4-[2-[6-hydroxy-5-hydroxymethyl-5,8a-dimethyl-(1S,2''S,4aS,5R,6R,8aS)-spiro[perhydronaphthalene-2,2''-oxirane]-1-yl]-(E)-ethylidene]-5-oxo-(3S)-tetrahydro-3-furanyl acetate

ID: ALA360826

Chembl Id: CHEMBL360826

PubChem CID: 44393882

Max Phase: Preclinical

Molecular Formula: C22H32O7

Molecular Weight: 408.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@H]1COC(=O)/C1=C/C[C@@H]1[C@@]2(CC[C@@H]3[C@](C)(CO)[C@H](O)CC[C@]31C)CO2

Standard InChI:  InChI=1S/C22H32O7/c1-13(24)29-15-10-27-19(26)14(15)4-5-17-20(2)8-7-18(25)21(3,11-23)16(20)6-9-22(17)12-28-22/h4,15-18,23,25H,5-12H2,1-3H3/b14-4+/t15-,16+,17+,18-,20-,21+,22-/m1/s1

Standard InChI Key:  NAURXZFHWXEHHU-WNSJHVJWSA-N

Alternative Forms

1. Parent:

   

   ALA360826

   [(3S,4E)-4-[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]ethylidene]-5-oxooxolan-3-yl] acetate

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: 408.49

Molecular Weight (Monoisotopic): 408.2148

AlogP: 1.75

#Rotatable Bonds: 4

Polar Surface Area: 105.59

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.25

CX LogD: 1.25

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: 3.08

References

1. Nanduri S, Nyavanandi VK, Thunuguntla SS, Kasu S, Pallerla MK, Ram PS, Rajagopal S, Kumar RA, Ramanujam R, Babu JM, Vyas K, Devi AS, Reddy GO, Akella V..  (2004)  Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents.,  14  (18): [PMID:15324893] [10.1016/j.bmcl.2004.06.090]

2. Chen SR, Li F, Ding MY, Wang D, Zhao Q, Wang Y, Zhou GC, Wang Y..  (2018)  Andrographolide derivative as STAT3 inhibitor that protects acute liver damage in mice.,  26  (18): [PMID:30228000] [10.1016/j.bmc.2018.09.002]

Source

Source(1):

• Scientific Literature