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

ID: ALA4761211

PubChem CID: 69121986

Max Phase: Preclinical

Molecular Formula: C23H30N2O7

Molecular Weight: 446.50

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H30N2O7/c1-25-10-9-22-18-12-3-5-15(26)19(18)32-20(22)13(7-8-23(22,31-2)16(25)11-12)24-14(21(29)30)4-6-17(27)28/h3,5,13-14,16,20,24,26H,4,6-11H2,1-2H3,(H,27,28)(H,29,30)/t13-,14-,16+,20-,22-,23+/m0/s1

Standard InChI Key:  IKXIQVMSQGSVLL-GYQVKVEVSA-N

Molfile:  

 
     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA4761211

   (2S)-2-[[(4R,4aS,7S,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]pentanedioic 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: 446.50

Molecular Weight (Monoisotopic): 446.2053

AlogP: 1.11

#Rotatable Bonds: 7

Polar Surface Area: 128.56

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.19

CX Basic pKa: 10.77

CX LogP: -4.06

CX LogD: -4.10

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: 1.60

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