NP-MRD: Showing NP-Card for methyl tortuosoate (NP0033102)

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Record Information

Version

2.0

Created at

2021-06-19 23:44:33 UTC

Updated at

2021-06-30 00:02:41 UTC

NP-MRD ID

NP0033102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl tortuosoate

Provided By

JEOL Database JEOL Logo

Description

Methyl tortuosoate belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions. methyl tortuosoate is found in Sarcophyton tortuosum. methyl tortuosoate was first documented in 2007 (PMID: 17595133). Based on a literature review very few articles have been published on methyl tortuosoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101443D          

 58 58  0  0  0  0            999 V2000
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   -1.6433   -4.3147   -2.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7058   -3.1608   -0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2258   -2.1171    1.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2658   -1.1198    2.4504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6644   -1.1650    3.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202101443D          

 58 58  0  0  0  0            999 V2000
   -1.6655   -4.8598   -4.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -4.3147   -2.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7892   -3.0219    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5488   -1.4206    3.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7249   -0.4925    3.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4350   -0.8668    2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9005   -2.1742    3.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898    0.5628    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3598    1.0235    2.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.0436    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9617    0.4609    2.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706    2.7584    2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6808    2.2218    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6610    2.3142    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    4.5802    1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950    4.2067    0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0320    4.2107    0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748    2.1907   -1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555    2.5691   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0936    0.0272   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2683   -0.3454   -3.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7263    1.1590   -3.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206    1.5465   -5.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388    2.5691   -3.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.2045   -3.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867    1.2195   -4.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207    0.5487   -3.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3336   -2.1930   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -1.8010    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5 26  1  0  0  0  0
 19 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 15  1  0  0  0  0
  7  8  2  0  0  0  0
 14 13  1  0  0  0  0
  5  3  1  0  0  0  0
 19 20  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  0  0  0  0
 20 21  1  0  0  0  0
 24 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 15  1  0  0  0  0
  3  2  1  0  0  0  0
 13 12  1  0  0  0  0
  2  1  1  0  0  0  0
 12 10  1  0  0  0  0
  3  4  2  0  0  0  0
 10  9  1  0  0  0  0
 15 16  1  0  0  0  0
  9  7  1  0  0  0  0
 10 11  1  0  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
 15 43  1  1  0  0  0
 13 39  1  0  0  0  0
 13 40  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 10 33  1  1  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
 20 49  1  1  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  6 30  1  0  0  0  0
 26 57  1  0  0  0  0
 26 58  1  0  0  0  0
 21 50  1  6  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
 22 53  1  0  0  0  0
 23 54  1  0  0  0  0
 23 55  1  0  0  0  0
 23 56  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033102

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O5/c1-13(2)18-12-19(23)15(4)8-6-7-14(3)9-17(22)10-16(11-20(18)24)21(25)26-5/h10,13-15,18H,6-9,11-12H2,1-5H3/b16-10+/t14-,15+,18-/m1/s1

> <INCHI_KEY>
FDULQXJIBZLYBH-CJFOREIUSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.482

> <EXACT_MASS>
364.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.7685101347019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1E,5R,9S,12R)-5,9-dimethyl-3,10,13-trioxo-12-(propan-2-yl)cyclotetradec-1-ene-1-carboxylate

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
4.602992297999999

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.882639801533546

> <JCHEM_PKA_STRONGEST_BASIC>
-6.646015545250161

> <JCHEM_POLAR_SURFACE_AREA>
77.51

> <JCHEM_REFRACTIVITY>
101.04699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1E,5R,9S,12R)-12-isopropyl-5,9-dimethyl-3,10,13-trioxocyclotetradec-1-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 58  0  0  0  0  0  0  0  0999 V2000
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   -1.6433   -4.3147   -2.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949   -3.3630   -2.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -2.9788   -3.5628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -2.8296   -1.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8390   -2.6014    0.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8856   -2.6063    1.6632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258   -2.1171    1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -1.1198    2.4504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6644   -1.1650    3.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622    0.3331    2.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694    0.6345    1.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371    2.0823    1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    2.4721    1.3902 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4321    3.9502    1.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0624    1.5943    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8215    0.7322    0.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255    1.8037   -1.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775    0.4926   -1.8205 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3464    0.6512   -3.3519 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2828    1.5332   -4.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7397    1.1903   -3.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334   -0.4767   -1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1447   -0.1182   -1.6131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4179   -1.8695   -1.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822   -4.0778   -4.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4630   -5.6066   -4.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -5.3538   -4.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291   -3.8007   -0.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7076   -1.6759    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7892   -3.0219    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5488   -1.4206    3.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7249   -0.4925    3.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4350   -0.8668    2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9005   -2.1742    3.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898    0.5628    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3598    1.0235    2.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.0436    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9617    0.4609    2.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706    2.7584    2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6808    2.2218    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6610    2.3142    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    4.5802    1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950    4.2067    0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0320    4.2107    0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748    2.1907   -1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555    2.5691   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0936    0.0272   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2683   -0.3454   -3.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7263    1.1590   -3.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206    1.5465   -5.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388    2.5691   -3.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.2045   -3.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867    1.2195   -4.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207    0.5487   -3.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3336   -2.1930   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -1.8010    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  2  0
  5 26  1  0
 19 17  1  0
 17 18  2  0
 17 15  1  0
  7  8  2  0
 14 13  1  0
  5  3  1  0
 19 20  1  0
 24 25  2  0
 26 24  1  0
 20 21  1  0
 24 20  1  0
 21 22  1  0
 21 23  1  0
 14 15  1  0
  3  2  1  0
 13 12  1  0
  2  1  1  0
 12 10  1  0
  3  4  2  0
 10  9  1  0
 15 16  1  0
  9  7  1  0
 10 11  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  1
 13 39  1  0
 13 40  1  0
 12 37  1  0
 12 38  1  0
 10 33  1  1
 19 47  1  0
 19 48  1  0
 20 49  1  1
  9 31  1  0
  9 32  1  0
  6 30  1  0
 26 57  1  0
 26 58  1  0
 21 50  1  6
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.666  -4.860  -4.223  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.643  -4.315  -2.903  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.695  -3.363  -2.715  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.098  -2.979  -3.563  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.708  -2.830  -1.322  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.706  -3.161  -0.481  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.839  -2.601   0.892  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.886  -2.606   1.663  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.226  -2.117   1.275  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.266  -1.120   2.450  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.664  -1.165   3.083  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.962   0.333   2.018  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.469   0.635   1.860  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.237   2.082   1.406  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.249   2.472   1.390  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.432   3.950   1.055  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.062   1.594   0.444  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.821   0.732   0.894  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.926   1.804  -1.058  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.178   0.493  -1.821  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.346   0.651  -3.352  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.283   1.533  -4.013  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.740   1.190  -3.694  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.033  -0.477  -1.519  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.145  -0.118  -1.613  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.418  -1.869  -1.034  0.00  0.00           C+0
HETATM   27  H   UNK     0      -1.882  -4.078  -4.958  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.463  -5.607  -4.268  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.715  -5.354  -4.450  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.529  -3.801  -0.780  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.708  -1.676   0.394  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.789  -3.022   1.538  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.549  -1.421   3.224  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.725  -0.493   3.945  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.435  -0.867   2.364  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.901  -2.174   3.437  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.490   0.563   1.083  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.360   1.024   2.773  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.027  -0.044   1.129  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.962   0.461   2.816  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.771   2.758   2.087  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.681   2.222   0.413  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.661   2.314   2.396  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.021   4.580   1.827  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.495   4.207   0.989  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.032   4.211   0.098  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.075   2.191  -1.274  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.656   2.569  -1.340  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.094   0.027  -1.434  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.268  -0.345  -3.807  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.726   1.159  -3.819  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.421   1.547  -5.100  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.339   2.569  -3.663  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.888   2.204  -3.309  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.887   1.220  -4.779  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.521   0.549  -3.272  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.334  -2.193  -1.541  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.663  -1.801   0.028  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6   26    3                                                  
CONECT    6    7    5   30                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9   10    7   31   32                                             
CONECT   10   12    9   11   33                                             
CONECT   11   10   34   35   36                                             
CONECT   12   13   10   37   38                                             
CONECT   13   14   12   39   40                                             
CONECT   14   13   15   41   42                                             
CONECT   15   17   14   16   43                                             
CONECT   16   15   44   45   46                                             
CONECT   17   19   18   15                                                  
CONECT   18   17                                                            
CONECT   19   17   20   47   48                                             
CONECT   20   19   21   24   49                                             
CONECT   21   20   22   23   50                                             
CONECT   22   21   51   52   53                                             
CONECT   23   21   54   55   56                                             
CONECT   24   25   26   20                                                  
CONECT   25   24                                                            
CONECT   26    5   24   57   58                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    6                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  116    0
END

RDKit          3D

58 58  0  0  0  0  0  0  0  0999 V2000
   -1.6655   -4.8598   -4.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -4.3147   -2.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949   -3.3630   -2.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -2.9788   -3.5628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -2.8296   -1.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058   -3.1608   -0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -2.6014    0.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8856   -2.6063    1.6632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258   -2.1171    1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -1.1198    2.4504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6644   -1.1650    3.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622    0.3331    2.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694    0.6345    1.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371    2.0823    1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    2.4721    1.3902 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4321    3.9502    1.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0624    1.5943    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8215    0.7322    0.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255    1.8037   -1.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775    0.4926   -1.8205 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3464    0.6512   -3.3519 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2828    1.5332   -4.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7397    1.1903   -3.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334   -0.4767   -1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1447   -0.1182   -1.6131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4179   -1.8695   -1.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822   -4.0778   -4.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4630   -5.6066   -4.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -5.3538   -4.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291   -3.8007   -0.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7076   -1.6759    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7892   -3.0219    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5488   -1.4206    3.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7249   -0.4925    3.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4350   -0.8668    2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9005   -2.1742    3.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898    0.5628    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3598    1.0235    2.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.0436    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9617    0.4609    2.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706    2.7584    2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6808    2.2218    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6610    2.3142    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    4.5802    1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950    4.2067    0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0320    4.2107    0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748    2.1907   -1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555    2.5691   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0936    0.0272   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2683   -0.3454   -3.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7263    1.1590   -3.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206    1.5465   -5.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388    2.5691   -3.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.2045   -3.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867    1.2195   -4.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207    0.5487   -3.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3336   -2.1930   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -1.8010    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  2  0
  5 26  1  0
 19 17  1  0
 17 18  2  0
 17 15  1  0
  7  8  2  0
 14 13  1  0
  5  3  1  0
 19 20  1  0
 24 25  2  0
 26 24  1  0
 20 21  1  0
 24 20  1  0
 21 22  1  0
 21 23  1  0
 14 15  1  0
  3  2  1  0
 13 12  1  0
  2  1  1  0
 12 10  1  0
  3  4  2  0
 10  9  1  0
 15 16  1  0
  9  7  1  0
 10 11  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  1
 13 39  1  0
 13 40  1  0
 12 37  1  0
 12 38  1  0
 10 33  1  1
 19 47  1  0
 19 48  1  0
 20 49  1  1
  9 31  1  0
  9 32  1  0
  6 30  1  0
 26 57  1  0
 26 58  1  0
 21 50  1  6
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl tortuosoic acid	Generator

Chemical Formula

C₂₁H₃₂O₅

Average Mass

364.4820 Da

Monoisotopic Mass

364.22497 Da

IUPAC Name

methyl (1E,5R,9S,12R)-5,9-dimethyl-3,10,13-trioxo-12-(propan-2-yl)cyclotetradec-1-ene-1-carboxylate

Traditional Name

methyl (1E,5R,9S,12R)-12-isopropyl-5,9-dimethyl-3,10,13-trioxocyclotetradec-1-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H32O5/c1-13(2)18-12-19(23)15(4)8-6-7-14(3)9-17(22)10-16(11-20(18)24)21(25)26-5/h10,13-15,18H,6-9,11-12H2,1-5H3/b16-10+/t14-,15+,18-/m1/s1

InChI Key

FDULQXJIBZLYBH-CJFOREIUSA-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
Sarcophyton tortuosum	JEOL database	Jia, R., et al, J. Nat. Prod. 70, 1158 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Cembrane diterpenoids

Alternative Parents

Substituents

Cembrane diterpenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	2.98	ALOGPS
logP	4.6	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.88	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.05 m³·mol⁻¹	ChemAxon
Polarizability	40.77 Å³	ChemAxon
Number of Rings	1	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

23286965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16756315

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jia R, Guo YW, Chen P, Yang YM, Mollo E, Gavagnin M, Cimino G: Biscembranoids and their probable biogenetic precursor from the Hainan soft coral Sarcophyton tortuosum. J Nat Prod. 2007 Jul;70(7):1158-66. doi: 10.1021/np060220b. Epub 2007 Jun 27. [PubMed:17595133 ]
Jia, R., et al. (2007). Jia, R., et al, J. Nat. Prod. 70, 1158 (2007). J. Nat. Prod..

Showing NP-Card for methyl tortuosoate (NP0033102)

MOL for NP0033102 (methyl tortuosoate)

3D MOL for NP0033102 (methyl tortuosoate)

3D SDF for NP0033102 (methyl tortuosoate)

3D-SDF for NP0033102 (methyl tortuosoate)

PDB for NP0033102 (methyl tortuosoate)

3D PDB for NP0033102 (methyl tortuosoate)

SMILES for NP0033102 (methyl tortuosoate)

INCHI for NP0033102 (methyl tortuosoate)

Structure for NP0033102 (methyl tortuosoate)

3D Structure for NP0033102 (methyl tortuosoate)