NP-MRD: Showing NP-Card for (1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate (NP0219396)

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Record Information

Version

2.0

Created at

2022-09-05 20:22:13 UTC

Updated at

2022-09-05 20:22:13 UTC

NP-MRD ID

NP0219396

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate

Description

12-O-(2-Methylbutyroyl)phorbol-13-dodecanoate belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. (1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate is found in Croton tiglium. Based on a literature review very few articles have been published on 12-O-(2-Methylbutyroyl)phorbol-13-dodecanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222222D          

 45 48  0  0  1  0            999 V2000
   -4.9906   -8.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110   -8.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5874   -7.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078   -8.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842   -7.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046   -7.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7810   -7.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0014   -7.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -8.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -8.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5577   -8.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372   -8.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -9.2864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -7.9362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7404   -8.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4704   -8.9858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9066   -9.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463  -10.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9499  -10.5646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826  -10.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791  -10.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8223  -11.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585  -12.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0105   -9.6094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2502  -10.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -9.4535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4931  -10.2107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0906   -8.6740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8685   -8.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5684   -8.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2656   -8.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9962   -8.7779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6633   -9.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0818  -10.2405    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8727  -10.4753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498  -11.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0020  -11.3870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5336  -11.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4437  -12.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229  -10.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2617  -10.1507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5506   -8.0503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0105   -7.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3474   -6.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181   -6.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 16 15  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 16  1  0  0  0  0
 24 25  1  6  0  0  0
 26 24  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 34 33  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 41 40  1  1  0  0  0
 26 41  1  0  0  0  0
 41 34  1  0  0  0  0
 28 42  1  0  0  0  0
 42 15  1  0  0  0  0
 42 43  1  1  0  0  0
 15 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
M  END


  Mrv1652309052222222D          

 45 48  0  0  1  0            999 V2000
   -4.9906   -8.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110   -8.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5874   -7.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078   -8.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842   -7.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046   -7.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7810   -7.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0014   -7.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -8.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -8.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5577   -8.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372   -8.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -9.2864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -7.9362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7404   -8.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4704   -8.9858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9066   -9.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463  -10.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9499  -10.5646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826  -10.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791  -10.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8223  -11.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585  -12.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0105   -9.6094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2502  -10.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -9.4535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4931  -10.2107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0906   -8.6740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8685   -8.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5684   -8.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2656   -8.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9962   -8.7779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6633   -9.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0818  -10.2405    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8727  -10.4753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498  -11.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0020  -11.3870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5336  -11.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4437  -12.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229  -10.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2617  -10.1507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5506   -8.0503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0105   -7.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3474   -6.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181   -6.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 16 15  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 16  1  0  0  0  0
 24 25  1  6  0  0  0
 26 24  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 34 33  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 41 40  1  1  0  0  0
 26 41  1  0  0  0  0
 41 34  1  0  0  0  0
 28 42  1  0  0  0  0
 42 15  1  0  0  0  0
 42 43  1  1  0  0  0
 15 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219396

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC(=O)O[C@]12[C@H]([C@@H]3C=C(CO)C[C@@]4(O)[C@@H](C=C(C)C4=O)[C@@]3(O)[C@H](C)[C@H]1OC(=O)C(C)CC)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C37H58O8/c1-8-10-11-12-13-14-15-16-17-18-29(39)45-37-30(34(37,6)7)27-20-26(22-38)21-35(42)28(19-24(4)31(35)40)36(27,43)25(5)32(37)44-33(41)23(3)9-2/h19-20,23,25,27-28,30,32,38,42-43H,8-18,21-22H2,1-7H3/t23?,25-,27+,28-,30-,32-,35-,36-,37-/m1/s1

> <INCHI_KEY>
HNUDFMQYCDPTHE-QPUDZDCCSA-N

> <FORMULA>
C37H58O8

> <MOLECULAR_WEIGHT>
630.863

> <EXACT_MASS>
630.413168828

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
103

> <JCHEM_AVERAGE_POLARIZABILITY>
73.79618721135222

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl dodecanoate

> <JCHEM_LOGP>
6.491112698666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.933225578957437

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.570370235711003

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7316135464895774

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
173.91870000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl dodecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.316 -15.318   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.861 -15.822   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.696 -14.814   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.241 -15.318   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.077 -14.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.622 -14.814   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.458 -13.806   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.003 -14.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.288 -15.822   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.744 -16.326   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.908 -15.318   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.363 -15.822   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.654 -17.335   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.527 -14.814   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.982 -15.318   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.478 -16.773   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.426 -17.898   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.873 -19.371   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.373 -19.721   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.821 -20.496   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.321 -20.146   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.268 -21.969   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.216 -23.094   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.486 -17.938   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.934 -19.411   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.998 -17.647   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.387 -19.060   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.503 -16.191   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.955 -15.678   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.261 -16.493   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.562 -15.670   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.926 -16.385   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.438 -18.023   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.353 -19.116   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.829 -19.554   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.666 -20.623   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      13.070 -21.256   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.329 -21.387   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.162 -22.918   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.189 -20.352   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.822 -18.948   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.494 -15.027   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.486 -13.863   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.115 -12.457   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.380 -12.791   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   42   43                                             
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   16   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   41                                             
CONECT   27   26                                                            
CONECT   28   26   29   42                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34                                                       
CONECT   34   33   35   36   41                                             
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   26   34                                                  
CONECT   42   28   15   43                                                  
CONECT   43   42   15   44   45                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Value	Source
12-O-(2-Methylbutyroyl)phorbol-13-dodecanoic acid	Generator

Chemical Formula

C₃₇H₅₈O₈

Average Mass

630.8630 Da

Monoisotopic Mass

630.41317 Da

IUPAC Name

(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl dodecanoate

Traditional Name

(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl dodecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(=O)O[C@]12[C@H]([C@@H]3C=C(CO)C[C@@]4(O)[C@@H](C=C(C)C4=O)[C@@]3(O)[C@H](C)[C@H]1OC(=O)C(C)CC)C2(C)C

InChI Identifier

InChI=1S/C37H58O8/c1-8-10-11-12-13-14-15-16-17-18-29(39)45-37-30(34(37,6)7)27-20-26(22-38)21-35(42)28(19-24(4)31(35)40)36(27,43)25(5)32(37)44-33(41)23(3)9-2/h19-20,23,25,27-28,30,32,38,42-43H,8-18,21-22H2,1-7H3/t23?,25-,27+,28-,30-,32-,35-,36-,37-/m1/s1

InChI Key

HNUDFMQYCDPTHE-QPUDZDCCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Croton tiglium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Phorbol esters

Alternative Parents

Substituents

Phorbol ester
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary 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	6.49	ChemAxon
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	173.92 m³·mol⁻¹	ChemAxon
Polarizability	73.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

418354

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

476549

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate (NP0219396)

MOL for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)

3D MOL for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)

3D SDF for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)

3D-SDF for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)

PDB for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)

3D PDB for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)

SMILES for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)

INCHI for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)

Structure for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)

3D Structure for NP0219396 ((1s,2s,6r,10s,11r,13s,14r,15r)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-[(2-methylbutanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl dodecanoate)