(+/-)-(1S,4R,9S)-10-(Benzo[d][1,3]dioxol-5-ylmethyl)-5-(3,4-dichlorophenyl)-3,3-dimethyl-9-(2-methylallyl)-1,2,3,4-tetrahydro-1,4-(epiminomethano)naphthalene

ID: ALA3347566

PubChem CID: 118718039

Max Phase: Preclinical

Molecular Formula: C31H31Cl2NO2

Molecular Weight: 520.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C[C@H]1[C@H]2c3c(-c4ccc(Cl)c(Cl)c4)cccc3[C@H](CC2(C)C)N1Cc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C31H31Cl2NO2/c1-18(2)12-25-30-29-21(20-9-10-23(32)24(33)14-20)6-5-7-22(29)26(15-31(30,3)4)34(25)16-19-8-11-27-28(13-19)36-17-35-27/h5-11,13-14,25-26,30H,1,12,15-17H2,2-4H3/t25-,26-,30-/m0/s1

Standard InChI Key:  IJCLLFSQOMIXGM-JCGRVDTESA-N

Molfile:  

     RDKit          2D

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    5.1210   -8.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279  -10.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0585  -10.6727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0882   -9.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702   -9.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -9.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860  -10.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7672   -7.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233   -8.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581  -11.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405  -12.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2258  -12.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8082  -12.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0292  -13.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2057  -13.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9450  -14.2718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6075  -14.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2775  -14.2822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444   -6.3816    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1818   -6.8861    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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  7 20  1  6
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 25 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347566

   ---

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: 520.50

Molecular Weight (Monoisotopic): 519.1732

AlogP: 8.79

#Rotatable Bonds: 5

Polar Surface Area: 21.70

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 9.13

CX LogP: 8.46

CX LogD: 6.74

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.31

Np Likeness Score: 0.06

References

1. Cifuentes-Pagano E, Saha J, Csányi G, Ghouleh IA, Sahoo S, Rodríguez A, Wipf P, Pagano PJ, Skoda EM..  (2013)  Bridged tetrahydroisoquinolines as selective NADPH oxidase 2 (Nox2) inhibitors.,  4  (7): [PMID:24466406] [10.1039/c3md00061c]

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

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data