17-Cyclopropylmethyl-3,14beta-dihydroxy-4,5r-epoxy-6alpha-[(2'-naphthalyl)acetamido]morphinan

ID: ALA495058

Chembl Id: CHEMBL495058

PubChem CID: 25232725

Max Phase: Preclinical

Molecular Formula: C31H32N2O4

Molecular Weight: 496.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5)c1ccc2ccccc2c1

Standard InChI:  InChI=1S/C31H32N2O4/c34-24-10-9-21-16-25-31(36)12-11-23(32-29(35)22-8-7-19-3-1-2-4-20(19)15-22)28-30(31,26(21)27(24)37-28)13-14-33(25)17-18-5-6-18/h1-4,7-10,15,18,23,25,28,34,36H,5-6,11-14,16-17H2,(H,32,35)/t23-,25+,28-,30-,31+/m0/s1

Standard InChI Key:  XZQMGGFIVXLGME-MFYRZQASSA-N

Alternative Forms

1. Parent:

   

   ALA495058

   N-[(4R,4aS,7S,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]naphthalene-2-carboxamide

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: 496.61

Molecular Weight (Monoisotopic): 496.2362

AlogP: 3.91

#Rotatable Bonds: 4

Polar Surface Area: 82.03

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.29

CX Basic pKa: 9.51

CX LogP: 3.36

CX LogD: 1.54

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.51

Np Likeness Score: 0.73

References

1. Li G, Aschenbach LC, Chen J, Cassidy MP, Stevens DL, Gabra BH, Selley DE, Dewey WL, Westkaemper RB, Zhang Y..  (2009)  Design, synthesis, and biological evaluation of 6alpha- and 6beta-N-heterocyclic substituted naltrexamine derivatives as mu opioid receptor selective antagonists.,  52  (5): [PMID:19199782] [10.1021/jm801272c]

2. Le Naour M, Lunzer MM, Powers MD, Portoghese PS..  (2012)  Opioid activity of spinally selective analogues of N-naphthoyl-β-naltrexamine in HEK-293 cells and mice.,  55  (2): [PMID:22136373] [10.1021/jm200902v]

Source

Source(1):

• Scientific Literature