(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-(benzylamino)-6-methylbenzoate

ID: ALA3105024

PubChem CID: 68036627

Max Phase: Preclinical

Molecular Formula: C35H41NO6

Molecular Weight: 571.71

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)cccc1NCc1ccccc1)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C35H41NO6/c1-19-10-9-13-26(36-17-22-11-7-6-8-12-22)27(19)32(40)42-31-20(2)16-34-21(3)14-25-28(33(25,4)5)24(30(34)39)15-23(18-37)29(38)35(31,34)41/h6-13,15-16,21,24-25,28-29,31,36-38,41H,14,17-18H2,1-5H3/t21-,24+,25-,28+,29-,31+,34+,35+/m1/s1

Standard InChI Key:  FFSAGCGDCQPIAA-VNEGOSELSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3105024

   [(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-(benzylamino)-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: 571.71

Molecular Weight (Monoisotopic): 571.2934

AlogP: 4.60

#Rotatable Bonds: 6

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: 1.49

CX LogP: 5.15

CX LogD: 5.15

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.30

Np Likeness Score: 1.90

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