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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015227

Secondary Accession Numbers

HMDB15227

Metabolite Identification

Common Name

Fluvastatin

Description

Fluvastatin, also known as fluvas or fluindostatin, belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond. In humans, fluvastatin is involved in the fluvastatin action pathway. Fluvastatin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Fluvastatin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1095
  Mrv0541 09041214332D          

 30 32  0  0  1  0            999 V2000
    4.8848    3.3294    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162   -0.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -1.1859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2913   -3.3294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2913   -1.9003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -1.1353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -1.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    0.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650   -2.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -2.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    0.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -1.1859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8162   -1.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -1.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -1.9003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6500   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650    1.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    1.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -2.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213    2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    1.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286    2.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -2.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
 18  2  1  6  0  0  0
 21  3  1  6  0  0  0
  4 30  1  0  0  0  0
  5 30  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
  9 16  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 17  2  0  0  0  0
 12 20  2  0  0  0  0
 15 24  2  0  0  0  0
 15 25  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  2  0  0  0  0
 24 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 30  1  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0015227
     RDKit          3D
Fluvastatin
 56 58  0  0  0  0  0  0  0  0999 V2000
   -1.1280   -4.1088    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256   -3.3070   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3625   -4.1145   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -2.0628   -0.0214 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -0.8262    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702   -0.6066    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9775    0.5430    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660    0.6681    0.4343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7892    0.5833    1.7849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9591    1.9695   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4508    2.0452    0.0453 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9401    3.2629   -0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1886    0.9447   -0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6749    1.1167   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1655    2.0544    0.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5312    0.2038   -1.0756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0506    0.1082    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0135    1.5596    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672    2.3153   -1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    3.6931   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    4.3849    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9450    5.7394    0.2886 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1113    3.6470    1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307    2.2722    1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2536   -0.6046   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5904   -0.2185   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6114   -1.1381   -0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3051   -2.4798   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785   -2.9016   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851   -1.9450   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0092   -4.7601    1.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2484   -4.7938    1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023   -3.4109    2.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610   -3.1581   -0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -5.1181   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542   -3.5688   -1.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -4.3522   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615   -1.4676    0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    1.4415    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -0.1761   -0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0574    1.0439    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4949    2.8168    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7270    2.0327   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584    1.9523    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386    3.7512    0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9262    0.9238   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9183   -0.0366   -0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1946   -0.7052   -1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7746    1.7651   -1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346    4.2785   -1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    4.1545    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2445    1.7269    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741    0.8514   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6434   -0.8217   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0970   -3.2140   -0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7325   -3.9532   -0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30  4  1  0
 24 18  1  0
 30 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  6
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  0
 13 46  1  0
 13 47  1  0
 16 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
 24 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
 29 56  1  0
M  END

1095
  Mrv0541 09041214332D          

 30 32  0  0  1  0            999 V2000
    4.8848    3.3294    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162   -0.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -1.1859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2913   -3.3294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2913   -1.9003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -1.1353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -1.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    0.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650   -2.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -2.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    0.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -1.1859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8162   -1.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -1.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -1.9003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6500   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650    1.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    1.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -2.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213    2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    1.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286    2.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -2.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
 18  2  1  6  0  0  0
 21  3  1  6  0  0  0
  4 30  1  0  0  0  0
  5 30  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
  9 16  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 17  2  0  0  0  0
 12 20  2  0  0  0  0
 15 24  2  0  0  0  0
 15 25  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  2  0  0  0  0
 24 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 30  1  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015227

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)N1C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C24H26FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30)/b12-11+/t18-,19-/m0/s1

> <INCHI_KEY>
FJLGEFLZQAZZCD-JUFISIKESA-N

> <FORMULA>
C24H26FNO4

> <MOLECULAR_WEIGHT>
411.4659

> <EXACT_MASS>
411.18458653

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
44.314175993841545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,5R,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
3.825949093666666

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.644783424148272

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5570100486599445

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8401489650869784

> <JCHEM_POLAR_SURFACE_AREA>
82.69

> <JCHEM_REFRACTIVITY>
114.85530000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fluvastatin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015227
     RDKit          3D
Fluvastatin
 56 58  0  0  0  0  0  0  0  0999 V2000
   -1.1280   -4.1088    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256   -3.3070   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3625   -4.1145   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -2.0628   -0.0214 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -0.8262    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702   -0.6066    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9775    0.5430    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660    0.6681    0.4343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7892    0.5833    1.7849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9591    1.9695   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4508    2.0452    0.0453 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9401    3.2629   -0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1886    0.9447   -0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6749    1.1167   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1655    2.0544    0.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5312    0.2038   -1.0756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0506    0.1082    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0135    1.5596    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672    2.3153   -1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    3.6931   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    4.3849    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9450    5.7394    0.2886 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1113    3.6470    1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307    2.2722    1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2536   -0.6046   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5904   -0.2185   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6114   -1.1381   -0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3051   -2.4798   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785   -2.9016   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851   -1.9450   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0092   -4.7601    1.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2484   -4.7938    1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023   -3.4109    2.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610   -3.1581   -0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -5.1181   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542   -3.5688   -1.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -4.3522   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615   -1.4676    0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    1.4415    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -0.1761   -0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0574    1.0439    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4949    2.8168    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7270    2.0327   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584    1.9523    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386    3.7512    0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9262    0.9238   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9183   -0.0366   -0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1946   -0.7052   -1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7746    1.7651   -1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346    4.2785   -1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    4.1545    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2445    1.7269    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741    0.8514   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6434   -0.8217   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0970   -3.2140   -0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7325   -3.9532   -0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30  4  1  0
 24 18  1  0
 30 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  6
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  0
 13 46  1  0
 13 47  1  0
 16 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
 24 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
 29 56  1  0
M  END

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1095                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  F   UNK     0       9.118   6.215   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0      12.724  -0.880   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      15.034  -2.214   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.344  -6.215   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      17.344  -3.547   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.205  -2.119   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.683  -3.583   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.104  -0.880   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -1.650   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.205   0.360   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -0.110   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.644  -0.880   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.655  -4.729   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.190  -3.901   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.683   1.823   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -2.420   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   0.660   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.954  -2.214   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.724  -3.547   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.414  -2.214   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.264  -3.547   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -1.650   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -0.110   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.655   2.969   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.190   2.141   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.034  -4.881   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.133   4.433   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.668   3.605   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.640   4.751   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.574  -4.881   0.000  0.00  0.00           C+0
CONECT    1   29                                                            
CONECT    2   18                                                            
CONECT    3   21                                                            
CONECT    4   30                                                            
CONECT    5   30                                                            
CONECT    6    7    8    9                                                  
CONECT    7    6   13   14                                                  
CONECT    8    6   10   12                                                  
CONECT    9    6   11   16                                                  
CONECT   10    8   11   15                                                  
CONECT   11    9   10   17                                                  
CONECT   12    8   20                                                       
CONECT   13    7                                                            
CONECT   14    7                                                            
CONECT   15   10   24   25                                                  
CONECT   16    9   22                                                       
CONECT   17   11   23                                                       
CONECT   18    2   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   12   18                                                       
CONECT   21    3   19   26                                                  
CONECT   22   16   23                                                       
CONECT   23   17   22                                                       
CONECT   24   15   27                                                       
CONECT   25   15   28                                                       
CONECT   26   21   30                                                       
CONECT   27   24   29                                                       
CONECT   28   25   29                                                       
CONECT   29    1   27   28                                                  
CONECT   30    4    5   26                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0015227
HETATM    1  C1  UNL     1      -1.128  -4.109   1.224  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.926  -3.307  -0.056  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.363  -4.114  -1.264  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.636  -2.063  -0.021  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.065  -0.826   0.091  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.370  -0.607   0.199  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.978   0.543   0.332  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.466   0.668   0.434  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.789   0.583   1.785  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.959   1.969  -0.093  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.451   2.045   0.045  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.940   3.263  -0.439  1.00  0.00           O  
HETATM   13  C10 UNL     1       5.189   0.945  -0.676  1.00  0.00           C  
HETATM   14  C11 UNL     1       6.675   1.117  -0.488  1.00  0.00           C  
HETATM   15  O3  UNL     1       7.165   2.054   0.179  1.00  0.00           O  
HETATM   16  O4  UNL     1       7.531   0.204  -1.076  1.00  0.00           O  
HETATM   17  C12 UNL     1      -2.051   0.108   0.086  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.014   1.560   0.164  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.867   2.315  -1.008  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.847   3.693  -0.943  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.967   4.385   0.245  1.00  0.00           C  
HETATM   22  F1  UNL     1      -1.945   5.739   0.289  1.00  0.00           F  
HETATM   23  C17 UNL     1      -2.111   3.647   1.404  1.00  0.00           C  
HETATM   24  C18 UNL     1      -2.131   2.272   1.335  1.00  0.00           C  
HETATM   25  C19 UNL     1      -3.254  -0.605  -0.033  1.00  0.00           C  
HETATM   26  C20 UNL     1      -4.590  -0.218  -0.092  1.00  0.00           C  
HETATM   27  C21 UNL     1      -5.611  -1.138  -0.211  1.00  0.00           C  
HETATM   28  C22 UNL     1      -5.305  -2.480  -0.275  1.00  0.00           C  
HETATM   29  C23 UNL     1      -3.978  -2.902  -0.218  1.00  0.00           C  
HETATM   30  C24 UNL     1      -2.985  -1.945  -0.098  1.00  0.00           C  
HETATM   31  H1  UNL     1      -2.009  -4.760   1.189  1.00  0.00           H  
HETATM   32  H2  UNL     1      -0.248  -4.794   1.354  1.00  0.00           H  
HETATM   33  H3  UNL     1      -1.102  -3.411   2.077  1.00  0.00           H  
HETATM   34  H4  UNL     1       0.161  -3.158  -0.135  1.00  0.00           H  
HETATM   35  H5  UNL     1      -1.757  -5.118  -0.939  1.00  0.00           H  
HETATM   36  H6  UNL     1      -2.054  -3.569  -1.924  1.00  0.00           H  
HETATM   37  H7  UNL     1      -0.471  -4.352  -1.878  1.00  0.00           H  
HETATM   38  H8  UNL     1       1.062  -1.468   0.171  1.00  0.00           H  
HETATM   39  H9  UNL     1       0.408   1.442   0.377  1.00  0.00           H  
HETATM   40  H10 UNL     1       2.965  -0.176  -0.083  1.00  0.00           H  
HETATM   41  H11 UNL     1       2.057   1.044   2.291  1.00  0.00           H  
HETATM   42  H12 UNL     1       2.495   2.817   0.469  1.00  0.00           H  
HETATM   43  H13 UNL     1       2.727   2.033  -1.179  1.00  0.00           H  
HETATM   44  H14 UNL     1       4.758   1.952   1.129  1.00  0.00           H  
HETATM   45  H15 UNL     1       5.439   3.751   0.248  1.00  0.00           H  
HETATM   46  H16 UNL     1       4.926   0.924  -1.736  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.918  -0.037  -0.182  1.00  0.00           H  
HETATM   48  H18 UNL     1       7.195  -0.705  -1.319  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.775   1.765  -1.931  1.00  0.00           H  
HETATM   50  H20 UNL     1      -1.735   4.279  -1.845  1.00  0.00           H  
HETATM   51  H21 UNL     1      -2.207   4.155   2.351  1.00  0.00           H  
HETATM   52  H22 UNL     1      -2.244   1.727   2.254  1.00  0.00           H  
HETATM   53  H23 UNL     1      -4.774   0.851  -0.037  1.00  0.00           H  
HETATM   54  H24 UNL     1      -6.643  -0.822  -0.256  1.00  0.00           H  
HETATM   55  H25 UNL     1      -6.097  -3.214  -0.368  1.00  0.00           H  
HETATM   56  H26 UNL     1      -3.733  -3.953  -0.266  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4   34
CONECT    3   35   36   37
CONECT    4    5   30
CONECT    5    6   17   17
CONECT    6    7    7   38
CONECT    7    8   39
CONECT    8    9   10   40
CONECT    9   41
CONECT   10   11   42   43
CONECT   11   12   13   44
CONECT   12   45
CONECT   13   14   46   47
CONECT   14   15   15   16
CONECT   16   48
CONECT   17   18   25
CONECT   18   19   19   24
CONECT   19   20   49
CONECT   20   21   21   50
CONECT   21   22   23
CONECT   23   24   24   51
CONECT   24   52
CONECT   25   26   26   30
CONECT   26   27   53
CONECT   27   28   28   54
CONECT   28   29   55
CONECT   29   30   30   56
END

HMDB0015227
     RDKit          3D
Fluvastatin
 56 58  0  0  0  0  0  0  0  0999 V2000
   -1.1280   -4.1088    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256   -3.3070   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3625   -4.1145   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -2.0628   -0.0214 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -0.8262    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702   -0.6066    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9775    0.5430    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660    0.6681    0.4343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7892    0.5833    1.7849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9591    1.9695   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4508    2.0452    0.0453 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9401    3.2629   -0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1886    0.9447   -0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6749    1.1167   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1655    2.0544    0.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5312    0.2038   -1.0756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0506    0.1082    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0135    1.5596    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672    2.3153   -1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    3.6931   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    4.3849    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9450    5.7394    0.2886 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1113    3.6470    1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307    2.2722    1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2536   -0.6046   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5904   -0.2185   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6114   -1.1381   -0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3051   -2.4798   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785   -2.9016   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851   -1.9450   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0092   -4.7601    1.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2484   -4.7938    1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023   -3.4109    2.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610   -3.1581   -0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -5.1181   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542   -3.5688   -1.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -4.3522   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615   -1.4676    0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    1.4415    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -0.1761   -0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0574    1.0439    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4949    2.8168    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7270    2.0327   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584    1.9523    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386    3.7512    0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9262    0.9238   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9183   -0.0366   -0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1946   -0.7052   -1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7746    1.7651   -1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346    4.2785   -1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    4.1545    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2445    1.7269    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741    0.8514   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6434   -0.8217   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0970   -3.2140   -0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7325   -3.9532   -0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30  4  1  0
 24 18  1  0
 30 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  6
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  0
 13 46  1  0
 13 47  1  0
 16 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
 24 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
 29 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-(3S,5R)-Fluvastatin	ChEBI
(3S,5R)-(-)-Fluvastatin	ChEBI
(3S,5R,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid	ChEBI
Fluvas	Kegg
(3S,5R,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate	Generator
Fluindostatin	HMDB
Fluvastatin sodium salt	HMDB
Fluvastatin sodium	HMDB
7-(3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl)-3,5-dihydroxy-6-heptenoate	HMDB
Lescol	HMDB

Chemical Formula

C₂₄H₂₆FNO₄

Average Molecular Weight

411.4659

Monoisotopic Molecular Weight

411.18458653

IUPAC Name

(3S,5R,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid

Traditional Name

fluvastatin

CAS Registry Number

93957-54-1

SMILES

CC(C)N1C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C24H26FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30)/b12-11+/t18-,19-/m0/s1

InChI Key

FJLGEFLZQAZZCD-JUFISIKESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Substituted pyrroles

Direct Parent

Phenylpyrroles

Alternative Parents

Substituents

3-phenylpyrrole
N-alkylindole
Indole
Indole or derivatives
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Fluorobenzene
Halobenzene
Halogenated fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Hydroxy acid
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

statin (synthetic) (CHEBI:5136 )
(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (CHEBI:5136 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015227)

Source

Exogenous

Exogenous (HMDB: HMDB0015227)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fluvastatin Action Pathway (PathBank: SMP0000119)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	194 - 197 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0044 g/L	Not Available
LogP	4.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0044 g/L	ALOGPS
logP	3.69	ALOGPS
logP	3.83	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.69 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	114.86 m³·mol⁻¹	ChemAxon
Polarizability	44.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	230.918	30932474
DeepCCS	[M+Na]+	206.287	30932474
AllCCS	[M+H]+	203.1	32859911
AllCCS	[M+H-H2O]+	200.5	32859911
AllCCS	[M+NH4]+	205.4	32859911
AllCCS	[M+Na]+	206.1	32859911
AllCCS	[M-H]-	201.7	32859911
AllCCS	[M+Na-2H]-	202.2	32859911
AllCCS	[M+HCOO]-	203.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.77 minutes	32390414
Predicted by Siyang on May 30, 2022	13.5486 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	48.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2690.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	266.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	196.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	197.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	631.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	513.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	72.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1183.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	540.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1420.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	217.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	124.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fluvastatin	CC(C)N1C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C12	5311.2	Standard polar	33892256
Fluvastatin	CC(C)N1C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C12	2816.9	Standard non polar	33892256
Fluvastatin	CC(C)N1C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C12	3359.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fluvastatin,1TMS,isomer #1	CC(C)N1C(/C=C/[C@@H](C[C@H](O)CC(=O)O)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3355.2	Semi standard non polar	33892256
Fluvastatin,1TMS,isomer #2	CC(C)N1C(/C=C/[C@H](O)C[C@@H](CC(=O)O)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3307.7	Semi standard non polar	33892256
Fluvastatin,1TMS,isomer #3	CC(C)N1C(/C=C/[C@H](O)C[C@H](O)CC(=O)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3299.7	Semi standard non polar	33892256
Fluvastatin,2TMS,isomer #1	CC(C)N1C(/C=C/[C@@H](C[C@@H](CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3324.9	Semi standard non polar	33892256
Fluvastatin,2TMS,isomer #2	CC(C)N1C(/C=C/[C@@H](C[C@H](O)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3310.5	Semi standard non polar	33892256
Fluvastatin,2TMS,isomer #3	CC(C)N1C(/C=C/[C@H](O)C[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3277.5	Semi standard non polar	33892256
Fluvastatin,3TMS,isomer #1	CC(C)N1C(/C=C/[C@@H](C[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3304.9	Semi standard non polar	33892256
Fluvastatin,1TBDMS,isomer #1	CC(C)N1C(/C=C/[C@@H](C[C@H](O)CC(=O)O)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3576.5	Semi standard non polar	33892256
Fluvastatin,1TBDMS,isomer #2	CC(C)N1C(/C=C/[C@H](O)C[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3522.8	Semi standard non polar	33892256
Fluvastatin,1TBDMS,isomer #3	CC(C)N1C(/C=C/[C@H](O)C[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3530.9	Semi standard non polar	33892256
Fluvastatin,2TBDMS,isomer #1	CC(C)N1C(/C=C/[C@@H](C[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3714.5	Semi standard non polar	33892256
Fluvastatin,2TBDMS,isomer #2	CC(C)N1C(/C=C/[C@@H](C[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3719.2	Semi standard non polar	33892256
Fluvastatin,2TBDMS,isomer #3	CC(C)N1C(/C=C/[C@H](O)C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3669.9	Semi standard non polar	33892256
Fluvastatin,3TBDMS,isomer #1	CC(C)N1C(/C=C/[C@@H](C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21	3862.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fluvastatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6229000000-e7e9a4f18c77b8a3f328	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluvastatin GC-MS (3 TMS) - 70eV, Positive	splash10-03g0-9113255000-bbcec21c7d8450380f53	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluvastatin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluvastatin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluvastatin 10V, Positive-QTOF	splash10-03xr-0082900000-af0bcdb98404aa7485cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluvastatin 20V, Positive-QTOF	splash10-01b9-0090000000-fbe9d82e356a4c40ed62	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluvastatin 40V, Positive-QTOF	splash10-00di-0290000000-4e6800fc8ed4bacd61c7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluvastatin 40V, Positive-QTOF	splash10-00di-0190000000-8d3aabcab51b7427b00c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluvastatin 20V, Positive-QTOF	splash10-01b9-0091000000-91a05c153cd55276cb1e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluvastatin 10V, Positive-QTOF	splash10-03xr-0064900000-6073674eb901911a6505	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 10V, Positive-QTOF	splash10-002f-0009100000-48400cafdfe7b1ae8e91	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 20V, Positive-QTOF	splash10-0fbc-2029000000-d4584fe54d4a4dee073e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 40V, Positive-QTOF	splash10-0f79-8196000000-fb302f9ef42c788b0d34	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 10V, Negative-QTOF	splash10-03di-2009600000-fceb838edec69ac58798	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 20V, Negative-QTOF	splash10-0pi1-6109100000-0037246c25ef1a9001ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 40V, Negative-QTOF	splash10-0a4i-9124000000-574e6db0baf9d8f4ad3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 10V, Negative-QTOF	splash10-03di-0007900000-94ec3a6470255ed0e510	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 20V, Negative-QTOF	splash10-0kmj-2009000000-f827f5fc9e84c0d8a8ee	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 40V, Negative-QTOF	splash10-01u3-5094000000-5b650479bc088483a8c2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 10V, Positive-QTOF	splash10-03dl-0019500000-b32ac44df58c44fecd76	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 20V, Positive-QTOF	splash10-00ou-0039000000-533fcd1fe96ff3c27509	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluvastatin 40V, Positive-QTOF	splash10-0079-0091000000-fb70ed9366fe79b510e5	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fluvastatin Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01095	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01095	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01095

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1265982

KEGG Compound ID

C07014

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fluvastatin

METLIN ID

Not Available

PubChem Compound

1548972

PDB ID

Not Available

ChEBI ID

5136

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). FDA label . .

Showing metabocard for Fluvastatin (HMDB0015227)

MOL for HMDB0015227 (Fluvastatin)

3D MOL for HMDB0015227 (Fluvastatin)

3D SDF for HMDB0015227 (Fluvastatin)

3D-SDF for HMDB0015227 (Fluvastatin)

PDB for HMDB0015227 (Fluvastatin)

3D PDB for HMDB0015227 (Fluvastatin)

SMILES for HMDB0015227 (Fluvastatin)

INCHI for HMDB0015227 (Fluvastatin)

Structure for HMDB0015227 (Fluvastatin)

3D Structure for HMDB0015227 (Fluvastatin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra