17-Cyclopropylmethyl-3,14beta-dihydroxy-4,5alpha-epoxy-6beta-[(3'-cyclopentanyl-4'-pyridyl)carboxamido]morphinan

ID: ALA4580789

PubChem CID: 146408966

Max Phase: Preclinical

Molecular Formula: C31H37N3O4

Molecular Weight: 515.65

Molecule Type: Unknown

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)c1ccncc1C1CCCC1

Standard InChI:  InChI=1S/C31H37N3O4/c35-24-8-7-20-15-25-31(37)11-9-23(33-29(36)21-10-13-32-16-22(21)19-3-1-2-4-19)28-30(31,26(20)27(24)38-28)12-14-34(25)17-18-5-6-18/h7-8,10,13,16,18-19,23,25,28,35,37H,1-6,9,11-12,14-15,17H2,(H,33,36)/t23-,25-,28+,30+,31-/m1/s1

Standard InChI Key:  JREDGYCNIRJYKG-PTSROERVSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4580789

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 515.65

Molecular Weight (Monoisotopic): 515.2784

AlogP: 3.81

#Rotatable Bonds: 5

Polar Surface Area: 94.92

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.29

CX Basic pKa: 9.51

CX LogP: 2.82

CX LogD: 1.00

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.56

Np Likeness Score: 0.76

References

1. Zheng Y, Obeng S, Wang H, Jali AM, Peddibhotla B, Williams DA, Zou C, Stevens DL, Dewey WL, Akbarali HI, Selley DE, Zhang Y..  (2019)  Design, Synthesis, and Biological Evaluation of the Third Generation 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4'-pyridyl)carboxamido]morphinan (NAP) Derivatives as μ/κ Opioid Receptor Dual Selective Ligands.,  62  (2): [PMID:30608693] [10.1021/acs.jmedchem.8b01158]

Source

Source(1):

• Scientific Literature