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

ID: ALA1933972

Chembl Id: CHEMBL1933972

Cas Number: 79233-05-9

PubChem CID: 21679044

Max Phase: Preclinical

Molecular Formula: C26H36O8

Molecular Weight: 476.57

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3,14,19-Ac-Andrographolide | Triacetylandrographolide|6V668B97GS|3,14,19-Triacetylandrographolide|Andrographolide 3,14,19-triacetate|Andrographolide triacetyl derivative [MI]|UNII-6V668B97GS|79233-05-9|2(3H)-Furanone, 4-(acetyloxy)-3-(2-((1R,4aS,5R,6R,8aS)-6-(acetyloxy)-5-((acetyloxy)methyl)decahydro-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-, (3E,4S)-|3,14,19-Ac-Andrographolide|CHEMBL1933972|NSC780381|NSC-780381

Canonical SMILES:  C=C1CC[C@@H]2[C@](C)(COC(C)=O)[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/C26H36O8/c1-15-7-10-22-25(5,12-11-23(34-18(4)29)26(22,6)14-32-16(2)27)20(15)9-8-19-21(33-17(3)28)13-31-24(19)30/h8,20-23H,1,7,9-14H2,2-6H3/b19-8+/t20-,21-,22+,23-,25+,26+/m1/s1

Standard InChI Key:  KJFJXGDQSMGFTO-GSGGYZLZSA-N

Alternative Forms

1. Parent:

   

   ALA1933972

   Triacetylandrographolide

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: 476.57

Molecular Weight (Monoisotopic): 476.2410

AlogP: 3.68

#Rotatable Bonds: 6

Polar Surface Area: 105.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 0

Heavy Atoms: 34

QED Weighted: 0.25

Np Likeness Score: 2.76

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]

2. Pandeti S, Sonkar R, Shukla A, Bhatia G, Tadigoppula N..  (2013)  Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity.,  69  [PMID:24090915] [10.1016/j.ejmech.2013.09.002]

3. Kandanur SG, Golakoti NR, Nanduri S..  (2015)  Synthesis and in vitro cytotoxicity of novel C-12 substituted-14-deoxy-andrographolide derivatives as potent anti-cancer agents.,  25  (24): [PMID:26561364] [10.1016/j.bmcl.2015.10.053]

4. Arsakhant P, Sirion U, Chairoungdua A, Suksen K, Piyachaturawat P, Suksamrarn A, Saeeng R..  (2020)  Design and synthesis of C-12 dithiocarbamate andrographolide analogues as an anticancer agent.,  30  (14): [PMID:32527561] [10.1016/j.bmcl.2020.127263]

Source

Source(1):

• Scientific Literature