(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-methylbenzoate

ID: ALA3105090

PubChem CID: 68036691

Max Phase: Preclinical

Molecular Formula: C28H34O6

Molecular Weight: 466.57

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)c1ccccc1C)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C28H34O6/c1-14-8-6-7-9-18(14)25(32)34-24-15(2)12-27-16(3)10-20-21(26(20,4)5)19(23(27)31)11-17(13-29)22(30)28(24,27)33/h6-9,11-12,16,19-22,24,29-30,33H,10,13H2,1-5H3/t16-,19+,20-,21+,22-,24+,27+,28+/m1/s1

Standard InChI Key:  PLCYLDKOPKFRJP-PBQDKQMHSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA3105090

   [(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-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: 466.57

Molecular Weight (Monoisotopic): 466.2355

AlogP: 2.99

#Rotatable Bonds: 3

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.13

CX Basic pKa: ┄

CX LogP: 3.30

CX LogD: 3.30

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.47

Np Likeness Score: 2.54

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