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

ID: ALA4740360

PubChem CID: 69122130

Max Phase: Preclinical

Molecular Formula: C22H28N2O7

Molecular Weight: 432.47

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H28N2O7/c1-24-8-7-21-17-11-3-4-14(25)18(17)31-19(21)12(23-13(20(28)29)10-16(26)27)5-6-22(21,30-2)15(24)9-11/h3-4,12-13,15,19,23,25H,5-10H2,1-2H3,(H,26,27)(H,28,29)/t12-,13-,15+,19-,21-,22+/m0/s1

Standard InChI Key:  MNYBENXVWGLZEJ-OXNBKUEFSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   37.6156  -11.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0283  -10.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8066  -11.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0159  -11.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4104  -11.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2111  -12.3817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6279   -9.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4145  -10.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8314   -9.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6279   -8.9891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0955  -10.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8413  -10.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8166  -11.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6097  -11.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0955   -9.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6139  -10.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2293  -11.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4328   -9.8063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2169  -12.6169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1970  -11.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1970  -12.5880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0283   -8.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4204  -12.6169    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.2388   -9.4431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   39.2499   -9.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0341  -12.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4409  -13.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4445  -11.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2617  -11.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2581  -13.3298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0305  -14.0344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.6710  -12.6238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.6746  -11.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  6  4  1  0
  7  2  1  0
  8  3  2  0
  9  8  1  0
 10 15  1  0
  1 11  1  1
 12  2  1  0
 13  4  1  0
 14  5  2  0
 15 11  1  0
 16  8  1  0
 17 13  1  0
  2 18  1  1
 13 19  1  6
 20 16  2  0
 21 14  1  0
 22 10  1  0
  4 23  1  1
  7 24  1  6
  5  6  1  0
  7 10  1  0
 12 17  1  0
  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
 29 32  1  0
 29 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740360

   (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]butanedioic 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: 432.47

Molecular Weight (Monoisotopic): 432.1897

AlogP: 0.72

#Rotatable Bonds: 6

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: 2.31

CX Basic pKa: 10.61

CX LogP: -4.35

CX LogD: -4.39

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: 1.56

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