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

ID: ALA4743953

PubChem CID: 69122411

Max Phase: Preclinical

Molecular Formula: C22H30N2O5

Molecular Weight: 402.49

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H30N2O5/c1-24-11-9-21-18-13-5-6-15(25)19(18)29-20(21)14(23-10-3-4-17(26)27)7-8-22(21,28-2)16(24)12-13/h5-6,14,16,20,23,25H,3-4,7-12H2,1-2H3,(H,26,27)/t14-,16+,20-,21-,22+/m0/s1

Standard InChI Key:  HAVQMMOFQDNJHT-MOSLHWROSA-N

Molfile:  

 
     RDKit          2D

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    4.8371  -18.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2192  -20.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2234  -18.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402  -18.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4368  -17.4293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044  -18.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6502  -18.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254  -20.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186  -20.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2416  -18.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0258  -21.0571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058  -19.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058  -21.0282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8371  -16.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292  -21.0571    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476  -17.8833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0588  -18.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8429  -21.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2497  -21.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0669  -21.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4763  -22.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0688  -23.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2968  -22.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
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  7  2  1  0
  8  3  2  0
  9  8  1  0
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  1 11  1  1
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 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
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743953

   4-[[(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]butanoic 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: 402.49

Molecular Weight (Monoisotopic): 402.2155

AlogP: 1.65

#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: 3.47

CX Basic pKa: 10.50

CX LogP: -1.18

CX LogD: -2.05

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.62

Np Likeness Score: 1.58

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