(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-(methylamino)benzoate

ID: ALA3102881

PubChem CID: 68036707

Max Phase: Preclinical

Molecular Formula: C28H34ClNO6

Molecular Weight: 516.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1cccc(Cl)c1C(=O)O[C@H]1C(C)=C[C@]23C(=O)[C@@H](C=C(CO)[C@@H](O)[C@]12O)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C28H34ClNO6/c1-13-11-27-14(2)9-17-21(26(17,3)4)16(23(27)33)10-15(12-31)22(32)28(27,35)24(13)36-25(34)20-18(29)7-6-8-19(20)30-5/h6-8,10-11,14,16-17,21-22,24,30-32,35H,9,12H2,1-5H3/t14-,16+,17-,21+,22-,24+,27+,28+/m1/s1

Standard InChI Key:  NCKXXTVKZTZRMQ-XUBYYPQFSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3102881

   [(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-(methylamino)benzoate

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: 516.03

Molecular Weight (Monoisotopic): 515.2075

AlogP: 3.38

#Rotatable Bonds: 4

Polar Surface Area: 116.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.13

CX Basic pKa: 1.73

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.36

Np Likeness Score: 2.31

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