Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:33:09 UTC
Update Date2022-03-07 02:55:16 UTC
HMDB IDHMDB0037314
Secondary Accession Numbers
  • HMDB37314
Metabolite Identification
Common NameNorartocarpanone
DescriptionNorartocarpanone belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, norartocarpanone is considered to be a flavonoid. Norartocarpanone has been detected, but not quantified in, fruits. This could make norartocarpanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Norartocarpanone.
Structure
Data?1563863009
SynonymsNot Available
Chemical FormulaC15H12O6
Average Molecular Weight288.2522
Monoisotopic Molecular Weight288.063388116
IUPAC Name2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namesteppogenin
CAS Registry Number56486-94-3
SMILES
OC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C15H12O6/c16-7-1-2-9(10(18)3-7)13-6-12(20)15-11(19)4-8(17)5-14(15)21-13/h1-5,13,16-19H,6H2
InChI KeyQBLQLKNOKUHRCH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
Substituents
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point255 - 257 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility824.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP2.07ALOGPS
logP2.53ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.88ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.27 m³·mol⁻¹ChemAxon
Polarizability28.13 ųChemAxon
Number of Rings3ChemAxon
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]+167.99731661259
DarkChem[M-H]-163.99331661259
DeepCCS[M+H]+166.9130932474
DeepCCS[M-H]-164.55330932474
DeepCCS[M-2H]-197.43930932474
DeepCCS[M+Na]+173.00430932474
AllCCS[M+H]+166.432859911
AllCCS[M+H-H2O]+162.732859911
AllCCS[M+NH4]+169.932859911
AllCCS[M+Na]+170.932859911
AllCCS[M-H]-165.432859911
AllCCS[M+Na-2H]-164.832859911
AllCCS[M+HCOO]-164.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorartocarpanoneOC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O14266.3Standard polar33892256
NorartocarpanoneOC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O13013.2Standard non polar33892256
NorartocarpanoneOC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O13097.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norartocarpanone,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C(O)=C12979.2Semi standard non polar33892256
Norartocarpanone,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC=C1C1CC(=O)C2=C(O)C=C(O)C=C2O12926.9Semi standard non polar33892256
Norartocarpanone,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1O)O22940.1Semi standard non polar33892256
Norartocarpanone,1TMS,isomer #4C[Si](C)(C)OC1=CC(O)=C2C(=O)CC(C3=CC=C(O)C=C3O)OC2=C12971.5Semi standard non polar33892256
Norartocarpanone,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C(O)=C12962.6Semi standard non polar33892256
Norartocarpanone,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C(O)=C12946.8Semi standard non polar33892256
Norartocarpanone,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C(O[Si](C)(C)C)=C12912.9Semi standard non polar33892256
Norartocarpanone,2TMS,isomer #4C[Si](C)(C)OC1=CC(O)=CC=C1C1CC(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C)O12917.7Semi standard non polar33892256
Norartocarpanone,2TMS,isomer #5C[Si](C)(C)OC1=CC(O)=C2C(=O)CC(C3=CC=C(O)C=C3O[Si](C)(C)C)OC2=C12905.0Semi standard non polar33892256
Norartocarpanone,2TMS,isomer #6C[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C(O)C=C3O)O2)C(O[Si](C)(C)C)=C12940.7Semi standard non polar33892256
Norartocarpanone,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C(O)=C12875.7Semi standard non polar33892256
Norartocarpanone,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C(O[Si](C)(C)C)=C12879.6Semi standard non polar33892256
Norartocarpanone,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C(O[Si](C)(C)C)=C12886.0Semi standard non polar33892256
Norartocarpanone,3TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C(O)C=C3O[Si](C)(C)C)O2)C(O[Si](C)(C)C)=C12853.7Semi standard non polar33892256
Norartocarpanone,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C(O[Si](C)(C)C)=C12920.5Semi standard non polar33892256
Norartocarpanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C(O)=C13262.0Semi standard non polar33892256
Norartocarpanone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C1CC(=O)C2=C(O)C=C(O)C=C2O13204.0Semi standard non polar33892256
Norartocarpanone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1O)O23225.5Semi standard non polar33892256
Norartocarpanone,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)CC(C3=CC=C(O)C=C3O)OC2=C13257.3Semi standard non polar33892256
Norartocarpanone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O)=C13509.3Semi standard non polar33892256
Norartocarpanone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O)=C13503.7Semi standard non polar33892256
Norartocarpanone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C13438.5Semi standard non polar33892256
Norartocarpanone,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C1CC(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)O13460.2Semi standard non polar33892256
Norartocarpanone,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)CC(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)OC2=C13421.6Semi standard non polar33892256
Norartocarpanone,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C(O)C=C3O)O2)C(O[Si](C)(C)C(C)(C)C)=C13491.5Semi standard non polar33892256
Norartocarpanone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O)=C13626.0Semi standard non polar33892256
Norartocarpanone,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O[Si](C)(C)C(C)(C)C)=C13601.5Semi standard non polar33892256
Norartocarpanone,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C13622.0Semi standard non polar33892256
Norartocarpanone,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O[Si](C)(C)C(C)(C)C)=C13561.6Semi standard non polar33892256
Norartocarpanone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O[Si](C)(C)C(C)(C)C)=C13771.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norartocarpanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0490000000-6b9257ef487bbf5b280b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norartocarpanone GC-MS (4 TMS) - 70eV, Positivesplash10-0imi-2420190000-d69f33ce6070e010921a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norartocarpanone 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 - Norartocarpanone 10V, Positive-QTOFsplash10-000i-0290000000-9910dd0b08a9b6831e762015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 20V, Positive-QTOFsplash10-000i-0980000000-98d5dfe9e50cacc3856b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 40V, Positive-QTOFsplash10-0f79-2910000000-6a49a7db32889325fa512015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 10V, Negative-QTOFsplash10-000i-0090000000-4b19f2e022b00086491d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 20V, Negative-QTOFsplash10-000i-0390000000-7a12ab87af82f880cbee2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 40V, Negative-QTOFsplash10-0pwi-5950000000-e3cc21d16f515f4cd2232015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 10V, Positive-QTOFsplash10-000i-0090000000-6ba2690e52ef797ececb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 20V, Positive-QTOFsplash10-0uds-0940000000-cb26dafebd1059de9c9b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 40V, Positive-QTOFsplash10-0udi-0900000000-5ed3e87ec31a61a942ee2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 10V, Negative-QTOFsplash10-000i-0090000000-fd96bbe1d8ed2e3ede5b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 20V, Negative-QTOFsplash10-0f79-0980000000-c6bfd4913da1e44ef31d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norartocarpanone 40V, Negative-QTOFsplash10-000i-0900000000-8d4818271eab4b80a22f2021-09-22Wishart 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 IDFDB016333
KNApSAcK IDC00008367
Chemspider ID10221696
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21596130
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1859751
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.. .