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

ID: ALA208244

Chembl Id: CHEMBL208244

PubChem CID: 44411425

Max Phase: Preclinical

Molecular Formula: C28H36O6

Molecular Weight: 468.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2[C@]3(C)COC(c4ccc(OC)cc4)O[C@@H]3CC[C@@]2(C)[C@@H]1C/C=C1/C(=O)OC[C@H]1O

Standard InChI:  InChI=1S/C28H36O6/c1-17-5-12-23-27(2,21(17)11-10-20-22(29)15-32-25(20)30)14-13-24-28(23,3)16-33-26(34-24)18-6-8-19(31-4)9-7-18/h6-10,21-24,26,29H,1,5,11-16H2,2-4H3/b20-10+/t21-,22-,23+,24-,26?,27+,28+/m1/s1

Standard InChI Key:  GGQLCHJDKBKVJS-PHQQLAFWSA-N

Alternative Forms

1. Parent:

   

   ALA208244

   (3E,4S)-3-[2-[(4aR,6aS,7R,10aS,10bR)-3-(4-methoxyphenyl)-6a,10b-dimethyl-8-methylidene-1,4a,5,6,7,9,10,10a-octahydronaphtho[2,1-d][1,3]dioxin-7-yl]ethylidene]-4-hydroxyoxolan-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: 468.59

Molecular Weight (Monoisotopic): 468.2512

AlogP: 4.73

#Rotatable Bonds: 4

Polar Surface Area: 74.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.52

CX Basic pKa: ┄

CX LogP: 4.67

CX LogD: 4.67

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.39

Np Likeness Score: 2.47

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