(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-aminobenzoate

ID: ALA3105097

PubChem CID: 76317401

Max Phase: Preclinical

Molecular Formula: C27H33NO6

Molecular Weight: 467.56

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)c1ccccc1N)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C27H33NO6/c1-13-11-26-14(2)9-18-20(25(18,3)4)17(22(26)31)10-15(12-29)21(30)27(26,33)23(13)34-24(32)16-7-5-6-8-19(16)28/h5-8,10-11,14,17-18,20-21,23,29-30,33H,9,12,28H2,1-4H3/t14-,17+,18-,20+,21-,23+,26+,27+/m1/s1

Standard InChI Key:  QAGNFHNGTPNOJC-QVFPCUKTSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA3105097

   [(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-aminobenzoate

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: 467.56

Molecular Weight (Monoisotopic): 467.2308

AlogP: 2.26

#Rotatable Bonds: 3

Polar Surface Area: 130.08

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.13

CX Basic pKa: 2.10

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: 2.73

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