(S)-3-(2-((4aR,6aS,7R,10aS,10bR)-3-(3-bromophenyl)-6a,10b-dimethyl-8-methylene-decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)-4-hydroxy-dihydrofuran-2(3H)-one

ID: ALA379280

Chembl Id: CHEMBL379280

PubChem CID: 44411113

Max Phase: Preclinical

Molecular Formula: C27H33BrO5

Molecular Weight: 517.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2[C@]3(C)COC(c4cccc(Br)c4)O[C@@H]3CC[C@@]2(C)[C@@H]1C/C=C1/C(=O)OC[C@H]1O

Standard InChI:  InChI=1S/C27H33BrO5/c1-16-7-10-22-26(2,20(16)9-8-19-21(29)14-31-24(19)30)12-11-23-27(22,3)15-32-25(33-23)17-5-4-6-18(28)13-17/h4-6,8,13,20-23,25,29H,1,7,9-12,14-15H2,2-3H3/b19-8+/t20-,21-,22+,23-,25?,26+,27+/m1/s1

Standard InChI Key:  BDVGVXANMCQRAX-OPDNHIMUSA-N

Alternative Forms

1. Parent:

   

   ALA379280

   (S)-3-(2-((4aR,6aS,7R,10aS,10bR)-3-(3-bromophenyl)-6a,10b-dimethyl-8-methylene-decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)-4-hydroxy-dihydrofuran-2(3H)-one

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: 517.46

Molecular Weight (Monoisotopic): 516.1511

AlogP: 5.49

#Rotatable Bonds: 3

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.52

CX Basic pKa: ┄

CX LogP: 5.60

CX LogD: 5.60

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 2.39

References

1. Dai GF, Xu HW, Wang JF, Liu FW, Liu HM..  (2006)  Studies on the novel alpha-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues.,  16  (10): [PMID:16504503] [10.1016/j.bmcl.2006.02.011]

2. Korzeniecki C, Priefer R..  (2021)  Targeting KRAS mutant cancers by preventing signaling transduction in the MAPK pathway.,  211  [PMID:33228976] [10.1016/j.ejmech.2020.113006]

Source

Source(1):

• Scientific Literature