(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-4-yl 2-chloro-6-methylbenzoate

ID: ALA3105105

PubChem CID: 68036574

Max Phase: Preclinical

Molecular Formula: C28H33ClO6

Molecular Weight: 501.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C[C@]23C(=O)[C@@H](C=C(CO)[C@@H](O)[C@]2(O)[C@H]1OC(=O)c1c(C)cccc1Cl)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C28H33ClO6/c1-13-7-6-8-19(29)20(13)25(33)35-24-14(2)11-27-15(3)9-18-21(26(18,4)5)17(23(27)32)10-16(12-30)22(31)28(24,27)34/h6-8,10-11,15,17-18,21-22,24,30-31,34H,9,12H2,1-5H3/t15-,17+,18-,21+,22-,24+,27+,28+/m1/s1

Standard InChI Key:  OPNQZGLIFZOFCT-BPQFZFCWSA-N

Molfile:  

     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
    8.9055  -10.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9484   -8.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3227   -9.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6220   -8.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8717  -10.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6266  -10.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2528  -11.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4719  -11.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1602   -9.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6789  -10.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1044  -11.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5520   -9.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4096   -8.9255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8795  -10.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7191  -11.8690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6982  -11.7393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2578  -12.2550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7273  -11.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5259  -11.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2328   -8.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3888   -8.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6965   -9.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1829   -8.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3811   -7.6709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2588   -9.7824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3839   -7.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9562   -8.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0170  -10.3124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020  -11.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5044  -12.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6871  -12.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896  -13.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7092  -14.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5304  -14.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9243  -13.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4825  -11.1803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7413  -13.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2693  -11.9023    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 22  3  1  0
 21  4  1  0
  2  4  1  0
  5  1  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  5  8  1  0
  9 10  2  0
 10 11  1  0
  5 11  1  0
  1  9  1  6
  3 12  1  0
  1 12  1  0
 12 13  2  0
 10 14  1  0
 11 15  1  1
  5 16  1  1
  8 17  1  1
  7 18  1  0
 18 19  1  0
  2 20  1  6
 22 21  1  0
 23 22  1  0
 21 23  1  0
 21 24  1  6
 22 25  1  6
 23 26  1  0
 23 27  1  0
  3 28  1  1
 15 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 29 36  2  0
 35 37  1  0
 31 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3105105

   [(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] 2-chloro-6-methylbenzoate

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: 501.02

Molecular Weight (Monoisotopic): 500.1966

AlogP: 3.64

#Rotatable Bonds: 3

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.13

CX Basic pKa: ┄

CX LogP: 3.91

CX LogD: 3.91

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.43

Np Likeness Score: 2.42

References

1. Grue-Sørensen G, Liang X, Månsson K, Vedsø P, Dahl Sørensen M, Soor A, Stahlhut M, Bertelsen M, Engell KM, Högberg T..  (2014)  Synthesis, biological evaluation and SAR of 3-benzoates of ingenol for treatment of actinic keratosis and non-melanoma skin cancer.,  24  (1): [PMID:24332494] [10.1016/j.bmcl.2013.11.073]

Source

Source(1):

• Scientific Literature