N-(alpha,alpha-dimethylallyl)-normorphine

ID: ALA3275459

PubChem CID: 90679039

Max Phase: Preclinical

Molecular Formula: C21H25NO3

Molecular Weight: 339.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)N1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5

Standard InChI:  InChI=1S/C21H25NO3/c1-4-20(2,3)22-10-9-21-13-6-8-16(24)19(21)25-18-15(23)7-5-12(17(18)21)11-14(13)22/h4-8,13-14,16,19,23-24H,1,9-11H2,2-3H3/t13-,14+,16-,19-,21-/m0/s1

Standard InChI Key:  IFBGAXGWARFTOB-AYHJQLAQSA-N

Molfile:  

     RDKit          2D

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   11.2440   -4.3677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9670   -5.2927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5499   -5.9802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4923   -7.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8129   -4.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0725   -8.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5032   -5.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7976   -5.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0891   -5.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7810   -8.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3678   -5.1565    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5214   -4.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8232   -4.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3748   -6.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1033   -5.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0946   -4.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4867   -8.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0690   -6.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2079   -8.4758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3694   -6.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8244   -5.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -6.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9858   -6.4496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4250   -5.6065    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0991   -5.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7921   -6.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0781   -7.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0980   -4.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 21 15  1  0
  6 27  2  0
 10 17  2  0
 27 26  1  0
 21 13  1  0
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 20 14  1  0
  4 23  1  0
 25 28  2  0
 16  5  2  0
 12  7  1  0
 27 20  1  0
 16  9  1  0
  8 22  1  1
 18 22  1  0
  3 18  1  0
 12  1  1  6
  4 26  2  0
  7  8  1  0
  7 24  1  1
 17  4  1  0
 21  3  1  0
 14  3  1  0
 19 17  1  0
  5 12  1  0
 21 25  1  0
 14  2  1  6
 14  9  1  0
 26  8  1  0
  9  8  1  0
 10  6  1  0
  9 11  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3275459

   (4R,4aR,7S,7aR,12bS)-3-(2-methylbut-3-en-2-yl)-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 339.44

Molecular Weight (Monoisotopic): 339.1834

AlogP: 2.53

#Rotatable Bonds: 2

Polar Surface Area: 52.93

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.27

CX Basic pKa: 9.27

CX LogP: 2.30

CX LogD: 0.67

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.81

Np Likeness Score: 2.23

References

1. DeGraw JI, Lawson JA, Crase JL, Johnson HL, Ellis M, Uyeno ET, Loew GH, Berkowitz DS..  (1978)  Analgesics. 1. Synthesis and analgesic properties of N-sec-alkyl- and N-tert-alkylnormorphines.,  21  (5): [PMID:207868] [10.1021/jm00203a002]

Source

Source(1):

• Scientific Literature