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(S)-N-sec-butyl-normorphine

ID: ALA3275461

PubChem CID: 90679041

Max Phase: Preclinical

Molecular Formula: C20H25NO3

Molecular Weight: 327.42

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H25NO3/c1-3-11(2)21-9-8-20-13-5-7-16(23)19(20)24-18-15(22)6-4-12(17(18)20)10-14(13)21/h4-7,11,13-14,16,19,22-23H,3,8-10H2,1-2H3/t11-,13-,14+,16-,19-,20-/m0/s1

Standard InChI Key:  DHWOEIFEZNBNSB-XKNMSPGRSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    4.5820  -11.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764  -12.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8734  -10.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765  -12.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2875  -10.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7700  -11.7461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1593  -11.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8624  -12.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789  -10.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539  -12.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345  -11.2769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636  -11.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5973   -9.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057  -10.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2710  -13.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8536  -11.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569  -13.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5653  -13.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9920  -13.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0281   -9.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092  -10.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2092  -10.9031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1524  -10.4532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7516  -10.5894    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8881  -11.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079  -10.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857   -9.6106    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
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 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  1
 26 27  1  0
M  END

Associated Targets(non-human)

Oprd1 Opioid receptor (994 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 327.42Molecular Weight (Monoisotopic): 327.1834AlogP: 2.37#Rotatable Bonds: 2
Polar Surface Area: 52.93Molecular Species: BASEHBA: 4HBD: 2
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 9.70CX Basic pKa: 10.48CX LogP: 1.94CX LogD: -0.05
Aromatic Rings: 1Heavy Atoms: 24QED Weighted: 0.82Np Likeness Score: 1.84

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