(E)-methyl 2-(3-ethyl-7a,12a-(epoxyethanoxy)-9-fluoro-1,2,3,4,6,7,12,12b-octahydro-8-methoxy indolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate

ID: ALA2396991

Chembl Id: CHEMBL2396991

PubChem CID: 16095099

Max Phase: Preclinical

Molecular Formula: C25H33FN2O6

Molecular Weight: 476.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H]1CN2CC[C@@]34OCCO[C@@]3(Nc3ccc(F)c(OC)c34)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC

Standard InChI:  InChI=1S/C25H33FN2O6/c1-5-15-13-28-9-8-24-21-19(7-6-18(26)22(21)31-3)27-25(24,34-11-10-33-24)20(28)12-16(15)17(14-30-2)23(29)32-4/h6-7,14-16,20,27H,5,8-13H2,1-4H3/b17-14+/t15-,16+,20+,24+,25+/m1/s1

Standard InChI Key:  VDHVQTLHHZZTMJ-GWNIIIPKSA-N

Alternative Forms

1. Parent:

   

   ALA2396991

   methyl (E)-2-[(1S,2S,4S,5S,10S)-5-ethyl-13-fluoro-12-methoxy-18,21-dioxa-7,17-diazapentacyclo[8.7.4.01,10.02,7.011,16]henicosa-11(16),12,14-trien-4-yl]-3-methoxyprop-2-enoate

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: 476.55

Molecular Weight (Monoisotopic): 476.2323

AlogP: 3.02

#Rotatable Bonds: 5

Polar Surface Area: 78.49

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.41

CX Basic pKa: 7.34

CX LogP: 2.85

CX LogD: 2.58

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.39

Np Likeness Score: 1.39

References

1. Raffa RB, Beckett JR, Brahmbhatt VN, Ebinger TM, Fabian CA, Nixon JR, Orlando ST, Rana CA, Tejani AH, Tomazic RJ..  (2013)  Orally active opioid compounds from a non-poppy source.,  56  (12): [PMID:23517479] [10.1021/jm400143z]

2. Smith MT, Kong D, Kuo A, Imam MZ, Williams CM..  (2022)  Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.,  65  (3.0): [PMID:34995453] [10.1021/acs.jmedchem.0c01915]

Source

Source(1):

• Scientific Literature