NP-MRD: Showing NP-Card for 12-O-tetradecanoylphorbol-13-acetate (NP0137754)

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Record Information

Version

2.0

Created at

2022-05-31 16:32:07 UTC

Updated at

2022-05-31 16:32:07 UTC

NP-MRD ID

NP0137754

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-O-tetradecanoylphorbol-13-acetate

Description

Phorbol 13-acetate 12-myristate, also known as 12-tetradecanoylphorbol 13-acetate or phorbol 12-myristate 13-acetate, belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. 12-O-tetradecanoylphorbol-13-acetate is found in Croton alnifolius, Croton tiglium, Euphorbia turczaninowii, Leptolyngbya tenuis and Wisteria brachybotrys. 12-O-tetradecanoylphorbol-13-acetate was first documented in 2002 (PMID: 12421969). Based on a literature review a small amount of articles have been published on phorbol 13-acetate 12-myristate (PMID: 15721302) (PMID: 15822940) (PMID: 16740769).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218322D          

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M  END

     RDKit          3D

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 13 70  1  0
 13 71  1  0
 12 68  1  0
 12 69  1  0
 11 66  1  0
 11 67  1  0
 10 64  1  0
 10 65  1  0
  9 62  1  0
  9 63  1  0
  8 60  1  0
  8 61  1  0
  7 58  1  0
  7 59  1  0
  6 56  1  0
  6 57  1  0
  5 54  1  0
  5 55  1  0
  4 52  1  0
  4 53  1  0
  3 50  1  0
  3 51  1  0
  2 48  1  0
  2 49  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
 43 98  1  0
 43 99  1  0
 43100  1  0
 38 92  1  0
 38 93  1  0
 38 94  1  0
 39 95  1  0
 39 96  1  0
 39 97  1  0
M  END


  Mrv1652305312218322D          

 49 52  0  0  1  0            999 V2000
   -0.4706   -5.0690    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581   -4.3545    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7726   -3.9420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5159   -3.5841    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -4.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2219   -4.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7363   -4.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5521   -4.7949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799   -3.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2219   -2.7862    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0461   -2.8232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6451   -2.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4668   -2.0041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1023   -1.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859   -0.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3437   -1.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -2.6027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6012   -3.4070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7726   -3.1170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7110   -2.2943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581   -2.7045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6563   -2.2920    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581   -1.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -3.1170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3708   -3.5295    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3708   -2.7045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853   -3.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853   -3.9420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7997   -2.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5142   -3.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287   -2.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -3.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6576   -2.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3721   -3.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0866   -2.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8010   -3.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5155   -2.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2300   -3.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9444   -2.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6589   -3.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3734   -2.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -3.9420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4813   -3.9420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8938   -4.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7188   -4.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4813   -5.3710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -4.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0563   -5.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5844   -5.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 21 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 24 42  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
 42 47  1  0  0  0  0
  2 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137754

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1

> <INCHI_KEY>
PHEDXBVPIONUQT-RGYGYFBISA-N

> <FORMULA>
C36H56O8

> <MOLECULAR_WEIGHT>
616.836

> <EXACT_MASS>
616.397518763

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
72.22581731074082

> <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)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl tetradecanoate

> <JCHEM_LOGP>
5.692159238333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.933225775162544

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.570370247698069

> <JCHEM_PKA_STRONGEST_BASIC>
-2.731613546488827

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
169.31830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0      -0.879  -9.462   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -0.109  -8.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.442  -7.358   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      -2.830  -6.690   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      -2.646  -8.319   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.148  -7.976   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.108  -9.180   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -6.631  -8.950   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.816  -6.588   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.148  -5.201   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.686  -5.270   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.937  -3.879   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.471  -3.741   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.924  -2.719   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.267  -1.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.508  -3.324   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.646  -4.858   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      -2.989  -6.360   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      -1.442  -5.818   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.327  -4.283   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.109  -5.048   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       1.225  -4.278   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      -0.109  -3.508   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.225  -5.818   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       2.559  -6.588   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0       2.559  -5.048   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.892  -5.818   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.892  -7.358   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.226  -5.048   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.560  -5.818   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.894  -5.048   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.227  -5.818   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.561  -5.048   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.895  -5.818   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.228  -5.048   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.562  -5.818   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.896  -5.048   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.229  -5.818   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      18.563  -5.048   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      19.897  -5.818   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.230  -5.048   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.225  -7.358   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.765  -7.358   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       3.535  -8.692   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.075  -8.692   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       2.765 -10.026   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       1.225  -8.898   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.972 -10.245   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.091 -10.433   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   42   47                                             
CONECT    3    2    4    5   19                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    3   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   26   42                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   24    2   43   47                                             
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   42    2   48   49                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  104    0
END

View in JSmol

Synonyms

Value	Source
12-O-Tetradecanoylphorbol 13-acetate	ChEBI
12-Tetradecanoylphorbol 13-acetate	ChEBI
Phorbol 12-myristate 13-acetate	ChEBI
Phorbol 12-tetradecanoate 13-acetate	ChEBI
Phorbol-12-myristate-13-acetate	ChEBI
PMA	ChEBI
Tetradecanoylphorbol acetate	ChEBI
TPA	ChEBI
12-O-Tetradecanoylphorbol 13-acetic acid	Generator
12-Tetradecanoylphorbol 13-acetic acid	Generator
Phorbol 12-myristic acid 13-acetic acid	Generator
Phorbol 12-tetradecanoic acid 13-acetic acid	Generator
Phorbol-12-myristic acid-13-acetic acid	Generator
Tetradecanoylphorbol acetic acid	Generator
Phorbol 13-acetic acid 12-myristic acid	Generator
12-O-Tetradecanoyl phorbol 13-acetate	MeSH
Tetradecanoylphorbol acetate, 4a alpha isomer	MeSH
13-Acetate, 12-O-tetradecanoyl phorbol	MeSH
Acetate, tetradecanoylphorbol	MeSH
Phorbol 13-acetate, 12-O-tetradecanoyl	MeSH
Phorbol myristate acetate	MeSH
Acetate, phorbol myristate	MeSH
Tetradecanoylphorbol acetate, 4a alpha-isomer	MeSH
12 Myristoyl 13 acetylphorbol	MeSH
12 O Tetradecanoyl phorbol 13 acetate	MeSH
12-Myristoyl-13-acetylphorbol	MeSH
Myristate acetate, phorbol	MeSH

Chemical Formula

C₃₆H₅₆O₈

Average Mass

616.8360 Da

Monoisotopic Mass

616.39752 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

16561-29-8

SMILES

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

InChI Identifier

InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1

InChI Key

PHEDXBVPIONUQT-RGYGYFBISA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Croton alnifolius	LOTUS Database	35616633
Croton tiglium	LOTUS Database	35616633
Euphorbia turczaninowii	LOTUS Database	35616633
Leptolyngbya tenuis	LOTUS Database	35616633
Wisteria brachybotrys	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

phorbol ester (CHEBI:37537 )
Tigliane and ingenane diterpenoids (C05151 )
Tiglianes (C05151 )
Tigliane and ingenane diterpenoids (LMPR0104330002 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

12-O-Tetradecanoylphorbol-13-acetate

METLIN ID

Not Available

PubChem Compound

27924

PDB ID

Not Available

ChEBI ID

37537

Good Scents ID

Not Available

References

General References

Swindle EJ, Hunt JA, Coleman JW: A comparison of reactive oxygen species generation by rat peritoneal macrophages and mast cells using the highly sensitive real-time chemiluminescent probe pholasin: inhibition of antigen-induced mast cell degranulation by macrophage-derived hydrogen peroxide. J Immunol. 2002 Nov 15;169(10):5866-73. doi: 10.4049/jimmunol.169.10.5866. [PubMed:12421969 ]
Jorgensen K, Skrede M, Cruciani V, Mikalsen SO, Slipicevic A, Florenes VA: Phorbol ester phorbol-12-myristate-13-acetate promotes anchorage-independent growth and survival of melanomas through MEK-independent activation of ERK1/2. Biochem Biophys Res Commun. 2005 Apr 1;329(1):266-74. doi: 10.1016/j.bbrc.2005.01.143. [PubMed:15721302 ]
Jiang P, Gan M, Huang H, Shen X, Wang S, Yao K: Proteome analysis of antiproliferative mechanism of 12-O-tetradecanoylphorbol 13-acetate on cultured nasopharyngeal carcinoma CNE2 cells. J Proteome Res. 2005 Mar-Apr;4(2):599-605. doi: 10.1021/pr0497677. [PubMed:15822940 ]
Zheng X, Chang RL, Cui XX, Avila GE, Hebbar V, Garzotto M, Shih WJ, Lin Y, Lu SE, Rabson AB, Kong AN, Conney AH: Effects of 12-O-tetradecanoylphorbol-13-acetate (TPA) in combination with paclitaxel (Taxol) on prostate Cancer LNCaP cells cultured in vitro or grown as xenograft tumors in immunodeficient mice. Clin Cancer Res. 2006 Jun 1;12(11 Pt 1):3444-51. doi: 10.1158/1078-0432.CCR-05-2823. [PubMed:16740769 ]

Showing NP-Card for 12-O-tetradecanoylphorbol-13-acetate (NP0137754)

MOL for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)

3D MOL for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)

3D SDF for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)

3D-SDF for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)

PDB for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)

3D PDB for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)

SMILES for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)

INCHI for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)

Structure for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)

3D Structure for NP0137754 (12-O-tetradecanoylphorbol-13-acetate)