NP-MRD: Showing NP-Card for carrizaloic acid (NP0025848)

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Record Information

Version

2.0

Created at

2021-06-19 17:52:01 UTC

Updated at

2021-06-29 23:51:02 UTC

NP-MRD ID

NP0025848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

carrizaloic acid

Provided By

JEOL Database JEOL Logo

Description

carrizaloic acid is found in Heliotropium huascoense. carrizaloic acid was first documented in 2001 (Villarroel, L., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119523D          

 45 46  0  0  0  0            999 V2000
   -0.2498    3.2678   -1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    1.9814   -0.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    1.7614    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4151    2.6047    1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6502    2.2705    2.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.0872    3.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    0.7755    4.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539    1.4686    5.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223   -0.3937    4.8386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6253    0.2395    2.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    0.5660    0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7269   -0.3677    0.0321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0792   -1.7276   -0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1838   -2.7536   -0.8379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0201   -2.2592   -2.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538   -3.0879    0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122   -4.0679   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9723   -5.1807   -1.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871   -3.9940   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -2.8491   -2.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -1.5788   -1.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4137   -1.1524   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394   -0.6311   -2.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    3.3135   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    4.0624   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8347    3.4156   -1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    3.5262    0.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    2.9381    3.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1367   -0.4679    5.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405   -0.6782    2.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    0.1479   -0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -0.5387    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331   -2.1709    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4011   -2.0117   -2.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7226   -3.0346   -2.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -1.3746   -1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8325   -3.9068    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922   -2.2421    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6044   -3.4030    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -4.8895   -2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547   -2.8233   -2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2358   -1.1460   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938   -1.8264    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841   -0.1342   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160    0.2587   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  3  2  1  0  0  0  0
 13 21  1  0  0  0  0
 14 17  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 10 11  2  0  0  0  0
 21 23  1  6  0  0  0
  2  1  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 11 12  1  0  0  0  0
 21 22  1  0  0  0  0
 11  3  1  0  0  0  0
 17 18  2  0  0  0  0
 12 13  1  0  0  0  0
  6  7  1  0  0  0  0
 13 14  1  0  0  0  0
  7  8  2  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  5 28  1  0  0  0  0
 10 30  1  0  0  0  0
  4 27  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  1  0  0  0
 19 40  1  0  0  0  0
 20 41  1  0  0  0  0
 23 45  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 22 42  1  0  0  0  0
 22 43  1  0  0  0  0
 22 44  1  0  0  0  0
  9 29  1  0  0  0  0
M  END

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
   -0.2498    3.2678   -1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    1.9814   -0.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    1.7614    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4151    2.6047    1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6502    2.2705    2.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.0872    3.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    0.7755    4.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539    1.4686    5.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223   -0.3937    4.8386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6253    0.2395    2.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    0.5660    0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7269   -0.3677    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -1.7276   -0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1838   -2.7536   -0.8379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0201   -2.2592   -2.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538   -3.0879    0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122   -4.0679   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9723   -5.1807   -1.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871   -3.9940   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -2.8491   -2.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -1.5788   -1.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4137   -1.1524   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394   -0.6311   -2.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    3.3135   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    4.0624   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8347    3.4156   -1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    3.5262    0.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    2.9381    3.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1367   -0.4679    5.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405   -0.6782    2.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    0.1479   -0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -0.5387    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331   -2.1709    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4011   -2.0117   -2.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7226   -3.0346   -2.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -1.3746   -1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8325   -3.9068    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922   -2.2421    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6044   -3.4030    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -4.8895   -2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547   -2.8233   -2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2358   -1.1460   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938   -1.8264    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841   -0.1342   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160    0.2587   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  3  2  1  0
 13 21  1  0
 14 17  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 10 11  2  0
 21 23  1  6
  2  1  1  0
 14 15  1  6
 14 16  1  0
 11 12  1  0
 21 22  1  0
 11  3  1  0
 17 18  2  0
 12 13  1  0
  6  7  1  0
 13 14  1  0
  7  8  2  0
  6 10  1  0
  7  9  1  0
  5 28  1  0
 10 30  1  0
  4 27  1  0
  1 24  1  0
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 13 33  1  1
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 23 45  1  0
 15 34  1  0
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 16 37  1  0
 16 38  1  0
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 22 42  1  0
 22 43  1  0
 22 44  1  0
  9 29  1  0
M  END


  Mrv1652306192119523D          

 45 46  0  0  0  0            999 V2000
   -0.2498    3.2678   -1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    1.9814   -0.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    1.7614    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4151    2.6047    1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6502    2.2705    2.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.0872    3.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    0.7755    4.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539    1.4686    5.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223   -0.3937    4.8386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6253    0.2395    2.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    0.5660    0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7269   -0.3677    0.0321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0792   -1.7276   -0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1838   -2.7536   -0.8379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0201   -2.2592   -2.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538   -3.0879    0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122   -4.0679   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9723   -5.1807   -1.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871   -3.9940   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -2.8491   -2.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -1.5788   -1.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4137   -1.1524   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394   -0.6311   -2.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    3.3135   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    4.0624   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8513    3.5262    0.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    2.9381    3.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1367   -0.4679    5.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405   -0.6782    2.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    0.1479   -0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4011   -2.0117   -2.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7226   -3.0346   -2.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -1.3746   -1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8325   -3.9068    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922   -2.2421    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6044   -3.4030    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -4.8895   -2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547   -2.8233   -2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2358   -1.1460   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938   -1.8264    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841   -0.1342   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160    0.2587   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  3  2  1  0  0  0  0
 13 21  1  0  0  0  0
 14 17  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 10 11  2  0  0  0  0
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  2  1  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 11 12  1  0  0  0  0
 21 22  1  0  0  0  0
 11  3  1  0  0  0  0
 17 18  2  0  0  0  0
 12 13  1  0  0  0  0
  6  7  1  0  0  0  0
 13 14  1  0  0  0  0
  7  8  2  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  5 28  1  0  0  0  0
 10 30  1  0  0  0  0
  4 27  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  1  0  0  0
 19 40  1  0  0  0  0
 20 41  1  0  0  0  0
 23 45  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 22 42  1  0  0  0  0
 22 43  1  0  0  0  0
 22 44  1  0  0  0  0
  9 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C(OC([H])([H])[H])C(=C1[H])C([H])([H])[C@]1([H])[C@](O[H])(C([H])=C([H])C(=O)C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O5/c1-17(2)14(18(3,22)8-7-15(17)19)10-12-9-11(16(20)21)5-6-13(12)23-4/h5-9,14,22H,10H2,1-4H3,(H,20,21)/t14-,18+/m0/s1

> <INCHI_KEY>
VWTHQOHALJUZPE-KBXCAEBGSA-N

> <FORMULA>
C18H22O5

> <MOLECULAR_WEIGHT>
318.369

> <EXACT_MASS>
318.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.70886950263471

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(1S,2R)-2-hydroxy-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]methyl}-4-methoxybenzoic acid

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
3.0780410423333344

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.325545957722301

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.338068305371332

> <JCHEM_PKA_STRONGEST_BASIC>
-3.093806460806274

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
87.45689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1S,2R)-2-hydroxy-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]methyl}-4-methoxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
   -0.2498    3.2678   -1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    1.9814   -0.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    1.7614    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4151    2.6047    1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6502    2.2705    2.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.0872    3.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    0.7755    4.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539    1.4686    5.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223   -0.3937    4.8386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6253    0.2395    2.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    0.5660    0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7269   -0.3677    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -1.7276   -0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1838   -2.7536   -0.8379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0201   -2.2592   -2.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538   -3.0879    0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122   -4.0679   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9723   -5.1807   -1.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871   -3.9940   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -2.8491   -2.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -1.5788   -1.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4137   -1.1524   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394   -0.6311   -2.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    3.3135   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    4.0624   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8347    3.4156   -1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    3.5262    0.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    2.9381    3.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1367   -0.4679    5.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405   -0.6782    2.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    0.1479   -0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -0.5387    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331   -2.1709    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4011   -2.0117   -2.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7226   -3.0346   -2.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -1.3746   -1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8325   -3.9068    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922   -2.2421    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6044   -3.4030    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -4.8895   -2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547   -2.8233   -2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2358   -1.1460   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938   -1.8264    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841   -0.1342   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160    0.2587   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  3  2  1  0
 13 21  1  0
 14 17  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 10 11  2  0
 21 23  1  6
  2  1  1  0
 14 15  1  6
 14 16  1  0
 11 12  1  0
 21 22  1  0
 11  3  1  0
 17 18  2  0
 12 13  1  0
  6  7  1  0
 13 14  1  0
  7  8  2  0
  6 10  1  0
  7  9  1  0
  5 28  1  0
 10 30  1  0
  4 27  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  1
 19 40  1  0
 20 41  1  0
 23 45  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
  9 29  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.250   3.268  -1.514  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.578   1.981  -0.999  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.343   1.761   0.334  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.415   2.605   1.152  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.650   2.271   2.490  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.134   1.087   3.023  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.413   0.776   4.446  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.054   1.469   5.214  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.122  -0.394   4.839  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.625   0.240   2.210  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.870   0.566   0.862  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.727  -0.368   0.032  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.079  -1.728  -0.370  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.184  -2.754  -0.838  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.020  -2.259  -2.033  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.154  -3.088   0.321  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.512  -4.068  -1.260  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.972  -5.181  -1.011  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.287  -3.994  -2.077  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.394  -2.849  -2.163  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.090  -1.579  -1.412  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.414  -1.152  -0.751  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.239  -0.631  -2.422  0.00  0.00           O+0
HETATM   24  H   UNK     0      -0.607   3.313  -2.547  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.752   4.062  -0.952  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.835   3.416  -1.530  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.851   3.526   0.780  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.244   2.938   3.112  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.137  -0.468   5.781  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.040  -0.678   2.623  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.111   0.148  -0.855  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.622  -0.539   0.640  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.633  -2.171   0.534  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.401  -2.012  -2.900  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.723  -3.035  -2.362  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.611  -1.375  -1.776  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.833  -3.907   0.053  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.792  -2.242   0.591  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.604  -3.403   1.215  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.001  -4.890  -2.614  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.255  -2.823  -2.829  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.236  -1.146  -1.478  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.694  -1.826   0.066  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.384  -0.134  -0.365  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.216   0.259  -2.020  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   11                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   29                                                       
CONECT   10   11    6   30                                                  
CONECT   11   10   12    3                                                  
CONECT   12   11   13   31   32                                             
CONECT   13   21   12   14   33                                             
CONECT   14   17   15   16   13                                             
CONECT   15   14   34   35   36                                             
CONECT   16   14   37   38   39                                             
CONECT   17   14   19   18                                                  
CONECT   18   17                                                            
CONECT   19   17   20   40                                                  
CONECT   20   19   21   41                                                  
CONECT   21   13   20   23   22                                             
CONECT   22   21   42   43   44                                             
CONECT   23   21   45                                                       
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   15                                                            
CONECT   35   15                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   16                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   22                                                            
CONECT   43   22                                                            
CONECT   44   22                                                            
CONECT   45   23                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   92    0
END

RDKit          3D

45 46  0  0  0  0  0  0  0  0999 V2000
   -0.2498    3.2678   -1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    1.9814   -0.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    1.7614    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4151    2.6047    1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6502    2.2705    2.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.0872    3.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    0.7755    4.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539    1.4686    5.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223   -0.3937    4.8386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6253    0.2395    2.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    0.5660    0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7269   -0.3677    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -1.7276   -0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1838   -2.7536   -0.8379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0201   -2.2592   -2.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538   -3.0879    0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122   -4.0679   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9723   -5.1807   -1.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871   -3.9940   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -2.8491   -2.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -1.5788   -1.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4137   -1.1524   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394   -0.6311   -2.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    3.3135   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    4.0624   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8347    3.4156   -1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    3.5262    0.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    2.9381    3.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1367   -0.4679    5.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405   -0.6782    2.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    0.1479   -0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -0.5387    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331   -2.1709    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4011   -2.0117   -2.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7226   -3.0346   -2.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -1.3746   -1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8325   -3.9068    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922   -2.2421    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6044   -3.4030    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -4.8895   -2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547   -2.8233   -2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2358   -1.1460   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938   -1.8264    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841   -0.1342   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160    0.2587   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  3  2  1  0
 13 21  1  0
 14 17  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 10 11  2  0
 21 23  1  6
  2  1  1  0
 14 15  1  6
 14 16  1  0
 11 12  1  0
 21 22  1  0
 11  3  1  0
 17 18  2  0
 12 13  1  0
  6  7  1  0
 13 14  1  0
  7  8  2  0
  6 10  1  0
  7  9  1  0
  5 28  1  0
 10 30  1  0
  4 27  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  1
 19 40  1  0
 20 41  1  0
 23 45  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
  9 29  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₂O₅

Average Mass

318.3690 Da

Monoisotopic Mass

318.14672 Da

IUPAC Name

3-{[(1S,2R)-2-hydroxy-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]methyl}-4-methoxybenzoic acid

Traditional Name

3-{[(1S,2R)-2-hydroxy-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]methyl}-4-methoxybenzoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C([H])=C(OC([H])([H])[H])C(=C1[H])C([H])([H])[C@]1([H])[C@](O[H])(C([H])=C([H])C(=O)C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C18H22O5/c1-17(2)14(18(3,22)8-7-15(17)19)10-12-9-11(16(20)21)5-6-13(12)23-4/h5-9,14,22H,10H2,1-4H3,(H,20,21)/t14-,18+/m0/s1

InChI Key

VWTHQOHALJUZPE-KBXCAEBGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Heliotropium huascoense	JEOL database	Villarroel, L., et al, J. Nat. Prod. 64, 1123 (2001)

Chemical Taxonomy

Classification

Not classified

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	2.56	ALOGPS
logP	3.08	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.46 m³·mol⁻¹	ChemAxon
Polarizability	33.71 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

Not Available

References

General References

Villarroel, L., et al. (2001). Villarroel, L., et al, J. Nat. Prod. 64, 1123 (2001). J. Nat. Prod..

Showing NP-Card for carrizaloic acid (NP0025848)

MOL for NP0025848 (carrizaloic acid)

3D MOL for NP0025848 (carrizaloic acid)

3D SDF for NP0025848 (carrizaloic acid)

3D-SDF for NP0025848 (carrizaloic acid)

PDB for NP0025848 (carrizaloic acid)

3D PDB for NP0025848 (carrizaloic acid)

SMILES for NP0025848 (carrizaloic acid)

INCHI for NP0025848 (carrizaloic acid)

Structure for NP0025848 (carrizaloic acid)

3D Structure for NP0025848 (carrizaloic acid)