(2R)-2-[(4,5alpha-Epoxy-3-hydroxy-14beta-methoxy-17-methyl-morphinan-6alpha-yl)-amino]-3-phenylpropionic Acid

ID: ALA4757240

PubChem CID: 162656415

Max Phase: Preclinical

Molecular Formula: C27H32N2O5

Molecular Weight: 464.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@@]12CC[C@H](N[C@H](Cc3ccccc3)C(=O)O)[C@@H]3Oc4c(O)ccc5c4[C@@]31CCN(C)[C@@H]2C5

Standard InChI:  InChI=1S/C27H32N2O5/c1-29-13-12-26-22-17-8-9-20(30)23(22)34-24(26)18(10-11-27(26,33-2)21(29)15-17)28-19(25(31)32)14-16-6-4-3-5-7-16/h3-9,18-19,21,24,28,30H,10-15H2,1-2H3,(H,31,32)/t18-,19+,21+,24-,26-,27+/m0/s1

Standard InChI Key:  SILMEZJWWQTRJT-MMUDNFAGSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4757240

   ---

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: 464.56

Molecular Weight (Monoisotopic): 464.2311

AlogP: 2.48

#Rotatable Bonds: 6

Polar Surface Area: 91.26

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.58

CX Basic pKa: 10.65

CX LogP: 0.54

CX LogD: -0.34

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.61

Np Likeness Score: 1.31

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