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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:09 UTC
Update Date2022-03-07 02:53:06 UTC
HMDB IDHMDB0031744
Secondary Accession Numbers
  • HMDB31744
Metabolite Identification
Common NameArtocarbene
DescriptionArtocarbene belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review a significant number of articles have been published on Artocarbene.
Structure
Data?1563862164
Synonyms
ValueSource
7-(2,4-Dihydroxystyryl)-5-hydroxy-2,2-dimethyl-2H-1-benzopyranHMDB
Chemical FormulaC19H18O4
Average Molecular Weight310.3438
Monoisotopic Molecular Weight310.120509064
IUPAC Name4-[(Z)-2-(5-hydroxy-2,2-dimethyl-2H-chromen-7-yl)ethenyl]benzene-1,3-diol
Traditional Name4-[(Z)-2-(5-hydroxy-2,2-dimethylchromen-7-yl)ethenyl]benzene-1,3-diol
CAS Registry Number194144-02-0
SMILES
CC1(C)OC2=CC(\C=C/C3=C(O)C=C(O)C=C3)=CC(O)=C2C=C1
InChI Identifier
InChI=1S/C19H18O4/c1-19(2)8-7-15-17(22)9-12(10-18(15)23-19)3-4-13-5-6-14(20)11-16(13)21/h3-11,20-22H,1-2H3/b4-3-
InChI KeyVPKBRABQIHPIEA-ARJAWSKDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • 2,2-dimethyl-1-benzopyran
  • Benzopyran
  • 1-benzopyran
  • Styrene
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.59 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP4ALOGPS
logP4.3ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.9ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity91.85 m³·mol⁻¹ChemAxon
Polarizability32.77 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]+181.93230932474
DeepCCS[M-H]-179.57430932474
DeepCCS[M-2H]-213.66530932474
DeepCCS[M+Na]+188.89330932474
AllCCS[M+H]+175.632859911
AllCCS[M+H-H2O]+171.932859911
AllCCS[M+NH4]+179.032859911
AllCCS[M+Na]+180.032859911
AllCCS[M-H]-175.332859911
AllCCS[M+Na-2H]-174.932859911
AllCCS[M+HCOO]-174.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ArtocarbeneCC1(C)OC2=CC(\C=C/C3=C(O)C=C(O)C=C3)=CC(O)=C2C=C14143.9Standard polar33892256
ArtocarbeneCC1(C)OC2=CC(\C=C/C3=C(O)C=C(O)C=C3)=CC(O)=C2C=C12890.2Standard non polar33892256
ArtocarbeneCC1(C)OC2=CC(\C=C/C3=C(O)C=C(O)C=C3)=CC(O)=C2C=C13194.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artocarbene,1TMS,isomer #1CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O)C=C3O[Si](C)(C)C)C=C2O12918.2Semi standard non polar33892256
Artocarbene,1TMS,isomer #2CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O[Si](C)(C)C)C=C3O)C=C2O12904.6Semi standard non polar33892256
Artocarbene,1TMS,isomer #3CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O)C=C3O)C=C2O[Si](C)(C)C)O12943.8Semi standard non polar33892256
Artocarbene,2TMS,isomer #1CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O)C=C3O[Si](C)(C)C)C=C2O[Si](C)(C)C)O12866.5Semi standard non polar33892256
Artocarbene,2TMS,isomer #2CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C=C2O12848.1Semi standard non polar33892256
Artocarbene,2TMS,isomer #3CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O[Si](C)(C)C)C=C3O)C=C2O[Si](C)(C)C)O12848.3Semi standard non polar33892256
Artocarbene,3TMS,isomer #1CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C=C2O[Si](C)(C)C)O12877.6Semi standard non polar33892256
Artocarbene,1TBDMS,isomer #1CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C=C2O13221.7Semi standard non polar33892256
Artocarbene,1TBDMS,isomer #2CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C=C2O13200.4Semi standard non polar33892256
Artocarbene,1TBDMS,isomer #3CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O)C=C3O)C=C2O[Si](C)(C)C(C)(C)C)O13257.5Semi standard non polar33892256
Artocarbene,2TBDMS,isomer #1CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)O13444.1Semi standard non polar33892256
Artocarbene,2TBDMS,isomer #2CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C=C2O13420.5Semi standard non polar33892256
Artocarbene,2TBDMS,isomer #3CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C=C2O[Si](C)(C)C(C)(C)C)O13424.9Semi standard non polar33892256
Artocarbene,3TBDMS,isomer #1CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)O13652.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artocarbene GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pn-0291000000-fec585b94f70aed3bc282017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artocarbene GC-MS (3 TMS) - 70eV, Positivesplash10-0ik9-1004590000-32fc410853eab601e92f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artocarbene 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 - Artocarbene 10V, Positive-QTOFsplash10-03di-0029000000-47594a3184680821d5812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 20V, Positive-QTOFsplash10-03di-1294000000-c4e865644b22b20c5c912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 40V, Positive-QTOFsplash10-0rki-4590000000-1db94ce0baddec135a462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 10V, Negative-QTOFsplash10-0a4i-0019000000-addcc9a5916d8529dd1b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 20V, Negative-QTOFsplash10-0a4i-0169000000-fbc33dc71f03101f4ba92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 40V, Negative-QTOFsplash10-0a6r-1690000000-123738ebbc562d5620772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 10V, Positive-QTOFsplash10-03di-0019000000-f93d01a5595bb135c3742021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 20V, Positive-QTOFsplash10-03yi-0193000000-bafc978f9cddbc157c432021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 40V, Positive-QTOFsplash10-0gb9-0290000000-d796470d38c60873f6122021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 10V, Negative-QTOFsplash10-0a4i-0009000000-a5477ba8add3d375c0082021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 20V, Negative-QTOFsplash10-0a4i-1049000000-4a9280f76345399d14a42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarbene 40V, Negative-QTOFsplash10-03dr-0190000000-df70e97dedf508bdefb02021-09-25Wishart 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 IDFDB008413
KNApSAcK IDC00054483
Chemspider ID30776916
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751188
PDB IDNot Available
ChEBI ID174233
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1827681
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.. .