(5Z)-3-[(E)-2-[(1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-octahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl]ethenyl]-5-[(2E)-3-phenylprop-2-en-1-ylidene]-2,5-dihydrofuran-2-one

ID: ALA205969

Chembl Id: CHEMBL205969

PubChem CID: 44411115

Max Phase: Preclinical

Molecular Formula: C29H34O5

Molecular Weight: 462.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(CO)[C@H]2CC[C@@]3(CO3)[C@@H](/C=C/C3=C/C(=C/C=C/c4ccccc4)OC3=O)[C@]2(C)CC[C@H]1O

Standard InChI:  InChI=1S/C29H34O5/c1-27-15-14-25(31)28(2,18-30)23(27)13-16-29(19-33-29)24(27)12-11-21-17-22(34-26(21)32)10-6-9-20-7-4-3-5-8-20/h3-12,17,23-25,30-31H,13-16,18-19H2,1-2H3/b9-6+,12-11+,22-10-/t23-,24-,25+,27+,28-,29+/m0/s1

Standard InChI Key:  HHKMCAJXRQBLRD-YLNSPZMLSA-N

Alternative Forms

1. Parent:

   

   ALA205969

   (5Z)-3-[(E)-2-[(1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]ethenyl]-5-[(E)-3-phenylprop-2-enylidene]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: 462.59

Molecular Weight (Monoisotopic): 462.2406

AlogP: 4.58

#Rotatable Bonds: 5

Polar Surface Area: 79.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.49

Np Likeness Score: 2.49

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]

Source

Source(1):

• Scientific Literature