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

ID: ALA1933969

Chembl Id: CHEMBL1933969

PubChem CID: 57403747

Max Phase: Preclinical

Molecular Formula: C22H32O6

Molecular Weight: 392.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 19-Ac-Andrographolide | 19-Ac-Andrographolide|CHEMBL1933969

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

Standard InChI:  InChI=1S/C22H32O6/c1-13-5-8-18-21(3,10-9-19(25)22(18,4)12-28-14(2)23)16(13)7-6-15-17(24)11-27-20(15)26/h6,16-19,24-25H,1,5,7-12H2,2-4H3/b15-6+/t16-,17-,18+,19-,21+,22+/m1/s1

Standard InChI Key:  GMRRWIJRHOAFQG-QJAZYMEMSA-N

Alternative Forms

1. Parent:

   

   ALA1933969

   19-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: 392.49

Molecular Weight (Monoisotopic): 392.2199

AlogP: 2.53

#Rotatable Bonds: 4

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.49

CX Basic pKa:

CX LogP: 2.10

CX LogD: 2.10

Aromatic Rings: 0

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: 3.37

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