Marvin  05101010082D          

 33 34  0  0  1  0            999 V2000
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   10.5152   -7.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6673   -6.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8198   -7.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9717   -6.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1243   -7.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2761   -6.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2761   -5.4183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4287   -7.4030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6673   -5.4183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9717   -5.4183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667  -10.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2186  -11.3767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3710  -10.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3710   -9.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2186   -8.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667   -9.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0667   -6.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6572  -10.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9142  -12.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2186   -3.4179    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  1  0  0  0
  5 11  1  1  0  0  0
 12 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 20  1  0  0  0  0
 27 29  1  0  0  0  0
 15 16  1  0  0  0  0
 17 30  1  0  0  0  0
 20 21  2  0  0  0  0
 30 31  1  0  0  0  0
 13 14  1  0  0  0  0
 31 32  1  0  0  0  0
 21 22  1  0  0  0  0
 21 33  1  0  0  0  0
 16 17  2  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
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 17 12  1  0  0  0  0
 14 24  1  0  0  0  0
 12 13  2  0  0  0  0
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 14 15  2  0  0  0  0
 24 26  1  0  0  0  0
 18 19  2  0  0  0  0
 15  1  1  0  0  0  0
M  END
> <ID>
CHEBI:3558

> <NAME>
cerivastatin

> <DEFINITION>
(3R,5S)-3,5-dihydroxyhept-6-enoic acid in which the (7E)-hydrogen is substituted by a 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl group. Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:503465

> <SYNONYM>
cerivastatin acid; Cerivastatin; (3R,5S,E)-7-(4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl)-3,5-dihydroxyhept-6-enoic acid; (3R,5S,6E)-7-(4-(p-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoic acid; (3R,5S,6E)-7-(4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl)-3,5-dihydroxy-6-heptenoic acid

> <IUPAC_NAME>
(3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid

> <INN>
cerivastatin

> <FORMULA>
C26H34FNO5

> <MASS>
459.55030

> <MONOISOTOPIC_MASS>
459.24210

> <CHARGE>
0

> <SMILES>
COCc1c(nc(C(C)C)c(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)c1-c1ccc(F)cc1)C(C)C

> <INCHI>
InChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1

> <INCHIKEY>
SEERZIQQUAZTOL-ANMDKAQQSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
8366578

> <CAS_REGISTRY_NUMBER>
145599-86-6

> <CHEMIDPLUS>
145599-86-6

> <DRUGBANK_ACCESSION>
DB00439

> <KEGG_COMPOUND_ACCESSION>
C07966

> <KEGG_DRUG_ACCESSION>
D07661

> <WIKIPEDIA_ACCESSION>
Cerivastatin

> <PUBMED_CITATION>
17560788; 18155906

$$$$