3-[(E)-2-[(1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-octahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl]ethenyl]-2,5-dihydrofuran-2-one

ID: ALA208071

Chembl Id: CHEMBL208071

PubChem CID: 44411339

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(CO)[C@H]2CC[C@@]3(CO3)[C@@H](/C=C/C3=CCOC3=O)[C@]2(C)CC[C@H]1O

Standard InChI:  InChI=1S/C20H28O5/c1-18-8-6-16(22)19(2,11-21)14(18)5-9-20(12-25-20)15(18)4-3-13-7-10-24-17(13)23/h3-4,7,14-16,21-22H,5-6,8-12H2,1-2H3/b4-3+/t14-,15-,16+,18+,19-,20+/m0/s1

Standard InChI Key:  HGHDAOIFBYJURD-BESDKJSGSA-N

Alternative Forms

1. Parent:

   

   ALA208071

   4-[(E)-2-[(1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]ethenyl]-2H-furan-5-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: 348.44

Molecular Weight (Monoisotopic): 348.1937

AlogP: 1.98

#Rotatable Bonds: 3

Polar Surface Area: 79.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: ┄

CX LogP: 1.52

CX LogD: 1.52

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: 3.45

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]

2. Wu ZW, Xu HW, Dai GF, Liu MJ, Zhu LP, Wu J, Wang YN, Wu FJ, Zhao D, Gao MF, Nie SS, Han W, Song JH, Liu HM..  (2013)  Improved inhibitory activities against tumor-cell migration and invasion by 15-benzylidene substitution derivatives of andrographolide.,  23  (23): [PMID:24120543] [10.1016/j.bmcl.2013.09.049]

3. Chen H, Ma YB, Huang XY, Geng CA, Zhao Y, Wang LJ, Guo RH, Liang WJ, Zhang XM, Chen JJ..  (2014)  Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents.,  24  (10): [PMID:24731274] [10.1016/j.bmcl.2014.03.060]

4. Sombut S, Bunthawong R, Sirion U, Kasemsuk T, Piyachaturawat P, Suksen K, Suksamrarn A, Saeeng R..  (2017)  Synthesis of 14-deoxy-11,12-didehydroandrographolide analogues as potential cytotoxic agents for cholangiocarcinoma.,  27  (23): [PMID:29097170] [10.1016/j.bmcl.2017.10.063]

Source

Source(1):

• Scientific Literature