NA

ID: ALA4763643

PubChem CID: 12038840

Max Phase: Preclinical

Molecular Formula: C21H28N2O5

Molecular Weight: 388.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H28N2O5/c1-11(19(25)26)22-13-6-7-21(27-3)15-10-12-4-5-14(24)17-16(12)20(21,18(13)28-17)8-9-23(15)2/h4-5,11,13,15,18,22,24H,6-10H2,1-3H3,(H,25,26)/t11-,13+,15+,18-,20-,21+/m0/s1

Standard InChI Key:  ZDYOGHURRMOUMQ-QYYSHDEWSA-N

Molfile:  

 
     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   14.6971  -10.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1098   -9.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8881  -10.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0974  -10.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4919  -10.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2926  -11.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7094   -8.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4960   -9.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9129   -8.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7094   -7.9367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1770   -9.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9228   -9.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8981  -10.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6912  -10.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1770   -8.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6954   -9.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3108  -10.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5143   -8.7539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2984  -11.5645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2785  -10.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2785  -11.5356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1098   -7.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5019  -11.5645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3203   -8.3907    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1156  -11.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5224  -12.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3314   -8.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5260  -10.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1131  -12.9827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3407  -12.2781    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  1
 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
 19 25  1  0
 25 26  1  0
 18 27  1  0
 25 28  1  1
 26 29  1  0
 26 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4763643

   (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]propanoic 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: 388.46

Molecular Weight (Monoisotopic): 388.1998

AlogP: 1.26

#Rotatable Bonds: 4

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: 1.48

CX Basic pKa: 10.55

CX LogP: -1.12

CX LogD: -1.99

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: 1.61

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