Casticin (CHEM024675)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:51:10 UTC
Update Date2016-11-09 01:17:56 UTC
Accession NumberCHEM024675
Identification
Common NameCasticin
ClassSmall Molecule
DescriptionA tetramethoxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6, 7 and 4' have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3',5-Dihydroxy-3,4',6,7-tetramethoxyflavoneChEBI
3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavoneChEBI
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-1-benzopyran-4-oneChEBI
Quercetagetin 3,6,7,4'-tetramethyl etherChEBI
VitexicarpinChEBI
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-benzopyran-4-one, 9ciHMDB
VX-5 CPDHMDB
Chemical FormulaC19H18O8
Average Molecular Mass374.341 g/mol
Monoisotopic Mass374.100 g/mol
CAS Registry Number479-91-4
IUPAC Name5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-chromen-4-one
Traditional Namecasticin
SMILESCOC1=C(O)C=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC)C=C2O1
InChI IdentifierInChI=1S/C19H18O8/c1-23-11-6-5-9(7-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3
InChI KeyPJQLSMYMOKWUJG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 3-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • 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 Solubility0.047 g/LALOGPS
logP2.71ALOGPS
logP2.4ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.82ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.04 m³·mol⁻¹ChemAxon
Polarizability37.66 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-0219000000-b10838d2170a87f5e165Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-0219000000-b10838d2170a87f5e165Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053v-0509000000-3c486251240acc73601fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uk9-2040950000-41a30081cfab516b49ecSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0009000000-d6ed5ef9f799861207f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0009000000-4d2c493586b5fcd4d1dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0009000000-30bcb251b9d26fc58a19Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014j-0029000000-cd7ecf683ac9e2989c0eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ba-0097000000-3aea04e29566d8b04391Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-4d2c493586b5fcd4d1dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-d6ed5ef9f799861207f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0009000000-30bcb251b9d26fc58a19Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014j-0029000000-cd7ecf683ac9e2989c0eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-01ba-0097000000-08ea29548c97e948b7bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-01ba-0097000000-3aea04e29566d8b04391Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-ecd3dc4f22417f1612ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014j-0029000000-8ec7d8150aa7af0de5f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-17db282d5ed22e89f45bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-a37f820453b95f34a4b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0109000000-aa9b05dea6c3bf2433b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-4916000000-34aca43cde82c271932bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-ba74d1d25778133e0c3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-971a885656c794ea67d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-1594000000-ba5dc940c1512a3bfc5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-15f06bca4340439c6e17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-f1599d663315c885ab8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-2915000000-f2d86e14d56da92c9ebbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-0766b1754fab3c43817bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0309000000-952e721a3f25d056f180Spectrum
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 IDHMDB0030660
FooDB IDFDB002570
Phenol Explorer IDNot Available
KNApSAcK IDC00004705
BiGG IDNot Available
BioCyc IDCPD-14856
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCasticin
Chemspider ID4474632
ChEBI ID69355
PubChem Compound ID5315263
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=21877688
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22407499
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23135489
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23464460
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23476684
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23761826
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23816816
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24126491
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24247269
10. Kobayakawa J, Sato-Nishimori F, Moriyasu M, Matsukawa Y: G2-M arrest and antimitotic activity mediated by casticin, a flavonoid isolated from Viticis Fructus (Vitex rotundifolia Linne fil.). Cancer Lett. 2004 May 10;208(1):59-64.
11. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.