4alpha-Phorbol 12,13-dinonanoate

ID: ALA130626

PubChem CID: 42638084

Max Phase: Preclinical

Molecular Formula: C38H60O8

Molecular Weight: 644.89

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4Alpha-Phorbol 12,13-Dinonanoate | CHEMBL130626|4alpha-Phorbol 12,13-dinonanoate|BDBM50277489

Canonical SMILES:  CCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@@H](C=C(CO)C[C@@]3(O)C(=O)C(C)=C[C@@H]23)[C@@H]2C(C)(C)[C@]12OC(=O)CCCCCCCC

Standard InChI:  InChI=1S/C38H60O8/c1-7-9-11-13-15-17-19-30(40)45-34-26(4)37(44)28(22-27(24-39)23-36(43)29(37)21-25(3)33(36)42)32-35(5,6)38(32,34)46-31(41)20-18-16-14-12-10-8-2/h21-22,26,28-29,32,34,39,43-44H,7-20,23-24H2,1-6H3/t26-,28+,29-,32-,34-,36+,37-,38-/m1/s1

Standard InChI Key:  MCOPJFWROQYMMR-VUQSLQLNSA-N

Molfile:  

     RDKit          2D

 49 52  0  0  0  0  0  0  0  0999 V2000
    1.4328  -27.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0448  -27.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8684  -27.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5961  -25.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3095  -26.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3104  -24.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934  -25.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186  -27.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694  -26.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441  -25.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103  -26.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2473  -27.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0936  -25.4779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9915  -26.8103    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671  -28.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9825  -28.6613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8375  -27.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417  -26.6417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972  -25.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7264  -27.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3126  -23.8806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210  -24.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0239  -25.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0173  -25.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7307  -25.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000  -26.5208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292  -24.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992  -23.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6013  -22.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541  -24.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6592  -23.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6740  -25.1016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125  -26.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542  -25.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164  -23.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298  -23.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453  -23.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587  -23.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742  -23.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877  -23.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3968  -23.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1118  -23.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4842  -23.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8892  -22.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7142  -22.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1193  -22.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9442  -22.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3493  -21.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1743  -21.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 23 25  1  0
  5  1  1  0
  9  4  1  0
  9 10  1  0
 10 11  2  0
 24 26  1  6
 11 12  1  0
 23 27  1  6
 12  8  1  0
 21 28  1  0
  8  2  1  0
 28 29  2  0
  4 13  1  6
 27 30  1  0
 30 31  1  0
  5 14  1  1
 30 32  2  0
  4  7  1  0
 25 33  1  0
  3 15  1  0
 25 34  1  0
  5 24  1  0
 28 35  1  0
 15 16  1  0
 35 36  1  0
 23  6  1  0
 36 37  1  0
  8 17  1  6
 37 38  1  0
  6  7  1  0
 38 39  1  0
  9 18  1  6
 39 40  1  0
  8  9  1  0
 40 41  1  0
 11 19  1  0
 41 42  1  0
  1  3  2  0
 31 43  1  0
 12 20  2  0
 43 44  1  0
  2  3  1  0
 44 45  1  0
  6 21  1  1
 45 46  1  0
  4  5  1  0
 46 47  1  0
  7 22  1  6
 47 48  1  0
 24 23  1  0
 48 49  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA130626

   4alpha-Phorbol 12,13-dinonanoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 644.89

Molecular Weight (Monoisotopic): 644.4288

AlogP: 6.53

#Rotatable Bonds: 17

Polar Surface Area: 130.36

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.57

CX Basic pKa: ┄

CX LogP: 6.84

CX LogD: 6.84

Aromatic Rings: ┄

Heavy Atoms: 46

QED Weighted: 0.09

Np Likeness Score: 2.21

References

1. Klausen TK, Pagani A, Minassi A, Ech-Chahad A, Prenen J, Owsianik G, Hoffmann EK, Pedersen SF, Appendino G, Nilius B..  (2009)  Modulation of the transient receptor potential vanilloid channel TRPV4 by 4alpha-phorbol esters: a structure-activity study.,  52  (9): [PMID:19361196] [10.1021/jm9001007]

Source

Source(1):

• Scientific Literature