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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:54:19 UTC

Update Date

2021-09-26 23:14:23 UTC

HMDB ID

HMDB0257813

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate

Description

Simvastatin belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. In humans, simvastatin is involved in the simvastatin action pathway. Simvastatin 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 Simvastatin. This compound has been identified in human blood as reported by (PMID: 31557052 ). (1r,3s,7r,8r,8as)-8-{2-[(2r,4s)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652305221921152D          

 30 32  0  0  0  0            999 V2000
    4.0954    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.4454    2.5855    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
    3.2704    4.0145    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
    0.0000    0.8250    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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    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
   -0.7145    2.0625    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
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  3  1  0  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 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19  9  1  0  0  0  0
 19 13  1  0  0  0  0
 20 10  1  0  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  0  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
 26 18  1  0  0  0  0
 27 22  2  0  0  0  0
 28 24  2  0  0  0  0
 29 19  1  0  0  0  0
 29 22  1  0  0  0  0
 30 21  1  0  0  0  0
 30 24  1  0  0  0  0
M  END

HMDB0257813
     RDKit          3D
(1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-...
 68 70  0  0  0  0  0  0  0  0999 V2000
   -2.3275    1.2437    3.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934    1.9491    2.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735    1.8645    1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    2.5896    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9537    2.5613    1.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1601    0.4271    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -0.4746    1.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695   -0.0904   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -1.4434   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -1.6895   -1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3183   -3.0002   -2.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6680   -3.6053   -2.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -3.9724   -1.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5959   -3.6122   -0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1575   -4.4362    0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9562   -3.9767    0.9948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0318   -2.4627    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -2.2029    1.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245   -1.9390   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002   -0.7986   -0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397    0.4876    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8223    1.5037   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525    2.8077    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8823    3.6479    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321    4.9450    0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    3.6807   -1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1246    2.9689   -2.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6249    3.4268   -3.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    1.7399   -1.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -2.1194   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3913    0.7871    3.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1176    1.9956    4.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    0.4350    3.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0302    1.3798    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376    2.9854    2.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4041    3.0831   -0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    3.3949    0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7718    1.9280   -0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6163    2.8788    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0739    3.4793    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    1.9403    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -1.9740    0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5192   -1.6672   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707   -0.8882   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597   -2.9083   -3.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5572   -4.5658   -3.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3197   -2.8987   -3.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1301   -3.8699   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427   -4.9871   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0605   -5.5253   -0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -4.5944    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -2.1541    1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -1.3431    2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6450   -3.0624    2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997   -2.1637    1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -2.8232   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093   -1.0514   -0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863   -0.5957   -1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8077    1.0144   -0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867    0.4952    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.0994   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557    2.7163    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631    3.3300   -0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738    3.2111    0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    5.0154    1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1402    3.2162   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1599    4.7389   -1.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -2.0716   -2.1349 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
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 19 30  1  0
 30  9  1  0
 30 14  1  0
 29 22  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 30 68  1  0
M  END


  Mrv1652305221921152D          

 30 32  0  0  0  0            999 V2000
    4.0954    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.4454    2.5855    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
    3.2704    4.0145    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
    0.0000    0.8250    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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    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
   -0.7145    2.0625    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
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  3  1  0  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 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19  9  1  0  0  0  0
 19 13  1  0  0  0  0
 20 10  1  0  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  0  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
 26 18  1  0  0  0  0
 27 22  2  0  0  0  0
 28 24  2  0  0  0  0
 29 19  1  0  0  0  0
 29 22  1  0  0  0  0
 30 21  1  0  0  0  0
 30 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257813

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)(C)C(=O)OC1CC(C)C=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3

> <INCHI_KEY>
RYMZZMVNJRMUDD-UHFFFAOYSA-N

> <FORMULA>
C25H38O5

> <MOLECULAR_WEIGHT>
418.5662

> <EXACT_MASS>
418.271924326

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.05186724336233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[2-(4-hydroxy-6-oxooxan-2-yl)ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
4.458201216333332

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.914537666911102

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8361812244930835

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
117.68339999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
simvastatin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257813
     RDKit          3D
(1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-...
 68 70  0  0  0  0  0  0  0  0999 V2000
   -2.3275    1.2437    3.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934    1.9491    2.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735    1.8645    1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    2.5896    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9537    2.5613    1.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1601    0.4271    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -0.4746    1.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695   -0.0904   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -1.4434   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -1.6895   -1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3183   -3.0002   -2.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6680   -3.6053   -2.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -3.9724   -1.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5959   -3.6122   -0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1575   -4.4362    0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9562   -3.9767    0.9948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0318   -2.4627    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -2.2029    1.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245   -1.9390   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002   -0.7986   -0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397    0.4876    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8223    1.5037   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525    2.8077    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8823    3.6479    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321    4.9450    0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    3.6807   -1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1246    2.9689   -2.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6249    3.4268   -3.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    1.7399   -1.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -2.1194   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3913    0.7871    3.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1176    1.9956    4.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    0.4350    3.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0302    1.3798    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376    2.9854    2.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4041    3.0831   -0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    3.3949    0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7718    1.9280   -0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6163    2.8788    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0739    3.4793    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    1.9403    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -1.9740    0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5192   -1.6672   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707   -0.8882   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597   -2.9083   -3.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5572   -4.5658   -3.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3197   -2.8987   -3.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1301   -3.8699   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427   -4.9871   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0605   -5.5253   -0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -4.5944    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -2.1541    1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -1.3431    2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6450   -3.0624    2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997   -2.1637    1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -2.8232   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093   -1.0514   -0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863   -0.5957   -1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8077    1.0144   -0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867    0.4952    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.0994   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557    2.7163    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631    3.3300   -0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738    3.2111    0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    5.0154    1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1402    3.2162   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1599    4.7389   -1.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -2.0716   -2.1349 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
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 19 30  1  0
 30  9  1  0
 30 14  1  0
 29 22  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 30 68  1  0
M  END

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       7.645   7.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.565   4.826   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.105   7.494   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667   6.160   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   19                                                       
CONECT   10    9   20                                                       
CONECT   11   15   17                                                       
CONECT   12   15   21                                                       
CONECT   13   18   19                                                       
CONECT   14   18   22                                                       
CONECT   15    2   11   12                                                  
CONECT   16    3    7   20                                                  
CONECT   17    8   11   23                                                  
CONECT   18   13   14   26                                                  
CONECT   19    9   13   29                                                  
CONECT   20   10   16   23                                                  
CONECT   21   12   23   30                                                  
CONECT   22   14   27   29                                                  
CONECT   23   17   20   21                                                  
CONECT   24   25   28   30                                                  
CONECT   25    4    5    6   24                                             
CONECT   26   18                                                            
CONECT   27   22                                                            
CONECT   28   24                                                            
CONECT   29   19   22                                                       
CONECT   30   21   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0257813
HETATM    1  C1  UNL     1      -2.327   1.244   3.461  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.093   1.949   2.364  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.273   1.864   1.061  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.093   2.590   0.006  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.954   2.561   1.245  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.160   0.427   0.746  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.605  -0.475   1.534  1.00  0.00           O  
HETATM    8  O2  UNL     1      -1.569  -0.090  -0.424  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.491  -1.443  -0.695  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.539  -1.690  -1.786  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.318  -3.000  -2.489  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.668  -3.605  -2.806  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.613  -3.972  -1.600  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.596  -3.612  -0.864  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.158  -4.436   0.026  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.956  -3.977   0.995  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.032  -2.463   1.109  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.351  -2.203   1.767  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.024  -1.939  -0.329  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.900  -0.799  -0.618  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.740   0.488   0.081  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.822   1.504  -0.366  1.00  0.00           C  
HETATM   23  C21 UNL     1       2.653   2.808   0.348  1.00  0.00           C  
HETATM   24  C22 UNL     1       3.882   3.648   0.037  1.00  0.00           C  
HETATM   25  O3  UNL     1       3.732   4.945   0.481  1.00  0.00           O  
HETATM   26  C23 UNL     1       4.165   3.681  -1.446  1.00  0.00           C  
HETATM   27  C24 UNL     1       3.125   2.969  -2.231  1.00  0.00           C  
HETATM   28  O4  UNL     1       2.625   3.427  -3.291  1.00  0.00           O  
HETATM   29  O5  UNL     1       2.698   1.740  -1.755  1.00  0.00           O  
HETATM   30  C25 UNL     1      -0.242  -2.119  -1.018  1.00  0.00           C  
HETATM   31  H1  UNL     1      -1.391   0.787   3.078  1.00  0.00           H  
HETATM   32  H2  UNL     1      -2.118   1.996   4.255  1.00  0.00           H  
HETATM   33  H3  UNL     1      -2.905   0.435   3.947  1.00  0.00           H  
HETATM   34  H4  UNL     1      -4.030   1.380   2.179  1.00  0.00           H  
HETATM   35  H5  UNL     1      -3.338   2.985   2.621  1.00  0.00           H  
HETATM   36  H6  UNL     1      -2.404   3.083  -0.714  1.00  0.00           H  
HETATM   37  H7  UNL     1      -3.686   3.395   0.480  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.772   1.928  -0.540  1.00  0.00           H  
HETATM   39  H9  UNL     1      -0.616   2.879   0.224  1.00  0.00           H  
HETATM   40  H10 UNL     1      -1.074   3.479   1.840  1.00  0.00           H  
HETATM   41  H11 UNL     1      -0.198   1.940   1.744  1.00  0.00           H  
HETATM   42  H12 UNL     1      -1.938  -1.974   0.210  1.00  0.00           H  
HETATM   43  H13 UNL     1      -3.519  -1.667  -1.313  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.471  -0.888  -2.527  1.00  0.00           H  
HETATM   45  H15 UNL     1      -1.760  -2.908  -3.426  1.00  0.00           H  
HETATM   46  H16 UNL     1      -3.557  -4.566  -3.358  1.00  0.00           H  
HETATM   47  H17 UNL     1      -4.320  -2.899  -3.359  1.00  0.00           H  
HETATM   48  H18 UNL     1      -4.130  -3.870  -1.828  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.943  -4.987  -1.565  1.00  0.00           H  
HETATM   50  H20 UNL     1       0.060  -5.525  -0.107  1.00  0.00           H  
HETATM   51  H21 UNL     1       1.516  -4.594   1.662  1.00  0.00           H  
HETATM   52  H22 UNL     1       0.167  -2.154   1.690  1.00  0.00           H  
HETATM   53  H23 UNL     1       2.331  -1.343   2.494  1.00  0.00           H  
HETATM   54  H24 UNL     1       2.645  -3.062   2.457  1.00  0.00           H  
HETATM   55  H25 UNL     1       3.200  -2.164   1.063  1.00  0.00           H  
HETATM   56  H26 UNL     1       1.668  -2.823  -0.821  1.00  0.00           H  
HETATM   57  H27 UNL     1       3.009  -1.051  -0.578  1.00  0.00           H  
HETATM   58  H28 UNL     1       1.786  -0.596  -1.743  1.00  0.00           H  
HETATM   59  H29 UNL     1       0.808   1.014  -0.300  1.00  0.00           H  
HETATM   60  H30 UNL     1       1.687   0.495   1.159  1.00  0.00           H  
HETATM   61  H31 UNL     1       3.832   1.099  -0.162  1.00  0.00           H  
HETATM   62  H32 UNL     1       2.556   2.716   1.433  1.00  0.00           H  
HETATM   63  H33 UNL     1       1.763   3.330  -0.073  1.00  0.00           H  
HETATM   64  H34 UNL     1       4.774   3.211   0.532  1.00  0.00           H  
HETATM   65  H35 UNL     1       3.778   5.015   1.467  1.00  0.00           H  
HETATM   66  H36 UNL     1       5.140   3.216  -1.696  1.00  0.00           H  
HETATM   67  H37 UNL     1       4.160   4.739  -1.835  1.00  0.00           H  
HETATM   68  H38 UNL     1      -0.031  -2.072  -2.135  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4    5    6
CONECT    4   36   37   38
CONECT    5   39   40   41
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   30   42
CONECT   10   11   43   44
CONECT   11   12   13   45
CONECT   12   46   47   48
CONECT   13   14   14   49
CONECT   14   15   30
CONECT   15   16   16   50
CONECT   16   17   51
CONECT   17   18   19   52
CONECT   18   53   54   55
CONECT   19   20   30   56
CONECT   20   21   57   58
CONECT   21   22   59   60
CONECT   22   23   29   61
CONECT   23   24   62   63
CONECT   24   25   26   64
CONECT   25   65
CONECT   26   27   66   67
CONECT   27   28   28   29
CONECT   30   68
END

HMDB0257813
     RDKit          3D
(1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-...
 68 70  0  0  0  0  0  0  0  0999 V2000
   -2.3275    1.2437    3.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934    1.9491    2.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735    1.8645    1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    2.5896    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9537    2.5613    1.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1601    0.4271    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -0.4746    1.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695   -0.0904   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -1.4434   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -1.6895   -1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3183   -3.0002   -2.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6680   -3.6053   -2.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -3.9724   -1.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5959   -3.6122   -0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1575   -4.4362    0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9562   -3.9767    0.9948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0318   -2.4627    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -2.2029    1.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245   -1.9390   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002   -0.7986   -0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397    0.4876    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8223    1.5037   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525    2.8077    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8823    3.6479    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321    4.9450    0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    3.6807   -1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1246    2.9689   -2.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6249    3.4268   -3.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    1.7399   -1.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -2.1194   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3913    0.7871    3.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1176    1.9956    4.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    0.4350    3.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0302    1.3798    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376    2.9854    2.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4041    3.0831   -0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    3.3949    0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7718    1.9280   -0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6163    2.8788    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0739    3.4793    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    1.9403    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -1.9740    0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5192   -1.6672   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707   -0.8882   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597   -2.9083   -3.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5572   -4.5658   -3.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3197   -2.8987   -3.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1301   -3.8699   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427   -4.9871   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0605   -5.5253   -0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -4.5944    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -2.1541    1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -1.3431    2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6450   -3.0624    2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997   -2.1637    1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -2.8232   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093   -1.0514   -0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863   -0.5957   -1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8077    1.0144   -0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867    0.4952    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.0994   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557    2.7163    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631    3.3300   -0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738    3.2111    0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    5.0154    1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1402    3.2162   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1599    4.7389   -1.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -2.0716   -2.1349 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
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 19 30  1  0
 30  9  1  0
 30 14  1  0
 29 22  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 30 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Simcor	MeSH

Chemical Formula

C₂₅H₃₈O₅

Average Molecular Weight

418.5662

Monoisotopic Molecular Weight

418.271924326

IUPAC Name

8-[2-(4-hydroxy-6-oxooxan-2-yl)ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate

Traditional Name

simvastatin

CAS Registry Number

Not Available

SMILES

CCC(C)(C)C(=O)OC1CC(C)C=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C12

InChI Identifier

InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3

InChI Key

RYMZZMVNJRMUDD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta valerolactone
Fatty acid ester
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Fatty acyl
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD66-17 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	4.51	ALOGPS
logP	4.46	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.68 m³·mol⁻¹	ChemAxon
Polarizability	48.05 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]-	235.732	30932474
DeepCCS	[M+Na]+	210.96	30932474
AllCCS	[M+H]+	205.4	32859911
AllCCS	[M+H-H2O]+	203.1	32859911
AllCCS	[M+NH4]+	207.5	32859911
AllCCS	[M+Na]+	208.1	32859911
AllCCS	[M-H]-	205.6	32859911
AllCCS	[M+Na-2H]-	207.1	32859911
AllCCS	[M+HCOO]-	208.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate	CCC(C)(C)C(=O)OC1CC(C)C=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C12	3821.8	Standard polar	33892256
(1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate	CCC(C)(C)C(=O)OC1CC(C)C=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C12	2968.3	Standard non polar	33892256
(1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate	CCC(C)(C)C(=O)OC1CC(C)C=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C12	3066.9	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 - (1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ums-8196300000-197594668af98450a5c6	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

FDB023580

KNApSAcK ID

Not Available

Chemspider ID

3866078

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Simvastatin

METLIN ID

Not Available

PubChem Compound

4677798

PDB ID

Not Available

ChEBI ID

91894

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate (HMDB0257813)

MOL for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

3D MOL for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

3D SDF for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

3D-SDF for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

PDB for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

3D PDB for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

SMILES for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

INCHI for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

Structure for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

3D Structure for HMDB0257813 ((1R,3S,7R,8R,8As)-8-{2-[(2R,4S)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra