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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:15:19 UTC

Update Date

2021-09-26 22:58:10 UTC

HMDB ID

HMDB0248085

Secondary Accession Numbers

None

Metabolite Identification

Common Name

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

Description

[(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate, also known as 6 methylcompactin or lovastatin, belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Based on a literature review very few articles have been published on [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). [(1s,3s,7r,8r,8as)-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2r)-2-methylbutanoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate 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


  Mrv1533004171521172D          

 29 31  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  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
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 18 29  1  0  0  0  0
  8 29  1  0  0  0  0
 13 29  1  0  0  0  0
M  END

HMDB0248085
     RDKit          3D
[(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,...
 65 67  0  0  0  0  0  0  0  0999 V2000
   -3.5643    4.3934   -0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1284    3.0040   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321    2.1499    0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7430    2.7406    1.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    0.7516   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.4348   -1.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.2717    0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0344   -1.5925    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0801   -2.5505    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0996   -3.7507    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5204   -3.2828   -1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298   -4.3069    0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -3.5691    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320   -4.2470    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6772   -3.5713    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5681   -2.1521   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661   -2.2033   -1.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4258   -1.3902    0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -0.1874    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428    0.8989    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    0.7921   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2225    2.2471   -0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7332    3.0795    0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7554    4.3934   -0.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1476    2.6123    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1076    1.1292    0.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2242    0.5132    0.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153    0.4426    0.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6964   -2.1526    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863    4.7528   -1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987    5.0899   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0771    4.4349    0.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2210    3.1120   -1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122    2.5540   -1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7614    2.1474    0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8019    2.9069    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5945    2.1105    2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927    3.7276    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1237   -1.6476   -0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7552   -2.8805    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0376   -2.0272    1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8153   -4.4771    0.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736   -2.3431   -1.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167   -3.1663   -1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -4.0770   -1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -5.3332   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6761   -5.3063    0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555   -4.0293    0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -1.7162   -0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537   -1.3027   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -2.3996   -2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0593   -3.0708   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015   -0.9651   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297    0.2642    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -0.5447    1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8847    1.2739   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.8179    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9777    0.1640   -1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    2.7078   -1.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621    2.1521   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453    2.9594    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407    4.9121    0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8110    3.0188   -0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4995    2.9604    1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375   -2.1344    1.9171 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
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 18 29  1  0
 29  8  1  0
 29 13  1  0
 28 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 29 65  1  0
M  END


  Mrv1533004171521172D          

 29 31  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  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
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 18 29  1  0  0  0  0
  8 29  1  0  0  0  0
 13 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248085

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3

> <INCHI_KEY>
PCZOHLXUXFIOCF-UHFFFAOYSA-N

> <FORMULA>
C24H36O5

> <MOLECULAR_WEIGHT>
404.547

> <EXACT_MASS>
404.256274259

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.47046294237815

> <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-methylbutanoate

> <ALOGPS_LOGP>
4.11

> <JCHEM_LOGP>
3.9021869143333325

> <ALOGPS_LOGS>
-4.22

> <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>
113.18239999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248085
     RDKit          3D
[(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,...
 65 67  0  0  0  0  0  0  0  0999 V2000
   -3.5643    4.3934   -0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1284    3.0040   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321    2.1499    0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7430    2.7406    1.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    0.7516   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.4348   -1.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.2717    0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0344   -1.5925    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0801   -2.5505    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0996   -3.7507    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5204   -3.2828   -1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298   -4.3069    0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -3.5691    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320   -4.2470    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6772   -3.5713    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5681   -2.1521   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661   -2.2033   -1.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4258   -1.3902    0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -0.1874    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428    0.8989    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    0.7921   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2225    2.2471   -0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7332    3.0795    0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7554    4.3934   -0.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1476    2.6123    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1076    1.1292    0.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2242    0.5132    0.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153    0.4426    0.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6964   -2.1526    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863    4.7528   -1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987    5.0899   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0771    4.4349    0.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2210    3.1120   -1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122    2.5540   -1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7614    2.1474    0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8019    2.9069    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5945    2.1105    2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927    3.7276    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1237   -1.6476   -0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7552   -2.8805    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0376   -2.0272    1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8153   -4.4771    0.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736   -2.3431   -1.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167   -3.1663   -1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -4.0770   -1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -5.3332   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6761   -5.3063    0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555   -4.0293    0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -1.7162   -0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537   -1.3027   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -2.3996   -2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0593   -3.0708   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015   -0.9651   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297    0.2642    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -0.5447    1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8847    1.2739   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.8179    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9777    0.1640   -1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    2.7078   -1.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621    2.1521   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453    2.9594    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407    4.9121    0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8110    3.0188   -0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4995    2.9604    1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375   -2.1344    1.9171 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
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 18 29  1  0
 29  8  1  0
 29 13  1  0
 28 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 29 65  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21                                                       
CONECT   29   18    8   13                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0248085
HETATM    1  C1  UNL     1      -3.564   4.393  -0.477  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.128   3.004  -0.858  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.832   2.150   0.357  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.743   2.741   1.185  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.575   0.752  -0.053  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.622   0.435  -1.289  1.00  0.00           O  
HETATM    7  O2  UNL     1      -2.279  -0.272   0.816  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.034  -1.593   0.450  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.080  -2.550   0.983  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.100  -3.751   0.051  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.520  -3.283  -1.304  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.730  -4.307   0.095  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.672  -3.569   0.420  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.632  -4.247   0.427  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.677  -3.571   0.062  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.568  -2.152  -0.354  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.666  -2.203  -1.888  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.426  -1.390   0.124  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.800  -0.187   0.934  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.543   0.899   0.321  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.893   0.792  -0.242  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.223   2.247  -0.753  1.00  0.00           C  
HETATM   23  C21 UNL     1       3.733   3.079   0.390  1.00  0.00           C  
HETATM   24  O3  UNL     1       3.755   4.393  -0.026  1.00  0.00           O  
HETATM   25  C22 UNL     1       5.148   2.612   0.669  1.00  0.00           C  
HETATM   26  C23 UNL     1       5.108   1.129   0.652  1.00  0.00           C  
HETATM   27  O4  UNL     1       6.224   0.513   0.637  1.00  0.00           O  
HETATM   28  O5  UNL     1       3.915   0.443   0.651  1.00  0.00           O  
HETATM   29  C24 UNL     1      -0.696  -2.153   0.795  1.00  0.00           C  
HETATM   30  H1  UNL     1      -4.286   4.753  -1.224  1.00  0.00           H  
HETATM   31  H2  UNL     1      -2.699   5.090  -0.517  1.00  0.00           H  
HETATM   32  H3  UNL     1      -4.077   4.435   0.512  1.00  0.00           H  
HETATM   33  H4  UNL     1      -2.221   3.112  -1.505  1.00  0.00           H  
HETATM   34  H5  UNL     1      -3.912   2.554  -1.497  1.00  0.00           H  
HETATM   35  H6  UNL     1      -3.761   2.147   0.971  1.00  0.00           H  
HETATM   36  H7  UNL     1      -0.802   2.907   0.644  1.00  0.00           H  
HETATM   37  H8  UNL     1      -1.594   2.111   2.085  1.00  0.00           H  
HETATM   38  H9  UNL     1      -2.093   3.728   1.553  1.00  0.00           H  
HETATM   39  H10 UNL     1      -2.124  -1.648  -0.673  1.00  0.00           H  
HETATM   40  H11 UNL     1      -2.755  -2.881   1.990  1.00  0.00           H  
HETATM   41  H12 UNL     1      -4.038  -2.027   1.021  1.00  0.00           H  
HETATM   42  H13 UNL     1      -3.815  -4.477   0.495  1.00  0.00           H  
HETATM   43  H14 UNL     1      -4.074  -2.343  -1.200  1.00  0.00           H  
HETATM   44  H15 UNL     1      -2.617  -3.166  -1.937  1.00  0.00           H  
HETATM   45  H16 UNL     1      -4.154  -4.077  -1.766  1.00  0.00           H  
HETATM   46  H17 UNL     1      -1.609  -5.333  -0.141  1.00  0.00           H  
HETATM   47  H18 UNL     1       0.676  -5.306   0.741  1.00  0.00           H  
HETATM   48  H19 UNL     1       2.656  -4.029   0.049  1.00  0.00           H  
HETATM   49  H20 UNL     1       2.560  -1.716  -0.022  1.00  0.00           H  
HETATM   50  H21 UNL     1       1.254  -1.303  -2.344  1.00  0.00           H  
HETATM   51  H22 UNL     1       2.701  -2.400  -2.207  1.00  0.00           H  
HETATM   52  H23 UNL     1       1.059  -3.071  -2.227  1.00  0.00           H  
HETATM   53  H24 UNL     1      -0.101  -0.965  -0.818  1.00  0.00           H  
HETATM   54  H25 UNL     1      -0.130   0.264   1.420  1.00  0.00           H  
HETATM   55  H26 UNL     1       1.341  -0.545   1.899  1.00  0.00           H  
HETATM   56  H27 UNL     1       0.885   1.274  -0.557  1.00  0.00           H  
HETATM   57  H28 UNL     1       1.485   1.818   1.011  1.00  0.00           H  
HETATM   58  H29 UNL     1       2.978   0.164  -1.145  1.00  0.00           H  
HETATM   59  H30 UNL     1       2.314   2.708  -1.150  1.00  0.00           H  
HETATM   60  H31 UNL     1       3.962   2.152  -1.553  1.00  0.00           H  
HETATM   61  H32 UNL     1       3.145   2.959   1.303  1.00  0.00           H  
HETATM   62  H33 UNL     1       4.341   4.912   0.586  1.00  0.00           H  
HETATM   63  H34 UNL     1       5.811   3.019  -0.140  1.00  0.00           H  
HETATM   64  H35 UNL     1       5.499   2.960   1.652  1.00  0.00           H  
HETATM   65  H36 UNL     1      -0.537  -2.134   1.917  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4    5   35
CONECT    4   36   37   38
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   29   39
CONECT    9   10   40   41
CONECT   10   11   12   42
CONECT   11   43   44   45
CONECT   12   13   13   46
CONECT   13   14   29
CONECT   14   15   15   47
CONECT   15   16   48
CONECT   16   17   18   49
CONECT   17   50   51   52
CONECT   18   19   29   53
CONECT   19   20   54   55
CONECT   20   21   56   57
CONECT   21   22   28   58
CONECT   22   23   59   60
CONECT   23   24   25   61
CONECT   24   62
CONECT   25   26   63   64
CONECT   26   27   27   28
CONECT   29   65
END

HMDB0248085
     RDKit          3D
[(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,...
 65 67  0  0  0  0  0  0  0  0999 V2000
   -3.5643    4.3934   -0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1284    3.0040   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321    2.1499    0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7430    2.7406    1.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    0.7516   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.4348   -1.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.2717    0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0344   -1.5925    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0801   -2.5505    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0996   -3.7507    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5204   -3.2828   -1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298   -4.3069    0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -3.5691    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320   -4.2470    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6772   -3.5713    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5681   -2.1521   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661   -2.2033   -1.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4258   -1.3902    0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -0.1874    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428    0.8989    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    0.7921   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2225    2.2471   -0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7332    3.0795    0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7554    4.3934   -0.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1476    2.6123    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1076    1.1292    0.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2242    0.5132    0.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153    0.4426    0.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6964   -2.1526    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863    4.7528   -1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987    5.0899   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0771    4.4349    0.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2210    3.1120   -1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122    2.5540   -1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7614    2.1474    0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8019    2.9069    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5945    2.1105    2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927    3.7276    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1237   -1.6476   -0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7552   -2.8805    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0376   -2.0272    1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8153   -4.4771    0.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736   -2.3431   -1.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167   -3.1663   -1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -4.0770   -1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -5.3332   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6761   -5.3063    0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555   -4.0293    0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -1.7162   -0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537   -1.3027   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -2.3996   -2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0593   -3.0708   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015   -0.9651   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297    0.2642    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -0.5447    1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8847    1.2739   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.8179    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9777    0.1640   -1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    2.7078   -1.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621    2.1521   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453    2.9594    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407    4.9121    0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8110    3.0188   -0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4995    2.9604    1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375   -2.1344    1.9171 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
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 18 29  1  0
 29  8  1  0
 29 13  1  0
 28 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 29 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoic acid	Generator
8-[2-(4-Hydroxy-6-oxooxan-2-yl)ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoic acid	HMDB
1 alpha-Isomer lovastatin	MeSH
6 Methylcompactin	MeSH
6-Methylcompactin	MeSH
Lovastatin	MeSH
Lovastatin, (1 alpha(s*))-isomer	MeSH
Lovastatin, 1 alpha isomer	MeSH
Lovastatin, 1 alpha-isomer	MeSH
Mevacor	MeSH
Mevinolin	MeSH
alpha-Isomer lovastatin, 1	MeSH

Chemical Formula

C₂₄H₃₆O₅

Average Molecular Weight

404.547

Monoisotopic Molecular Weight

404.256274259

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3

InChI Key

PCZOHLXUXFIOCF-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 (CPD-5561 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	4.11	ALOGPS
logP	3.9	ChemAxon
logS	-4.2	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	113.18 m³·mol⁻¹	ChemAxon
Polarizability	45.47 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]-	233.482	30932474
DeepCCS	[M+Na]+	208.71	30932474
AllCCS	[M+H]+	202.5	32859911
AllCCS	[M+H-H2O]+	200.1	32859911
AllCCS	[M+NH4]+	204.8	32859911
AllCCS	[M+Na]+	205.4	32859911
AllCCS	[M-H]-	202.0	32859911
AllCCS	[M+Na-2H]-	203.3	32859911
AllCCS	[M+HCOO]-	204.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	20.2522 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.74 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3387.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	471.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	232.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	241.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	922.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	892.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1685.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	667.0 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	1868.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	515.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	510.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	219.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	406.1 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
[(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate	CCC(C)C(=O)OC1CC(C)C=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C12	3986.7	Standard polar	33892256
[(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate	CCC(C)C(=O)OC1CC(C)C=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C12	2970.4	Standard non polar	33892256
[(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate	CCC(C)C(=O)OC1CC(C)C=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C12	3075.5	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 - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-9178000000-6352f962ed86ad11e025	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate 10V, Positive-QTOF	splash10-0udi-0639000000-eafeab6df7f06e9163fa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate 20V, Positive-QTOF	splash10-0zfr-0779100000-bcae8dd132d13bedd53a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate 40V, Positive-QTOF	splash10-0002-5910000000-fbd748584824d73a46b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate 10V, Negative-QTOF	splash10-0udi-2009700000-27af578df8eacf4701fc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate 20V, Negative-QTOF	splash10-0udi-7319100000-a73693c27dab1a42183d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate 40V, Negative-QTOF	splash10-05tf-8934000000-3647418daa0b7aba2d48	2021-10-12	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3962

PDB ID

Not Available

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

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 [(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate (HMDB0248085)

MOL for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

3D MOL for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

3D SDF for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

3D-SDF for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

PDB for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

3D PDB for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

SMILES for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

INCHI for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

Structure for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

3D Structure for HMDB0248085 ([(1S,3S,7R,8R,8As)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methylbutanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra