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

ID: ALA4741308

PubChem CID: 69122329

Max Phase: Preclinical

Molecular Formula: C21H28N2O6

Molecular Weight: 404.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H28N2O6/c1-23-8-7-20-16-11-3-4-14(25)17(16)29-18(20)12(22-13(10-24)19(26)27)5-6-21(20,28-2)15(23)9-11/h3-4,12-13,15,18,22,24-25H,5-10H2,1-2H3,(H,26,27)/t12-,13-,15+,18-,20-,21+/m0/s1

Standard InChI Key:  IZZFNAUKHJUKPH-IPYZYDJNSA-N

Molfile:  

 
     RDKit          2D

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   35.7872   -2.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5655   -3.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.1735   -2.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5903   -1.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3869   -0.8585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8544   -2.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6003   -2.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5755   -3.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.1917   -1.6757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9758   -4.4863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9559   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9559   -4.4574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7872   -0.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1793   -4.4863    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   35.9977   -1.3125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.0089   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7930   -4.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1998   -5.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2034   -3.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0206   -3.7838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0170   -5.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7894   -5.9038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  1 11  1  1
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  2 18  1  1
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 20 16  2  0
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  4 23  1  1
  7 24  1  6
  5  6  1  0
  7 10  1  0
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  7  9  1  0
 20 14  1  0
 18 25  1  0
 19 26  1  0
 26 27  1  0
 26 28  1  1
 28 29  1  0
 27 30  2  0
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741308

   (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]-3-hydroxypropanoic 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: 404.46

Molecular Weight (Monoisotopic): 404.1947

AlogP: 0.23

#Rotatable Bonds: 5

Polar Surface Area: 111.49

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.38

CX Basic pKa: 9.63

CX LogP: -2.21

CX LogD: -3.03

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: 1.67

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