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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:23:51 UTC
Update Date2022-03-07 02:55:38 UTC
HMDB IDHMDB0038113
Secondary Accession Numbers
  • HMDB38113
Metabolite Identification
Common Name5-Deoxykievitone hydrate
Description5-Deoxykievitone hydrate belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position. 5-Deoxykievitone hydrate has been detected, but not quantified in, gram beans (Vigna mungo) and pulses. This could make 5-deoxykievitone hydrate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Deoxykievitone hydrate.
Structure
Data?1563863142
Synonyms
ValueSource
5-Deoxykievitone hydric acidGenerator
7,2',4'-Trihydroxy-8-(3-hydroxy-3-methylbutyl)isoflavanoneHMDB
Chemical FormulaC20H22O6
Average Molecular Weight358.3851
Monoisotopic Molecular Weight358.141638436
IUPAC Name3-(2,4-dihydroxyphenyl)-7-hydroxy-8-(3-hydroxy-3-methylbutyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5-deoxykievitone hydrate
CAS Registry NumberNot Available
SMILES
CC(C)(O)CCC1=C(O)C=CC2=C1OCC(C2=O)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C20H22O6/c1-20(2,25)8-7-13-16(22)6-5-14-18(24)15(10-26-19(13)14)12-4-3-11(21)9-17(12)23/h3-6,9,15,21-23,25H,7-8,10H2,1-2H3
InChI KeyBYQKGWSQMLLYGJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct Parent8-prenylated isoflavanones
Alternative Parents
Substituents
  • 8-prenylated isoflavanone
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary alcohol
  • Ketone
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.03 g/LALOGPS
logP2.8ALOGPS
logP2.74ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)8.08ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity96.91 m³·mol⁻¹ChemAxon
Polarizability37.19 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]+184.70331661259
DarkChem[M-H]-180.8231661259
DeepCCS[M+H]+186.55530932474
DeepCCS[M-H]-184.19730932474
DeepCCS[M-2H]-218.4430932474
DeepCCS[M+Na]+193.98730932474
AllCCS[M+H]+186.432859911
AllCCS[M+H-H2O]+183.332859911
AllCCS[M+NH4]+189.232859911
AllCCS[M+Na]+190.032859911
AllCCS[M-H]-189.132859911
AllCCS[M+Na-2H]-189.232859911
AllCCS[M+HCOO]-189.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Deoxykievitone hydrateCC(C)(O)CCC1=C(O)C=CC2=C1OCC(C2=O)C1=C(O)C=C(O)C=C14716.8Standard polar33892256
5-Deoxykievitone hydrateCC(C)(O)CCC1=C(O)C=CC2=C1OCC(C2=O)C1=C(O)C=C(O)C=C13218.1Standard non polar33892256
5-Deoxykievitone hydrateCC(C)(O)CCC1=C(O)C=CC2=C1OCC(C2=O)C1=C(O)C=C(O)C=C13515.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Deoxykievitone hydrate,1TMS,isomer #1CC(C)(CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O)C=C1O)C2=O)O[Si](C)(C)C3366.2Semi standard non polar33892256
5-Deoxykievitone hydrate,1TMS,isomer #2CC(C)(O)CCC1=C(O[Si](C)(C)C)C=CC2=C1OCC(C1=CC=C(O)C=C1O)C2=O3223.2Semi standard non polar33892256
5-Deoxykievitone hydrate,1TMS,isomer #3CC(C)(O)CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O)C=C1O[Si](C)(C)C)C2=O3213.3Semi standard non polar33892256
5-Deoxykievitone hydrate,1TMS,isomer #4CC(C)(O)CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C)C=C1O)C2=O3231.6Semi standard non polar33892256
5-Deoxykievitone hydrate,2TMS,isomer #1CC(C)(CCC1=C(O[Si](C)(C)C)C=CC2=C1OCC(C1=CC=C(O)C=C1O)C2=O)O[Si](C)(C)C3259.6Semi standard non polar33892256
5-Deoxykievitone hydrate,2TMS,isomer #2CC(C)(CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C)C=C1O)C2=O)O[Si](C)(C)C3251.3Semi standard non polar33892256
5-Deoxykievitone hydrate,2TMS,isomer #3CC(C)(CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O)C=C1O[Si](C)(C)C)C2=O)O[Si](C)(C)C3244.3Semi standard non polar33892256
5-Deoxykievitone hydrate,2TMS,isomer #4CC(C)(O)CCC1=C(O[Si](C)(C)C)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C)C=C1O)C2=O3128.7Semi standard non polar33892256
5-Deoxykievitone hydrate,2TMS,isomer #5CC(C)(O)CCC1=C(O[Si](C)(C)C)C=CC2=C1OCC(C1=CC=C(O)C=C1O[Si](C)(C)C)C2=O3118.0Semi standard non polar33892256
5-Deoxykievitone hydrate,2TMS,isomer #6CC(C)(O)CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C2=O3105.5Semi standard non polar33892256
5-Deoxykievitone hydrate,3TMS,isomer #1CC(C)(CCC1=C(O[Si](C)(C)C)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C)C=C1O)C2=O)O[Si](C)(C)C3161.0Semi standard non polar33892256
5-Deoxykievitone hydrate,3TMS,isomer #2CC(C)(CCC1=C(O[Si](C)(C)C)C=CC2=C1OCC(C1=CC=C(O)C=C1O[Si](C)(C)C)C2=O)O[Si](C)(C)C3141.8Semi standard non polar33892256
5-Deoxykievitone hydrate,3TMS,isomer #3CC(C)(CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C2=O)O[Si](C)(C)C3138.8Semi standard non polar33892256
5-Deoxykievitone hydrate,3TMS,isomer #4CC(C)(O)CCC1=C(O[Si](C)(C)C)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C2=O3066.2Semi standard non polar33892256
5-Deoxykievitone hydrate,4TMS,isomer #1CC(C)(CCC1=C(O[Si](C)(C)C)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C2=O)O[Si](C)(C)C3136.4Semi standard non polar33892256
5-Deoxykievitone hydrate,1TBDMS,isomer #1CC(C)(CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O)C=C1O)C2=O)O[Si](C)(C)C(C)(C)C3638.2Semi standard non polar33892256
5-Deoxykievitone hydrate,1TBDMS,isomer #2CC(C)(O)CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OCC(C1=CC=C(O)C=C1O)C2=O3493.8Semi standard non polar33892256
5-Deoxykievitone hydrate,1TBDMS,isomer #3CC(C)(O)CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C2=O3477.4Semi standard non polar33892256
5-Deoxykievitone hydrate,1TBDMS,isomer #4CC(C)(O)CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C2=O3503.1Semi standard non polar33892256
5-Deoxykievitone hydrate,2TBDMS,isomer #1CC(C)(CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OCC(C1=CC=C(O)C=C1O)C2=O)O[Si](C)(C)C(C)(C)C3781.5Semi standard non polar33892256
5-Deoxykievitone hydrate,2TBDMS,isomer #2CC(C)(CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C2=O)O[Si](C)(C)C(C)(C)C3798.4Semi standard non polar33892256
5-Deoxykievitone hydrate,2TBDMS,isomer #3CC(C)(CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C2=O)O[Si](C)(C)C(C)(C)C3766.4Semi standard non polar33892256
5-Deoxykievitone hydrate,2TBDMS,isomer #4CC(C)(O)CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C2=O3617.4Semi standard non polar33892256
5-Deoxykievitone hydrate,2TBDMS,isomer #5CC(C)(O)CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OCC(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C2=O3585.0Semi standard non polar33892256
5-Deoxykievitone hydrate,2TBDMS,isomer #6CC(C)(O)CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C2=O3589.1Semi standard non polar33892256
5-Deoxykievitone hydrate,3TBDMS,isomer #1CC(C)(CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C2=O)O[Si](C)(C)C(C)(C)C3881.2Semi standard non polar33892256
5-Deoxykievitone hydrate,3TBDMS,isomer #2CC(C)(CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OCC(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C2=O)O[Si](C)(C)C(C)(C)C3827.0Semi standard non polar33892256
5-Deoxykievitone hydrate,3TBDMS,isomer #3CC(C)(CCC1=C(O)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C2=O)O[Si](C)(C)C(C)(C)C3847.3Semi standard non polar33892256
5-Deoxykievitone hydrate,3TBDMS,isomer #4CC(C)(O)CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C2=O3718.5Semi standard non polar33892256
5-Deoxykievitone hydrate,4TBDMS,isomer #1CC(C)(CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C2=O)O[Si](C)(C)C(C)(C)C3966.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Deoxykievitone hydrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-052u-9286000000-b1a01c05da42c40549392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Deoxykievitone hydrate GC-MS (4 TMS) - 70eV, Positivesplash10-001i-4240059000-2e009041d291bade46412017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Deoxykievitone hydrate 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 - 5-Deoxykievitone hydrate 10V, Positive-QTOFsplash10-0006-0129000000-262af4f4fde1672568d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 20V, Positive-QTOFsplash10-00du-2869000000-df5003be81787c9f757b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 40V, Positive-QTOFsplash10-0abi-1921000000-d36e2f586cd7f86aeaf32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 10V, Negative-QTOFsplash10-0a4i-0019000000-84f61beb5265d87a85572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 20V, Negative-QTOFsplash10-0a4i-0459000000-626a70cb3e9421ef94f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 40V, Negative-QTOFsplash10-0a4i-4910000000-362e6a0aa9122311c6ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 10V, Positive-QTOFsplash10-0006-0098000000-6ab5c7bb1bcc515456e82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 20V, Positive-QTOFsplash10-002r-0942000000-96169fc69591914276872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 40V, Positive-QTOFsplash10-025j-1920000000-73ccbb5d00343eec13872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 10V, Negative-QTOFsplash10-0a4r-0009000000-c60463c289f4f1ada3252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 20V, Negative-QTOFsplash10-053j-1297000000-74c0648dad9075e625572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxykievitone hydrate 40V, Negative-QTOFsplash10-001r-3931000000-a7dda8e796b0e6b06b4d2021-09-22Wishart 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 IDFDB017338
KNApSAcK IDC00009956
Chemspider ID24842910
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257380
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.. .