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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:25 UTC
Update Date2022-03-07 02:52:43 UTC
HMDB IDHMDB0030852
Secondary Accession Numbers
  • HMDB30852
Metabolite Identification
Common NameAsperxanthone
DescriptionAsperxanthone, also known as TMC 256C2 or flavasperone, belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Asperxanthone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Asperxanthone.
Structure
Data?1563862048
Synonyms
ValueSource
Antibiotic TMC 256c2ChEBI
AsperxanthonChEBI
TMC 256c2ChEBI
5-Hydroxy-8,10-dimethoxy-2-methyl-4H-naphtho[1,2-b]pyran-4-one, 9ciHMDB
FlavasperoneHMDB
AsperxanthoneChEBI
Chemical FormulaC16H14O5
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name5-hydroxy-8,10-dimethoxy-2-methyl-4H-benzo[h]chromen-4-one
Traditional Name5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one
CAS Registry Number3566-99-2
SMILES
COC1=CC(OC)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C1
InChI Identifier
InChI=1S/C16H14O5/c1-8-4-11(17)15-12(18)6-9-5-10(19-2)7-13(20-3)14(9)16(15)21-8/h4-7,18H,1-3H3
InChI KeyARXPDHLVDOYIPX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • Chromone
  • 2-naphthol
  • Benzopyran
  • 1-benzopyran
  • Naphthalene
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.079 g/LALOGPS
logP2.95ALOGPS
logP2.89ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.4ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.46 m³·mol⁻¹ChemAxon
Polarizability29.24 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
DeepCCS[M+H]+173.55130932474
DeepCCS[M-H]-171.19330932474
DeepCCS[M-2H]-204.0830932474
DeepCCS[M+Na]+179.64430932474
AllCCS[M+H]+163.832859911
AllCCS[M+H-H2O]+160.032859911
AllCCS[M+NH4]+167.332859911
AllCCS[M+Na]+168.332859911
AllCCS[M-H]-168.132859911
AllCCS[M+Na-2H]-167.532859911
AllCCS[M+HCOO]-166.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AsperxanthoneCOC1=CC(OC)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C14042.7Standard polar33892256
AsperxanthoneCOC1=CC(OC)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C12708.9Standard non polar33892256
AsperxanthoneCOC1=CC(OC)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C12703.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Asperxanthone,1TMS,isomer #1COC1=CC(OC)=C2C(=C1)C=C(O[Si](C)(C)C)C1=C2OC(C)=CC1=O2895.0Semi standard non polar33892256
Asperxanthone,1TBDMS,isomer #1COC1=CC(OC)=C2C(=C1)C=C(O[Si](C)(C)C(C)(C)C)C1=C2OC(C)=CC1=O3085.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Asperxanthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g0-0190000000-63920300296fa73fc6f82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asperxanthone GC-MS (1 TMS) - 70eV, Positivesplash10-006x-3039000000-f28c7fa3d08e69eb1ecb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asperxanthone 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 - Asperxanthone 10V, Positive-QTOFsplash10-000i-0090000000-de1606154f2a2faca2042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 20V, Positive-QTOFsplash10-000i-0090000000-bca81911b2811ca93c192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 40V, Positive-QTOFsplash10-014r-1090000000-6090504d235c75f5e3502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 10V, Negative-QTOFsplash10-000i-0090000000-6ce0c2acfdede9a11d512016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 20V, Negative-QTOFsplash10-000i-0090000000-df2ba0a5599ddcef0c612016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 40V, Negative-QTOFsplash10-000i-2290000000-ff5174e06bbefd010cd82016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 10V, Positive-QTOFsplash10-000i-0090000000-b239d41c6032c85540b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 20V, Positive-QTOFsplash10-000i-0090000000-56020f0820eed7b460842021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 40V, Positive-QTOFsplash10-015j-0190000000-6691e283e1ff3d05dc242021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 10V, Negative-QTOFsplash10-000i-0090000000-14912e1703be5edd027d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 20V, Negative-QTOFsplash10-000i-0090000000-14912e1703be5edd027d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperxanthone 40V, Negative-QTOFsplash10-0a4i-1090000000-1fdfc323058c65ba3cb82021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB002811
KNApSAcK IDC00054889
Chemspider ID4678011
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5748546
PDB IDNot Available
ChEBI ID133814
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.. .