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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-07-09 16:14:52 UTC

Update Date

2021-09-14 15:48:25 UTC

HMDB ID

HMDB0061047

Secondary Accession Numbers

HMDB61047

Metabolite Identification

Common Name

simvastatin hydroxy acid

Description

simvastatin hydroxy acid belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. Simvastatin is a hypolipidemic drug used to control elevated cholesterol, or hypercholesterolemia. simvastatin hydroxy acid is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, simvastatin hydroxy acid is involved in simvastatin action pathway. It is a member of the statin class of pharmaceuticals. Simvastatin is a synthetic derivate of a fermentation product of Aspergillus terreus. simvastatin hydroxy acid is a metabolite of simvastatin. The drug is marketed generically and under the trade name Zocor.

Structure

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


  Mrv0541 07091309142D          

 31 32  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  2  0  0  0  0
 10  9  1  0  0  0  0
 15  2  1  1  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  3  1  6  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 17 11  2  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  6  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 22 14  1  0  0  0  0
 23 17  1  1  0  0  0
 23 20  1  0  0  0  0
 23 21  1  0  0  0  0
 25  4  1  0  0  0  0
 25  5  1  0  0  0  0
 25  6  1  0  0  0  0
 25 24  1  0  0  0  0
 18 26  1  6  0  0  0
 19 27  1  6  0  0  0
 28 22  2  0  0  0  0
 29 22  1  0  0  0  0
 30 24  2  0  0  0  0
 21 31  1  1  0  0  0
 31 24  1  0  0  0  0
M  END

HMDB0061047
     RDKit          3D
simvastatin hydroxy acid
 71 72  0  0  0  0  0  0  0  0999 V2000
   -5.7109   -0.8486   -0.9867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141   -1.6759   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4370   -1.8077   -0.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5770   -2.6459    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778   -2.5308   -2.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -0.4999   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -0.1897   -2.1386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    0.4315    0.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    1.6754   -0.2548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8694    2.7584    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415    2.6063    1.5290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2977    1.4426    1.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    2.3853    2.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0101    1.9925    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437    1.8099    2.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8214    0.7423    2.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5356   -0.1448    1.7048 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5090   -1.2672    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2391    0.5243    0.4006 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2449    0.6333   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126    1.2961   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6737    1.0502    0.1805 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5644    1.2285    1.5464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4568   -0.2121   -0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.2034   -1.5520 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8374    0.9193   -1.6519 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781   -1.4370   -1.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4520   -1.5164   -3.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2267   -0.6605   -3.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2812   -2.5788   -3.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359    1.7439    0.5844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5184   -0.3825   -0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -0.0504   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1441   -1.4870   -1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2474   -2.7172   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -1.3235    0.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6251   -2.8581   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1227   -3.5931    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -2.0696    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017   -1.8091   -2.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185   -3.0662   -2.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4178   -3.2260   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743    1.8033   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7471    2.6463   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    3.7785   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    3.5087    1.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9715    1.6602    2.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9216    1.2720    0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305    0.5260    2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775    2.5785    3.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578    2.5288    3.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266    0.5567    3.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4487   -0.6624    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551   -2.1917    2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103   -1.6248    0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242   -1.1027    2.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5342   -0.2315   -0.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    0.9907   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4504   -0.4497   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9127    1.1537   -1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4142    2.4512   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490    1.8601   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3865    0.8824    1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -1.1394    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3798   -0.1334    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -0.2487   -2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3827    0.9336   -0.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7438   -1.3742   -0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863   -2.3630   -1.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1902   -2.7236   -2.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    2.6761    0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 19 31  1  0
 31  9  1  0
 31 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  5 42  1  0
  9 43  1  6
 10 44  1  0
 10 45  1  0
 11 46  1  1
 12 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  1
 18 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  6
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  6
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  6
 26 67  1  0
 27 68  1  0
 27 69  1  0
 30 70  1  0
 31 71  1  6
M  END


  Mrv0541 07091309142D          

 31 32  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  2  0  0  0  0
 10  9  1  0  0  0  0
 15  2  1  1  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  3  1  6  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 17 11  2  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  6  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 22 14  1  0  0  0  0
 23 17  1  1  0  0  0
 23 20  1  0  0  0  0
 23 21  1  0  0  0  0
 25  4  1  0  0  0  0
 25  5  1  0  0  0  0
 25  6  1  0  0  0  0
 25 24  1  0  0  0  0
 18 26  1  6  0  0  0
 19 27  1  6  0  0  0
 28 22  2  0  0  0  0
 29 22  1  0  0  0  0
 30 24  2  0  0  0  0
 21 31  1  1  0  0  0
 31 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061047

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O6/c1-6-25(4,5)24(30)31-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-18(26)13-19(27)14-22(28)29/h7-8,11,15-16,18-21,23,26-27H,6,9-10,12-14H2,1-5H3,(H,28,29)/t15-,16-,18+,19+,20-,21-,23-/m0/s1

> <INCHI_KEY>
XWLXKKNPFMNSFA-HGQWONQESA-N

> <FORMULA>
C25H40O6

> <MOLECULAR_WEIGHT>
436.5815

> <EXACT_MASS>
436.282489012

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
49.231820654996575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
3.7937300916666645

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.890242521747759

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.212298804304306

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7214650667185314

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
121.17559999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061047
     RDKit          3D
simvastatin hydroxy acid
 71 72  0  0  0  0  0  0  0  0999 V2000
   -5.7109   -0.8486   -0.9867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141   -1.6759   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4370   -1.8077   -0.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5770   -2.6459    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778   -2.5308   -2.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -0.4999   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -0.1897   -2.1386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    0.4315    0.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    1.6754   -0.2548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8694    2.7584    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415    2.6063    1.5290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2977    1.4426    1.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    2.3853    2.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0101    1.9925    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437    1.8099    2.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8214    0.7423    2.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5356   -0.1448    1.7048 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5090   -1.2672    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2391    0.5243    0.4006 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2449    0.6333   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126    1.2961   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6737    1.0502    0.1805 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5644    1.2285    1.5464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4568   -0.2121   -0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.2034   -1.5520 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8374    0.9193   -1.6519 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781   -1.4370   -1.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4520   -1.5164   -3.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2267   -0.6605   -3.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2812   -2.5788   -3.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359    1.7439    0.5844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5184   -0.3825   -0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -0.0504   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1441   -1.4870   -1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2474   -2.7172   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -1.3235    0.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6251   -2.8581   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1227   -3.5931    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -2.0696    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017   -1.8091   -2.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185   -3.0662   -2.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4178   -3.2260   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743    1.8033   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7471    2.6463   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    3.7785   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    3.5087    1.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9715    1.6602    2.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9216    1.2720    0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305    0.5260    2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775    2.5785    3.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578    2.5288    3.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266    0.5567    3.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4487   -0.6624    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551   -2.1917    2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103   -1.6248    0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242   -1.1027    2.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5342   -0.2315   -0.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    0.9907   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4504   -0.4497   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9127    1.1537   -1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4142    2.4512   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490    1.8601   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3865    0.8824    1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -1.1394    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3798   -0.1334    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -0.2487   -2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3827    0.9336   -0.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7438   -1.3742   -0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863   -2.3630   -1.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1902   -2.7236   -2.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    2.6761    0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 19 31  1  0
 31  9  1  0
 31 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  5 42  1  0
  9 43  1  6
 10 44  1  0
 10 45  1  0
 11 46  1  1
 12 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  1
 18 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  6
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  6
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  6
 26 67  1  0
 27 68  1  0
 27 69  1  0
 30 70  1  0
 31 71  1  6
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.437   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.003   5.390   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   25                                                            
CONECT    5   25                                                            
CONECT    6    1   25                                                       
CONECT    7    8   16                                                       
CONECT    8    7   17                                                       
CONECT    9   10   18                                                       
CONECT   10    9   20                                                       
CONECT   11   15   17                                                       
CONECT   12   15   21                                                       
CONECT   13   18   19                                                       
CONECT   14   19   22                                                       
CONECT   15    2   11   12                                                  
CONECT   16    3    7   20                                                  
CONECT   17    8   11   23                                                  
CONECT   18    9   13   26                                                  
CONECT   19   13   14   27                                                  
CONECT   20   10   16   23                                                  
CONECT   21   12   23   31                                                  
CONECT   22   14   28   29                                                  
CONECT   23   17   20   21                                                  
CONECT   24   25   30   31                                                  
CONECT   25    4    5    6   24                                             
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   22                                                            
CONECT   29   22                                                            
CONECT   30   24                                                            
CONECT   31   21   24                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

COMPND    HMDB0061047
HETATM    1  C1  UNL     1      -5.711  -0.849  -0.987  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.814  -1.676  -0.103  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.437  -1.808  -0.715  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.577  -2.646   0.208  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.578  -2.531  -2.034  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.795  -0.500  -0.966  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.480  -0.190  -2.139  1.00  0.00           O  
HETATM    8  O2  UNL     1      -2.509   0.431   0.021  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.893   1.675  -0.255  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.869   2.758   0.126  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.341   2.606   1.529  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.298   1.443   1.701  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.192   2.385   2.422  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.010   1.992   1.988  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.044   1.810   2.988  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.821   0.742   2.849  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.536  -0.145   1.705  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.509  -1.267   1.651  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.239   0.524   0.401  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.245   0.633  -0.637  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.513   1.296  -0.661  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.674   1.050   0.181  1.00  0.00           C  
HETATM   23  O3  UNL     1       3.564   1.228   1.546  1.00  0.00           O  
HETATM   24  C21 UNL     1       4.457  -0.212  -0.139  1.00  0.00           C  
HETATM   25  C22 UNL     1       4.995  -0.203  -1.552  1.00  0.00           C  
HETATM   26  O4  UNL     1       5.837   0.919  -1.652  1.00  0.00           O  
HETATM   27  C23 UNL     1       5.878  -1.437  -1.717  1.00  0.00           C  
HETATM   28  C24 UNL     1       6.452  -1.516  -3.070  1.00  0.00           C  
HETATM   29  O5  UNL     1       6.227  -0.661  -3.962  1.00  0.00           O  
HETATM   30  O6  UNL     1       7.281  -2.579  -3.391  1.00  0.00           O  
HETATM   31  C25 UNL     1      -0.636   1.744   0.584  1.00  0.00           C  
HETATM   32  H1  UNL     1      -6.518  -0.383  -0.399  1.00  0.00           H  
HETATM   33  H2  UNL     1      -5.122  -0.050  -1.478  1.00  0.00           H  
HETATM   34  H3  UNL     1      -6.144  -1.487  -1.796  1.00  0.00           H  
HETATM   35  H4  UNL     1      -5.247  -2.717  -0.111  1.00  0.00           H  
HETATM   36  H5  UNL     1      -4.810  -1.323   0.928  1.00  0.00           H  
HETATM   37  H6  UNL     1      -1.625  -2.858  -0.289  1.00  0.00           H  
HETATM   38  H7  UNL     1      -3.123  -3.593   0.406  1.00  0.00           H  
HETATM   39  H8  UNL     1      -2.362  -2.070   1.128  1.00  0.00           H  
HETATM   40  H9  UNL     1      -3.702  -1.809  -2.871  1.00  0.00           H  
HETATM   41  H10 UNL     1      -2.618  -3.066  -2.213  1.00  0.00           H  
HETATM   42  H11 UNL     1      -4.418  -3.226  -2.063  1.00  0.00           H  
HETATM   43  H12 UNL     1      -1.674   1.803  -1.337  1.00  0.00           H  
HETATM   44  H13 UNL     1      -3.747   2.646  -0.550  1.00  0.00           H  
HETATM   45  H14 UNL     1      -2.474   3.779  -0.031  1.00  0.00           H  
HETATM   46  H15 UNL     1      -3.920   3.509   1.826  1.00  0.00           H  
HETATM   47  H16 UNL     1      -4.971   1.660   2.561  1.00  0.00           H  
HETATM   48  H17 UNL     1      -4.922   1.272   0.824  1.00  0.00           H  
HETATM   49  H18 UNL     1      -3.730   0.526   2.010  1.00  0.00           H  
HETATM   50  H19 UNL     1      -2.378   2.579   3.492  1.00  0.00           H  
HETATM   51  H20 UNL     1       0.158   2.529   3.811  1.00  0.00           H  
HETATM   52  H21 UNL     1       1.627   0.557   3.563  1.00  0.00           H  
HETATM   53  H22 UNL     1      -0.449  -0.662   2.079  1.00  0.00           H  
HETATM   54  H23 UNL     1       1.055  -2.192   2.131  1.00  0.00           H  
HETATM   55  H24 UNL     1       1.710  -1.625   0.608  1.00  0.00           H  
HETATM   56  H25 UNL     1       2.424  -1.103   2.245  1.00  0.00           H  
HETATM   57  H26 UNL     1      -0.534  -0.232  -0.035  1.00  0.00           H  
HETATM   58  H27 UNL     1       0.692   0.991  -1.603  1.00  0.00           H  
HETATM   59  H28 UNL     1       1.450  -0.450  -1.003  1.00  0.00           H  
HETATM   60  H29 UNL     1       2.913   1.154  -1.741  1.00  0.00           H  
HETATM   61  H30 UNL     1       2.414   2.451  -0.714  1.00  0.00           H  
HETATM   62  H31 UNL     1       4.449   1.860  -0.089  1.00  0.00           H  
HETATM   63  H32 UNL     1       4.386   0.882   1.960  1.00  0.00           H  
HETATM   64  H33 UNL     1       3.985  -1.139   0.155  1.00  0.00           H  
HETATM   65  H34 UNL     1       5.380  -0.133   0.515  1.00  0.00           H  
HETATM   66  H35 UNL     1       4.240  -0.249  -2.335  1.00  0.00           H  
HETATM   67  H36 UNL     1       6.383   0.934  -0.842  1.00  0.00           H  
HETATM   68  H37 UNL     1       6.744  -1.374  -0.998  1.00  0.00           H  
HETATM   69  H38 UNL     1       5.286  -2.363  -1.540  1.00  0.00           H  
HETATM   70  H39 UNL     1       8.190  -2.724  -2.956  1.00  0.00           H  
HETATM   71  H40 UNL     1      -0.130   2.676   0.249  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4    5    6
CONECT    4   37   38   39
CONECT    5   40   41   42
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   31   43
CONECT   10   11   44   45
CONECT   11   12   13   46
CONECT   12   47   48   49
CONECT   13   14   14   50
CONECT   14   15   31
CONECT   15   16   16   51
CONECT   16   17   52
CONECT   17   18   19   53
CONECT   18   54   55   56
CONECT   19   20   31   57
CONECT   20   21   58   59
CONECT   21   22   60   61
CONECT   22   23   24   62
CONECT   23   63
CONECT   24   25   64   65
CONECT   25   26   27   66
CONECT   26   67
CONECT   27   28   68   69
CONECT   28   29   29   30
CONECT   30   70
CONECT   31   71
END

HMDB0061047
     RDKit          3D
simvastatin hydroxy acid
 71 72  0  0  0  0  0  0  0  0999 V2000
   -5.7109   -0.8486   -0.9867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141   -1.6759   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4370   -1.8077   -0.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5770   -2.6459    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778   -2.5308   -2.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -0.4999   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -0.1897   -2.1386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    0.4315    0.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    1.6754   -0.2548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8694    2.7584    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415    2.6063    1.5290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2977    1.4426    1.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    2.3853    2.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0101    1.9925    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437    1.8099    2.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8214    0.7423    2.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5356   -0.1448    1.7048 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5090   -1.2672    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2391    0.5243    0.4006 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2449    0.6333   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126    1.2961   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6737    1.0502    0.1805 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5644    1.2285    1.5464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4568   -0.2121   -0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.2034   -1.5520 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8374    0.9193   -1.6519 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781   -1.4370   -1.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4520   -1.5164   -3.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2267   -0.6605   -3.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2812   -2.5788   -3.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359    1.7439    0.5844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5184   -0.3825   -0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -0.0504   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1441   -1.4870   -1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2474   -2.7172   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -1.3235    0.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6251   -2.8581   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1227   -3.5931    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -2.0696    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017   -1.8091   -2.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185   -3.0662   -2.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4178   -3.2260   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743    1.8033   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7471    2.6463   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    3.7785   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    3.5087    1.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9715    1.6602    2.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9216    1.2720    0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305    0.5260    2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775    2.5785    3.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578    2.5288    3.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266    0.5567    3.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4487   -0.6624    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551   -2.1917    2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103   -1.6248    0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242   -1.1027    2.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5342   -0.2315   -0.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    0.9907   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4504   -0.4497   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9127    1.1537   -1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4142    2.4512   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490    1.8601   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3865    0.8824    1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -1.1394    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3798   -0.1334    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -0.2487   -2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3827    0.9336   -0.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7438   -1.3742   -0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863   -2.3630   -1.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1902   -2.7236   -2.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    2.6761    0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 19 31  1  0
 31  9  1  0
 31 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  5 42  1  0
  9 43  1  6
 10 44  1  0
 10 45  1  0
 11 46  1  1
 12 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  1
 18 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  6
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  6
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  6
 26 67  1  0
 27 68  1  0
 27 69  1  0
 30 70  1  0
 31 71  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₅H₄₀O₆

Average Molecular Weight

436.5815

Monoisotopic Molecular Weight

436.282489012

IUPAC Name

(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

Traditional Name

(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12

InChI Identifier

InChI=1S/C25H40O6/c1-6-25(4,5)24(30)31-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-18(26)13-19(27)14-22(28)29/h7-8,11,15-16,18-21,23,26-27H,6,9-10,12-14H2,1-5H3,(H,28,29)/t15-,16-,18+,19+,20-,21-,23-/m0/s1

InChI Key

XWLXKKNPFMNSFA-HGQWONQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Fatty alcohol
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Branched fatty acid
Hydroxy fatty acid
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Kidney (HMDB: HMDB0061047)
Liver (HMDB: HMDB0061047)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Cytoplasm (HMDB: HMDB0061047)
Membrane (HMDB: HMDB0061047)

Source

Endogenous

Endogenous (HMDB: HMDB0061047)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	4.22	ALOGPS
logP	3.79	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	121.18 m³·mol⁻¹	ChemAxon
Polarizability	49.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	204.297	31661259
DarkChem	[M-H]-	203.355	31661259
DeepCCS	[M-2H]-	242.597	30932474
DeepCCS	[M+Na]+	216.808	30932474
AllCCS	[M+H]+	210.4	32859911
AllCCS	[M+H-H2O]+	208.4	32859911
AllCCS	[M+NH4]+	212.2	32859911
AllCCS	[M+Na]+	212.7	32859911
AllCCS	[M-H]-	206.2	32859911
AllCCS	[M+Na-2H]-	208.2	32859911
AllCCS	[M+HCOO]-	210.6	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.	7.35 minutes	32390414
Predicted by Siyang on May 30, 2022	15.8159 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3107.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	240.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	167.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	744.0 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	646.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1282.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	605.5 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	1721.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	486.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	208.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	196.6 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	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
simvastatin hydroxy acid	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12	4955.4	Standard polar	33892256
simvastatin hydroxy acid	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12	3060.8	Standard non polar	33892256
simvastatin hydroxy acid	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12	3060.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
simvastatin hydroxy acid,1TMS,isomer #1	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@H](C[C@@H](O)CC(=O)O)O[Si](C)(C)C)[C@H]21	3085.6	Semi standard non polar	33892256
simvastatin hydroxy acid,1TMS,isomer #2	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@H](CC(=O)O)O[Si](C)(C)C)[C@H]21	3058.5	Semi standard non polar	33892256
simvastatin hydroxy acid,1TMS,isomer #3	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(=O)O[Si](C)(C)C)[C@H]21	3098.6	Semi standard non polar	33892256
simvastatin hydroxy acid,2TMS,isomer #1	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@H](C[C@H](CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]21	3085.3	Semi standard non polar	33892256
simvastatin hydroxy acid,2TMS,isomer #2	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@H](C[C@@H](O)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]21	3114.8	Semi standard non polar	33892256
simvastatin hydroxy acid,2TMS,isomer #3	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]21	3084.9	Semi standard non polar	33892256
simvastatin hydroxy acid,3TMS,isomer #1	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@H](C[C@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]21	3107.0	Semi standard non polar	33892256
simvastatin hydroxy acid,1TBDMS,isomer #1	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@H](C[C@@H](O)CC(=O)O)O[Si](C)(C)C(C)(C)C)[C@H]21	3336.7	Semi standard non polar	33892256
simvastatin hydroxy acid,1TBDMS,isomer #2	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@H](CC(=O)O)O[Si](C)(C)C(C)(C)C)[C@H]21	3305.7	Semi standard non polar	33892256
simvastatin hydroxy acid,1TBDMS,isomer #3	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(=O)O[Si](C)(C)C(C)(C)C)[C@H]21	3359.6	Semi standard non polar	33892256
simvastatin hydroxy acid,2TBDMS,isomer #1	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[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@H]21	3555.2	Semi standard non polar	33892256
simvastatin hydroxy acid,2TBDMS,isomer #2	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[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@H]21	3589.5	Semi standard non polar	33892256
simvastatin hydroxy acid,2TBDMS,isomer #3	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[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@H]21	3562.3	Semi standard non polar	33892256
simvastatin hydroxy acid,3TBDMS,isomer #1	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[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@H]21	3766.8	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 - simvastatin hydroxy acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-7059500000-c243b36c156bda159855	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - simvastatin hydroxy acid GC-MS (3 TMS) - 70eV, Positive	splash10-000i-9011268000-0c0a34c8ff37ede6ad2c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - simvastatin hydroxy acid 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 10V, Positive-QTOF	splash10-0gb9-1002900000-7362cb6a6a11e6093e9a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 20V, Positive-QTOF	splash10-0fka-6019400000-56d1e64c65fbe3fa7611	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 40V, Positive-QTOF	splash10-006t-9042000000-4f898d33e5ead5caa9ca	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 10V, Negative-QTOF	splash10-00kr-1005900000-0f83a291da02d48fa8f9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 20V, Negative-QTOF	splash10-06dr-6209300000-d5da9d18a4ce425dff92	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 40V, Negative-QTOF	splash10-06dl-9143000000-cd063b22825d93d74346	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 10V, Positive-QTOF	splash10-00di-0639000000-16d77d094f4540672add	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 20V, Positive-QTOF	splash10-01b9-1494000000-dcda16883d6a6707f1bf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 40V, Positive-QTOF	splash10-05fr-9300000000-5f14291065079c0f8acc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 10V, Negative-QTOF	splash10-014i-2709700000-b55ceac33087e36a0f1f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 20V, Negative-QTOF	splash10-014r-7910000000-df19f5932336d8f894e4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - simvastatin hydroxy acid 40V, Negative-QTOF	splash10-014m-3129000000-7b87e19bea3b4485aace	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

64718

PDB ID

SIM

ChEBI ID

Not Available

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

Not Available

Showing metabocard for simvastatin hydroxy acid (HMDB0061047)

MOL for HMDB0061047 (simvastatin hydroxy acid)

3D MOL for HMDB0061047 (simvastatin hydroxy acid)

3D SDF for HMDB0061047 (simvastatin hydroxy acid)

3D-SDF for HMDB0061047 (simvastatin hydroxy acid)

PDB for HMDB0061047 (simvastatin hydroxy acid)

3D PDB for HMDB0061047 (simvastatin hydroxy acid)

SMILES for HMDB0061047 (simvastatin hydroxy acid)

INCHI for HMDB0061047 (simvastatin hydroxy acid)

Structure for HMDB0061047 (simvastatin hydroxy acid)

3D Structure for HMDB0061047 (simvastatin hydroxy acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra