(1R,2R,2aR,10aS)-1,10,10-Trimethyl-2-(3,4,5-trimethoxyphenyl)-1,2,2a,4,10,10a-hexahydro-3H-cyclobuta[4,5]pyrano[3,2-c]-quinolin-3-one

ID: ALA3261007

Chembl Id: CHEMBL3261007

PubChem CID: 78426192

Max Phase: Preclinical

Molecular Formula: C26H29NO5

Molecular Weight: 435.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2[C@@H](C)[C@H]3[C@@H]2c2c(c4ccccc4[nH]c2=O)OC3(C)C)cc(OC)c1OC

Standard InChI:  InChI=1S/C26H29NO5/c1-13-19(14-11-17(29-4)24(31-6)18(12-14)30-5)20-21-23(32-26(2,3)22(13)20)15-9-7-8-10-16(15)27-25(21)28/h7-13,19-20,22H,1-6H3,(H,27,28)/t13-,19+,20+,22+/m1/s1

Standard InChI Key:  JTYASLGJTZDIAO-NOMGZSDZSA-N

Alternative Forms

1. Parent:

   

   ALA3261007

   (11R,12R,13R,14S)-13,15,15-trimethyl-12-(3,4,5-trimethoxyphenyl)-16-oxa-8-azatetracyclo[8.6.0.02,7.011,14]hexadeca-1(10),2,4,6-tetraen-9-one

Molecule Features

Natural Product: Yes

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: 435.52

Molecular Weight (Monoisotopic): 435.2046

AlogP: 4.86

#Rotatable Bonds: 4

Polar Surface Area: 69.78

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.79

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 3.44

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.63

Np Likeness Score: 0.86

References

1. Neve JE, Wijesekera HP, Duffy S, Jenkins ID, Ripper JA, Teague SJ, Campitelli M, Garavelas A, Nikolakopoulos G, Le PV, de A Leone P, Pham NB, Shelton P, Fraser N, Carroll AR, Avery VM, McCrae C, Williams N, Quinn RJ..  (2014)  Euodenine A: a small-molecule agonist of human TLR4.,  57  (4): [PMID:24471857] [10.1021/jm401321v]

Source

Source(1):

• Scientific Literature