Artocarpin (CHEM024873)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:58:53 UTC
Update Date2016-11-09 01:17:58 UTC
Accession NumberCHEM024873
Identification
Common NameArtocarpin
ClassSmall Molecule
DescriptionA trihydroxyflavone that is flavone substituted by hydroxy groups at positions 5, 2', and 4', a methoxy group at position 7, a prenyl group at position 3 and a (1E)-3-methylbut-1-enyl group at position 6. Isolated from Artocarpus heterophyllus and Artocarpus integrifolia, it exhibits antineoplastic activity.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass436.497 g/mol
Monoisotopic Mass436.189 g/mol
CAS Registry Number7608-44-8
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
SMILESCOC1=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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0016900000-b6a66201932d08b82d02Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000i-1000029000-6e75e6ccb1941c992db7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0159-0590000000-6545d7dadecee8a4f74fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029100000-b05a8e20e23cb267e253Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0002900010-8da91c9103874a49a7faSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a4i-0191000000-bd435bd5fa1fd964bc2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-01p9-0007900000-e9660f3601ab50e32862Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0bt9-0095000000-af0abacc4b61c8c1f999Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0000900000-0edef93ed272697afd8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029100000-b05a8e20e23cb267e253Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0002900010-8da91c9103874a49a7faSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a4i-0191000000-bd435bd5fa1fd964bc2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-01p9-0007900000-e9660f3601ab50e32862Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0bt9-0095000000-af0abacc4b61c8c1f999Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0000900000-0edef93ed272697afd8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0029100000-b05a8e20e23cb267e253Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0191000000-bd435bd5fa1fd964bc2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-01p9-0007900000-e9660f3601ab50e32862Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0bt9-0095000000-af0abacc4b61c8c1f999Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0a4i-0191000000-bd435bd5fa1fd964bc2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0095000000-c149b87b1a12b52906ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1005900000-d8d4a3082742081f6e69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-017r-4009300000-cb731e983db7d2669e38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dr-6393100000-9fca685296e8905c5773Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-dd022c2539a92356788eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0014900000-bfa7024d47d949dc121bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2925100000-b56b4bc0809997d590adSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030849
FooDB IDFDB002808
Phenol Explorer IDNot Available
KNApSAcK IDC00004032
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4572407
ChEBI ID65439
PubChem Compound ID5458461
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11902840
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15165133
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20082761
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20544395
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21941923
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.