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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:51 UTC
Update Date2022-03-07 02:52:41 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. 13alpha-Hydroxydolineone has been detected, but not quantified in, jicamas (Pachyrhizus erosus) and pulses. This could make 13alpha-hydroxydolineone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 13alpha-Hydroxydolineone.
Structure
Data?1563862033
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point194 - 195 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility432.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.79831661259
DarkChem[M-H]-178.69131661259
DeepCCS[M-2H]-216.92830932474
DeepCCS[M+Na]+192.15630932474
AllCCS[M+H]+181.632859911
AllCCS[M+H-H2O]+178.332859911
AllCCS[M+NH4]+184.632859911
AllCCS[M+Na]+185.432859911
AllCCS[M-H]-184.332859911
AllCCS[M+Na-2H]-183.232859911
AllCCS[M+HCOO]-182.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
13alpha-HydroxydolineoneOC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O4790.6Standard polar33892256
13alpha-HydroxydolineoneOC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O3002.9Standard non polar33892256
13alpha-HydroxydolineoneOC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O3106.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
13alpha-Hydroxydolineone,1TMS,isomer #1C[Si](C)(C)OC12C(=O)C3=CC4=C(C=C3OC1COC1=CC3=C(C=C12)OCO3)OC=C43262.7Semi standard non polar33892256
13alpha-Hydroxydolineone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC12C(=O)C3=CC4=C(C=C3OC1COC1=CC3=C(C=C12)OCO3)OC=C43533.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 13alpha-Hydroxydolineone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-2913000000-506dee24db7b8cf3a6182017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13alpha-Hydroxydolineone GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-9343200000-96d8036ba9a77c71c6612017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13alpha-Hydroxydolineone 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 - 13alpha-Hydroxydolineone 10V, Positive-QTOFsplash10-0udi-0009000000-586b0b4a691c1edcb5c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 20V, Positive-QTOFsplash10-0w29-0619000000-7dcbda7eea674461b5902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 40V, Positive-QTOFsplash10-03di-1900000000-ebb97846d21913823d472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 10V, Negative-QTOFsplash10-0udi-0109000000-128203575629f8eed5f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 20V, Negative-QTOFsplash10-0udi-0409000000-4a49f6ba37c665e7bd7c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 40V, Negative-QTOFsplash10-0a4i-1900000000-ba731628889bb11154772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 10V, Positive-QTOFsplash10-0udi-0009000000-6b09288367f287c3aa7b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 20V, Positive-QTOFsplash10-0udi-0009000000-75ec90160a6d1d79cb222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 40V, Positive-QTOFsplash10-0ika-0922000000-46a80340180660ae59452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 10V, Negative-QTOFsplash10-0udi-0009000000-fbaae7d8d0a33f870dc02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 20V, Negative-QTOFsplash10-0udi-0009000000-9850b65af18c86bc4c3e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 40V, Negative-QTOFsplash10-0f7c-0917000000-8afcc2a79ad23f675c7f2021-09-23Wishart 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 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
MarkerDB IDNot Available
Good Scents IDrw1822501
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
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