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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11)transporters (3) Show 14 proteins XML

enzymes (11)transporters (3) Show 14 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014372

Secondary Accession Numbers

HMDB14372

Metabolite Identification

Common Name

Lovastatin

Description

Lovastatin is a cholesterol-lowering agent that belongs to the class of medications called statins. It was the second agent of this class discovered. It was discovered by Alfred Alberts and his team at Merck in 1978 after screening only 18 compounds over 2 weeks. The agent, also known as mevinolin, was isolated from the fungi Aspergillus terreus. Research on this compound was suddenly shut down in 1980 and the drug was not approved until 1987. Interesting, Akira Endo at Sankyo Co. (Japan) patented lovastatin isolated from Monascus ruber four months before Merck. Lovastatin was found to be 2 times more potent than its predecessor, mevastatin, the first discovered statin. Like mevastatin, lovastatin is structurally similar to hydroxymethylglutarate (HMG), a substituent of HMG-Coenzyme A (HMG-CoA), a substrate of the cholesterol biosynthesis pathway via the mevalonic acid pathway. Lovastatin is a competitive inhibitor of HMG-CoA reductase with a binding affinity 20,000 times greater than HMG-CoA. Lovastatin differs structurally from mevastatin by a single methyl group at the 6 position. Lovastatin is a prodrug that is activated by in vivo hydrolysis of the lactone ring. It, along with mevastatin, has served as one of the lead compounds for the development of the synthetic compounds used today.

Structure

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

227
  Mrv0541 02231214322D          

 30 32  0  0  1  0            999 V2000
    3.0790    0.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9312   -1.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736   -2.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6313   -2.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.6952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5309    1.2542    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0790    1.2827    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2785    1.6781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7935    2.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215    0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.5202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0790    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2310    0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2785    2.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309    2.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9914    1.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.8165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6500    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5023   -1.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4928   -2.0457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -2.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.7798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9217   -2.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884    1.0352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  1 23  1  0  0  0  0
  2 19  1  0  0  0  0
  2 26  1  0  0  0  0
 22  3  1  6  0  0  0
  4 23  2  0  0  0  0
  5 26  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 30  1  6  0  0  0
  7  9  1  0  0  0  0
  7 11  1  6  0  0  0
  8 12  1  0  0  0  0
  9 16  1  0  0  0  0
  9 18  1  6  0  0  0
 10 14  2  0  0  0  0
 10 17  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  1  0  0  0
 19 15  1  1  0  0  0
 16 17  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  1  0  0  0
 27 29  1  0  0  0  0
M  END

HMDB0014372
     RDKit          3D
Lovastatin
 65 67  0  0  0  0  0  0  0  0999 V2000
    4.8259   -2.4941   -3.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9685   -2.2065   -2.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.7324   -2.0842 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9848    0.0034   -1.9375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -0.5337   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811   -1.5299   -0.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972    0.7000   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4093    0.8309    0.5890 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1000    1.7719    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4764    3.0380    0.8472 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9557    2.9868    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    3.2979   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249    2.6470   -0.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    2.9597   -2.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2635    2.4054   -2.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9014    1.5050   -1.1736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7158    2.3669   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699    0.6755   -0.4617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5130   -0.1581    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584   -1.1114    0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1189   -1.8854    1.2616 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1668   -2.8662    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687   -2.9014    1.7318 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9137   -4.2012    1.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0539   -2.6609    3.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -1.5024    3.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0213   -1.0438    4.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050   -1.0039    2.2718 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413    1.5791    0.1539 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7492   -3.5825   -3.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8783   -2.2467   -3.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935   -1.9240   -4.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297   -2.7731   -2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5413   -2.5556   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1723   -0.4211   -3.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    1.0856   -1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013   -0.4899   -1.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409   -0.1187   -2.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722   -0.1314    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3519    2.0492    2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    1.2970    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    3.9448    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3572    1.9630    0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5243    3.6505    1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    3.2902   -0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054    4.0906   -1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3963    3.6165   -2.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7926    2.6307   -3.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5452    0.7829   -1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792    3.4348   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3268    2.4193    0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738    2.0002   -0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4042    0.0112   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543    0.4828    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7742   -0.7317    1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3677   -0.5419   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1522   -1.8476   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2481   -2.4715    1.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7535   -3.8991    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5109   -2.5792   -0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1626   -2.2283    1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6651   -4.2056    2.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0451   -2.4930    3.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6226   -3.5477    3.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009    2.1032    1.0371 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  6
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  1
 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  6
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  6
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  1
 22 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 25 63  1  0
 25 64  1  0
 29 65  1  1
M  END

227
  Mrv0541 02231214322D          

 30 32  0  0  1  0            999 V2000
    3.0790    0.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9312   -1.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736   -2.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6313   -2.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.6952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5309    1.2542    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0790    1.2827    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2785    1.6781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7935    2.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215    0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.5202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0790    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2310    0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2785    2.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309    2.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9914    1.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.8165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6500    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5023   -1.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4928   -2.0457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -2.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.7798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9217   -2.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884    1.0352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  1 23  1  0  0  0  0
  2 19  1  0  0  0  0
  2 26  1  0  0  0  0
 22  3  1  6  0  0  0
  4 23  2  0  0  0  0
  5 26  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 30  1  6  0  0  0
  7  9  1  0  0  0  0
  7 11  1  6  0  0  0
  8 12  1  0  0  0  0
  9 16  1  0  0  0  0
  9 18  1  6  0  0  0
 10 14  2  0  0  0  0
 10 17  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  1  0  0  0
 19 15  1  1  0  0  0
 16 17  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  1  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014372

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)[C@@H](C)CC

> <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/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1

> <INCHI_KEY>
PCZOHLXUXFIOCF-BXMDZJJMSA-N

> <FORMULA>
C24H36O5

> <MOLECULAR_WEIGHT>
404.5396

> <EXACT_MASS>
404.256274262

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
46.112664928862706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-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>
113.18239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lovastatin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014372
     RDKit          3D
Lovastatin
 65 67  0  0  0  0  0  0  0  0999 V2000
    4.8259   -2.4941   -3.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9685   -2.2065   -2.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.7324   -2.0842 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9848    0.0034   -1.9375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -0.5337   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811   -1.5299   -0.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972    0.7000   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4093    0.8309    0.5890 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1000    1.7719    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4764    3.0380    0.8472 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9557    2.9868    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    3.2979   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249    2.6470   -0.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    2.9597   -2.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2635    2.4054   -2.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9014    1.5050   -1.1736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7158    2.3669   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699    0.6755   -0.4617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5130   -0.1581    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584   -1.1114    0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1189   -1.8854    1.2616 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1668   -2.8662    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687   -2.9014    1.7318 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9137   -4.2012    1.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0539   -2.6609    3.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -1.5024    3.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0213   -1.0438    4.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050   -1.0039    2.2718 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413    1.5791    0.1539 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7492   -3.5825   -3.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8783   -2.2467   -3.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935   -1.9240   -4.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297   -2.7731   -2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5413   -2.5556   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1723   -0.4211   -3.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    1.0856   -1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013   -0.4899   -1.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409   -0.1187   -2.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722   -0.1314    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3519    2.0492    2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    1.2970    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    3.9448    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3572    1.9630    0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5243    3.6505    1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    3.2902   -0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054    4.0906   -1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3963    3.6165   -2.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7926    2.6307   -3.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5452    0.7829   -1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792    3.4348   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3268    2.4193    0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738    2.0002   -0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4042    0.0112   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543    0.4828    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7742   -0.7317    1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3677   -0.5419   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1522   -1.8476   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2481   -2.4715    1.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7535   -3.8991    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5109   -2.5792   -0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1626   -2.2283    1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6651   -4.2056    2.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0451   -2.4930    3.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6226   -3.5477    3.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009    2.1032    1.0371 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  6
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  1
 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  6
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  6
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  1
 22 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 25 63  1  0
 25 64  1  0
 29 65  1  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 227                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.747   0.854   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.072  -2.310   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.044  -4.573   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080   0.854   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      12.378  -4.635   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.081   3.164   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.458   2.341   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747   2.394   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.853   3.132   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   4.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.440   0.801   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   3.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   4.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747   5.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.765   0.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.853   4.736   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.458   5.528   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.184   2.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.747  -1.524   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080   5.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.404  -2.279   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.387  -3.819   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414   0.084   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.711  -4.604   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414  -1.456   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.054  -3.849   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080  -2.226   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.747  -2.226   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.080  -3.766   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       7.072   1.932   0.000  0.00  0.00           H+0
CONECT    1    8   23                                                       
CONECT    2   19   26                                                       
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   26                                                            
CONECT    6    7    8   10   30                                             
CONECT    7    6    9   11                                                  
CONECT    8    1    6   12                                                  
CONECT    9    7   16   18                                                  
CONECT   10    6   14   17                                                  
CONECT   11    7   15                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   10   13                                                       
CONECT   15   11   19                                                       
CONECT   16    9   17                                                       
CONECT   17   10   16                                                       
CONECT   18    9                                                            
CONECT   19    2   15   21                                                  
CONECT   20   13                                                            
CONECT   21   19   22                                                       
CONECT   22    3   21   24                                                  
CONECT   23    1    4   25                                                  
CONECT   24   22   26                                                       
CONECT   25   23   27   28                                                  
CONECT   26    2    5   24                                                  
CONECT   27   25   29                                                       
CONECT   28   25                                                            
CONECT   29   27                                                            
CONECT   30    6                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0014372
HETATM    1  C1  UNL     1       4.826  -2.494  -3.443  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.968  -2.207  -2.231  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.676  -0.732  -2.084  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.985   0.003  -1.938  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.771  -0.534  -0.952  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.381  -1.530  -0.297  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.297   0.700  -0.532  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.409   0.831   0.589  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.100   1.772   1.553  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.476   3.038   0.847  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.956   2.987   0.531  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.714   3.298  -0.395  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.625   2.647  -0.757  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.081   2.960  -2.005  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.263   2.405  -2.165  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.901   1.505  -1.174  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.716   2.367  -0.242  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.870   0.676  -0.462  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.513  -0.158   0.612  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.558  -1.111   0.060  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.119  -1.885   1.262  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.167  -2.866   0.852  1.00  0.00           C  
HETATM   23  C21 UNL     1      -5.369  -2.901   1.732  1.00  0.00           C  
HETATM   24  O3  UNL     1      -5.914  -4.201   1.656  1.00  0.00           O  
HETATM   25  C22 UNL     1      -5.054  -2.661   3.190  1.00  0.00           C  
HETATM   26  C23 UNL     1      -4.151  -1.502   3.394  1.00  0.00           C  
HETATM   27  O4  UNL     1      -4.021  -1.044   4.549  1.00  0.00           O  
HETATM   28  O5  UNL     1      -3.505  -1.004   2.272  1.00  0.00           O  
HETATM   29  C24 UNL     1       0.141   1.579   0.154  1.00  0.00           C  
HETATM   30  H1  UNL     1       4.749  -3.583  -3.648  1.00  0.00           H  
HETATM   31  H2  UNL     1       5.878  -2.247  -3.152  1.00  0.00           H  
HETATM   32  H3  UNL     1       4.493  -1.924  -4.329  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.030  -2.773  -2.234  1.00  0.00           H  
HETATM   34  H5  UNL     1       4.541  -2.556  -1.337  1.00  0.00           H  
HETATM   35  H6  UNL     1       3.172  -0.421  -3.045  1.00  0.00           H  
HETATM   36  H7  UNL     1       4.848   1.086  -1.766  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.601  -0.490  -1.161  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.541  -0.119  -2.891  1.00  0.00           H  
HETATM   39  H10 UNL     1       1.172  -0.131   1.042  1.00  0.00           H  
HETATM   40  H11 UNL     1       1.352   2.049   2.347  1.00  0.00           H  
HETATM   41  H12 UNL     1       2.961   1.297   2.067  1.00  0.00           H  
HETATM   42  H13 UNL     1       2.308   3.945   1.500  1.00  0.00           H  
HETATM   43  H14 UNL     1       4.357   1.963   0.688  1.00  0.00           H  
HETATM   44  H15 UNL     1       4.524   3.651   1.215  1.00  0.00           H  
HETATM   45  H16 UNL     1       4.125   3.290  -0.507  1.00  0.00           H  
HETATM   46  H17 UNL     1       2.105   4.091  -1.035  1.00  0.00           H  
HETATM   47  H18 UNL     1       0.396   3.616  -2.717  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.793   2.631  -3.084  1.00  0.00           H  
HETATM   49  H20 UNL     1      -2.545   0.783  -1.754  1.00  0.00           H  
HETATM   50  H21 UNL     1      -2.779   3.435  -0.604  1.00  0.00           H  
HETATM   51  H22 UNL     1      -2.327   2.419   0.776  1.00  0.00           H  
HETATM   52  H23 UNL     1      -3.774   2.000  -0.303  1.00  0.00           H  
HETATM   53  H24 UNL     1      -0.404   0.011  -1.195  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.054   0.483   1.355  1.00  0.00           H  
HETATM   55  H26 UNL     1      -0.774  -0.732   1.207  1.00  0.00           H  
HETATM   56  H27 UNL     1      -3.368  -0.542  -0.443  1.00  0.00           H  
HETATM   57  H28 UNL     1      -2.152  -1.848  -0.635  1.00  0.00           H  
HETATM   58  H29 UNL     1      -2.248  -2.472   1.651  1.00  0.00           H  
HETATM   59  H30 UNL     1      -3.753  -3.899   0.732  1.00  0.00           H  
HETATM   60  H31 UNL     1      -4.511  -2.579  -0.182  1.00  0.00           H  
HETATM   61  H32 UNL     1      -6.163  -2.228   1.359  1.00  0.00           H  
HETATM   62  H33 UNL     1      -6.665  -4.206   2.310  1.00  0.00           H  
HETATM   63  H34 UNL     1      -6.045  -2.493   3.704  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.623  -3.548   3.680  1.00  0.00           H  
HETATM   65  H36 UNL     1      -0.301   2.103   1.037  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

HMDB0014372
     RDKit          3D
Lovastatin
 65 67  0  0  0  0  0  0  0  0999 V2000
    4.8259   -2.4941   -3.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9685   -2.2065   -2.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.7324   -2.0842 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9848    0.0034   -1.9375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -0.5337   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811   -1.5299   -0.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972    0.7000   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4093    0.8309    0.5890 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1000    1.7719    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4764    3.0380    0.8472 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9557    2.9868    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    3.2979   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249    2.6470   -0.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    2.9597   -2.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2635    2.4054   -2.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9014    1.5050   -1.1736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7158    2.3669   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699    0.6755   -0.4617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5130   -0.1581    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584   -1.1114    0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1189   -1.8854    1.2616 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1668   -2.8662    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687   -2.9014    1.7318 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9137   -4.2012    1.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0539   -2.6609    3.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -1.5024    3.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0213   -1.0438    4.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050   -1.0039    2.2718 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413    1.5791    0.1539 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7492   -3.5825   -3.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8783   -2.2467   -3.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935   -1.9240   -4.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297   -2.7731   -2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5413   -2.5556   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1723   -0.4211   -3.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    1.0856   -1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013   -0.4899   -1.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409   -0.1187   -2.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722   -0.1314    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3519    2.0492    2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    1.2970    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    3.9448    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3572    1.9630    0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5243    3.6505    1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    3.2902   -0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054    4.0906   -1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3963    3.6165   -2.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7926    2.6307   -3.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5452    0.7829   -1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792    3.4348   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3268    2.4193    0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738    2.0002   -0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4042    0.0112   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543    0.4828    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7742   -0.7317    1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3677   -0.5419   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1522   -1.8476   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2481   -2.4715    1.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7535   -3.8991    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5109   -2.5792   -0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1626   -2.2283    1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6651   -4.2056    2.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0451   -2.4930    3.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6226   -3.5477    3.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009    2.1032    1.0371 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  6
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  1
 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  6
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  6
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  1
 22 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 25 63  1  0
 25 64  1  0
 29 65  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1S,3R,7S,8S,8AR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrate	ChEBI
2beta,6alpha-Dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinic acid lactone	ChEBI
6alpha-Methylcompactin	ChEBI
Mevacor	ChEBI
Mevinolin	ChEBI
MK-803	ChEBI
ML-530b	ChEBI
(1S,3R,7S,8S,8AR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyric acid	Generator
2b,6a-Dimethyl-8a-(2-methyl-1-oxobutoxy)-mevinate lactone	Generator
2b,6a-Dimethyl-8a-(2-methyl-1-oxobutoxy)-mevinic acid lactone	Generator
2beta,6alpha-Dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinate lactone	Generator
2Β,6α-dimethyl-8α-(2-methyl-1-oxobutoxy)-mevinate lactone	Generator
2Β,6α-dimethyl-8α-(2-methyl-1-oxobutoxy)-mevinic acid lactone	Generator
6a-Methylcompactin	Generator
6Α-methylcompactin	Generator
6 alpha-Methylcompactin	HMDB
1 alpha-Isomer lovastatin	HMDB
6 Methylcompactin	HMDB
6-Methylcompactin	HMDB
Lovastatin, 1 alpha-isomer	HMDB
alpha-Isomer lovastatin, 1	HMDB
Lovastatin, (1 alpha(s*))-isomer	HMDB
Lovastatin, 1 alpha isomer	HMDB
Monacolin K	HMDB

Chemical Formula

C₂₄H₃₆O₅

Average Molecular Weight

404.5396

Monoisotopic Molecular Weight

404.256274262

IUPAC Name

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

Traditional Name

lovastatin

CAS Registry Number

75330-75-5

SMILES

[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)[C@@H](C)CC

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/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1

InChI Key

PCZOHLXUXFIOCF-BXMDZJJMSA-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

polyketide (CHEBI:40303 )
fatty acid ester (CHEBI:40303 )
delta-lactone (CHEBI:40303 )
carbobicyclic compound (CHEBI:40303 )
statin (naturally occurring) (CHEBI:40303 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014372)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Lovastatin Pathway (HMDB: HMDB0014372)
Lovastatin Action Pathway (PathBank: SMP0000099)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.024 g/L	Not Available
LogP	4.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
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	46.11 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
DarkChem	[M+H]+	195.078	31661259
DarkChem	[M-H]-	191.008	31661259
DeepCCS	[M-2H]-	244.547	30932474
DeepCCS	[M+Na]+	219.322	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
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.89 minutes	32390414
Predicted by Siyang on May 30, 2022	20.2522 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.72 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
Lovastatin	[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)[C@@H](C)CC	4237.5	Standard polar	33892256
Lovastatin	[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)[C@@H](C)CC	2904.4	Standard non polar	33892256
Lovastatin	[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)[C@@H](C)CC	3174.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lovastatin,1TMS,isomer #1	CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O[Si](C)(C)C)CC(=O)O3)[C@H]21	2996.7	Semi standard non polar	33892256
Lovastatin,1TBDMS,isomer #1	CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)O3)[C@H]21	3235.6	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Lovastatin Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00227	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00227	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00227

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000547

Chemspider ID

48085

KEGG Compound ID

C07074

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lovastatin

METLIN ID

Not Available

PubChem Compound

53232

PDB ID

803

ChEBI ID

40303

Food Biomarker Ontology

Not Available

VMH ID

LVST

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bobek P, Ozdin L, Galbavy S: Dose- and time-dependent hypocholesterolemic effect of oyster mushroom (Pleurotus ostreatus) in rats. Nutrition. 1998 Mar;14(3):282-6. [PubMed:9583372 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Serum paraoxonase/lactonase 3

General function:: Involved in arylesterase activity
Specific function:: Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:: PON3
Uniprot ID:: Q15166
Molecular weight:: 39607.185

References

Draganov DI, Stetson PL, Watson CE, Billecke SS, La Du BN: Rabbit serum paraoxonase 3 (PON3) is a high density lipoprotein-associated lactonase and protects low density lipoprotein against oxidation. J Biol Chem. 2000 Oct 27;275(43):33435-42. [PubMed:10931838 ]

Enzyme Details

2. 3-hydroxy-3-methylglutaryl-coenzyme A reductase

General function:: Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:: Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:: HMGCR
Uniprot ID:: P04035
Molecular weight:: 97475.155

References

Abe Y, Suzuki T, Ono C, Iwamoto K, Hosobuchi M, Yoshikawa H: Molecular cloning and characterization of an ML-236B (compactin) biosynthetic gene cluster in Penicillium citrinum. Mol Genet Genomics. 2002 Jul;267(5):636-46. Epub 2002 Jun 28. [PubMed:12172803 ]
Miyazaki A, Koieyama T, Shimada Y, Kikuchi T, Nezu H, Ito K, Kasanuki N, Koga T: Effects of pravastatin sodium on mevalonate metabolism in common marmosets. J Biochem. 2002 Sep;132(3):395-400. [PubMed:12204108 ]
Buxbaum JD, Geoghagen NS, Friedhoff LT: Cholesterol depletion with physiological concentrations of a statin decreases the formation of the Alzheimer amyloid Abeta peptide. J Alzheimers Dis. 2001 Apr;3(2):221-229. [PubMed:12214063 ]
Baranova NA, Kreier VG, Egorov NS: [Concentration on Diapak C 16 capsules of lovastatin, mevinolinic acid and other inhibitors of biosynthesis of sterins produced by Penicillium citrinum 89]. Antibiot Khimioter. 2002;47(4):3-6. [PubMed:12369143 ]
Farina HG, Bublik DR, Alonso DF, Gomez DE: Lovastatin alters cytoskeleton organization and inhibits experimental metastasis of mammary carcinoma cells. Clin Exp Metastasis. 2002;19(6):551-9. [PubMed:12405293 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Podar K, Tai YT, Hideshima T, Vallet S, Richardson PG, Anderson KC: Emerging therapies for multiple myeloma. Expert Opin Emerg Drugs. 2009 Mar;14(1):99-127. doi: 10.1517/14728210802676278 . [PubMed:19249983 ]
Dimitroulakos J, Marhin WH, Tokunaga J, Irish J, Gullane P, Penn LZ, Kamel-Reid S: Microarray and biochemical analysis of lovastatin-induced apoptosis of squamous cell carcinomas. Neoplasia. 2002 Jul-Aug;4(4):337-46. [PubMed:12082550 ]

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Neuvonen PJ, Niemi M, Backman JT: Drug interactions with lipid-lowering drugs: mechanisms and clinical relevance. Clin Pharmacol Ther. 2006 Dec;80(6):565-81. [PubMed:17178259 ]
Cohen LH, van Leeuwen RE, van Thiel GC, van Pelt JF, Yap SH: Equally potent inhibitors of cholesterol synthesis in human hepatocytes have distinguishable effects on different cytochrome P450 enzymes. Biopharm Drug Dispos. 2000 Dec;21(9):353-64. [PubMed:11523064 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Cohen LH, van Leeuwen RE, van Thiel GC, van Pelt JF, Yap SH: Equally potent inhibitors of cholesterol synthesis in human hepatocytes have distinguishable effects on different cytochrome P450 enzymes. Biopharm Drug Dispos. 2000 Dec;21(9):353-64. [PubMed:11523064 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Cohen LH, van Leeuwen RE, van Thiel GC, van Pelt JF, Yap SH: Equally potent inhibitors of cholesterol synthesis in human hepatocytes have distinguishable effects on different cytochrome P450 enzymes. Biopharm Drug Dispos. 2000 Dec;21(9):353-64. [PubMed:11523064 ]

Enzyme Details

6. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

8. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

9. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Tornio A, Pasanen MK, Laitila J, Neuvonen PJ, Backman JT: Comparison of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors (statins) as inhibitors of cytochrome P450 2C8. Basic Clin Pharmacol Toxicol. 2005 Aug;97(2):104-8. [PubMed:15998357 ]
Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

10. Integrin alpha-L

General function:: Involved in cell adhesion
Specific function:: Integrin alpha-L/beta-2 is a receptor for ICAM1, ICAM2, ICAM3 and ICAM4. It is involved in a variety of immune phenomena including leukocyte-endothelial cell interaction, cytotoxic T-cell mediated killing, and antibody dependent killing by granulocytes and monocytes
Gene Name:: ITGAL
Uniprot ID:: P20701
Molecular weight:: 128768.5

References

Kallen J, Welzenbach K, Ramage P, Geyl D, Kriwacki R, Legge G, Cottens S, Weitz-Schmidt G, Hommel U: Structural basis for LFA-1 inhibition upon lovastatin binding to the CD11a I-domain. J Mol Biol. 1999 Sep 10;292(1):1-9. [PubMed:10493852 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Hsiang B, Zhu Y, Wang Z, Wu Y, Sasseville V, Yang WP, Kirchgessner TG: A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters. J Biol Chem. 1999 Dec 24;274(52):37161-8. [PubMed:10601278 ]
Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [PubMed:15716364 ]

Enzyme Details

2. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Wang E, Casciano CN, Clement RP, Johnson WW: HMG-CoA reductase inhibitors (statins) characterized as direct inhibitors of P-glycoprotein. Pharm Res. 2001 Jun;18(6):800-6. [PubMed:11474784 ]
Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372 ]

Enzyme Details

3. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612 ]
Hsiang B, Zhu Y, Wang Z, Wu Y, Sasseville V, Yang WP, Kirchgessner TG: A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters. J Biol Chem. 1999 Dec 24;274(52):37161-8. [PubMed:10601278 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Showing metabocard for Lovastatin (HMDB0014372)

MOL for HMDB0014372 (Lovastatin)

3D MOL for HMDB0014372 (Lovastatin)

3D SDF for HMDB0014372 (Lovastatin)

3D-SDF for HMDB0014372 (Lovastatin)

PDB for HMDB0014372 (Lovastatin)

3D PDB for HMDB0014372 (Lovastatin)

SMILES for HMDB0014372 (Lovastatin)

INCHI for HMDB0014372 (Lovastatin)

Structure for HMDB0014372 (Lovastatin)

3D Structure for HMDB0014372 (Lovastatin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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Transporters

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