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Showing metabocard for 13alpha-Hydroxydolineone (HMDB0030756)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:51 UTC
Update Date2019-07-23 06:07:13 UTC
HMDB IDHMDB0030756
Secondary Accession Numbers
  • HMDB30756
Metabolite Identification
Common Name13alpha-Hydroxydolineone
Description13alpha-Hydroxydolineone 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, 13alpha-hydroxydolineone is considered to be a flavonoid lipid molecule. 13alpha-Hydroxydolineone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 13alpha-Hydroxydolineone has been detected, but not quantified in, jicama and pulses. This could make 13alpha-hydroxydolineone a potential biomarker for the consumption of these foods.
Structure
Data?1563862033
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
13a-HydroxydolineoneGenerator
13Α-hydroxydolineoneGenerator
Chemical FormulaC19H12O7
Average Molecular Weight352.2944
Monoisotopic Molecular Weight352.058302738
IUPAC Name1-hydroxy-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-hydroxydolineone
CAS Registry Number28617-71-2
SMILES
OC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O
InChI Identifier
InChI=1S/C19H12O7/c20-18-10-3-9-1-2-22-12(9)5-13(10)26-17-7-23-14-6-16-15(24-8-25-16)4-11(14)19(17,18)21/h1-6,17,21H,7-8H2
InChI KeyHLEAVDSSZUIWQI-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
  • Alkyl aryl ether
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Tertiary alcohol
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen 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 Point194 - 195 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP2.08ALOGPS
logP1.91ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.03ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area87.36 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.75 m³·mol⁻¹ChemAxon
Polarizability34.33 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, Positivesplash10-0096-2913000000-506dee24db7b8cf3a618Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-9343200000-96d8036ba9a77c71c661Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-586b0b4a691c1edcb5c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-0619000000-7dcbda7eea674461b590Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1900000000-ebb97846d21913823d47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-128203575629f8eed5f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0409000000-4a49f6ba37c665e7bd7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-ba731628889bb1115477Spectrum
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 IDFDB002688
KNApSAcK IDC00009582
Chemspider ID24842945
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13885696
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

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
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
13alpha-Hydroxydolineone → 3,4,5-trihydroxy-6-({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