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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:57 UTC
Update Date2022-03-07 02:52:41 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 (+)-12a-Hydroxypachyrrhizone has been detected, but not quantified in, jicamas (Pachyrhizus erosus) and pulses. This could make (+)-12a-hydroxypachyrrhizone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (+)-12a-Hydroxypachyrrhizone.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point214 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility242.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.06131661259
DarkChem[M-H]-185.69631661259
DeepCCS[M+H]+183.28930932474
DeepCCS[M-H]-180.93130932474
DeepCCS[M-2H]-215.13430932474
DeepCCS[M+Na]+190.36230932474
AllCCS[M+H]+188.132859911
AllCCS[M+H-H2O]+185.032859911
AllCCS[M+NH4]+190.932859911
AllCCS[M+Na]+191.732859911
AllCCS[M-H]-191.032859911
AllCCS[M+Na-2H]-190.332859911
AllCCS[M+HCOO]-189.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-12a-HydroxypachyrrhizoneCOC1=C2OC=CC2=CC2=C1OC1COC3=CC4=C(OCO4)C=C3C1(O)C2=O4917.2Standard polar33892256
(+)-12a-HydroxypachyrrhizoneCOC1=C2OC=CC2=CC2=C1OC1COC3=CC4=C(OCO4)C=C3C1(O)C2=O3144.4Standard non polar33892256
(+)-12a-HydroxypachyrrhizoneCOC1=C2OC=CC2=CC2=C1OC1COC3=CC4=C(OCO4)C=C3C1(O)C2=O3238.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-12a-Hydroxypachyrrhizone,1TMS,isomer #1COC1=C2OC3COC4=CC5=C(C=C4C3(O[Si](C)(C)C)C(=O)C2=CC2=C1OC=C2)OCO53397.0Semi standard non polar33892256
(+)-12a-Hydroxypachyrrhizone,1TBDMS,isomer #1COC1=C2OC3COC4=CC5=C(C=C4C3(O[Si](C)(C)C(C)(C)C)C(=O)C2=CC2=C1OC=C2)OCO53628.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+)-12a-Hydroxypachyrrhizone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w29-1904000000-a2f427427f0f2d8e9a592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-12a-Hydroxypachyrrhizone GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8720900000-c6eb4c2dc06607fa6cdc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-12a-Hydroxypachyrrhizone 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 - (+)-12a-Hydroxypachyrrhizone 10V, Positive-QTOFsplash10-001i-0009000000-b2cf40f2dd30efbe1ba12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 20V, Positive-QTOFsplash10-000x-0609000000-e09584ee78f54c4a4c172016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 40V, Positive-QTOFsplash10-0006-0900000000-00b82f54344392298bd82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 10V, Negative-QTOFsplash10-001i-0109000000-322453f12e0fc17b5b1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 20V, Negative-QTOFsplash10-001i-0309000000-1a337fe3391f3ff275ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 40V, Negative-QTOFsplash10-000i-1901000000-229f6a7d76bccc6e6a7d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 10V, Positive-QTOFsplash10-001i-0009000000-04cc6acdc6d39b2af0df2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 20V, Positive-QTOFsplash10-001i-0009000000-17fbb6ab70d81459819e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 40V, Positive-QTOFsplash10-001l-1597000000-aca4eded395b377383582021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 10V, Negative-QTOFsplash10-001i-0009000000-1d2bc93c7df9fb7c3dcd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 20V, Negative-QTOFsplash10-001i-0009000000-eb32d48d8f366a5d5d8f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-12a-Hydroxypachyrrhizone 40V, Negative-QTOFsplash10-0fa9-0629000000-326b5d48ec272e2a10942021-09-24Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1822651
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