(2S)-6-Amino-2-[(4,5alpha-epoxy-3-hydroxy-14beta-methoxy-17-methylmorphinan-6beta-yl)amino]hexanoic Acid

ID: ALA4741873

PubChem CID: 69122070

Max Phase: Preclinical

Molecular Formula: C24H35N3O5

Molecular Weight: 445.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@@]12CC[C@@H](N[C@@H](CCCCN)C(=O)O)[C@@H]3Oc4c(O)ccc5c4[C@@]31CCN(C)[C@@H]2C5

Standard InChI:  InChI=1S/C24H35N3O5/c1-27-12-10-23-19-14-6-7-17(28)20(19)32-21(23)15(8-9-24(23,31-2)18(27)13-14)26-16(22(29)30)5-3-4-11-25/h6-7,15-16,18,21,26,28H,3-5,8-13,25H2,1-2H3,(H,29,30)/t15-,16+,18-,21+,23+,24-/m1/s1

Standard InChI Key:  NKIQDONKAOALDB-FDDRLWOQSA-N

Molfile:  

 
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   14.9695   -2.1792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741873

   (2S)-2-[[(4R,4aS,7R,7aR,12bS)-9-hydroxy-4a-methoxy-3-methyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]amino]-6-aminohexanoic acid

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: 445.56

Molecular Weight (Monoisotopic): 445.2577

AlogP: 1.37

#Rotatable Bonds: 8

Polar Surface Area: 117.28

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.63

CX Basic pKa: 10.82

CX LogP: -1.64

CX LogD: -4.56

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.44

Np Likeness Score: 1.65

References

1. Spetea M,Rief SB,Haddou TB,Fink M,Kristeva E,Mittendorfer H,Haas S,Hummer N,Follia V,Guerrieri E,Asim MF,Sturm S,Schmidhammer H.  (2019)  Synthesis, Biological, and Structural Explorations of New Zwitterionic Derivatives of 14- O-Methyloxymorphone, as Potent μ/δ Opioid Agonists and Peripherally Selective Antinociceptives.,  62  (2): [PMID:30571123] [10.1021/acs.jmedchem.8b01327]

Source

Source(1):

• Scientific Literature