(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 2,6-dichlorobenzoate

ID: ALA3105104

PubChem CID: 68036617

Max Phase: Preclinical

Molecular Formula: C27H30Cl2O6

Molecular Weight: 521.44

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(Cl)cccc1Cl)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C27H30Cl2O6/c1-12-10-26-13(2)8-16-20(25(16,3)4)15(22(26)32)9-14(11-30)21(31)27(26,34)23(12)35-24(33)19-17(28)6-5-7-18(19)29/h5-7,9-10,13,15-16,20-21,23,30-31,34H,8,11H2,1-4H3/t13-,15+,16-,20+,21-,23+,26+,27+/m1/s1

Standard InChI Key:  WCRDBPZZXRNSOP-VZNJPERDSA-N

Molfile:  

     RDKit          2D

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    8.8717  -10.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5259  -11.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   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
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    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 Cl  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
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  2  4  1  0
  5  1  1  0
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  6  7  2  0
  7  8  1  0
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  9 10  2  0
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  1  9  1  6
  3 12  1  0
  1 12  1  0
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  7 18  1  0
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  2 20  1  6
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 21 23  1  0
 21 24  1  6
 22 25  1  6
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  3 28  1  1
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 32 33  2  0
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 31 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3105104

   [(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] 2,6-dichlorobenzoate

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: 521.44

Molecular Weight (Monoisotopic): 520.1419

AlogP: 3.99

#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: 4.00

CX LogD: 4.00

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.41

Np Likeness Score: 2.46

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