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Record Information
Version2.0
Created at2022-03-17 21:03:09 UTC
Updated at2022-03-17 21:03:09 UTC
NP-MRD IDNP0048849
Secondary Accession NumbersNone
Natural Product Identification
Common NameCirsiliol
Description Cirsiliol is found in Achillea ageratum, Achillea millefolium, Achillea setacea, Ageratina havanensis, Aloysia citrodora, Fridericia platyphylla, Artemisia annua, Artemisia xanthochroa, Baccharis flabellata, Baccharis genistelloides, Brickellia dentata, Calanticaria greggii, Centaurea gigantea, Cirsium lineare, Ferula aucheri, Isodon angustifolius, Isodon japonicus, Isodon rubescens, Isodon tenuifolius, Lantana fucata , Lantana montevidensis, Leucocyclus formosus, Lippia citriodora , Phyla nodiflora, Lycopus europaeus, Ocimum kilimandscharicum, Passiflora menispermifolia, Salvia columbariae , Salvia dorrii, Salvia guaranitica, Salvia guranitica, Salvia hypoleuca, Salvia lavandulaefolia, Salvia limbata, Salvia lineata, Salvia macrosiphon, Salvia montbretii, Salvia rhyacophila, Salvia stenophylla , Salvia verbenaca , Sideritis leucantha, Teucrium chamaedrys, Teucrium divaricatum, Teucrium gnaphalodes, Teucrium kotschyanum, Teucrium montanum, Teucrium nudicaule, Teucrium oliverianum, Teucrium polium, Teucrium stocksianum, Thymus herba-barona and Wilkesia hobdyi. Cirsiliol was first documented in 2013 (PMID: 23902763).
Structure
Thumb
Synonyms
ValueSource
3',4',5-Trihydroxy-6,7-dimethoxyflavoneChEBI
6,7-Dimethoxy-5,3',4'-trihydroxyflavoneChEBI
3',4',5-Trihydroxy-6,7-dimethoxy-flavoneMeSH
Chemical FormulaC17H14O7
Average Mass330.2889 Da
Monoisotopic Mass330.07395 Da
IUPAC Name2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one
Traditional Namecirsiliol
CAS Registry Number34334-69-5
SMILES
COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1OC
InChI Identifier
InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3
InChI KeyIMEYGBIXGJLUIS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
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
  • 7-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.05ALOGPS
logP2.39ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.57ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.84 m³·mol⁻¹ChemAxon
Polarizability32.84 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016700
KNApSAcK IDC00001033
Chemspider IDNot Available
KEGG Compound IDC10033
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound160237
PDB IDNot Available
ChEBI ID3719
Good Scents IDNot Available
References
General References
  1. Uehara A, Kitajima J, Kokubugata G, Iwashina T: Further characterization of foliar flavonoids in Crossostephium chinense and their geographic variation. Nat Prod Commun. 2014 Feb;9(2):163-4. [PubMed:24689280 ]
  2. Kang J, Kim E, Kim W, Seong KM, Youn H, Kim JW, Kim J, Youn B: Rhamnetin and cirsiliol induce radiosensitization and inhibition of epithelial-mesenchymal transition (EMT) by miR-34a-mediated suppression of Notch-1 expression in non-small cell lung cancer cell lines. J Biol Chem. 2013 Sep 20;288(38):27343-27357. doi: 10.1074/jbc.M113.490482. Epub 2013 Jul 31. [PubMed:23902763 ]
  3. Lin FJ, Yen FL, Chen PC, Wang MC, Lin CN, Lee CW, Ko HH: HPLC-fingerprints and antioxidant constituents of Phyla nodiflora. ScientificWorldJournal. 2014;2014:528653. doi: 10.1155/2014/528653. Epub 2014 Jul 20. [PubMed:25140335 ]