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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:56:58 UTC
Update Date2022-03-07 02:54:41 UTC
HMDB IDHMDB0035903
Secondary Accession Numbers
  • HMDB35903
Metabolite Identification
Common NameEnokipodin A
DescriptionEnokipodin A, also known as avarol, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Enokipodin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, enokipodin a has been detected, but not quantified in, mushrooms. This could make enokipodin a a potential biomarker for the consumption of these foods.
Structure
Data?1563862790
Synonyms
ValueSource
AvarolHMDB
Enokipodin aMeSH
Chemical FormulaC15H20O3
Average Molecular Weight248.3175
Monoisotopic Molecular Weight248.141244506
IUPAC Name1,5,12,12-tetramethyl-8-oxatricyclo[7.2.1.0²,⁷]dodeca-2(7),3,5-triene-4,9-diol
Traditional Name1,5,12,12-tetramethyl-8-oxatricyclo[7.2.1.0²,⁷]dodeca-2(7),3,5-triene-4,9-diol
CAS Registry Number306951-07-5
SMILES
CC1=CC2=C(C=C1O)C1(C)CCC(O)(O2)C1(C)C
InChI Identifier
InChI=1S/C15H20O3/c1-9-7-12-10(8-11(9)16)14(4)5-6-15(17,18-12)13(14,2)3/h7-8,16-17H,5-6H2,1-4H3
InChI KeyKANVQRLDTGOSBL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent1-benzopyrans
Alternative Parents
Substituents
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Hemiacetal
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Point138.5 - 138.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP3.04ALOGPS
logP3.45ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.19ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.46 m³·mol⁻¹ChemAxon
Polarizability27.48 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]+155.86731661259
DarkChem[M-H]-155.42731661259
DeepCCS[M+H]+164.63630932474
DeepCCS[M-H]-162.27830932474
DeepCCS[M-2H]-195.16430932474
DeepCCS[M+Na]+170.72930932474
AllCCS[M+H]+156.432859911
AllCCS[M+H-H2O]+152.732859911
AllCCS[M+NH4]+159.932859911
AllCCS[M+Na]+160.932859911
AllCCS[M-H]-164.932859911
AllCCS[M+Na-2H]-164.832859911
AllCCS[M+HCOO]-164.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Enokipodin ACC1=CC2=C(C=C1O)C1(C)CCC(O)(O2)C1(C)C3116.9Standard polar33892256
Enokipodin ACC1=CC2=C(C=C1O)C1(C)CCC(O)(O2)C1(C)C1980.6Standard non polar33892256
Enokipodin ACC1=CC2=C(C=C1O)C1(C)CCC(O)(O2)C1(C)C2057.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Enokipodin A,1TMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCC(O)(O2)C1(C)C2079.4Semi standard non polar33892256
Enokipodin A,1TMS,isomer #2CC1=CC2=C(C=C1O)C1(C)CCC(O[Si](C)(C)C)(O2)C1(C)C2025.7Semi standard non polar33892256
Enokipodin A,2TMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCC(O[Si](C)(C)C)(O2)C1(C)C2089.7Semi standard non polar33892256
Enokipodin A,1TBDMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCC(O)(O2)C1(C)C2363.2Semi standard non polar33892256
Enokipodin A,1TBDMS,isomer #2CC1=CC2=C(C=C1O)C1(C)CCC(O[Si](C)(C)C(C)(C)C)(O2)C1(C)C2314.3Semi standard non polar33892256
Enokipodin A,2TBDMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCC(O[Si](C)(C)C(C)(C)C)(O2)C1(C)C2622.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Enokipodin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2490000000-2cf3034e97b3b0000e1b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enokipodin A GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5109000000-1830e9b3dc94ee03cd212017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enokipodin 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 - Enokipodin A 10V, Positive-QTOFsplash10-0002-0190000000-6b3131112da3f69c3cb62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 20V, Positive-QTOFsplash10-0002-0790000000-ec951199fc6a8f30a0ff2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 40V, Positive-QTOFsplash10-0zmi-9720000000-c4b8b0eed0bf42b74a0b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 10V, Negative-QTOFsplash10-0002-0290000000-19a854b5f932db85ac712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 20V, Negative-QTOFsplash10-0002-0290000000-11652c6a6135dce21dd52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 40V, Negative-QTOFsplash10-0a4i-3930000000-036665e036ad304fc2cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 10V, Negative-QTOFsplash10-0002-0090000000-7b3a58b796a0e42639592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 20V, Negative-QTOFsplash10-0002-0090000000-3c5fa023f431202efe2b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 40V, Negative-QTOFsplash10-00di-0930000000-ab8db158a47aa0509b1a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 10V, Positive-QTOFsplash10-001j-0090000000-21a321c486f0c8463d192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 20V, Positive-QTOFsplash10-00dj-0790000000-f28d6a1afee8fb61273d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enokipodin A 40V, Positive-QTOFsplash10-05r3-9310000000-1461b423e32a6b290f152021-09-22Wishart 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 IDFDB014688
KNApSAcK IDNot Available
Chemspider ID10190206
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21578749
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.. .