NP-MRD: Showing NP-Card for lovastatin (NP0306349)

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Record Information

Version

2.0

Created at

2022-09-10 22:46:08 UTC

Updated at

2022-09-10 22:46:08 UTC

NP-MRD ID

NP0306349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lovastatin

Description

Lovastatin, also known as mevacor or MK-803, belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Lovastatin is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, lovastatin is involved in lovastatin action pathway. lovastatin is found in Apis cerana, Cephalotrichum nanum, Nectriopsis rexiana and Pleurotus ostreatus. lovastatin was first documented in 1997 (PMID: 18642339). Lovastatin is a potentially toxic compound (PMID: 11375168) (PMID: 11389707) (PMID: 11483865).

Structure

MOL 3D MOL SDF 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

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
   -2.3006    4.9718    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4902    3.5676    0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8495    2.5513   -0.1447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4059    2.6931   -1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    1.1784    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7598    0.9451    1.4010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5343    0.0407   -0.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7316   -1.2515    0.2072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8151   -1.9448   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -3.1621    0.1877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5266   -3.7352   -0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778   -4.0889   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763   -3.5793    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2342   -4.5220   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4729   -4.2085    0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6854   -2.8361    0.7517 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4604   -2.9192    2.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -1.8087    0.0721 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2800   -0.4607    0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697   -0.2479   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1689    1.1685    0.2849 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2803    2.2419   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1253    3.4595   -0.5823 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0709    3.5561    0.4603 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9315    3.1035   -1.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    1.9256   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6204    1.4973   -2.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4763    1.3559   -0.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6252   -2.1349    0.5432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2612    5.3247   -0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379    5.0567   -0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057    5.6877    1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542    3.3320    0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9576    3.4671    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7870    2.7884   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6297    2.3420   -2.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    3.7707   -1.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3316    2.0856   -1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475   -1.1209    1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6990   -1.3168   -0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020   -2.3409   -1.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2605   -2.8250    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3203   -3.3146    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8162   -3.4213   -1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5865   -4.8337   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704   -5.1027   -0.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527   -5.5141   -0.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3398   -4.8237    0.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7231   -2.5266    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994   -3.3019    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6838   -3.6799    2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2263   -1.9871    2.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432   -2.0266   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236    0.3935    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928   -0.3643    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4506   -0.8958    0.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7210   -0.3840   -1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2318    1.1957    1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485    1.8809   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4607    2.5052    0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450    4.3725   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9650    3.6868    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5534    3.9694   -2.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1950    2.7995   -2.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4890   -2.2351    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
 29  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
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  1  0
 13 29  1  0
 28 21  1  0
 18 29  1  0
 29 65  1  1
  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  1
 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
  3 35  1  6
  4 36  1  0
  4 37  1  0
  4 38  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
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>
NP0306349

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

404.5396 Da

Monoisotopic Mass

404.25627 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Cephalotrichum nanum	LOTUS Database	35616633
Nectriopsis rexiana	LOTUS Database	35616633
Pleurotus ostreatus	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted 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	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

External Links

HMDB ID

HMDB0014372

DrugBank ID

DB00227

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Hajjaj H, Niederberger P, Duboc P: Lovastatin biosynthesis by Aspergillus terreus in a chemically defined medium. Appl Environ Microbiol. 2001 Jun;67(6):2596-602. doi: 10.1128/AEM.67.6.2596-2602.2001. [PubMed:11375168 ]
Sahu K, Sharma R, Gupta A, Gulati S, Agarwal D, Kumar A, Bhandari M: Effect of lovastatin, an HMG CoA reductase inhibitor, on acute renal allograft rejection. Clin Transplant. 2001 Jun;15(3):173-5. doi: 10.1034/j.1399-0012.2001.150305.x. [PubMed:11389707 ]
Unlu S, Clunn G, Schachter M, Demoliou-Mason C, Hughes AD: Action of an HMG CoA reductase inhibitor, lovastatin, on apoptosis of untransformed and ts-SV40 transformed human smooth muscle cells derived from saphenous vein. J Cardiovasc Pharmacol. 2001 Aug;38(2):161-73. doi: 10.1097/00005344-200108000-00001. [PubMed:11483865 ]
Yang F, Weber TW, Gainer JL, Carta G: Synthesis of lovastatin with immobilized Candida rugosa lipase in organic solvents: Effects of reaction conditions on initial rates. Biotechnol Bioeng. 1997 Dec 20;56(6):671-80. doi: 10.1002/(SICI)1097-0290(19971220)56:6<671::AID-BIT10>3.0.CO;2-B. [PubMed:18642339 ]
LOTUS database [Link]

Showing NP-Card for lovastatin (NP0306349)

MOL for NP0306349 (lovastatin)

3D MOL for NP0306349 (lovastatin)

3D SDF for NP0306349 (lovastatin)

3D-SDF for NP0306349 (lovastatin)

PDB for NP0306349 (lovastatin)

3D PDB for NP0306349 (lovastatin)

SMILES for NP0306349 (lovastatin)

INCHI for NP0306349 (lovastatin)

Structure for NP0306349 (lovastatin)

3D Structure for NP0306349 (lovastatin)