(R)-1-Phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol hydrochloride

ID: ALA1467585

Cas Number: 81702-42-3

PubChem CID: 6852375

Product Number: S275412, Order Now?

Max Phase: Preclinical

Molecular Formula: C16H18ClNO2

Molecular Weight: 255.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Oc1cc2c(cc1O)[C@@H](c1ccccc1)CNCC2

Standard InChI:  InChI=1S/C16H17NO2.ClH/c18-15-8-12-6-7-17-10-14(13(12)9-16(15)19)11-4-2-1-3-5-11;/h1-5,8-9,14,17-19H,6-7,10H2;1H/t14-;/m1./s1

Standard InChI Key:  YEWHJCLOUYPAOH-PFEQFJNWSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    2.1214   -0.0243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    1.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0721    0.8007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648    0.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9099   -0.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648    1.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504   -0.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    0.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7263   -0.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    1.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    1.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7142    0.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9099    1.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3310   -1.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379   -1.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7142    1.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1475   -2.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7543   -1.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3591   -2.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0
  2 10  1  0
  3 12  1  0
  3 16  1  0
  4  5  1  0
  4  6  2  0
  4  7  1  0
  5  9  1  6
  5 12  1  0
  6 11  1  0
  6 13  1  0
  7  8  2  0
  8 10  1  0
  9 14  2  0
  9 15  1  0
 10 11  2  0
 13 16  1  0
 14 17  1  0
 15 18  2  0
 17 19  2  0
 18 19  1  0
M  END

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: 255.32

Molecular Weight (Monoisotopic): 255.1259

AlogP: 2.38

#Rotatable Bonds: 1

Polar Surface Area: 52.49

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.28

CX Basic pKa: 9.25

CX LogP: 1.88

CX LogD: 0.32

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.69

Np Likeness Score: 0.88

References

1. Kaiser C, Dandridge PA, Garvey E, Hahn RA, Sarau HM, Setler PE, Bass LS, Clardy J..  (1982)  Absolute stereochemistry and dopaminergic activity of enantiomers of 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine.,  25  (6): [PMID:6980283] [10.1021/jm00348a017]

2. PubChem BioAssay data set, 

3. Clark AH, McCorvy JD, Watts VJ, Nichols DE..  (2011)  Assessment of dopamine D₁ receptor affinity and efficacy of three tetracyclic conformationally-restricted analogs of SKF38393.,  19  (18): [PMID:21862338] [10.1016/j.bmc.2011.07.057]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays