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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:59:03 UTC
Update Date2022-03-07 02:53:39 UTC
HMDB IDHMDB0033271
Secondary Accession Numbers
  • HMDB33271
Metabolite Identification
Common NameFoetidin
DescriptionFoetidin belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Foetidin has been detected, but not quantified in, green vegetables and herbs and spices. This could make foetidin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Foetidin.
Structure
Data?1563862379
Synonyms
ValueSource
FoetidinMeSH
Chemical FormulaC24H30O4
Average Molecular Weight382.4926
Monoisotopic Molecular Weight382.214409448
IUPAC Name4-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methoxy]-2H-chromen-2-one
Traditional Name4-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl)methoxy]chromen-2-one
CAS Registry Number97165-40-7
SMILES
CC1(C)C(O)CCC2(C)C(COC3=CC(=O)OC4=CC=CC=C34)C(=C)CCC12
InChI Identifier
InChI=1S/C24H30O4/c1-15-9-10-20-23(2,3)21(25)11-12-24(20,4)17(15)14-27-19-13-22(26)28-18-8-6-5-7-16(18)19/h5-8,13,17,20-21,25H,1,9-12,14H2,2-4H3
InChI KeyWLYRUZQGIVCRDD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Cyclic alcohol
  • Heteroaromatic compound
  • Vinylogous ester
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point176 - 178 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0027 g/LALOGPS
logP4.78ALOGPS
logP3.85ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity109.77 m³·mol⁻¹ChemAxon
Polarizability42.49 ųChemAxon
Number of Rings4ChemAxon
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]+189.31131661259
DarkChem[M-H]-187.52231661259
DeepCCS[M-2H]-228.40630932474
DeepCCS[M+Na]+203.63430932474
AllCCS[M+H]+195.132859911
AllCCS[M+H-H2O]+192.532859911
AllCCS[M+NH4]+197.532859911
AllCCS[M+Na]+198.132859911
AllCCS[M-H]-197.132859911
AllCCS[M+Na-2H]-197.232859911
AllCCS[M+HCOO]-197.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FoetidinCC1(C)C(O)CCC2(C)C(COC3=CC(=O)OC4=CC=CC=C34)C(=C)CCC123502.4Standard polar33892256
FoetidinCC1(C)C(O)CCC2(C)C(COC3=CC(=O)OC4=CC=CC=C34)C(=C)CCC123127.0Standard non polar33892256
FoetidinCC1(C)C(O)CCC2(C)C(COC3=CC(=O)OC4=CC=CC=C34)C(=C)CCC123527.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Foetidin,1TMS,isomer #1C=C1CCC2C(C)(C)C(O[Si](C)(C)C)CCC2(C)C1COC1=CC(=O)OC2=CC=CC=C123288.5Semi standard non polar33892256
Foetidin,1TBDMS,isomer #1C=C1CCC2C(C)(C)C(O[Si](C)(C)C(C)(C)C)CCC2(C)C1COC1=CC(=O)OC2=CC=CC=C123495.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Foetidin GC-MS (Non-derivatized) - 70eV, Positivesplash10-1000-0349000000-4f014c8988449a28bb092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Foetidin GC-MS (1 TMS) - 70eV, Positivesplash10-004r-4091600000-3c1ba15b99c03218974e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Foetidin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Foetidin 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 - Foetidin 10V, Positive-QTOFsplash10-0159-0029000000-d8799a3cb9bd3d56eb912016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 20V, Positive-QTOFsplash10-0159-0349000000-6def0ceb4b4fa4160d392016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 40V, Positive-QTOFsplash10-0w2c-2930000000-f295c6738d384108dd872016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 10V, Negative-QTOFsplash10-01q9-0209000000-51bf5da61c1f098c77b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 20V, Negative-QTOFsplash10-03e9-1509000000-db14fc4ff9ba82c601462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 40V, Negative-QTOFsplash10-00kf-9810000000-cf7d76b906b96be5fc762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 10V, Negative-QTOFsplash10-001i-0009000000-3eb349f8710b3ffdc26e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 20V, Negative-QTOFsplash10-03ei-0629000000-a62eac07e457b67a38b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 40V, Negative-QTOFsplash10-0006-8922000000-a89b4ecdc7fd48e013592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 10V, Positive-QTOFsplash10-03e9-0978000000-1e11bad01e66d767d9522021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 20V, Positive-QTOFsplash10-0w2i-0694000000-03470b36f9fac2931e2e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Foetidin 40V, Positive-QTOFsplash10-00kf-4930000000-9626892ea247d2062ae42021-09-23Wishart 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 IDFDB011294
KNApSAcK IDC00019794
Chemspider ID35013573
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73202223
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.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Foetidin → (1,1,4a-trimethyl-6-methylidene-5-{[(2-oxo-2H-chromen-4-yl)oxy]methyl}-decahydronaphthalen-2-yl)oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Foetidin → 6-[(1,1,4a-trimethyl-6-methylidene-5-{[(2-oxo-2H-chromen-4-yl)oxy]methyl}-decahydronaphthalen-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails