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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:24 UTC
Update Date2022-03-07 02:52:43 UTC
HMDB IDHMDB0030849
Secondary Accession Numbers
  • HMDB30849
Metabolite Identification
Common NameArtocarpin
DescriptionArtocarpin, also known as artocarpin lectin, belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position. Artocarpin has been detected, but not quantified in, a few different foods, such as breadfruits (Artocarpus altilis), fruits, and jackfruits (Artocarpus heterophyllus). This could make artocarpin a potential biomarker for the consumption of these foods. Artocarpin 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 Artocarpin.
Structure
Data?1563862047
Synonyms
ValueSource
2',4',5-Trihydroxy-7-methoxy-6-(3-methyl-1-butenyl)-3-(3-methyl-2-butenyl)flavoneChEBI
5-Hydroxy-7-methoxy-3-(3-methyl-2-butenyl)-6-(3-methyl-1-butenyl)-2-(2,4-dihydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
Artocarpin lectinMeSH
2-(2,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-6-(3-methyl-1-butenyl)-3-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ciHMDB
Chemical FormulaC26H28O6
Average Molecular Weight436.4969
Monoisotopic Molecular Weight436.188588628
IUPAC Name2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methylbut-1-en-1-yl]-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Name2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methylbut-1-en-1-yl]-3-(3-methylbut-2-en-1-yl)chromen-4-one
CAS Registry Number7608-44-8
SMILES
COC1=CC2=C(C(O)=C1\C=C\C(C)C)C(=O)C(CC=C(C)C)=C(O2)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C26H28O6/c1-14(2)6-9-18-21(31-5)13-22-23(24(18)29)25(30)19(10-7-15(3)4)26(32-22)17-11-8-16(27)12-20(17)28/h6-9,11-14,27-29H,10H2,1-5H3/b9-6+
InChI KeyKRGDFVQWQJIMEK-RMKNXTFCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent3-prenylated flavones
Alternative Parents
Substituents
  • 3-prenylated flavone
  • 7-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Styrene
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Point174 - 175 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0027 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0026 g/LALOGPS
logP5.18ALOGPS
logP6.01ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)7.98ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity127.45 m³·mol⁻¹ChemAxon
Polarizability48.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+208.82430932474
DeepCCS[M-H]-206.42930932474
DeepCCS[M-2H]-239.31230932474
DeepCCS[M+Na]+214.73730932474
AllCCS[M+H]+207.532859911
AllCCS[M+H-H2O]+204.932859911
AllCCS[M+NH4]+209.832859911
AllCCS[M+Na]+210.532859911
AllCCS[M-H]-205.532859911
AllCCS[M+Na-2H]-205.732859911
AllCCS[M+HCOO]-206.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ArtocarpinCOC1=CC2=C(C(O)=C1\C=C\C(C)C)C(=O)C(CC=C(C)C)=C(O2)C1=C(O)C=C(O)C=C15464.1Standard polar33892256
ArtocarpinCOC1=CC2=C(C(O)=C1\C=C\C(C)C)C(=O)C(CC=C(C)C)=C(O2)C1=C(O)C=C(O)C=C13539.4Standard non polar33892256
ArtocarpinCOC1=CC2=C(C(O)=C1\C=C\C(C)C)C(=O)C(CC=C(C)C)=C(O2)C1=C(O)C=C(O)C=C13698.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artocarpin,1TMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O)O23591.7Semi standard non polar33892256
Artocarpin,1TMS,isomer #2COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O[Si](C)(C)C)O23561.9Semi standard non polar33892256
Artocarpin,1TMS,isomer #3COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C)C=C1O)O23594.8Semi standard non polar33892256
Artocarpin,2TMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C)C=C1O)O23500.4Semi standard non polar33892256
Artocarpin,2TMS,isomer #2COC1=CC2=C(C(O[Si](C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O[Si](C)(C)C)O23475.5Semi standard non polar33892256
Artocarpin,2TMS,isomer #3COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)O23498.9Semi standard non polar33892256
Artocarpin,3TMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)O23470.4Semi standard non polar33892256
Artocarpin,1TBDMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O)O23839.9Semi standard non polar33892256
Artocarpin,1TBDMS,isomer #2COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)O23807.2Semi standard non polar33892256
Artocarpin,1TBDMS,isomer #3COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)O23854.9Semi standard non polar33892256
Artocarpin,2TBDMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)O23948.7Semi standard non polar33892256
Artocarpin,2TBDMS,isomer #2COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)O23911.2Semi standard non polar33892256
Artocarpin,2TBDMS,isomer #3COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)O23970.8Semi standard non polar33892256
Artocarpin,3TBDMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)O24066.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artocarpin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0016900000-b6a66201932d08b82d022017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artocarpin GC-MS (3 TMS) - 70eV, Positivesplash10-000i-1000029000-6e75e6ccb1941c992db72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artocarpin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 10V, Negative-QTOFsplash10-0159-0590000000-6545d7dadecee8a4f74f2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 30V, Negative-QTOFsplash10-03di-0029100000-b05a8e20e23cb267e2532017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF , Negative-QTOFsplash10-000i-0002900010-8da91c9103874a49a7fa2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 50V, Negative-QTOFsplash10-0a4i-0191000000-bd435bd5fa1fd964bc2a2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 20V, Negative-QTOFsplash10-01p9-0007900000-e9660f3601ab50e328622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 40V, Negative-QTOFsplash10-0bt9-0095000000-af0abacc4b61c8c1f9992017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 10V, Negative-QTOFsplash10-000i-0000900000-0edef93ed272697afd8a2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 30V, Negative-QTOFsplash10-03di-0029100000-b05a8e20e23cb267e2532017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF , Negative-QTOFsplash10-000i-0002900010-8da91c9103874a49a7fa2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 50V, Negative-QTOFsplash10-0a4i-0191000000-bd435bd5fa1fd964bc2a2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 20V, Negative-QTOFsplash10-01p9-0007900000-e9660f3601ab50e328622017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin ESI-TOF 40V, Negative-QTOFsplash10-0bt9-0095000000-af0abacc4b61c8c1f9992017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOFsplash10-000i-0000900000-0edef93ed272697afd8a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOFsplash10-03di-0029100000-b05a8e20e23cb267e2532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOFsplash10-0a4i-0191000000-bd435bd5fa1fd964bc2a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOFsplash10-01p9-0007900000-e9660f3601ab50e328622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOFsplash10-0bt9-0095000000-af0abacc4b61c8c1f9992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin 50V, Positive-QTOFsplash10-0a4i-0191000000-bd435bd5fa1fd964bc2a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Artocarpin 40V, Positive-QTOFsplash10-0bt9-0095000000-c149b87b1a12b52906eb2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarpin 10V, Positive-QTOFsplash10-000i-1005900000-d8d4a3082742081f6e692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarpin 20V, Positive-QTOFsplash10-017r-4009300000-cb731e983db7d2669e382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarpin 40V, Positive-QTOFsplash10-06dr-6393100000-9fca685296e8905c57732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarpin 10V, Negative-QTOFsplash10-000i-0000900000-dd022c2539a92356788e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarpin 20V, Negative-QTOFsplash10-000i-0014900000-bfa7024d47d949dc121b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artocarpin 40V, Negative-QTOFsplash10-0a4i-2925100000-b56b4bc0809997d590ad2016-08-03Wishart 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 IDFDB002808
KNApSAcK IDC00004032
Chemspider ID4572407
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5458461
PDB IDNot Available
ChEBI ID65439
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1823161
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.. .