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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 401019118
| Name = Nepetin | Name = Nepetin
| ImageFile = Nepetin.PNG | ImageFile = Nepetin.svg
| ImageSize = 200px
| ImageName = Chemical structure of nepetin
| ImageAlt = Chemical structure of nepetin | ImageAlt = Chemical structure of nepetin
| ImageFile1 = Nepetin molecule ball.png
| IUPACName = 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
| ImageSize1 = 220
| OtherNames = 6-Methoxyluteolin<br>6-methoxy 5,7,3',4'-tetrahydroxyflavone
| ImageAlt1 = Ball-and-stick model of nepetin
|Section1= {{Chembox Identifiers
| IUPACName = 3′,4′,5,7-Tetrahydroxy-6-methoxyflavone
| SystematicName = 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4''H''-1-benzopyran-4-one
| OtherNames = 6-Methoxyluteolin
|Section1={{Chembox Identifiers
| CASNo = 520-11-6 | CASNo = 520-11-6
| CASNo_Ref = | CASNo_Ref = {{cascite|correct|??}}
| CASOther = | CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = I3O7LF3GED
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 172350
| PubChem = 5317284 | PubChem = 5317284
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| SMILES =
| InChI = | ChemSpiderID = 4476172
| SMILES = COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O
| InChI = 1/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3
| InChIKey = FHHSEFRSDKWJKJ-UHFFFAOYAR
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = FHHSEFRSDKWJKJ-UHFFFAOYSA-N
| MeSHName = | MeSHName =
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>16</sub>H<sub>12</sub>O<sub>7</sub> | Formula = C<sub>16</sub>H<sub>12</sub>O<sub>7</sub>
| MolarMass = 316.26 g/mol | MolarMass = 316.26 g/mol
| ExactMass = 316.058303 u
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = <!-- °C --> | MeltingPt =
| BoilingPt = <!-- °C --> | BoilingPt =
| Solubility = | Solubility =
}} }}
}} }}
'''Nepetin''' is an ]. It can be found in '']''<ref></ref>. '''Nepetin''' is the 6-methoxy derivative of the pentahydroxyflavone ], an ]. It can be found in '']''.<ref>{{Cite web |url=http://cat.inist.fr/?aModele=afficheN&cpsidt=16354923 |title=Cytotoxic activity of nepetin, a flavonoid from Eupatorium ballotaefolium HBK. Militao G. C. G., Albuquerque M. R. J. R., Pessoa O. D. L., Pessoa C., Moraes M. E. A., De Moraes M. O., Costa-Lotufo L. V., Pharmazie, 2004, vol. 59, no12, pp. 965-966 |access-date=2010-04-06 |archive-date=2012-08-28 |archive-url=https://web.archive.org/web/20120828034645/http://cat.inist.fr/?aModele=afficheN&cpsidt=16354923 |url-status=dead }}</ref>


==Glycosides== == Glycosides ==
] is the 7-glucoside of nepetin. ] is the 7-glucoside of nepetin.


==References== == References ==
{{reflist}} {{reflist}}


{{flavone}} {{flavone}}


] ]
] ]
] ]


{{polyphenol-stub}} {{aromatic-stub}}

Latest revision as of 02:18, 24 December 2024

Nepetin
Chemical structure of nepetin
Ball-and-stick model of nepetin
Names
IUPAC name 3′,4′,5,7-Tetrahydroxy-6-methoxyflavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one
Other names 6-Methoxyluteolin
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3Key: FHHSEFRSDKWJKJ-UHFFFAOYSA-N
  • InChI=1/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3Key: FHHSEFRSDKWJKJ-UHFFFAOYAR
SMILES
  • COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O
Properties
Chemical formula C16H12O7
Molar mass 316.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

Nepetin is the 6-methoxy derivative of the pentahydroxyflavone 6-hydroxyluteolin, an O-methylated flavone. It can be found in Eupatorium ballotaefolium.

Glycosides

Nepitrin is the 7-glucoside of nepetin.

References

  1. "Cytotoxic activity of nepetin, a flavonoid from Eupatorium ballotaefolium HBK. Militao G. C. G., Albuquerque M. R. J. R., Pessoa O. D. L., Pessoa C., Moraes M. E. A., De Moraes M. O., Costa-Lotufo L. V., Pharmazie, 2004, vol. 59, no12, pp. 965-966". Archived from the original on 2012-08-28. Retrieved 2010-04-06.
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
of luteolin
Acetylated
  • Artocarpetin A
  • Artoindonesianin P
  • Sulfated glycosidesTheograndin I and II
    Polymers
    Drugs
    Stub icon

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