(1R,2R,4aS,5R,8aS)-5-((E)-2-((S)-4-acetoxy-2-oxodihydrofuran-3(2H)-ylidene)ethyl)-1-(hydroxymethyl)-1,4a-dimethyl-6-methylenedecahydronaphthalen-2-yl acetate

ID: ALA1933973

Chembl Id: CHEMBL1933973

PubChem CID: 57401998

Max Phase: Preclinical

Molecular Formula: C24H34O7

Molecular Weight: 434.53

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3,14-Ac-Andrographolide | 3,14-Ac-Andrographolide|CHEMBL1933973

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

Standard InChI:  InChI=1S/C24H34O7/c1-14-6-9-20-23(4,11-10-21(31-16(3)27)24(20,5)13-25)18(14)8-7-17-19(30-15(2)26)12-29-22(17)28/h7,18-21,25H,1,6,8-13H2,2-5H3/b17-7+/t18-,19-,20+,21-,23+,24+/m1/s1

Standard InChI Key:  SCOKHRNHLUUYSL-IZQYNGGQSA-N

Alternative Forms

1. Parent:

   

   ALA1933973

   3,14-Ac-Andrographolide

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: 434.53

Molecular Weight (Monoisotopic): 434.2305

AlogP: 3.10

#Rotatable Bonds: 5

Polar Surface Area: 99.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.54

CX LogD: 2.54

Aromatic Rings: 0

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: 2.86

References

1. Sirion U, Kasemsook S, Suksen K, Piyachaturawat P, Suksamrarn A, Saeeng R..  (2012)  New substituted C-19-andrographolide analogues with potent cytotoxic activities.,  22  (1): [PMID:22154665] [10.1016/j.bmcl.2011.11.085]

Source

Source(1):

• Scientific Literature