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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:57 UTC
Update Date2019-07-23 06:07:16 UTC
HMDB IDHMDB0030774
Secondary Accession Numbers
  • HMDB30774
Metabolite Identification
Common Name(+)-12a-Hydroxypachyrrhizone
Description(+)-12a-Hydroxypachyrrhizone belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Thus, (+)-12a-hydroxypachyrrhizone is considered to be a flavonoid lipid molecule (+)-12a-Hydroxypachyrrhizone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (+)-12a-Hydroxypachyrrhizone has been detected, but not quantified in, jicama and pulses. This could make (+)-12a-hydroxypachyrrhizone a potential biomarker for the consumption of these foods.
Structure
Data?1563862036
Synonyms
ValueSource
12a-HydroxypachyrrhizoneHMDB
Chemical FormulaC20H14O8
Average Molecular Weight382.3204
Monoisotopic Molecular Weight382.068867424
IUPAC Name1-hydroxy-16-methoxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one
Traditional Name12a-hydroxypachyrrhizone
CAS Registry Number28768-44-7
SMILES
COC1=C2OC=CC2=CC2=C1OC1COC3=CC4=C(OCO4)C=C3C1(O)C2=O
InChI Identifier
InChI=1S/C20H14O8/c1-23-18-16-9(2-3-24-16)4-10-17(18)28-15-7-25-12-6-14-13(26-8-27-14)5-11(12)20(15,22)19(10)21/h2-6,15,22H,7-8H2,1H3
InChI KeyDDGYXSWHWAQNRQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassRotenoids
Direct ParentRotenones
Alternative Parents
Substituents
  • Rotenone or derivatives
  • Isoflavanone
  • Isoflavan
  • Furanochromone
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzodioxole
  • Benzofuran
  • Aryl alkyl ketone
  • Aryl ketone
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Heteroaromatic compound
  • Furan
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point214 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP1.87ALOGPS
logP1.75ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.01ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area96.59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.22 m³·mol⁻¹ChemAxon
Polarizability37.27 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w29-1904000000-a2f427427f0f2d8e9a59Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8720900000-c6eb4c2dc06607fa6cdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-b2cf40f2dd30efbe1ba1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0609000000-e09584ee78f54c4a4c17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-00b82f54344392298bd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0109000000-322453f12e0fc17b5b1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0309000000-1a337fe3391f3ff275adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1901000000-229f6a7d76bccc6e6a7dSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB002709
KNApSAcK IDC00009586
Chemspider ID4476915
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318311
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

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
(+)-12a-Hydroxypachyrrhizone → 3,4,5-trihydroxy-6-({16-methoxy-24-oxo-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-1-yl}oxy)oxane-2-carboxylic aciddetails