5-(4-fluorobenzylidene)-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: ALA206838

Chembl Id: CHEMBL206838

PubChem CID: 16121615

Max Phase: Preclinical

Molecular Formula: C27H31FO4

Molecular Weight: 438.54

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/c2ccc(F)cc2)OC1=O

Standard InChI:  InChI=1S/C27H31FO4/c1-17-4-11-23-26(2,13-12-24(30)27(23,3)16-29)22(17)10-7-19-15-21(32-25(19)31)14-18-5-8-20(28)9-6-18/h5-10,14-15,22-24,29-30H,1,4,11-13,16H2,2-3H3/b10-7+,21-14-/t22-,23+,24-,26+,27+/m1/s1

Standard InChI Key:  PLOBXVKQXDTHQC-BJYXGBJASA-N

Alternative Forms

1. Parent:

   

   ALA206838

   (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-[(4-fluorophenyl)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: 438.54

Molecular Weight (Monoisotopic): 438.2206

AlogP: 4.95

#Rotatable Bonds: 4

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: 2.27

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]

3. Wu ZW, Xu HW, Dai GF, Liu MJ, Zhu LP, Wu J, Wang YN, Wu FJ, Zhao D, Gao MF, Nie SS, Han W, Song JH, Liu HM..  (2013)  Improved inhibitory activities against tumor-cell migration and invasion by 15-benzylidene substitution derivatives of andrographolide.,  23  (23): [PMID:24120543] [10.1016/j.bmcl.2013.09.049]

Source

Source(1):

• Scientific Literature