(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 naphthalene-2-carboxylate

ID: ALA3105027

PubChem CID: 76324779

Max Phase: Preclinical

Molecular Formula: C31H34O6

Molecular Weight: 502.61

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)c1ccc2ccccc2c1)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C31H34O6/c1-16-14-30-17(2)11-23-24(29(23,3)4)22(26(30)34)13-21(15-32)25(33)31(30,36)27(16)37-28(35)20-10-9-18-7-5-6-8-19(18)12-20/h5-10,12-14,17,22-25,27,32-33,36H,11,15H2,1-4H3/t17-,22+,23-,24+,25-,27+,30+,31+/m1/s1

Standard InChI Key:  IXYHNFDSJUFSHJ-ACECJHEDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3105027

   [(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] naphthalene-2-carboxylate

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: 502.61

Molecular Weight (Monoisotopic): 502.2355

AlogP: 3.83

#Rotatable Bonds: 3

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.13

CX Basic pKa: ┄

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.44

Np Likeness Score: 2.48

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]

2. Liu Q, Li W, Huang L, Asada Y, Morris-Natschke SL, Chen CH, Lee KH, Koike K..  (2018)  Identification, structural modification, and dichotomous effects on human immunodeficiency virus type 1 (HIV-1) replication of ingenane esters from Euphorbia kansui.,  156  [PMID:30031972] [10.1016/j.ejmech.2018.07.020]

Source

Source(1):

• Scientific Literature