5-(3-bromobenzylidene)-3-(2-((1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decahydronaphthalen-1-yl)vinyl)furan-2(5H)-one

ID: ALA207747

Chembl Id: CHEMBL207747

PubChem CID: 44411420

Max Phase: Preclinical

Molecular Formula: C27H31BrO4

Molecular Weight: 499.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1/C=C/C1=C/C(=C/c2cccc(Br)c2)OC1=O

Standard InChI:  InChI=1S/C27H31BrO4/c1-17-7-10-23-26(2,12-11-24(30)27(23,3)16-29)22(17)9-8-19-15-21(32-25(19)31)14-18-5-4-6-20(28)13-18/h4-6,8-9,13-15,22-24,29-30H,1,7,10-12,16H2,2-3H3/b9-8+,21-14-/t22-,23+,24-,26+,27+/m1/s1

Standard InChI Key:  VCHJXZHYNNUKQU-JWFBKGCASA-N

Alternative Forms

1. Parent:

   

   ALA207747

   (5Z)-3-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-5-[(3-bromophenyl)methylidene]furan-2-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: 499.45

Molecular Weight (Monoisotopic): 498.1406

AlogP: 5.57

#Rotatable Bonds: 4

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.97

CX LogD: 4.97

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: 2.33

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. Xu HW, Dai GF, Liu GZ, Wang JF, Liu HM..  (2007)  Synthesis of andrographolide derivatives: a new family of alpha-glucosidase inhibitors.,  15  (12): [PMID:17428667] [10.1016/j.bmc.2007.03.063]

Source

Source(1):

• Scientific Literature