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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:25:10 UTC
Update Date2022-03-07 02:56:03 UTC
HMDB IDHMDB0039066
Secondary Accession Numbers
  • HMDB39066
Metabolite Identification
Common Name6',7'-Dihydroxybergamottin
Description6',7'-Dihydroxybergamottin belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. 6',7'-Dihydroxybergamottin has been detected, but not quantified in, citrus. This could make 6',7'-dihydroxybergamottin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6',7'-Dihydroxybergamottin.
Structure
Data?1563863306
Synonyms
ValueSource
4-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-oneHMDB
LepiochlorinHMDB
6,7-DHBMeSH
6',7'-DihydroxybergamottinMeSH
Chemical FormulaC21H24O6
Average Molecular Weight372.417
Monoisotopic Molecular Weight372.157288493
IUPAC Name4-{[(2Z)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one
Traditional Name4-{[(2Z)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}furo[3,2-g]chromen-7-one
CAS Registry Number71339-34-9
SMILES
C\C(CCC(O)C(C)(C)O)=C\COC1=C2C=COC2=CC2=C1C=CC(=O)O2
InChI Identifier
InChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8-
InChI KeyIXZUPBUEKFXTSD-JYRVWZFOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
Alternative Parents
Substituents
  • Psoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Fatty alcohol
  • Alkyl aryl ether
  • Pyranone
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Tertiary alcohol
  • Furan
  • 1,2-diol
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • 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 Point104 - 106 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.18 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP3.4ALOGPS
logP2.67ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity102.12 m³·mol⁻¹ChemAxon
Polarizability39.65 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
DarkChem[M+H]+187.63131661259
DarkChem[M-H]-185.37831661259
DeepCCS[M+H]+190.83830932474
DeepCCS[M-H]-188.28330932474
DeepCCS[M-2H]-222.77130932474
DeepCCS[M+Na]+198.23430932474
AllCCS[M+H]+189.032859911
AllCCS[M+H-H2O]+186.332859911
AllCCS[M+NH4]+191.432859911
AllCCS[M+Na]+192.132859911
AllCCS[M-H]-191.832859911
AllCCS[M+Na-2H]-192.032859911
AllCCS[M+HCOO]-192.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6',7'-DihydroxybergamottinC\C(CCC(O)C(C)(C)O)=C\COC1=C2C=COC2=CC2=C1C=CC(=O)O24059.5Standard polar33892256
6',7'-DihydroxybergamottinC\C(CCC(O)C(C)(C)O)=C\COC1=C2C=COC2=CC2=C1C=CC(=O)O23015.5Standard non polar33892256
6',7'-DihydroxybergamottinC\C(CCC(O)C(C)(C)O)=C\COC1=C2C=COC2=CC2=C1C=CC(=O)O23232.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6',7'-Dihydroxybergamottin,1TMS,isomer #1C/C(=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2)CCC(O[Si](C)(C)C)C(C)(C)O3171.4Semi standard non polar33892256
6',7'-Dihydroxybergamottin,1TMS,isomer #2C/C(=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2)CCC(O)C(C)(C)O[Si](C)(C)C3212.3Semi standard non polar33892256
6',7'-Dihydroxybergamottin,2TMS,isomer #1C/C(=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2)CCC(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C3179.4Semi standard non polar33892256
6',7'-Dihydroxybergamottin,1TBDMS,isomer #1C/C(=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)O3410.6Semi standard non polar33892256
6',7'-Dihydroxybergamottin,1TBDMS,isomer #2C/C(=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2)CCC(O)C(C)(C)O[Si](C)(C)C(C)(C)C3449.3Semi standard non polar33892256
6',7'-Dihydroxybergamottin,2TBDMS,isomer #1C/C(=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)O[Si](C)(C)C(C)(C)C3625.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6',7'-Dihydroxybergamottin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9044000000-941ed62632b71a13305d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6',7'-Dihydroxybergamottin GC-MS (2 TMS) - 70eV, Positivesplash10-0kji-8894750000-911d6c503b24adefc3d32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6',7'-Dihydroxybergamottin 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 - 6',7'-Dihydroxybergamottin 10V, Positive-QTOFsplash10-05fr-0219000000-60828bda7a2eb1b2b8382016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 20V, Positive-QTOFsplash10-0zni-6898000000-9b3d898ebda6aef35d942016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 40V, Positive-QTOFsplash10-0ktr-9230000000-58a1d646ec73e9fb68062016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 10V, Negative-QTOFsplash10-0fk9-0029000000-739b06d1a0a3b5242e1b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 20V, Negative-QTOFsplash10-0udi-0395000000-0b1e14b4c9f49fd157672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 40V, Negative-QTOFsplash10-0a4i-2920000000-580ae694ecab81deb6402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 10V, Positive-QTOFsplash10-0f79-0029000000-53d804be2c67f474ea3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 20V, Positive-QTOFsplash10-0f79-1159000000-3f605d41a0289f2dbcba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 40V, Positive-QTOFsplash10-0kdr-7892000000-2bf483e2025be4fe392a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 10V, Negative-QTOFsplash10-00di-0019000000-492869cd0ced7b279ef42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 20V, Negative-QTOFsplash10-0pb9-9188000000-c36742fd1abb17e618182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6',7'-Dihydroxybergamottin 40V, Negative-QTOFsplash10-0zfr-2980000000-541760eb3e74dd26805c2021-09-22Wishart 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 IDFDB018565
KNApSAcK IDC00047681
Chemspider ID35014735
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link6',7'-Dihydroxybergamottin
METLIN IDNot Available
PubChem Compound131752532
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1873951
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.. .