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

ID: ALA4760163

PubChem CID: 69122001

Max Phase: Preclinical

Molecular Formula: C22H29N3O6

Molecular Weight: 431.49

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H29N3O6/c1-25-8-7-21-17-11-3-4-14(26)18(17)31-19(21)12(24-13(20(28)29)10-16(23)27)5-6-22(21,30-2)15(25)9-11/h3-4,12-13,15,19,24,26H,5-10H2,1-2H3,(H2,23,27)(H,28,29)/t12-,13+,15-,19+,21+,22-/m1/s1

Standard InChI Key:  VJFNAJWMIIUIKO-YQSLKQGWSA-N

Molfile:  

 
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   38.8950   -5.0971    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.7134   -1.9233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4760163

   (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]-4-amino-4-oxobutanoic 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: 431.49

Molecular Weight (Monoisotopic): 431.2056

AlogP: 0.12

#Rotatable Bonds: 6

Polar Surface Area: 134.35

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.22

CX Basic pKa: 9.57

CX LogP: -2.61

CX LogD: -3.43

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: 1.50

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