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

ID: ALA4530500

PubChem CID: 153536692

Max Phase: Preclinical

Molecular Formula: C26H28N4O6

Molecular Weight: 492.53

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)c1ccncc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C26H28N4O6/c31-19-4-3-15-11-20-26(33)7-5-17(28-24(32)16-6-9-27-12-18(16)30(34)35)23-25(26,21(15)22(19)36-23)8-10-29(20)13-14-1-2-14/h3-4,6,9,12,14,17,20,23,31,33H,1-2,5,7-8,10-11,13H2,(H,28,32)/t17-,20-,23+,25+,26-/m1/s1

Standard InChI Key:  XTJYQGUVQMWMBO-VWGUVZQXSA-N

Molfile:  

 
     RDKit          2D

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M  CHG  2  36   1  37  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4530500

   ---

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: 492.53

Molecular Weight (Monoisotopic): 492.2009

AlogP: 2.06

#Rotatable Bonds: 5

Polar Surface Area: 138.06

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.08

CX Basic pKa: 9.50

CX LogP: 1.09

CX LogD: -0.73

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.43

Np Likeness Score: 0.41

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