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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:00:51 UTC
Update Date2022-03-07 02:54:21 UTC
HMDB IDHMDB0035070
Secondary Accession Numbers
  • HMDB35070
Metabolite Identification
Common Name12alpha-Hydroxymunduserone
Description12alpha-Hydroxymunduserone 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, 12alpha-hydroxymunduserone is considered to be a flavonoid. 12alpha-Hydroxymunduserone has been detected, but not quantified in, jicamas (Pachyrhizus erosus) and pulses. This could make 12alpha-hydroxymunduserone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 12alpha-Hydroxymunduserone.
Structure
Data?1563862660
Synonyms
ValueSource
12a-HydroxymunduseroneGenerator
12Α-hydroxymunduseroneGenerator
Chemical FormulaC19H18O7
Average Molecular Weight358.342
Monoisotopic Molecular Weight358.10525293
IUPAC Name12a-hydroxy-2,3,9-trimethoxy-6,6a,12,12a-tetrahydro-5,7-dioxatetraphen-12-one
Traditional Name12a-hydroxymunduserone
CAS Registry Number66280-24-8
SMILES
COC1=CC2=C(C=C1)C(=O)C1(O)C(COC3=C1C=C(OC)C(OC)=C3)O2
InChI Identifier
InChI=1S/C19H18O7/c1-22-10-4-5-11-13(6-10)26-17-9-25-14-8-16(24-3)15(23-2)7-12(14)19(17,21)18(11)20/h4-8,17,21H,9H2,1-3H3
InChI KeyAPAWOEBSLLGWDF-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
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP1.98ALOGPS
logP1.65ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.08ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.53 m³·mol⁻¹ChemAxon
Polarizability36.13 ųChemAxon
Number of Rings4ChemAxon
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]+185.11431661259
DarkChem[M-H]-184.5231661259
DeepCCS[M+H]+185.34130932474
DeepCCS[M-H]-182.98330932474
DeepCCS[M-2H]-216.79730932474
DeepCCS[M+Na]+192.02530932474
AllCCS[M+H]+184.432859911
AllCCS[M+H-H2O]+181.332859911
AllCCS[M+NH4]+187.232859911
AllCCS[M+Na]+188.132859911
AllCCS[M-H]-187.632859911
AllCCS[M+Na-2H]-187.332859911
AllCCS[M+HCOO]-187.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12alpha-HydroxymunduseroneCOC1=CC2=C(C=C1)C(=O)C1(O)C(COC3=C1C=C(OC)C(OC)=C3)O24588.1Standard polar33892256
12alpha-HydroxymunduseroneCOC1=CC2=C(C=C1)C(=O)C1(O)C(COC3=C1C=C(OC)C(OC)=C3)O23053.3Standard non polar33892256
12alpha-HydroxymunduseroneCOC1=CC2=C(C=C1)C(=O)C1(O)C(COC3=C1C=C(OC)C(OC)=C3)O22865.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12alpha-Hydroxymunduserone,1TMS,isomer #1COC1=CC=C2C(=O)C3(O[Si](C)(C)C)C4=CC(OC)=C(OC)C=C4OCC3OC2=C12913.9Semi standard non polar33892256
12alpha-Hydroxymunduserone,1TBDMS,isomer #1COC1=CC=C2C(=O)C3(O[Si](C)(C)C(C)(C)C)C4=CC(OC)=C(OC)C=C4OCC3OC2=C13153.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12alpha-Hydroxymunduserone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-0904000000-cf2499ece1ea08af4bcf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12alpha-Hydroxymunduserone GC-MS (1 TMS) - 70eV, Positivesplash10-0gi9-6903600000-3491124f65f968aa812e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12alpha-Hydroxymunduserone 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 - 12alpha-Hydroxymunduserone 10V, Positive-QTOFsplash10-0a4i-0009000000-442152adfe24223e3d642016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 20V, Positive-QTOFsplash10-0pb9-0429000000-2c602cbd9e1de222b5962016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 40V, Positive-QTOFsplash10-0uki-2900000000-39adfadf04ddc1de448a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 10V, Negative-QTOFsplash10-0a4i-0009000000-99c28e807d2e56358f722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 20V, Negative-QTOFsplash10-0a4i-0129000000-f7d80f31b8f0a6eeed182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 40V, Negative-QTOFsplash10-000b-2922000000-2941848f4efb713851492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 10V, Negative-QTOFsplash10-0a4i-0009000000-f52033267e0ba5a1ec2d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 20V, Negative-QTOFsplash10-0a4i-0239000000-e98f8ce7a9793417e4512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 40V, Negative-QTOFsplash10-052r-1953000000-e6f34babec2a244dc4d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 10V, Positive-QTOFsplash10-0a4i-0009000000-0bfcdd2d4921747632622021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 20V, Positive-QTOFsplash10-0a4i-0339000000-aedd56d9baf1ddaad7062021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12alpha-Hydroxymunduserone 40V, Positive-QTOFsplash10-0uki-0952000000-7dc313ec1069ea1143252021-09-24Wishart 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 IDFDB013694
KNApSAcK IDC00009580
Chemspider ID24842959
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14427372
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .