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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:08:04 UTC
Update Date2022-03-07 02:55:55 UTC
HMDB IDHMDB0038789
Secondary Accession Numbers
  • HMDB38789
Metabolite Identification
Common NameTorvanol A
DescriptionTorvanol A belongs to the class of organic compounds known as 6-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C6 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Torvanol A has been detected, but not quantified in, fruits. This could make torvanol a a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Torvanol A.
Structure
Data?1563863258
Synonyms
ValueSource
4-Sulfate-2'-hydroxy-6,3'-dimethoxy-5'-(2-propenoic acid)isoflavoneHMDB
(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoateGenerator
(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulphooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoateGenerator
(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulphooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoic acidGenerator
Torvanol aMeSH
Chemical FormulaC20H20O10S
Average Molecular Weight452.432
Monoisotopic Molecular Weight452.07771755
IUPAC Name(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoic acid
Traditional Name(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(OCC(C2OS(O)(=O)=O)C2=C(O)C(OC)=CC(\C=C\C(O)=O)=C2)C=C1
InChI Identifier
InChI=1S/C20H20O10S/c1-27-12-4-5-16-14(9-12)20(30-31(24,25)26)15(10-29-16)13-7-11(3-6-18(21)22)8-17(28-2)19(13)23/h3-9,15,20,23H,10H2,1-2H3,(H,21,22)(H,24,25,26)/b6-3+
InChI KeyXKGLTSPFQHSIDD-ZZXKWVIFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C6 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent6-O-methylated isoflavonoids
Alternative Parents
Substituents
  • 3p-methoxyisoflavonoid-skeleton
  • 6-methoxyisoflavonoid-skeleton
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Isoflavan
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • Phenol
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Benzenoid
  • Sulfuric acid monoester
  • Monocyclic benzene moiety
  • Organic sulfuric acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP0.71ALOGPS
logP2.21ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.82 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.32 m³·mol⁻¹ChemAxon
Polarizability43.44 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+204.57130932474
DeepCCS[M-H]-202.17630932474
DeepCCS[M-2H]-235.05930932474
DeepCCS[M+Na]+210.49630932474
AllCCS[M+H]+204.032859911
AllCCS[M+H-H2O]+201.532859911
AllCCS[M+NH4]+206.332859911
AllCCS[M+Na]+207.032859911
AllCCS[M-H]-200.932859911
AllCCS[M+Na-2H]-201.432859911
AllCCS[M+HCOO]-202.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Torvanol ACOC1=CC2=C(OCC(C2OS(O)(=O)=O)C2=C(O)C(OC)=CC(\C=C\C(O)=O)=C2)C=C16607.7Standard polar33892256
Torvanol ACOC1=CC2=C(OCC(C2OS(O)(=O)=O)C2=C(O)C(OC)=CC(\C=C\C(O)=O)=C2)C=C13506.9Standard non polar33892256
Torvanol ACOC1=CC2=C(OCC(C2OS(O)(=O)=O)C2=C(O)C(OC)=CC(\C=C\C(O)=O)=C2)C=C13908.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Torvanol A,1TMS,isomer #1COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O)=CC(OC)=C3O[Si](C)(C)C)C(OS(=O)(=O)O)C2=C13831.7Semi standard non polar33892256
Torvanol A,1TMS,isomer #2COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C3O)C(OS(=O)(=O)O)C2=C13908.5Semi standard non polar33892256
Torvanol A,1TMS,isomer #3COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O)=CC(OC)=C3O)C(OS(=O)(=O)O[Si](C)(C)C)C2=C13924.6Semi standard non polar33892256
Torvanol A,2TMS,isomer #1COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C3O[Si](C)(C)C)C(OS(=O)(=O)O)C2=C13741.4Semi standard non polar33892256
Torvanol A,2TMS,isomer #2COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O)=CC(OC)=C3O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)C2=C13765.1Semi standard non polar33892256
Torvanol A,2TMS,isomer #3COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C3O)C(OS(=O)(=O)O[Si](C)(C)C)C2=C13774.3Semi standard non polar33892256
Torvanol A,3TMS,isomer #1COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C3O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)C2=C13647.6Semi standard non polar33892256
Torvanol A,3TMS,isomer #1COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C3O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)C2=C13853.3Standard non polar33892256
Torvanol A,1TBDMS,isomer #1COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O)=CC(OC)=C3O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O)C2=C14128.7Semi standard non polar33892256
Torvanol A,1TBDMS,isomer #2COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C3O)C(OS(=O)(=O)O)C2=C14212.7Semi standard non polar33892256
Torvanol A,1TBDMS,isomer #3COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O)=CC(OC)=C3O)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C2=C14169.8Semi standard non polar33892256
Torvanol A,2TBDMS,isomer #1COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C3O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O)C2=C14297.8Semi standard non polar33892256
Torvanol A,2TBDMS,isomer #2COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O)=CC(OC)=C3O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C2=C14270.0Semi standard non polar33892256
Torvanol A,2TBDMS,isomer #3COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C3O)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C2=C14317.8Semi standard non polar33892256
Torvanol A,3TBDMS,isomer #1COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C3O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C2=C14388.9Semi standard non polar33892256
Torvanol A,3TBDMS,isomer #1COC1=CC=C2OCC(C3=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C3O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C2=C14653.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Torvanol A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abi-3027900000-baf45560c65975951c122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Torvanol A GC-MS (2 TMS) - 70eV, Positivesplash10-001r-3003290000-f34674c633daafd43c662017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Torvanol A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Torvanol A 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 - Torvanol A 10V, Positive-QTOFsplash10-0udr-0032900000-27242b6806ac9814dc412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 20V, Positive-QTOFsplash10-001i-1289600000-cf272207a7973c01be652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 40V, Positive-QTOFsplash10-053s-2972000000-5c8cb6f82407dc55bd652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 10V, Negative-QTOFsplash10-0udi-0011900000-2a140fa1fc4cf0c2b2c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 20V, Negative-QTOFsplash10-0abc-0349400000-36c4587d222bc11038ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 40V, Negative-QTOFsplash10-055f-4905100000-1c053ba47c661f6df5c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 10V, Negative-QTOFsplash10-0udi-0001900000-0e067ff09b04caacd1942021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 20V, Negative-QTOFsplash10-004i-0009300000-29f537d22516fb434cb22021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 40V, Negative-QTOFsplash10-004i-1019100000-72be5ece49a101b4cc402021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 10V, Positive-QTOFsplash10-000i-0001900000-bc60c5bf0f4ab6e7b8b62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 20V, Positive-QTOFsplash10-0a4i-0209200000-f61bb6650ff689b75f0e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torvanol A 40V, Positive-QTOFsplash10-0a6r-0209100000-f512a90e7a2ec6b335f62021-09-25Wishart 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 IDFDB018213
KNApSAcK IDC00019212
Chemspider ID4479588
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5321987
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.. .