Ingenol 3-(2-methylaminobenzoate)

ID: ALA3105098

PubChem CID: 76310178

Max Phase: Preclinical

Molecular Formula: C28H35NO6

Molecular Weight: 481.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1ccccc1C(=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/C28H35NO6/c1-14-12-27-15(2)10-19-21(26(19,3)4)18(23(27)32)11-16(13-30)22(31)28(27,34)24(14)35-25(33)17-8-6-7-9-20(17)29-5/h6-9,11-12,15,18-19,21-22,24,29-31,34H,10,13H2,1-5H3/t15-,18+,19-,21+,22-,24+,27+,28+/m1/s1

Standard InChI Key:  GBNPWIIHHOENSI-YXKOJEMPSA-N

Molfile:  

     RDKit          2D

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  1  2  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3105098

   [(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-(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: 481.59

Molecular Weight (Monoisotopic): 481.2464

AlogP: 2.72

#Rotatable Bonds: 4

Polar Surface Area: 116.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.13

CX Basic pKa: 2.12

CX LogP: 2.91

CX LogD: 2.91

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.39

Np Likeness Score: 2.53

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