Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:45 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030579
Secondary Accession Numbers
  • HMDB30579
Metabolite Identification
Common NameC.I. Natural Red 20
DescriptionC.I. Natural Red 20 belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Based on a literature review very few articles have been published on C.I. Natural Red 20.
Structure
Data?1563862006
Synonyms
ValueSource
Alkanet extractHMDB
Alkanna redHMDB
AlkanninHMDB
Anchusa acidHMDB
AnchusinHMDB
C.I. 75530HMDB
2-((1R)-1-Hydroxy-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthoquinoneMeSH
5,8-Dihydroxy-2-((1R)-1-hydroxy-4-methyl-3-penten-1-yl)-1,4-naphthalenedioneMeSH
Isoarnebin 4MeSH
Shikonin, (+)-isomerMeSH
Chemical FormulaC16H16O5
Average Molecular Weight288.2952
Monoisotopic Molecular Weight288.099773622
IUPAC Name5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
Traditional Name5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione
CAS Registry Number517-88-4
SMILES
CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O
InChI Identifier
InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3
InChI KeyNEZONWMXZKDMKF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aromatic monoterpenoid
  • Bicyclic monoterpenoid
  • Monoterpenoid
  • Aryl ketone
  • Quinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point116 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.19ALOGPS
logP3.01ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.6ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.82 m³·mol⁻¹ChemAxon
Polarizability29.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.49231661259
DarkChem[M-H]-165.07231661259
DeepCCS[M+H]+166.75230932474
DeepCCS[M-H]-164.39430932474
DeepCCS[M-2H]-197.2830932474
DeepCCS[M+Na]+172.84630932474
AllCCS[M+H]+167.132859911
AllCCS[M+H-H2O]+163.632859911
AllCCS[M+NH4]+170.432859911
AllCCS[M+Na]+171.432859911
AllCCS[M-H]-169.032859911
AllCCS[M+Na-2H]-168.832859911
AllCCS[M+HCOO]-168.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
C.I. Natural Red 20CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O3976.5Standard polar33892256
C.I. Natural Red 20CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O2286.8Standard non polar33892256
C.I. Natural Red 20CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O2522.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
C.I. Natural Red 20,1TMS,isomer #1CC(C)=CCC(O[Si](C)(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O2478.9Semi standard non polar33892256
C.I. Natural Red 20,1TMS,isomer #2CC(C)=CCC(O)C1=CC(=O)C2=C(O[Si](C)(C)C)C=CC(O)=C2C1=O2609.4Semi standard non polar33892256
C.I. Natural Red 20,1TMS,isomer #3CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O[Si](C)(C)C)=C2C1=O2591.5Semi standard non polar33892256
C.I. Natural Red 20,2TMS,isomer #1CC(C)=CCC(O[Si](C)(C)C)C1=CC(=O)C2=C(O[Si](C)(C)C)C=CC(O)=C2C1=O2538.0Semi standard non polar33892256
C.I. Natural Red 20,2TMS,isomer #2CC(C)=CCC(O[Si](C)(C)C)C1=CC(=O)C2=C(O)C=CC(O[Si](C)(C)C)=C2C1=O2526.9Semi standard non polar33892256
C.I. Natural Red 20,2TMS,isomer #3CC(C)=CCC(O)C1=CC(=O)C2=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C2C1=O2591.4Semi standard non polar33892256
C.I. Natural Red 20,3TMS,isomer #1CC(C)=CCC(O[Si](C)(C)C)C1=CC(=O)C2=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C2C1=O2572.6Semi standard non polar33892256
C.I. Natural Red 20,1TBDMS,isomer #1CC(C)=CCC(O[Si](C)(C)C(C)(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O2754.9Semi standard non polar33892256
C.I. Natural Red 20,1TBDMS,isomer #2CC(C)=CCC(O)C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C2C1=O2855.1Semi standard non polar33892256
C.I. Natural Red 20,1TBDMS,isomer #3CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O2842.5Semi standard non polar33892256
C.I. Natural Red 20,2TBDMS,isomer #1CC(C)=CCC(O[Si](C)(C)C(C)(C)C)C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C2C1=O3041.3Semi standard non polar33892256
C.I. Natural Red 20,2TBDMS,isomer #2CC(C)=CCC(O[Si](C)(C)C(C)(C)C)C1=CC(=O)C2=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3035.6Semi standard non polar33892256
C.I. Natural Red 20,2TBDMS,isomer #3CC(C)=CCC(O)C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3073.5Semi standard non polar33892256
C.I. Natural Red 20,3TBDMS,isomer #1CC(C)=CCC(O[Si](C)(C)C(C)(C)C)C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3263.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ml-9280000000-b0844b9158a9ed8540c02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (3 TMS) - 70eV, Positivesplash10-01yc-9400800000-80ea5d873c7acc0809bf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 10V, Positive-QTOFsplash10-00dr-0090000000-075012fc8e371dc2176e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 20V, Positive-QTOFsplash10-0fy9-3690000000-91f11e32821de969fc962016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 40V, Positive-QTOFsplash10-0gbc-9230000000-192f49a494c02eaf64b32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 10V, Negative-QTOFsplash10-000i-0090000000-d06cd6d33d99ce2f26d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 20V, Negative-QTOFsplash10-000i-2790000000-649136aee6eabbfaaf172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 40V, Negative-QTOFsplash10-000i-2900000000-bbd3966288658c0b712f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 10V, Negative-QTOFsplash10-000i-0090000000-1b01e1b5bd30ed06ec252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 20V, Negative-QTOFsplash10-000i-0390000000-6df930f27a9fb74ab9f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 40V, Negative-QTOFsplash10-000i-4940000000-69c7d5eecdd1133dee732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 10V, Positive-QTOFsplash10-000i-0190000000-cbace8aa536e09d6a1572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 20V, Positive-QTOFsplash10-000m-1690000000-7b5921dde568b56f4d512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - C.I. Natural Red 20 40V, Positive-QTOFsplash10-0a4l-8960000000-5d996db7d5d10d3d385c2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002470
KNApSAcK IDNot Available
Chemspider ID5019
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .