((6S,11R)-3-Cyclopropylmethyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl)-phenyl-amine

ID: ALA2367916

Chembl Id: CHEMBL2367916

PubChem CID: 73351393

Max Phase: Preclinical

Molecular Formula: C24H30N2

Molecular Weight: 346.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1[C@H]2Cc3ccc(Nc4ccccc4)cc3[C@@]1(C)CCN2CC1CC1

Standard InChI:  InChI=1S/C24H30N2/c1-17-23-14-19-10-11-21(25-20-6-4-3-5-7-20)15-22(19)24(17,2)12-13-26(23)16-18-8-9-18/h3-7,10-11,15,17-18,23,25H,8-9,12-14,16H2,1-2H3/t17-,23+,24-/m0/s1

Standard InChI Key:  FUMBLBJFVJXVBV-VWMXVWASSA-N

Alternative Forms

1. Parent:

   

   ALA2367916

   (3-Cyclopropylmethyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl)-phenyl-amine

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: 346.52

Molecular Weight (Monoisotopic): 346.2409

AlogP: 5.36

#Rotatable Bonds: 4

Polar Surface Area: 15.27

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.63

CX LogP: 5.45

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: 0.38

References

1. Wentland MP, Xu G, Cioffi CL, Ye Y, Duan W, Cohen DJ, Colasurdo AM, Bidlack JM..  (2000)  8-Aminocyclazocine analogues: synthesis and structure-activity relationships.,  10  (2): [PMID:10673107] [10.1016/s0960-894x(99)00670-8]

2. Wentland MP, Xu G, Cioffi CL, Ye Y, Duan W, Cohen DJ, Colasurdo AM, Bidlack JM..  (2000)  8-Aminocyclazocine analogues: synthesis and structure-activity relationships.,  10  (2): [PMID:10673107] [10.1016/s0960-894x(99)00670-8]

3. Wentland MP, Xu G, Cioffi CL, Ye Y, Duan W, Cohen DJ, Colasurdo AM, Bidlack JM..  (2000)  8-Aminocyclazocine analogues: synthesis and structure-activity relationships.,  10  (2): [PMID:10673107] [10.1016/s0960-894x(99)00670-8]

4. Wentland MP, Sun X, Ye Y, Lou R, Bidlack JM..  (2003)  Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 2: 8-formamidocyclazocine analogues.,  13  (11): [PMID:12749896] [10.1016/s0960-894x(03)00295-6]

5. Wentland MP, Duan W, Cohen DJ, Bidlack JM..  (2000)  Selective protection and functionalization of morphine: synthesis and opioid receptor binding properties of 3-amino-3-desoxymorphine derivatives.,  43  (19): [PMID:11000010] [10.1021/jm000119i]

6. Wentland MP, Ye Y, Cioffi CL, Lou R, Zhou Q, Xu G, Duan W, Dehnhardt CM, Sun X, Cohen DJ, Bidlack JM..  (2003)  Syntheses and opioid receptor binding affinities of 8-amino-2,6-methano-3-benzazocines.,  46  (5): [PMID:12593663] [10.1021/jm020429w]

7. Wentland MP, Ye Y, Cioffi CL, Lou R, Zhou Q, Xu G, Duan W, Dehnhardt CM, Sun X, Cohen DJ, Bidlack JM..  (2003)  Syntheses and opioid receptor binding affinities of 8-amino-2,6-methano-3-benzazocines.,  46  (5): [PMID:12593663] [10.1021/jm020429w]

8. Wentland MP, Ye Y, Cioffi CL, Lou R, Zhou Q, Xu G, Duan W, Dehnhardt CM, Sun X, Cohen DJ, Bidlack JM..  (2003)  Syntheses and opioid receptor binding affinities of 8-amino-2,6-methano-3-benzazocines.,  46  (5): [PMID:12593663] [10.1021/jm020429w]

9. Turnaturi R, Marrazzo A, Parenti C, Pasquinucci L..  (2018)  Benzomorphan scaffold for opioid analgesics and pharmacological tools development: A comprehensive review.,  148  [PMID:29477074] [10.1016/j.ejmech.2018.02.046]

Source

Source(1):

• Scientific Literature