NP-MRD: Showing NP-Card for compactin (NP0293972)

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Record Information

Version

1.0

Created at

2022-09-10 02:16:44 UTC

Updated at

2022-09-10 02:16:44 UTC

NP-MRD ID

NP0293972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

compactin

Description

Mevinic acid, also known as compactin acid or mevastatin acid, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. compactin is found in Penicillium citrinum and Penicillium javanicum. It was first documented in 1976 (PMID: 1010803). Mevinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 16042349).

Structure

MOL 3D MOL SDF PDB SMILES InChI

114
  Mrv0541 02241205582D          

 36 37  0  0  0  0            999 V2000
   -4.3691    1.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991    0.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7489   -0.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3987   -0.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -0.4994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8586   -1.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8291    0.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0189    1.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788    0.4361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6687    0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1286   -0.0317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3185    0.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484    0.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7617    1.0597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0317    1.8393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8419    1.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3820    1.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1119    0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3820   -0.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317   -0.3435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3018    0.4361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4917    2.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484   -1.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -1.9026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3018   -1.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8419   -2.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -2.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0522    0.3257    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7020   -0.1420    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    1.3438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552    1.9317    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406   -0.8952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6828   -1.3508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  7  1  0  0  0  0
  9  3  1  1  0  0  0
 11  4  1  1  0  0  0
 22  5  1  6  0  0  0
  5 25  1  0  0  0  0
  6 25  2  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
  9 30  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 31  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 14 23  1  0  0  0  0
 14 32  1  6  0  0  0
 15 16  1  0  0  0  0
 15 24  1  1  0  0  0
 15 33  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 23  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
 22 34  1  1  0  0  0
 23 35  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  1  0  0  0
 26 36  1  1  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 65 66  0  0  0  0  0  0  0  0999 V2000
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    4.8397    0.1954    1.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    1.6260    1.1610 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.0789    1.7148    0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2111    2.4168    1.0873 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7411    1.0812   -0.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893    1.1253   -1.2912 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7998    1.6501   -2.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8816    0.8084   -3.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -0.4801   -2.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820   -1.0455   -1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5901   -2.3063   -1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271   -2.9870   -0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422   -2.4285   -0.6271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4021   -2.8093   -1.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370   -0.9420   -0.3929 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9478   -0.3475    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043   -0.4754   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3441    0.2296   -0.2445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4033    0.0779   -1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7148   -0.2843    1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    0.3454    1.8060 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6250    1.7391    1.9517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2464    0.0561    1.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7966    0.3255    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2041   -0.6027   -0.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9089    1.6209   -0.3213 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063   -0.3087   -1.5633 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1770   -0.2701    3.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450   -0.4040    2.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454   -1.6285    2.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9842   -0.3024    0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285    0.2391    1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1486    2.0393    0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    1.8957    3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0967    3.4081    2.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5290    2.7678    2.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456    1.7354   -0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8618    1.6624   -3.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201    2.7182   -2.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6462    0.6024   -4.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    1.4132   -3.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1082   -0.9683   -2.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -2.7162   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975   -3.9373   -0.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690   -2.8536    0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775   -3.4524   -1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7306   -1.9823   -2.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841   -3.4692   -2.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551   -0.8344    0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8210    0.7078    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995   -0.9040    1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4695   -1.5019   -1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9093    0.0428   -1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0959    1.3210   -0.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3852    0.7791   -1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316   -0.1910    1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -1.4045    1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7630    0.0240    2.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0181    2.2171    1.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8816    0.6036    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4827   -1.0363    1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7796    2.0985   -0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -0.3414   -2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
 20 19  1  0
 19 18  1  0
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 17 15  1  0
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 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  8  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
  8 29  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 28  1  0
 26 27  2  0
 29 17  1  0
 29 12  1  0
 20 56  1  1
 21 57  1  0
 19 54  1  0
 19 55  1  0
 18 52  1  0
 18 53  1  0
 17 51  1  1
 15 47  1  1
 16 48  1  0
 16 49  1  0
 16 50  1  0
 14 46  1  0
 13 45  1  0
 11 44  1  0
 10 42  1  0
 10 43  1  0
  9 40  1  0
  9 41  1  0
  8 39  1  1
  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
 29 65  1  6
 22 58  1  0
 22 59  1  0
 23 60  1  1
 24 61  1  0
 25 62  1  0
 25 63  1  0
 28 64  1  0
M  END

114
  Mrv0541 02241205582D          

 36 37  0  0  0  0            999 V2000
   -4.3691    1.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991    0.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7489   -0.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3987   -0.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -0.4994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8586   -1.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8291    0.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0189    1.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788    0.4361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6687    0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1286   -0.0317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.0484    0.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0317    1.8393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8419    1.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3820    1.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1119    0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3820   -0.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317   -0.3435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3018    0.4361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4917    2.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484   -1.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -1.9026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3018   -1.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8419   -2.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -2.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0522    0.3257    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7020   -0.1420    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    1.3438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552    1.9317    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406   -0.8952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7284    0.3257    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -1.3508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  7  1  0  0  0  0
  9  3  1  1  0  0  0
 11  4  1  1  0  0  0
 22  5  1  6  0  0  0
  5 25  1  0  0  0  0
  6 25  2  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
  9 30  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 31  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 14 23  1  0  0  0  0
 14 32  1  6  0  0  0
 15 16  1  0  0  0  0
 15 24  1  1  0  0  0
 15 33  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 23  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
 22 34  1  1  0  0  0
 23 35  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  1  0  0  0
 26 36  1  1  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0293972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(CC[C@@]1([H])[C@@]([H])(C)C=CC2=CCC[C@]([H])(OC(=O)[C@@]([H])(C)CC)[C@]12[H])C[C@@]([H])(O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H36O6/c1-4-14(2)23(28)29-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-17(24)12-18(25)13-21(26)27/h6,8-9,14-15,17-20,22,24-25H,4-5,7,10-13H2,1-3H3,(H,26,27)/t14-,15-,17+,18+,19-,20-,22-/m0/s1

> <INCHI_KEY>
BOZILQFLQYBIIY-INTXDZFKSA-N

> <FORMULA>
C23H36O6

> <MOLECULAR_WEIGHT>
408.5283

> <EXACT_MASS>
408.251188884

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.31285271778316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
2.9506966933333336

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.890242521752814

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.212298804304482

> <JCHEM_PKA_STRONGEST_BASIC>
-2.721465066714238

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
112.126

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
compactin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 114                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -8.156   2.851   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -7.652   0.232   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -5.131  -0.641   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.611  -1.514   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.414  -0.932   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.603  -2.678   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.148   1.687   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.635   1.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.627   0.814   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.115   1.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.107  -0.059   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.595   0.232   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.090   1.687   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.422   1.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.926   3.433   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.438   3.724   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.446   2.560   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.942   1.105   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.950  -0.059   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.446  -1.514   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.934  -1.805   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.926  -0.641   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.430   0.814   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.918   4.597   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.090  -2.387   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.918  -3.552   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.430  -3.261   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.438  -4.425   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.414  -5.007   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      -5.697   0.608   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.177  -0.265   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.469   2.508   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.850   3.606   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.569  -1.671   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.360   0.608   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.275  -2.521   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    9                                                            
CONECT    4   11                                                            
CONECT    5   22   25                                                       
CONECT    6   25                                                            
CONECT    7    1    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    3    8   10   30                                             
CONECT   10    9   11                                                       
CONECT   11    4   10   12   31                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   23   32                                             
CONECT   15   14   16   24   33                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    5   21   23   34                                             
CONECT   23   14   18   22   35                                             
CONECT   24   15                                                            
CONECT   25    5    6   26                                                  
CONECT   26   25   27   29   36                                             
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30    9                                                            
CONECT   31   11                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
CONECT   36   26                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
Compactin acid	ChEBI
Mevastatin (acid form)	ChEBI
Mevastatin acid	ChEBI
Mevastatin hydroxy acid	ChEBI
ML 236b acid	ChEBI
ML-236b acid	ChEBI
Mevinate	Generator

Chemical Formula

C₂₃H₃₆O₆

Average Mass

408.5283 Da

Monoisotopic Mass

408.25119 Da

IUPAC Name

(3R,5R)-7-[(1S,2S,8S,8aR)-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

Traditional Name

compactin

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CC[C@@]1([H])[C@@]([H])(C)C=CC2=CCC[C@]([H])(OC(=O)[C@@]([H])(C)CC)[C@]12[H])C[C@@]([H])(O)CC(O)=O

InChI Identifier

InChI=1S/C23H36O6/c1-4-14(2)23(28)29-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-17(24)12-18(25)13-21(26)27/h6,8-9,14-15,17-20,22,24-25H,4-5,7,10-13H2,1-3H3,(H,26,27)/t14-,15-,17+,18+,19-,20-,22-/m0/s1

InChI Key

BOZILQFLQYBIIY-INTXDZFKSA-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
Penicillium citrinum	LOTUS Database	35616633
Penicillium javanicum	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	4.03	ALOGPS
logP	2.95	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	112.13 m³·mol⁻¹	ChemAxon
Polarizability	45.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

446154

PDB ID

Not Available

ChEBI ID

39508

Good Scents ID

Not Available

References

General References

Endo A, Kuroda M, Tsujita Y: ML-236A, ML-236B, and ML-236C, new inhibitors of cholesterogenesis produced by Penicillium citrinium. J Antibiot (Tokyo). 1976 Dec;29(12):1346-8. doi: 10.7164/antibiotics.29.1346. [PubMed:1010803 ]
Weber D, Gorzalczany S, Martino V, Acevedo C, Sterner O, Anke T: Metabolites from endophytes of the medicinal plant Erythrina crista-galli. Z Naturforsch C J Biosci. 2005 May-Jun;60(5-6):467-77. doi: 10.1515/znc-2005-5-616. [PubMed:16042349 ]
LOTUS database [Link]

Showing NP-Card for compactin (NP0293972)

MOL for NP0293972 (compactin)

3D MOL for NP0293972 (compactin)

3D SDF for NP0293972 (compactin)

3D-SDF for NP0293972 (compactin)

PDB for NP0293972 (compactin)

3D PDB for NP0293972 (compactin)

SMILES for NP0293972 (compactin)

INCHI for NP0293972 (compactin)

Structure for NP0293972 (compactin)

3D Structure for NP0293972 (compactin)