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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:50:19 UTC
Update Date2022-03-07 02:55:24 UTC
HMDB IDHMDB0037586
Secondary Accession Numbers
  • HMDB37586
Metabolite Identification
Common NameGancaonin V
DescriptionGancaonin V belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. Gancaonin V has been detected, but not quantified in, herbs and spices. This could make gancaonin V a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Gancaonin V.
Structure
Data?1563863056
Synonyms
ValueSource
1-Isopentenyl-2,4,6,7-tetrahydroxy-9,10-dihydrophenanthreneHMDB
Chemical FormulaC19H20O4
Average Molecular Weight312.3597
Monoisotopic Molecular Weight312.136159128
IUPAC Name8-(3-methylbut-2-en-1-yl)-9,10-dihydrophenanthrene-2,3,5,7-tetrol
Traditional Name8-(3-methylbut-2-en-1-yl)-9,10-dihydrophenanthrene-2,3,5,7-tetrol
CAS Registry Number134958-57-9
SMILES
CC(C)=CCC1=C2CCC3=CC(O)=C(O)C=C3C2=C(O)C=C1O
InChI Identifier
InChI=1S/C19H20O4/c1-10(2)3-5-12-13-6-4-11-7-16(21)17(22)8-14(11)19(13)18(23)9-15(12)20/h3,7-9,20-23H,4-6H2,1-2H3
InChI KeyUEXOPXIMQJMWKA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassHydrophenanthrenes
Direct ParentHydrophenanthrenes
Alternative Parents
Substituents
  • Hydrophenanthrene
  • 1-naphthol
  • 2-naphthol
  • Naphthalene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.01ALOGPS
logP4.7ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.88ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity91.64 m³·mol⁻¹ChemAxon
Polarizability34.43 ųChemAxon
Number of Rings3ChemAxon
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]+175.85231661259
DarkChem[M-H]-173.99931661259
DeepCCS[M+H]+174.41830932474
DeepCCS[M-H]-172.0630932474
DeepCCS[M-2H]-205.6430932474
DeepCCS[M+Na]+180.86730932474
AllCCS[M+H]+175.232859911
AllCCS[M+H-H2O]+171.832859911
AllCCS[M+NH4]+178.232859911
AllCCS[M+Na]+179.132859911
AllCCS[M-H]-178.732859911
AllCCS[M+Na-2H]-178.232859911
AllCCS[M+HCOO]-177.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gancaonin VCC(C)=CCC1=C2CCC3=CC(O)=C(O)C=C3C2=C(O)C=C1O4798.7Standard polar33892256
Gancaonin VCC(C)=CCC1=C2CCC3=CC(O)=C(O)C=C3C2=C(O)C=C1O3020.9Standard non polar33892256
Gancaonin VCC(C)=CCC1=C2CCC3=CC(O)=C(O)C=C3C2=C(O)C=C1O3197.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gancaonin V,1TMS,isomer #1CC(C)=CCC1=C(O)C=C(O)C2=C1CCC1=CC(O[Si](C)(C)C)=C(O)C=C123057.6Semi standard non polar33892256
Gancaonin V,1TMS,isomer #2CC(C)=CCC1=C(O)C=C(O)C2=C1CCC1=CC(O)=C(O[Si](C)(C)C)C=C123019.0Semi standard non polar33892256
Gancaonin V,1TMS,isomer #3CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1CCC1=CC(O)=C(O)C=C123040.4Semi standard non polar33892256
Gancaonin V,1TMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1CCC1=CC(O)=C(O)C=C123012.8Semi standard non polar33892256
Gancaonin V,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1CCC1=CC(O[Si](C)(C)C)=C(O)C=C122877.3Semi standard non polar33892256
Gancaonin V,2TMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1CCC1=CC(O[Si](C)(C)C)=C(O)C=C122885.2Semi standard non polar33892256
Gancaonin V,2TMS,isomer #3CC(C)=CCC1=C(O)C=C(O)C2=C1CCC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C122903.5Semi standard non polar33892256
Gancaonin V,2TMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1CCC1=CC(O)=C(O[Si](C)(C)C)C=C122853.6Semi standard non polar33892256
Gancaonin V,2TMS,isomer #5CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1CCC1=CC(O)=C(O[Si](C)(C)C)C=C122894.8Semi standard non polar33892256
Gancaonin V,2TMS,isomer #6CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1CCC1=CC(O)=C(O)C=C122865.1Semi standard non polar33892256
Gancaonin V,3TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1CCC1=CC(O[Si](C)(C)C)=C(O)C=C122854.9Semi standard non polar33892256
Gancaonin V,3TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1CCC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C122826.2Semi standard non polar33892256
Gancaonin V,3TMS,isomer #3CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1CCC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C122854.0Semi standard non polar33892256
Gancaonin V,3TMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1CCC1=CC(O)=C(O[Si](C)(C)C)C=C122850.9Semi standard non polar33892256
Gancaonin V,4TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1CCC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C122885.4Semi standard non polar33892256
Gancaonin V,1TBDMS,isomer #1CC(C)=CCC1=C(O)C=C(O)C2=C1CCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C123344.3Semi standard non polar33892256
Gancaonin V,1TBDMS,isomer #2CC(C)=CCC1=C(O)C=C(O)C2=C1CCC1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C123309.7Semi standard non polar33892256
Gancaonin V,1TBDMS,isomer #3CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1CCC1=CC(O)=C(O)C=C123312.9Semi standard non polar33892256
Gancaonin V,1TBDMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1CCC1=CC(O)=C(O)C=C123304.6Semi standard non polar33892256
Gancaonin V,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1CCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C123423.4Semi standard non polar33892256
Gancaonin V,2TBDMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1CCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C123417.0Semi standard non polar33892256
Gancaonin V,2TBDMS,isomer #3CC(C)=CCC1=C(O)C=C(O)C2=C1CCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C123459.1Semi standard non polar33892256
Gancaonin V,2TBDMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1CCC1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C123382.5Semi standard non polar33892256
Gancaonin V,2TBDMS,isomer #5CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1CCC1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C123413.4Semi standard non polar33892256
Gancaonin V,2TBDMS,isomer #6CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1CCC1=CC(O)=C(O)C=C123393.7Semi standard non polar33892256
Gancaonin V,3TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1CCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C123531.8Semi standard non polar33892256
Gancaonin V,3TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1CCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C123512.7Semi standard non polar33892256
Gancaonin V,3TBDMS,isomer #3CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1CCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C123535.6Semi standard non polar33892256
Gancaonin V,3TBDMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1CCC1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C123523.6Semi standard non polar33892256
Gancaonin V,4TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1CCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C123653.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gancaonin V GC-MS (Non-derivatized) - 70eV, Positivesplash10-0535-2090000000-cefc67aa6229ad6b0df82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gancaonin V GC-MS (4 TMS) - 70eV, Positivesplash10-000i-1000190000-5c8236522106244cd6542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gancaonin V GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 10V, Positive-QTOFsplash10-03di-0049000000-039a9ebb2e93e78f000d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 20V, Positive-QTOFsplash10-0bt9-2492000000-6cc96fb7704152c231d42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 40V, Positive-QTOFsplash10-0f79-6690000000-3a250572e1f06d5a61762016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 10V, Negative-QTOFsplash10-03di-0009000000-965d65e89c56d434c3d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 20V, Negative-QTOFsplash10-03di-0039000000-b184f546715c1013ba062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 40V, Negative-QTOFsplash10-0006-1190000000-bd0a6318973507fb74242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 10V, Negative-QTOFsplash10-03di-0009000000-1436f13e3f3f2b9feffe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 20V, Negative-QTOFsplash10-03di-0029000000-fa3b581581ba1a8d9cb22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 40V, Negative-QTOFsplash10-004i-0090000000-230de61e9045ce6ad0742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 10V, Positive-QTOFsplash10-0a4i-0091000000-24dbc4b471b3cb0ae6d82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 20V, Positive-QTOFsplash10-0a4i-0091000000-205e500f30f6572a73d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gancaonin V 40V, Positive-QTOFsplash10-01p9-2970000000-f3d5af8f29e70a627e842021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB016690
KNApSAcK IDC00015194
Chemspider ID421878
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound480817
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1862481
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.. .