(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-amino-6-fluorobenzoate

ID: ALA3105109

PubChem CID: 68036696

Max Phase: Preclinical

Molecular Formula: C27H32FNO6

Molecular Weight: 485.55

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(N)cccc1F)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C27H32FNO6/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,8,11,29H2,1-4H3/t13-,15+,16-,20+,21-,23+,26+,27+/m1/s1

Standard InChI Key:  ARVNFCMZJZSEMH-VZNJPERDSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA3105109

   [(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-amino-6-fluorobenzoate

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: 485.55

Molecular Weight (Monoisotopic): 485.2214

AlogP: 2.40

#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: 1.42

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.29

Np Likeness Score: 2.42

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