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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:32 UTC
HMDB IDHMDB14435
Secondary Accession NumbersNone
Metabolite Identification
Common NameBleomycin
DescriptionA complex of related glycopeptide antibiotics from Streptomyces verticillus consisting of bleomycin A2 and B2 (B2 CAS # 9060-10-0). It inhibits DNA metabolism and is used as an antineoplastic, especially for solid tumors. Bleomycin A2 is used as the representative structure for Bleomycin.
Structure
Thumb
Synonyms
ValueSource
BleocinHMDB
BleomicinHMDB
Bleomycin a2HMDB
Bleomycin sulfateHMDB
Bleomycin sulphateHMDB
BLMHMDB
Chemical FormulaC55H84N17O21S3
Average Molecular Weight1415.552
Monoisotopic Molecular Weight1414.518979905
IUPAC Name(3-{[2-(2-{2-[(2S,3R)-2-[(2S,3S,4R)-4-[(2S,3R)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-[(3-{[4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-(1H-imidazol-5-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium
Traditional Namebleomycin
CAS Registry Number11056-06-7
SMILES
C[C@@H](O)[C@H](NC(=O)[C@@H](C)[C@H](O)[C@@H](C)NC(=O)[C@@H](NC(=O)C1=C(C)C(N)=NC(=N1)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(OC(N)=O)C1O)C1=CN=CN1)C(=O)NCCC1=NC(=CS1)C1=NC(=CS1)C(=O)NCCC[S+](C)C
InChI Identifier
InChI=1S/C55H83N17O21S3/c1-20-33(69-46(72-44(20)58)25(12-31(57)76)64-13-24(56)45(59)82)50(86)71-35(41(26-14-61-19-65-26)91-54-43(39(80)37(78)29(15-73)90-54)92-53-40(81)42(93-55(60)88)38(79)30(16-74)89-53)51(87)66-22(3)36(77)21(2)47(83)70-34(23(4)75)49(85)63-10-8-32-67-28(18-94-32)52-68-27(17-95-52)48(84)62-9-7-11-96(5)6/h14,17-19,21-25,29-30,34-43,53-54,64,73-75,77-81H,7-13,15-16,56H2,1-6H3,(H13-,57,58,59,60,61,62,63,65,66,69,70,71,72,76,82,83,84,85,86,87,88)/p+1/t21-,22+,23+,24-,25-,29?,30?,34-,35-,36-,37?,38?,39?,40?,41-,42?,43?,53?,54?/m0/s1
InChI KeyInChIKey=OYVAGSVQBOHSSS-WXFSZRTFSA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hybrid glycopeptides. These are compounds containing a carbohydrate component linked linked to a hybrid peptide component.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHybrid glycopeptides
Alternative Parents
Substituents
  • Hybrid glycopeptide
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • N-acyl-alpha amino acid or derivatives
  • Gamma amino acid or derivatives
  • Alpha-amino acid amide
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyrimidine-6-carboxylic acid or derivatives
  • Thiazolecarboxylic acid or derivatives
  • Thiazolecarboxamide
  • Aralkylamine
  • Aminopyrimidine
  • 2,4-disubstituted 1,3-thiazole
  • Fatty acyl
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Oxane
  • N-acyl-amine
  • Fatty amide
  • Saccharide
  • Heteroaromatic compound
  • Thiazole
  • Imidazole
  • Azole
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid amide
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antibiotics, Antineoplastic
  • Antimetabolites
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point71 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.82e-02 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.028 mg/mLALOGPS
logP-0.52ALOGPS
logP-9.7ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.34ChemAxon
pKa (Strongest Basic)7.67ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count28ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area627.07 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity344.16 m3·mol-1ChemAxon
Polarizability142.03 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00290
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00290
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-1 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-0 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00290
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4514492
KEGG Compound IDC06854
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBleomycin
NuGOwiki LinkHMDB14435
Metagene LinkHMDB14435
METLIN IDNot Available
PubChem Compound5360373
PDB IDNot Available
ChEBI ID22907
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Claussen CA, Long EC: Nucleic Acid recognition by metal complexes of bleomycin. Chem Rev. 1999 Sep 8;99(9):2797-816. [11749501 ]

Enzymes

General function:
Involved in DNA ligase (ATP) activity
Specific function:
Interacts with DNA-repair protein XRCC1 and can correct defective DNA strand-break repair and sister chromatid exchange following treatment with ionizing radiation and alkylating agents.
Gene Name:
LIG3
Uniprot ID:
P49916
Molecular weight:
106017.03
References
  1. Rose JL, Reeves KC, Likhotvorik RI, Hoyt DG: Base excision repair proteins are required for integrin-mediated suppression of bleomycin-induced DNA breakage in murine lung endothelial cells. J Pharmacol Exp Ther. 2007 Apr;321(1):318-26. Epub 2007 Jan 3. [17202402 ]
General function:
Involved in DNA ligase (ATP) activity
Specific function:
DNA ligase that seals nicks in double-stranded DNA during DNA replication, DNA recombination and DNA repair.
Gene Name:
LIG1
Uniprot ID:
P18858
Molecular weight:
101735.11
References
  1. Rose JL, Reeves KC, Likhotvorik RI, Hoyt DG: Base excision repair proteins are required for integrin-mediated suppression of bleomycin-induced DNA breakage in murine lung endothelial cells. J Pharmacol Exp Ther. 2007 Apr;321(1):318-26. Epub 2007 Jan 3. [17202402 ]