(+/-)-(1S,4R,9S)-5-Bromo-3,3-Dimethyl-9-(2-methylallyl)-10-(thiophen-2-ylmethyl)-1,2,3,4-tetrahydro-1,4-(epiminomethano)naphthalene

ID: ALA3733336

PubChem CID: 127024185

Max Phase: Preclinical

Molecular Formula: C22H26BrNS

Molecular Weight: 416.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C[C@H]1[C@H]2c3c(Br)cccc3[C@H](CC2(C)C)N1Cc1ccsc1

Standard InChI:  InChI=1S/C22H26BrNS/c1-14(2)10-18-21-20-16(6-5-7-17(20)23)19(11-22(21,3)4)24(18)12-15-8-9-25-13-15/h5-9,13,18-19,21H,1,10-12H2,2-4H3/t18-,19-,21-/m0/s1

Standard InChI Key:  NMUFGVINDAIMKX-ZJOUEHCJSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    2.7650   -0.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720   -1.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1591   -0.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1140   -1.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4468   -0.7559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4468    0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1140    1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1591    0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720    1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650    0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9296    0.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -0.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7269    1.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087   -0.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4721    2.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6578    2.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7196    3.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626    1.2238    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516   -0.5405    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503   -1.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4761    2.7317    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0464   -0.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4020   -1.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3981   -0.2327    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6392    1.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1742    0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  2  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  0
  7  6  1  0
  8  7  1  0
  3  8  2  0
  8  9  1  0
  9 10  2  0
 10  1  1  0
 11  7  1  0
 11 12  1  0
  4 12  1  0
 11 13  1  0
 11 14  1  0
  6 15  1  1
 15 16  1  0
 16 17  2  0
 16 18  1  0
  7 19  1  6
  4 20  1  6
  5 21  1  0
  9 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3733336

   ---

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: 416.43

Molecular Weight (Monoisotopic): 415.0969

AlogP: 6.92

#Rotatable Bonds: 4

Polar Surface Area: 3.24

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.93

CX LogP: 6.53

CX LogD: 5.89

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: -0.40

References

1.  (2014)  Tetrahydroisoquinolines as selective nadph oxidase 2 inhibitors, 

Source

Source(1):

• Patent Bioactivity Data