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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-17 17:44:56 UTC
Update Date2019-11-12 17:22:31 UTC
HMDB IDHMDB0132757
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,7-dihydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-4-yl]-3,4-dihydro-2H-1-benzopyran-4-one
Description5,7-dihydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-4-yl]-3,4-dihydro-2h-1-benzopyran-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 5,7-dihydroxy-2-{5-hydroxy-9,13,13-trimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-4-yl}-3,4-dihydro-2h-1-benzopyran-4-one. It is generated by cyp2b6 enzyme via a hydroxylation-of-methyl-carbon-adjacent-to-aliphatic-ring reaction. This hydroxylation-of-methyl-carbon-adjacent-to-aliphatic-ring occurs in humans.
Structure
Data?1563875963
SynonymsNot Available
Chemical FormulaC25H26O7
Average Molecular Weight438.476
Monoisotopic Molecular Weight438.167853177
IUPAC Name5,7-dihydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-trien-4-yl]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5,7-dihydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-trien-4-yl]-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
CC1(CO)C2CCC3(C)OC4=C(C=C(C5CC(=O)C6=C(O)C=C(O)C=C6O5)C(O)=C4)C1C23
InChI Identifier
InChI=1S/C25H26O7/c1-24(10-26)14-3-4-25(2)23(14)22(24)13-7-12(15(28)8-19(13)32-25)18-9-17(30)21-16(29)5-11(27)6-20(21)31-18/h5-8,14,18,22-23,26-29H,3-4,9-10H2,1-2H3
InChI KeyRYWQZJIWKMYJTI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 3'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 3'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct Parent3'-prenylated flavanones
Alternative Parents
Substituents
  • 3'-prenylated flavanone
  • Pyranoflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.13ALOGPS
logP3.25ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)7.85ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity115.41 m³·mol⁻¹ChemAxon
Polarizability45.9 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009l-2700097000-24a2f23491b25e7d6077JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05e9-2008900000-ac27c940cb5f7a4c8dfbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0110900000-e1a35e08deb531315bfdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uki-0930800000-1facf648aa9787535ad6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-0940000000-a97f59866ff67de8d95dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-e2469b05a71c46ee584eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05n0-0102900000-7417bc21ccb255b99725JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-1549200000-d8baac6bfd81191c608cJSpectraViewer
Biological Properties
Cellular LocationsNot Available
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

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
5,7-dihydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-4-yl]-3,4-dihydro-2H-1-benzopyran-4-one → {[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)-5-hydroxy-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-13-yl]methoxy}sulfonic 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
5,7-dihydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-4-yl]-3,4-dihydro-2H-1-benzopyran-4-one → 6-{[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5,7-dihydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-4-yl]-3,4-dihydro-2H-1-benzopyran-4-one → 3,4,5-trihydroxy-6-({5-hydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-4-yl]-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl}oxy)oxane-2-carboxylic aciddetails
5,7-dihydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-4-yl]-3,4-dihydro-2H-1-benzopyran-4-one → 3,4,5-trihydroxy-6-({7-hydroxy-2-[5-hydroxy-13-(hydroxymethyl)-9,13-dimethyl-8-oxatetracyclo[7.4.1.0²,⁷.0¹²,¹⁴]tetradeca-2(7),3,5-trien-4-yl]-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl}oxy)oxane-2-carboxylic aciddetails