NP-MRD: Showing NP-Card for (1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate (NP0221676)

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Record Information

Version

2.0

Created at

2022-09-05 23:19:12 UTC

Updated at

2022-09-05 23:19:12 UTC

NP-MRD ID

NP0221676

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate

Description

12-Deoxyphorbaldehyde-13-(9Z)-octadecanoate-20-acetate belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. (1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate is found in Euphorbia fischeriana. Based on a literature review very few articles have been published on 12-Deoxyphorbaldehyde-13-(9Z)-octadecanoate-20-acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201192D          

 47 50  0  0  1  0            999 V2000
   -4.3218   -2.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5117   -1.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9716   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214   -3.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113   -2.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2712   -3.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390   -3.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791   -3.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -3.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1592   -3.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6191   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -1.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993   -1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394   -2.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496   -1.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3998   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6698   -1.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399   -3.0220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6698   -3.8016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8903   -3.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666   -4.0716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4871   -3.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4225   -4.8817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6653   -4.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2021   -5.1518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4770   -5.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403   -6.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4814   -7.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057   -7.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6889   -6.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5132   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2478   -5.8655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207   -6.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -6.1429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4008   -6.9338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278   -6.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890   -7.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4185   -5.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -5.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -4.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7254   -5.3229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8257   -4.6117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4494   -4.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2024   -4.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0236   -3.4792    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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
 23 24  1  6  0  0  0
 25 23  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  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
 32 34  2  0  0  0  0
 29 35  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 43 42  1  1  0  0  0
 43 36  1  0  0  0  0
 25 43  1  0  0  0  0
 27 44  1  0  0  0  0
 44 21  1  0  0  0  0
 44 45  1  1  0  0  0
 21 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
M  END


  Mrv1652309062201192D          

 47 50  0  0  1  0            999 V2000
   -4.3218   -2.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5117   -1.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9716   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214   -3.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113   -2.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2712   -3.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390   -3.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791   -3.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -3.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1592   -3.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6191   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -1.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993   -1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394   -2.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496   -1.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3998   -2.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6698   -1.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399   -3.0220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6698   -3.8016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8903   -3.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666   -4.0716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4871   -3.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4225   -4.8817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6653   -4.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2021   -5.1518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4770   -5.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403   -6.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4814   -7.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057   -7.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6889   -6.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5132   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2478   -5.8655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207   -6.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -6.1429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4008   -6.9338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278   -6.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890   -7.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4185   -5.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -5.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -4.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7254   -5.3229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8257   -4.6117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4494   -4.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2024   -4.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0236   -3.4792    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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
 23 24  1  6  0  0  0
 25 23  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  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
 32 34  2  0  0  0  0
 29 35  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 43 42  1  1  0  0  0
 43 36  1  0  0  0  0
 25 43  1  0  0  0  0
 27 44  1  0  0  0  0
 44 21  1  0  0  0  0
 44 45  1  1  0  0  0
 21 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221676

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(=O)O[C@@]12C[C@@H](C)[C@]3(O)[C@@H]4C=C(C)C(=O)[C@@]4(O)CC(COC(C)=O)=C[C@H]3[C@@H]1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H62O7/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-34(42)47-39-25-29(3)40(45)32(35(39)37(39,5)6)24-31(27-46-30(4)41)26-38(44)33(40)23-28(2)36(38)43/h14-15,23-24,29,32-33,35,44-45H,7-13,16-22,25-27H2,1-6H3/b15-14-/t29-,32+,33-,35-,38-,39+,40-/m1/s1

> <INCHI_KEY>
FRLZOANJBWVXPT-LWDNIVNZSA-N

> <FORMULA>
C40H62O7

> <MOLECULAR_WEIGHT>
654.929

> <EXACT_MASS>
654.449554336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
79.41900315454576

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6R,10S,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl (9Z)-octadec-9-enoate

> <JCHEM_LOGP>
8.141859121666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.0376938454448

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.575740432290779

> <JCHEM_PKA_STRONGEST_BASIC>
-3.271835701321244

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
187.57620000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6R,10S,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl (9Z)-octadec-9-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.067  -3.895   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.555  -3.604   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.547  -4.768   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.035  -4.477   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.027  -5.641   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.514  -5.350   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.506  -6.514   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.006  -6.223   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.014  -7.387   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.526  -7.096   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.031  -5.641   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.022  -4.477   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.526  -3.022   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.039  -2.731   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.047  -3.895   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.559  -3.604   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.567  -4.768   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.080  -4.477   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.584  -3.022   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.088  -5.641   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.584  -7.096   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.128  -6.592   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.964  -7.600   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.509  -7.096   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.255  -9.113   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.842  -8.501   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.711  -9.617   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.224 -11.069   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.408 -12.375   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.232 -13.677   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.771 -13.614   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.486 -12.250   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.025 -12.188   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.663 -10.949   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.879 -12.552   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.786 -11.467   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.348 -12.943   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.279 -11.780   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.646 -13.185   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.514 -10.443   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.984 -10.276   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.550  -9.303   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.954  -9.936   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.875  -8.609   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.039  -7.600   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      13.445  -8.229   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.111  -6.495   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                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   44   45                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   43                                             
CONECT   26   25                                                            
CONECT   27   25   28   44                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29   36                                                       
CONECT   36   35   37   38   43                                             
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   36   25                                                  
CONECT   44   27   21   45                                                  
CONECT   45   44   21   46   47                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

View in JSmol

Synonyms

Value	Source
12-Deoxyphorbaldehyde-13-(9Z)-octadecanoic acid-20-acetic acid	Generator

Chemical Formula

C₄₀H₆₂O₇

Average Mass

654.9290 Da

Monoisotopic Mass

654.44955 Da

IUPAC Name

(1R,2S,6R,10S,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl (9Z)-octadec-9-enoate

Traditional Name

(1R,2S,6R,10S,11R,13S,15R)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl (9Z)-octadec-9-enoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)O[C@@]12C[C@@H](C)[C@]3(O)[C@@H]4C=C(C)C(=O)[C@@]4(O)CC(COC(C)=O)=C[C@H]3[C@@H]1C2(C)C

InChI Identifier

InChI=1S/C40H62O7/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-34(42)47-39-25-29(3)40(45)32(35(39)37(39,5)6)24-31(27-46-30(4)41)26-38(44)33(40)23-28(2)36(38)43/h14-15,23-24,29,32-33,35,44-45H,7-13,16-22,25-27H2,1-6H3/b15-14-/t29-,32+,33-,35-,38-,39+,40-/m1/s1

InChI Key

FRLZOANJBWVXPT-LWDNIVNZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia fischeriana	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
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	8.14	ChemAxon
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	187.58 m³·mol⁻¹	ChemAxon
Polarizability	79.42 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

9709550

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11534767

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate (NP0221676)

MOL for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)

3D MOL for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)

3D SDF for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)

3D-SDF for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)

PDB for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)

3D PDB for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)

SMILES for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)

INCHI for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)

Structure for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)

3D Structure for NP0221676 ((1r,2s,6r,10s,11r,13s,15r)-8-[(acetyloxy)methyl]-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl (9z)-octadec-9-enoate)