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

ID: ALA206839

PubChem CID: 44411130

Max Phase: Preclinical

Molecular Formula: C27H42O5

Molecular Weight: 446.63

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H42O5/c1-5-6-7-8-9-24-31-17-27(4)22-13-10-18(2)20(26(22,3)15-14-23(27)32-24)12-11-19-21(28)16-30-25(19)29/h11,20-24,28H,2,5-10,12-17H2,1,3-4H3/b19-11+/t20-,21-,22+,23-,24?,26+,27+/m1/s1

Standard InChI Key:  DCXFVNBGNQKMPY-YGKPVBKJSA-N

Molfile:  

     RDKit          2D

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  4 34  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA206839

   (3E,4S)-3-[2-[(4aR,6aS,7R,10aS,10bR)-3-hexyl-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: 446.63

Molecular Weight (Monoisotopic): 446.3032

AlogP: 5.32

#Rotatable Bonds: 7

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.52

CX Basic pKa: ┄

CX LogP: 5.53

CX LogD: 5.53

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.25

Np Likeness Score: 2.81

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