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

ID: ALA3085528

Chembl Id: CHEMBL3085528

PubChem CID: 10016044

Max Phase: Preclinical

Molecular Formula: C18H25NO

Molecular Weight: 271.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H25NO/c1-12-17-9-14-5-6-15(20)10-16(14)18(12,2)7-8-19(17)11-13-3-4-13/h5-6,10,12-13,17,20H,3-4,7-9,11H2,1-2H3/t12-,17+,18-/m0/s1

Standard InChI Key:  YQYVFVRQLZMJKJ-RZAIGCCYSA-N

Alternative Forms

1. Parent:

   

   ALA3085528

   (cyclazocine)2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid

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: 271.40

Molecular Weight (Monoisotopic): 271.1936

AlogP: 3.33

#Rotatable Bonds: 2

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.94

CX Basic pKa: 10.78

CX LogP: 2.92

CX LogD: 0.81

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.89

Np Likeness Score: 1.43

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. Crivori P, Cruciani G, Carrupt PA, Testa B..  (2000)  Predicting blood-brain barrier permeation from three-dimensional molecular structure.,  43  (11): [PMID:10841799] [10.1021/jm990968+]

3. Wentland MP, Lou R, Ye Y, Cohen DJ, Richardson GP, Bidlack JM..  (2001)  8-Carboxamidocyclazocine analogues: redefining the structure-activity relationships of 2,6-methano-3-benzazocines.,  11  (5): [PMID:11266156] [10.1016/s0960-894x(01)00014-2]

4. VanAlstine MA, Wentland MP, Cohen DJ, Bidlack JM..  (2007)  Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 5. Opioid receptor binding properties of N-((4'-phenyl)-phenethyl) analogues of 8-CAC.,  17  (23): [PMID:17935988] [10.1016/j.bmcl.2007.09.082]

5. Katz R, Osborne SF, Ionescu F..  (1977)  Application of the Free-Wilson technique to structurally related series of homologues. Quantitative structure-activity relationship studies of narcotic analgetics.,  20  (11): [PMID:21292] [10.1021/jm00221a012]

6. 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