(E)-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)furan-2(3H)-one

ID: ALA2436162

Chembl Id: CHEMBL2436162

Cas Number: 134418-28-3

PubChem CID: 6473762

Max Phase: Preclinical

Molecular Formula: C20H28O4

Molecular Weight: 332.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1C/C=C1\C=COC1=O

Standard InChI:  InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5,9,11,15-17,21-22H,1,4,6-8,10,12H2,2-3H3/b14-5+/t15-,16+,17-,19+,20+/m1/s1

Standard InChI Key:  YIIRVUDGRKEWBV-FZOOCBFYSA-N

Alternative Forms

1. Parent:

   

   ALA2436162

   Dehydroandrographolide

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: 332.44

Molecular Weight (Monoisotopic): 332.1988

AlogP: 3.12

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.59

CX LogD: 2.59

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.47

Np Likeness Score: 3.34

References

1. 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]

2. Nguyen VS, Loh XY, Wijaya H, Wang J, Lin Q, Lam Y, Wong WS, Mok YK..  (2015)  Specificity and inhibitory mechanism of andrographolide and its analogues as antiasthma agents on NF-κB p50.,  78  (2): [PMID:25615020] [10.1021/np5007179]

3. Song Z, Huang S, He Y, Li J, Lin K, Xue X..  (2018)  Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives.,  157  [PMID:30144698] [10.1016/j.ejmech.2018.08.046]

4. Xu Y, Wei H, Wang J, Wang W, Gao J..  (2019)  Synthesis of andrographolide analogues and their neuroprotection and neurite outgrowth-promoting activities.,  27  (11): [PMID:31014564] [10.1016/j.bmc.2019.04.025]

5. Tran QTN,Tan DWS,Wong WSF,Chai CLL.  (2020)  From irreversible to reversible covalent inhibitors: Harnessing the andrographolide scaffold for anti-inflammatory action.,  204  [PMID:32712435] [10.1016/j.ejmech.2020.112481]

6. Zhang S, Zhang Y, Fang Y, Chen H, Hao M, Tan Q, Hu C, Zhou H, Xu J, Gu Q..  (2021)  Synthesis and evaluation of andrographolide derivatives as potent anti-osteoporosis agents in vitro and in vivo.,  213  [PMID:33485256] [10.1016/j.ejmech.2021.113185]

Source

Source(1):

• Scientific Literature