N-Cyclopropylmethyl-7alpha-4'-(N'-phenylacetyl)aminophenyl-6,14-endoethanotetrahydronorthebaine

ID: ALA4522335

PubChem CID: 155543078

Max Phase: Preclinical

Molecular Formula: C38H42N2O4

Molecular Weight: 590.76

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c3c1O[C@H]1[C@@]4(OC)CC[C@@]5(C[C@@H]4c4ccc(NC(=O)Cc6ccccc6)cc4)[C@@H](C2)N(CC2CC2)CC[C@]315

Standard InChI:  InChI=1S/C38H42N2O4/c1-42-30-15-12-27-21-31-36-16-17-38(43-2,35-37(36,33(27)34(30)44-35)18-19-40(31)23-25-8-9-25)29(22-36)26-10-13-28(14-11-26)39-32(41)20-24-6-4-3-5-7-24/h3-7,10-15,25,29,31,35H,8-9,16-23H2,1-2H3,(H,39,41)/t29-,31-,35-,36-,37+,38-/m1/s1

Standard InChI Key:  FLSSYBVMHIZHOY-ZGELKJLSSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4522335

   ---

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: 590.76

Molecular Weight (Monoisotopic): 590.3145

AlogP: 6.27

#Rotatable Bonds: 8

Polar Surface Area: 60.03

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 10.05

CX LogP: 5.82

CX LogD: 3.22

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.34

Np Likeness Score: 0.44

References

1. Xiao L, Wang Y, Zhang M, Wu W, Kong L, Ma Y, Xu X, Liu X, He Q, Qian Y, Sun H, Wu H, Lin C, Huang H, Ye R, Jiang S, Ye RF, Yuan C, Fang S, Xue D, Yang X, Chen H, Zheng Y, Yu L, Xie Q, Zheng L, Fu W, Li W, Qiu Z, Liu J, Shao L..  (2019)  Discovery of a Highly Selective and Potent κ Opioid Receptor Agonist from N-Cyclopropylmethyl-7α-phenyl-6,14-endoethanotetrahydronorthebaines with Reduced Central Nervous System (CNS) Side Effects Navigated by the Message-Address Concept.,  62  (24): [PMID:31738550] [10.1021/acs.jmedchem.9b00857]

Source

Source(1):

• Scientific Literature