Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:52 UTC
HMDB IDHMDB0015132
Secondary Accession Numbers
  • HMDB15132
Metabolite Identification
Common NameDoxorubicin
DescriptionDoxorubicin, also known as adriamycin or adriblastina, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. Thus, doxorubicin is considered to be an aromatic polyketide lipid molecule. Doxorubicin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Doxorubicin exists in all living organisms, ranging from bacteria to humans. Within humans, doxorubicin participates in a number of enzymatic reactions. In particular, doxorubicin can be converted into doxorubicinol deoxaglycone through the action of the enzymes nad(p)H dehydrogenase [quinone] 1, nadph--cytochrome P450 reductase, and xanthine dehydrogenase/oxidase. In addition, doxorubicin can be converted into doxorubicinol; which is mediated by the enzymes carbonyl reductase [nadph] 1, carbonyl reductase [nadph] 3, aldo-keto reductase family 1 member C3, and alcohol dehydrogenase [nadp(+)]. In humans, doxorubicin is involved in doxorubicin metabolism pathway. Doxorubicin is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. People often experience red discoloration of the urine for a few days.
Structure
Data?1582753262
Synonyms
ValueSource
(1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosideChEBI
(8S-cis)-10-((3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedioneChEBI
14-HydroxydaunomycinChEBI
14-HydroxydaunorubicineChEBI
AdriamycinChEBI
DoxorubicineChEBI
DoxorubicinumChEBI
ADRKegg
AdriblastinaKegg
(1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosideGenerator
(1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosideGenerator
(8S-cis)-10-((3-Amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedioneGenerator
(8S-cis)-10-((3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedioneGenerator
AdriablastinHMDB
AdriblastinHMDB
Baxter brand OF doxorubicin hydrochlorideHMDB
Doxorubicin hydrochlorideHMDB
Doxorubicina ferrer farmHMDB
Ferrer brand OF doxorubicin hydrochlorideHMDB
Onkoworks brand OF doxorubicin hydrochlorideHMDB
Urokit doxo-cellHMDB
Ribosepharm brand OF doxorubicin hydrochlorideHMDB
AdrimedacHMDB
Bedford brand OF doxorubicin hydrochlorideHMDB
Doxorubicin hexalHMDB
Doxorubicin NCHMDB
Doxorubicina funkHMDB
DoxotecHMDB
Kenfarma brand OF doxorubicin hydrochlorideHMDB
Prasfarma brand OF doxorubicin hydrochlorideHMDB
RubexHMDB
Tedec meiji brand OF doxorubicin hydrochlorideHMDB
Cell pharm brand OF doxorubicin hydrochlorideHMDB
AdriblastineHMDB
Columbia brand OF doxorubicin hydrochlorideHMDB
Doxo cellHMDB
Doxo-cellHMDB
Elan brand OF doxorubicin hydrochlorideHMDB
FarmiblastinaHMDB
Lemery brand OF doxorubicin hydrochlorideHMDB
MyocetHMDB
OnkodoxHMDB
RibodoxoHMDB
AdriablastineHMDB
Bristol-myers squibb brand OF doxorubicin hydrochlorideHMDB
DoxolemHMDB
Doxorubicina tedecHMDB
Doxorubicine baxterHMDB
Hexal brand OF doxorubicin hydrochlorideHMDB
Hydrochloride, doxorubicinHMDB
Neocorp brand OF doxorubicin hydrochlorideHMDB
Pfizer brand OF doxorubicin hydrochlorideHMDB
Urokit doxo cellHMDB
Medac brand OF doxorubicin hydrochlorideHMDB
Chemical FormulaC27H29NO11
Average Molecular Weight543.5193
Monoisotopic Molecular Weight543.174060775
IUPAC Name(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
Traditional Namedoxorubicin
CAS Registry Number23214-92-8
SMILES
COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O
InChI Identifier
InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
InChI KeyAOJJSUZBOXZQNB-TZSSRYMLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point204 - 205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.18 g/LNot Available
LogP-0.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available226.977http://allccs.zhulab.cn/database/detail?ID=AllCCS00001404
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.18 g/LALOGPS
logP1.41ALOGPS
logP0.92ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)9.53ChemAxon
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area206.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity134.59 m³·mol⁻¹ChemAxon
Polarizability53.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+221.43731661259
DarkChem[M-H]-213.69431661259
DeepCCS[M+H]+219.21130932474
DeepCCS[M-H]-217.38630932474
DeepCCS[M-2H]-250.89330932474
DeepCCS[M+Na]+224.81730932474
AllCCS[M+H]+222.432859911
AllCCS[M+H-H2O]+220.832859911
AllCCS[M+NH4]+223.832859911
AllCCS[M+Na]+224.232859911
AllCCS[M-H]-222.032859911
AllCCS[M+Na-2H]-223.632859911
AllCCS[M+HCOO]-225.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DoxorubicinCOC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O4544.9Standard polar33892256
DoxorubicinCOC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O4387.7Standard non polar33892256
DoxorubicinCOC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O4769.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Doxorubicin,1TMS,isomer #1COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4420.9Semi standard non polar33892256
Doxorubicin,1TMS,isomer #2COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4422.5Semi standard non polar33892256
Doxorubicin,1TMS,isomer #3COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4401.2Semi standard non polar33892256
Doxorubicin,1TMS,isomer #4COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4372.1Semi standard non polar33892256
Doxorubicin,1TMS,isomer #5COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4443.1Semi standard non polar33892256
Doxorubicin,1TMS,isomer #6COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4428.9Semi standard non polar33892256
Doxorubicin,1TMS,isomer #7COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4396.0Semi standard non polar33892256
Doxorubicin,2TMS,isomer #1COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4345.1Semi standard non polar33892256
Doxorubicin,2TMS,isomer #10COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4335.6Semi standard non polar33892256
Doxorubicin,2TMS,isomer #11COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4290.5Semi standard non polar33892256
Doxorubicin,2TMS,isomer #12COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4336.5Semi standard non polar33892256
Doxorubicin,2TMS,isomer #13COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4284.8Semi standard non polar33892256
Doxorubicin,2TMS,isomer #14COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4294.2Semi standard non polar33892256
Doxorubicin,2TMS,isomer #15COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4294.6Semi standard non polar33892256
Doxorubicin,2TMS,isomer #16COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4301.5Semi standard non polar33892256
Doxorubicin,2TMS,isomer #17COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4314.4Semi standard non polar33892256
Doxorubicin,2TMS,isomer #18COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4253.2Semi standard non polar33892256
Doxorubicin,2TMS,isomer #19COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4310.3Semi standard non polar33892256
Doxorubicin,2TMS,isomer #2COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4328.0Semi standard non polar33892256
Doxorubicin,2TMS,isomer #20COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4321.3Semi standard non polar33892256
Doxorubicin,2TMS,isomer #21COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4325.6Semi standard non polar33892256
Doxorubicin,2TMS,isomer #22COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4389.0Semi standard non polar33892256
Doxorubicin,2TMS,isomer #3COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4292.8Semi standard non polar33892256
Doxorubicin,2TMS,isomer #4COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4329.9Semi standard non polar33892256
Doxorubicin,2TMS,isomer #5COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4297.8Semi standard non polar33892256
Doxorubicin,2TMS,isomer #6COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4308.1Semi standard non polar33892256
Doxorubicin,2TMS,isomer #7COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4335.8Semi standard non polar33892256
Doxorubicin,2TMS,isomer #8COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4292.7Semi standard non polar33892256
Doxorubicin,2TMS,isomer #9COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4310.2Semi standard non polar33892256
Doxorubicin,3TMS,isomer #1COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4262.1Semi standard non polar33892256
Doxorubicin,3TMS,isomer #10COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4220.2Semi standard non polar33892256
Doxorubicin,3TMS,isomer #11COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4207.0Semi standard non polar33892256
Doxorubicin,3TMS,isomer #12COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4207.6Semi standard non polar33892256
Doxorubicin,3TMS,isomer #13COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4206.0Semi standard non polar33892256
Doxorubicin,3TMS,isomer #14COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4252.2Semi standard non polar33892256
Doxorubicin,3TMS,isomer #15COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4243.0Semi standard non polar33892256
Doxorubicin,3TMS,isomer #16COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4299.4Semi standard non polar33892256
Doxorubicin,3TMS,isomer #17COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4241.6Semi standard non polar33892256
Doxorubicin,3TMS,isomer #18COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4246.1Semi standard non polar33892256
Doxorubicin,3TMS,isomer #19COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4235.2Semi standard non polar33892256
Doxorubicin,3TMS,isomer #2COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4229.9Semi standard non polar33892256
Doxorubicin,3TMS,isomer #20COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4237.7Semi standard non polar33892256
Doxorubicin,3TMS,isomer #21COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4213.4Semi standard non polar33892256
Doxorubicin,3TMS,isomer #22COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4220.7Semi standard non polar33892256
Doxorubicin,3TMS,isomer #23COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4191.5Semi standard non polar33892256
Doxorubicin,3TMS,isomer #24COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4209.0Semi standard non polar33892256
Doxorubicin,3TMS,isomer #25COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4216.5Semi standard non polar33892256
Doxorubicin,3TMS,isomer #26COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4255.7Semi standard non polar33892256
Doxorubicin,3TMS,isomer #27COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4295.1Semi standard non polar33892256
Doxorubicin,3TMS,isomer #28COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4224.4Semi standard non polar33892256
Doxorubicin,3TMS,isomer #29COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4211.1Semi standard non polar33892256
Doxorubicin,3TMS,isomer #3COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4266.8Semi standard non polar33892256
Doxorubicin,3TMS,isomer #30COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4245.9Semi standard non polar33892256
Doxorubicin,3TMS,isomer #31COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4215.4Semi standard non polar33892256
Doxorubicin,3TMS,isomer #32COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4189.2Semi standard non polar33892256
Doxorubicin,3TMS,isomer #33COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4225.9Semi standard non polar33892256
Doxorubicin,3TMS,isomer #34COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4295.1Semi standard non polar33892256
Doxorubicin,3TMS,isomer #35COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4223.4Semi standard non polar33892256
Doxorubicin,3TMS,isomer #36COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4211.5Semi standard non polar33892256
Doxorubicin,3TMS,isomer #37COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4225.6Semi standard non polar33892256
Doxorubicin,3TMS,isomer #38COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4259.1Semi standard non polar33892256
Doxorubicin,3TMS,isomer #39COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4248.6Semi standard non polar33892256
Doxorubicin,3TMS,isomer #4COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4201.5Semi standard non polar33892256
Doxorubicin,3TMS,isomer #40COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4305.5Semi standard non polar33892256
Doxorubicin,3TMS,isomer #41COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4321.7Semi standard non polar33892256
Doxorubicin,3TMS,isomer #5COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4266.9Semi standard non polar33892256
Doxorubicin,3TMS,isomer #6COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4232.6Semi standard non polar33892256
Doxorubicin,3TMS,isomer #7COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4249.8Semi standard non polar33892256
Doxorubicin,3TMS,isomer #8COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4228.7Semi standard non polar33892256
Doxorubicin,3TMS,isomer #9COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4244.6Semi standard non polar33892256
Doxorubicin,4TMS,isomer #1COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4184.0Semi standard non polar33892256
Doxorubicin,4TMS,isomer #10COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4196.6Semi standard non polar33892256
Doxorubicin,4TMS,isomer #11COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4250.7Semi standard non polar33892256
Doxorubicin,4TMS,isomer #12COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4180.6Semi standard non polar33892256
Doxorubicin,4TMS,isomer #13COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4155.7Semi standard non polar33892256
Doxorubicin,4TMS,isomer #14COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4192.3Semi standard non polar33892256
Doxorubicin,4TMS,isomer #15COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4156.1Semi standard non polar33892256
Doxorubicin,4TMS,isomer #16COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4196.2Semi standard non polar33892256
Doxorubicin,4TMS,isomer #17COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4219.4Semi standard non polar33892256
Doxorubicin,4TMS,isomer #18COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4261.5Semi standard non polar33892256
Doxorubicin,4TMS,isomer #19COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4150.2Semi standard non polar33892256
Doxorubicin,4TMS,isomer #2COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4187.3Semi standard non polar33892256
Doxorubicin,4TMS,isomer #20COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4180.4Semi standard non polar33892256
Doxorubicin,4TMS,isomer #21COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4184.1Semi standard non polar33892256
Doxorubicin,4TMS,isomer #22COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4230.5Semi standard non polar33892256
Doxorubicin,4TMS,isomer #23COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4188.5Semi standard non polar33892256
Doxorubicin,4TMS,isomer #24COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4267.6Semi standard non polar33892256
Doxorubicin,4TMS,isomer #25COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4267.8Semi standard non polar33892256
Doxorubicin,4TMS,isomer #26COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4178.3Semi standard non polar33892256
Doxorubicin,4TMS,isomer #27COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4172.8Semi standard non polar33892256
Doxorubicin,4TMS,isomer #28COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4192.5Semi standard non polar33892256
Doxorubicin,4TMS,isomer #29COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4164.7Semi standard non polar33892256
Doxorubicin,4TMS,isomer #3COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4160.8Semi standard non polar33892256
Doxorubicin,4TMS,isomer #30COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4185.8Semi standard non polar33892256
Doxorubicin,4TMS,isomer #31COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4219.2Semi standard non polar33892256
Doxorubicin,4TMS,isomer #32COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4263.3Semi standard non polar33892256
Doxorubicin,4TMS,isomer #33COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4146.6Semi standard non polar33892256
Doxorubicin,4TMS,isomer #34COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4149.5Semi standard non polar33892256
Doxorubicin,4TMS,isomer #35COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4178.1Semi standard non polar33892256
Doxorubicin,4TMS,isomer #36COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4244.7Semi standard non polar33892256
Doxorubicin,4TMS,isomer #37COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4184.2Semi standard non polar33892256
Doxorubicin,4TMS,isomer #38COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4256.0Semi standard non polar33892256
Doxorubicin,4TMS,isomer #39COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4288.1Semi standard non polar33892256
Doxorubicin,4TMS,isomer #4COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4218.0Semi standard non polar33892256
Doxorubicin,4TMS,isomer #40COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4158.5Semi standard non polar33892256
Doxorubicin,4TMS,isomer #41COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4176.6Semi standard non polar33892256
Doxorubicin,4TMS,isomer #42COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4195.7Semi standard non polar33892256
Doxorubicin,4TMS,isomer #43COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4266.3Semi standard non polar33892256
Doxorubicin,4TMS,isomer #44COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4161.3Semi standard non polar33892256
Doxorubicin,4TMS,isomer #45COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4226.4Semi standard non polar33892256
Doxorubicin,4TMS,isomer #46COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O4267.7Semi standard non polar33892256
Doxorubicin,4TMS,isomer #47COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4186.7Semi standard non polar33892256
Doxorubicin,4TMS,isomer #48COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4241.7Semi standard non polar33892256
Doxorubicin,4TMS,isomer #49COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4268.3Semi standard non polar33892256
Doxorubicin,4TMS,isomer #5COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4167.9Semi standard non polar33892256
Doxorubicin,4TMS,isomer #50COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4278.2Semi standard non polar33892256
Doxorubicin,4TMS,isomer #6COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4124.3Semi standard non polar33892256
Doxorubicin,4TMS,isomer #7COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4194.3Semi standard non polar33892256
Doxorubicin,4TMS,isomer #8COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4138.8Semi standard non polar33892256
Doxorubicin,4TMS,isomer #9COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O4213.6Semi standard non polar33892256
Doxorubicin,1TBDMS,isomer #1COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4637.4Semi standard non polar33892256
Doxorubicin,1TBDMS,isomer #2COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4627.2Semi standard non polar33892256
Doxorubicin,1TBDMS,isomer #3COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4606.6Semi standard non polar33892256
Doxorubicin,1TBDMS,isomer #4COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4627.4Semi standard non polar33892256
Doxorubicin,1TBDMS,isomer #5COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4663.1Semi standard non polar33892256
Doxorubicin,1TBDMS,isomer #6COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4624.7Semi standard non polar33892256
Doxorubicin,1TBDMS,isomer #7COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4631.4Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #1COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4787.7Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #10COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4737.8Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #11COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4748.7Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #12COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4782.3Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #13COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4766.4Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #14COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4739.7Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #15COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4731.9Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #16COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4784.4Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #17COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4741.6Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #18COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4753.0Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #19COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4753.8Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #2COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4768.5Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #20COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4778.1Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #21COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4752.5Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #22COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4822.5Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #3COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4754.4Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #4COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4758.6Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #5COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4730.2Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #6COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4759.1Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #7COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4780.7Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #8COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4770.3Semi standard non polar33892256
Doxorubicin,2TBDMS,isomer #9COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4756.5Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #1COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4886.3Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #10COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4877.5Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #11COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4827.6Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #12COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4877.3Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #13COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4819.1Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #14COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4837.1Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #15COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4814.5Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #16COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4961.4Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #17COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4923.7Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #18COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4914.4Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #19COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4869.9Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #2COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4867.4Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #20COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4892.1Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #21COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4918.6Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #22COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4860.7Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #23COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4894.1Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #24COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4867.4Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #25COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4871.5Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #26COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4851.1Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #27COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4943.0Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #28COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4915.3Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #29COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4845.0Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #3COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4858.9Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #30COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4867.7Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #31COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4855.0Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #32COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4881.1Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #33COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4819.4Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #34COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4957.9Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #35COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4857.4Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #36COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4904.4Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #37COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4860.9Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #38COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4952.8Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #39COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4840.7Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #4COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4817.2Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #40COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4975.1Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #41COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4965.5Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #5COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O4858.3Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #6COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4901.9Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #7COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O4893.7Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #8COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4849.5Semi standard non polar33892256
Doxorubicin,3TBDMS,isomer #9COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](C)O3)C(O)=C1C2=O4878.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100210000-2b807cbc2c92b3239ce22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (2 TMS) - 70eV, Positivesplash10-0fl0-4910224000-4bfde6a587c553084e352017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxorubicin GC-MS (TMS_2_17) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxorubicin LC-ESI-qTof , Positive-QTOFsplash10-006t-0109000000-ac65f689e3fa439adddc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxorubicin , positive-QTOFsplash10-006t-0109000000-ac65f689e3fa439adddc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxorubicin 35V, Positive-QTOFsplash10-03k9-0309000000-868891bb4c99d599c2842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxorubicin 35V, Negative-QTOFsplash10-0002-0009000000-5b676bfe14711ba000d62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 10V, Positive-QTOFsplash10-00ov-0005390000-f948ee4b89881c04094f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 20V, Positive-QTOFsplash10-00l2-1319310000-6809908c73812c7294b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 40V, Positive-QTOFsplash10-0pea-4109100000-aa6428ee7c0e41ed2d972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 10V, Negative-QTOFsplash10-01ox-0002390000-1d86ac1de2afc3f4ce0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 20V, Negative-QTOFsplash10-08fv-5209740000-2da58c964c8e55c74f5e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 40V, Negative-QTOFsplash10-08fr-7207900000-9dd3041a50cddfad58dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 10V, Positive-QTOFsplash10-004j-0409070000-1f754ac056625a678f5e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 20V, Positive-QTOFsplash10-01u1-2619140000-93871ebd236804cb7e032021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 40V, Positive-QTOFsplash10-03e9-4910200000-64c8902380be8a1fd1832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 10V, Negative-QTOFsplash10-000t-0009000000-c2261d7295031ec8b1a32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 20V, Negative-QTOFsplash10-00kr-0009000000-c0d23b7b41211d5bcf7d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxorubicin 40V, Negative-QTOFsplash10-0006-1009230000-adab49e4224b716b7c2f2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00997 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00997 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00997
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID29400
KEGG Compound IDC01661
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDoxorubicin
METLIN IDNot Available
PubChem Compound31703
PDB IDNot Available
ChEBI ID28748
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Weiss RB: The anthracyclines: will we ever find a better doxorubicin? Semin Oncol. 1992 Dec;19(6):670-86. [PubMed:1462166 ]
  2. Minotti G: Reactions of adriamycin with microsomal iron and lipids. Free Radic Res Commun. 1989;7(3-6):143-8. [PubMed:2555273 ]
  3. Tan C, Tasaka H, Yu KP, Murphy ML, Karnofsky DA: Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease. Clinical evaluation with special reference to childhood leukemia. Cancer. 1967 Mar;20(3):333-53. [PubMed:4290058 ]
  4. Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C: Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng. 1969 Nov;11(6):1101-10. [PubMed:5365804 ]
  5. Di Marco A, Gaetani M, Scarpinato B: Adriamycin (NSC-123,127): a new antibiotic with antitumor activity. Cancer Chemother Rep. 1969 Feb;53(1):33-7. [PubMed:5772652 ]
  6. Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, Inventi-Solari A, Filippini S, Torti F, Colombo AL, Hutchinson CR: Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene. J Bacteriol. 1999 Jan;181(1):305-18. [PubMed:9864344 ]
  7. Mordente A, Meucci E, Silvestrini A, Martorana GE, Giardina B: New developments in anthracycline-induced cardiotoxicity. Curr Med Chem. 2009;16(13):1656-72. [PubMed:19442138 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Lu H, Chen CS, Waxman DJ: Potentiation of methoxymorpholinyl doxorubicin antitumor activity by P450 3A4 gene transfer. Cancer Gene Ther. 2009 May;16(5):393-404. doi: 10.1038/cgt.2008.93. Epub 2008 Nov 14. [PubMed:19011599 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Masek V, Anzenbacherova E, Etrych T, Strohalm J, Ulbrich K, Anzenbacher P: Interaction of N-(2-hydroxypropyl)methacrylamide copolymer-doxorubicin conjugates with human liver microsomal cytochromes P450: comparison with free doxorubicin. Drug Metab Dispos. 2011 Sep;39(9):1704-10. doi: 10.1124/dmd.110.037986. Epub 2011 Jun 3. [PubMed:21642392 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular weight:
174383.9
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Rody A, Karn T, Gatje R, Ahr A, Solbach C, Kourtis K, Munnes M, Loibl S, Kissler S, Ruckhaberle E, Holtrich U, von Minckwitz G, Kaufmann M: Gene expression profiling of breast cancer patients treated with docetaxel, doxorubicin, and cyclophosphamide within the GEPARTRIO trial: HER-2, but not topoisomerase II alpha and microtubule-associated protein tau, is highly predictive of tumor response. Breast. 2007 Feb;16(1):86-93. Epub 2006 Sep 28. [PubMed:17010609 ]
  3. Koehn H, Magan N, Isaacs RJ, Stowell KM: Differential regulation of DNA repair protein Rad51 in human tumour cell lines exposed to doxorubicin. Anticancer Drugs. 2007 Apr;18(4):419-25. [PubMed:17351394 ]
  4. Hayashi S, Hatashita M, Matsumoto H, Shioura H, Kitai R, Kano E: Enhancement of radiosensitivity by topoisomerase II inhibitor, amrubicin and amrubicinol, in human lung adenocarcinoma A549 cells and kinetics of apoptosis and necrosis induction. Int J Mol Med. 2006 Nov;18(5):909-15. [PubMed:17016621 ]
  5. Azarova AM, Lyu YL, Lin CP, Tsai YC, Lau JY, Wang JC, Liu LF: Roles of DNA topoisomerase II isozymes in chemotherapy and secondary malignancies. Proc Natl Acad Sci U S A. 2007 Jun 26;104(26):11014-9. Epub 2007 Jun 19. [PubMed:17578914 ]
  6. Menendez JA, Vellon L, Lupu R: DNA topoisomerase IIalpha (TOP2A) inhibitors up-regulate fatty acid synthase gene expression in SK-Br3 breast cancer cells: in vitro evidence for a 'functional amplicon' involving FAS, Her-2/neu and TOP2A genes. Int J Mol Med. 2006 Dec;18(6):1081-7. [PubMed:17089011 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular weight:
171589.5
References
  1. Loe DW, Almquist KC, Cole SP, Deeley RG: ATP-dependent 17 beta-estradiol 17-(beta-D-glucuronide) transport by multidrug resistance protein (MRP). Inhibition by cholestatic steroids. J Biol Chem. 1996 Apr 19;271(16):9683-9. [PubMed:8621644 ]
  2. Godinot N, Iversen PW, Tabas L, Xia X, Williams DC, Dantzig AH, Perry WL 3rd: Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey. Mol Cancer Ther. 2003 Mar;2(3):307-16. [PubMed:12657726 ]
  3. Tribull TE, Bruner RH, Bain LJ: The multidrug resistance-associated protein 1 transports methoxychlor and protects the seminiferous epithelium from injury. Toxicol Lett. 2003 Apr 30;142(1-2):61-70. [PubMed:12765240 ]
  4. Nunoya K, Grant CE, Zhang D, Cole SP, Deeley RG: Molecular cloning and pharmacological characterization of rat multidrug resistance protein 1 (mrp1). Drug Metab Dispos. 2003 Aug;31(8):1016-26. [PubMed:12867490 ]
  5. Stride BD, Grant CE, Loe DW, Hipfner DR, Cole SP, Deeley RG: Pharmacological characterization of the murine and human orthologs of multidrug-resistance protein in transfected human embryonic kidney cells. Mol Pharmacol. 1997 Sep;52(3):344-53. [PubMed:9281595 ]
  6. Wong IL, Chan KF, Tsang KH, Lam CY, Zhao Y, Chan TH, Chow LM: Modulation of multidrug resistance protein 1 (MRP1/ABCC1)-mediated multidrug resistance by bivalent apigenin homodimers and their derivatives. J Med Chem. 2009 Sep 10;52(17):5311-22. doi: 10.1021/jm900194w. [PubMed:19725578 ]
  7. Tao LY, Liang YJ, Wang F, Chen LM, Yan YY, Dai CL, Fu LW: Cediranib (recentin, AZD2171) reverses ABCB1- and ABCC1-mediated multidrug resistance by inhibition of their transport function. Cancer Chemother Pharmacol. 2009 Oct;64(5):961-9. doi: 10.1007/s00280-009-0949-1. Epub 2009 Mar 3. [PubMed:19255759 ]
  8. Zheng LS, Wang F, Li YH, Zhang X, Chen LM, Liang YJ, Dai CL, Yan YY, Tao LY, Mi YJ, Yang AK, To KK, Fu LW: Vandetanib (Zactima, ZD6474) antagonizes ABCC1- and ABCG2-mediated multidrug resistance by inhibition of their transport function. PLoS One. 2009;4(4):e5172. doi: 10.1371/journal.pone.0005172. Epub 2009 Apr 23. [PubMed:19390592 ]
General function:
Involved in ATP binding
Specific function:
May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4) and N-ethylmaleimide S-glutathione (NEM-GS)
Gene Name:
ABCC6
Uniprot ID:
O95255
Molecular weight:
164904.8
References
  1. Cai J, Daoud R, Alqawi O, Georges E, Pelletier J, Gros P: Nucleotide binding and nucleotide hydrolysis properties of the ABC transporter MRP6 (ABCC6). Biochemistry. 2002 Jun 25;41(25):8058-67. [PubMed:12069597 ]
  2. Belinsky MG, Chen ZS, Shchaveleva I, Zeng H, Kruh GD: Characterization of the drug resistance and transport properties of multidrug resistance protein 6 (MRP6, ABCC6). Cancer Res. 2002 Nov 1;62(21):6172-7. [PubMed:12414644 ]
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular weight:
169341.1
References
  1. Zeng H, Chen ZS, Belinsky MG, Rea PA, Kruh GD: Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32. [PubMed:11585759 ]
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Fardel O, Lecureur V, Daval S, Corlu A, Guillouzo A: Up-regulation of P-glycoprotein expression in rat liver cells by acute doxorubicin treatment. Eur J Biochem. 1997 May 15;246(1):186-92. [PubMed:9210482 ]
  2. Gao J, Murase O, Schowen RL, Aube J, Borchardt RT: A functional assay for quantitation of the apparent affinities of ligands of P-glycoprotein in Caco-2 cells. Pharm Res. 2001 Feb;18(2):171-6. [PubMed:11405287 ]
  3. Takara K, Tanigawara Y, Komada F, Nishiguchi K, Sakaeda T, Okumura K: Cellular pharmacokinetic aspects of reversal effect of itraconazole on P-glycoprotein-mediated resistance of anticancer drugs. Biol Pharm Bull. 1999 Dec;22(12):1355-9. [PubMed:10746169 ]
  4. Jutabha P, Wempe MF, Anzai N, Otomo J, Kadota T, Endou H: Xenopus laevis oocytes expressing human P-glycoprotein: probing trans- and cis-inhibitory effects on [3H]vinblastine and [3H]digoxin efflux. Pharmacol Res. 2010 Jan;61(1):76-84. doi: 10.1016/j.phrs.2009.07.002. Epub 2009 Jul 21. [PubMed:19631272 ]
  5. Li D, Jang SH, Kim J, Wientjes MG, Au JL: Enhanced drug-induced apoptosis associated with P-glycoprotein overexpression is specific to antimicrotubule agents. Pharm Res. 2003 Jan;20(1):45-50. [PubMed:12608535 ]
  6. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]
  7. Kim S, Kim SS, Bang YJ, Kim SJ, Lee BJ: In vitro activities of native and designed peptide antibiotics against drug sensitive and resistant tumor cell lines. Peptides. 2003 Jul;24(7):945-53. [PubMed:14499271 ]
  8. Ambudkar SV, Lelong IH, Zhang J, Cardarelli CO, Gottesman MM, Pastan I: Partial purification and reconstitution of the human multidrug-resistance pump: characterization of the drug-stimulatable ATP hydrolysis. Proc Natl Acad Sci U S A. 1992 Sep 15;89(18):8472-6. [PubMed:1356264 ]
  9. Kusunoki N, Takara K, Tanigawara Y, Yamauchi A, Ueda K, Komada F, Ku Y, Kuroda Y, Saitoh Y, Okumura K: Inhibitory effects of a cyclosporin derivative, SDZ PSC 833, on transport of doxorubicin and vinblastine via human P-glycoprotein. Jpn J Cancer Res. 1998 Nov;89(11):1220-8. [PubMed:9914792 ]
  10. Li YC, Fung KP, Kwok TT, Lee CY, Suen YK, Kong SK: Mitochondria-targeting drug oligomycin blocked P-glycoprotein activity and triggered apoptosis in doxorubicin-resistant HepG2 cells. Chemotherapy. 2004 Jun;50(2):55-62. [PubMed:15211078 ]
  11. Sieczkowski E, Lehner C, Ambros PF, Hohenegger M: Double impact on p-glycoprotein by statins enhances doxorubicin cytotoxicity in human neuroblastoma cells. Int J Cancer. 2010 May 1;126(9):2025-35. doi: 10.1002/ijc.24885. [PubMed:19739078 ]
  12. Bray J, Sludden J, Griffin MJ, Cole M, Verrill M, Jamieson D, Boddy AV: Influence of pharmacogenetics on response and toxicity in breast cancer patients treated with doxorubicin and cyclophosphamide. Br J Cancer. 2010 Mar 16;102(6):1003-9. doi: 10.1038/sj.bjc.6605587. Epub 2010 Feb 23. [PubMed:20179710 ]
  13. Tao LY, Liang YJ, Wang F, Chen LM, Yan YY, Dai CL, Fu LW: Cediranib (recentin, AZD2171) reverses ABCB1- and ABCC1-mediated multidrug resistance by inhibition of their transport function. Cancer Chemother Pharmacol. 2009 Oct;64(5):961-9. doi: 10.1007/s00280-009-0949-1. Epub 2009 Mar 3. [PubMed:19255759 ]
  14. Woodahl EL, Crouthamel MH, Bui T, Shen DD, Ho RJ: MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8. doi: 10.1007/s00280-008-0906-4. Epub 2009 Jan 4. [PubMed:19123050 ]
General function:
Involved in ATP binding
Specific function:
Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular weight:
72313.5
References
  1. Suzuki M, Suzuki H, Sugimoto Y, Sugiyama Y: ABCG2 transports sulfated conjugates of steroids and xenobiotics. J Biol Chem. 2003 Jun 20;278(25):22644-9. Epub 2003 Apr 7. [PubMed:12682043 ]
  2. Wang X, Furukawa T, Nitanda T, Okamoto M, Sugimoto Y, Akiyama S, Baba M: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Mol Pharmacol. 2003 Jan;63(1):65-72. [PubMed:12488537 ]
  3. Ozvegy C, Litman T, Szakacs G, Nagy Z, Bates S, Varadi A, Sarkadi B: Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells. Biochem Biophys Res Commun. 2001 Jul 6;285(1):111-7. [PubMed:11437380 ]
  4. Allen JD, Van Dort SC, Buitelaar M, van Tellingen O, Schinkel AH: Mouse breast cancer resistance protein (Bcrp1/Abcg2) mediates etoposide resistance and transport, but etoposide oral availability is limited primarily by P-glycoprotein. Cancer Res. 2003 Mar 15;63(6):1339-44. [PubMed:12649196 ]
  5. An Y, Ongkeko WM: ABCG2: the key to chemoresistance in cancer stem cells? Expert Opin Drug Metab Toxicol. 2009 Dec;5(12):1529-42. doi: 10.1517/17425250903228834. [PubMed:19708828 ]
  6. Tiwari AK, Sodani K, Wang SR, Kuang YH, Ashby CR Jr, Chen X, Chen ZS: Nilotinib (AMN107, Tasigna) reverses multidrug resistance by inhibiting the activity of the ABCB1/Pgp and ABCG2/BCRP/MXR transporters. Biochem Pharmacol. 2009 Jul 15;78(2):153-61. doi: 10.1016/j.bcp.2009.04.002. Epub 2009 Apr 11. [PubMed:19427995 ]
  7. Dai CL, Liang YJ, Wang YS, Tiwari AK, Yan YY, Wang F, Chen ZS, Tong XZ, Fu LW: Sensitization of ABCG2-overexpressing cells to conventional chemotherapeutic agent by sunitinib was associated with inhibiting the function of ABCG2. Cancer Lett. 2009 Jun 28;279(1):74-83. doi: 10.1016/j.canlet.2009.01.027. Epub 2009 Feb 18. [PubMed:19232821 ]
  8. Zheng LS, Wang F, Li YH, Zhang X, Chen LM, Liang YJ, Dai CL, Yan YY, Tao LY, Mi YJ, Yang AK, To KK, Fu LW: Vandetanib (Zactima, ZD6474) antagonizes ABCC1- and ABCG2-mediated multidrug resistance by inhibition of their transport function. PLoS One. 2009;4(4):e5172. doi: 10.1371/journal.pone.0005172. Epub 2009 Apr 23. [PubMed:19390592 ]
General function:
Involved in transporter activity
Specific function:
High affinity carnitine transporter; the uptake is partially sodium-ion dependent. Thought to mediate the L-carnitine secretion mechanism from testis epididymal epithelium into the lumen which is involved in the maturation of spermatozoa. Also transports organic cations such as tetraethylammonium (TEA) and doxorubicin. The uptake of TEA is inhibited by various organic cations. The uptake of doxorubicin is sodium-independent
Gene Name:
SLC22A16
Uniprot ID:
Q86VW1
Molecular weight:
64613.6
References
  1. Bray J, Sludden J, Griffin MJ, Cole M, Verrill M, Jamieson D, Boddy AV: Influence of pharmacogenetics on response and toxicity in breast cancer patients treated with doxorubicin and cyclophosphamide. Br J Cancer. 2010 Mar 16;102(6):1003-9. doi: 10.1038/sj.bjc.6605587. Epub 2010 Feb 23. [PubMed:20179710 ]

Only showing the first 10 proteins. There are 12 proteins in total.