N-tert-amyl-normorphine

ID: ALA3275458

PubChem CID: 90679038

Max Phase: Preclinical

Molecular Formula: C21H27NO3

Molecular Weight: 341.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(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/C21H27NO3/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/h5-8,13-14,16,19,23-24H,4,9-11H2,1-3H3/t13-,14+,16-,19-,21-/m0/s1

Standard InChI Key:  LBVIZSXBIANHRT-AYHJQLAQSA-N

Molfile:  

     RDKit          2D

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    5.1544   -3.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487   -4.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458   -3.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8489   -4.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599   -3.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3424   -4.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317   -3.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4348   -4.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4514   -2.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7263   -4.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9069   -3.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4360   -4.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1696   -1.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781   -2.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8434   -5.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -4.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4293   -5.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1377   -6.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5645   -6.1037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6005   -1.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1816   -3.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -3.2348    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -2.7848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3240   -2.9211    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4605   -3.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1803   -2.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562   -2.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -1.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  2  0
  5  1  1  0
  6  5  1  0
  7  3  1  0
  8  2  1  0
  9  3  1  0
 10  7  1  0
 11 16  1  0
  1 12  1  1
 13 14  1  0
 14  5  1  0
 15  4  1  0
 16 12  1  0
 17  8  2  0
 18 17  1  0
 19 15  1  0
 14 20  1  6
 21 11  1  0
  5 22  1  1
  3 23  1  1
  7 24  1  6
  4  6  1  0
  7 11  1  0
  9 13  2  0
  8 10  1  0
 18 15  2  0
 21 25  1  0
 21 26  1  0
 21 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3275458

   (4R,4aR,7S,7aR,12bS)-3-(2-methylbutan-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: 341.45

Molecular Weight (Monoisotopic): 341.1991

AlogP: 2.76

#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: 9.82

CX Basic pKa: 10.63

CX LogP: 2.07

CX LogD: 0.02

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.81

Np Likeness Score: 1.80

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