[(6S)-4-(3'-Cyanobiphenyl-4-yl)-2,3,9-trimethyl-6H-1-thia-5,7,8,9a-tetraazacyclopenta[e]azulen-6-yl]acetic acid methyl ester

ID: ALA3771129

PubChem CID: 15978962

Max Phase: Preclinical

Molecular Formula: C27H23N5O2S

Molecular Weight: 481.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C[C@@H]1N=C(c2ccc(-c3cccc(C#N)c3)cc2)c2c(sc(C)c2C)-n2c(C)nnc21

Standard InChI:  InChI=1S/C27H23N5O2S/c1-15-16(2)35-27-24(15)25(29-22(13-23(33)34-4)26-31-30-17(3)32(26)27)20-10-8-19(9-11-20)21-7-5-6-18(12-21)14-28/h5-12,22H,13H2,1-4H3/t22-/m0/s1

Standard InChI Key:  NCPYGYYERXQFSF-QFIPXVFZSA-N

Molfile:  

     RDKit          2D

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    3.1584   -2.7155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9871    1.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4121   -2.5707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086   -3.2948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1266    3.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149    4.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7214    5.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    8.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5626    9.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715   10.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1623   11.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1354    8.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4111   11.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6 20  1  0
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 30 31  2  0
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 11  2  1  1
  4 33  1  0
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 29 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3771129

   methyl 2-[(9S)-7-[4-(3-cyanophenyl)phenyl]-4,5,13-trimethyl-3-thia-1,8,11,12-tetrazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaen-9-yl]acetate

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: 481.58

Molecular Weight (Monoisotopic): 481.1572

AlogP: 5.25

#Rotatable Bonds: 4

Polar Surface Area: 93.16

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.45

CX LogP: 5.10

CX LogD: 5.10

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: -1.05

References

1. Endo J, Hikawa H, Hamada M, Ishibuchi S, Fujie N, Sugiyama N, Tanaka M, Kobayashi H, Sugahara K, Oshita K, Iwata K, Ooike S, Murata M, Sumichika H, Chiba K, Adachi K..  (2016)  A phenotypic drug discovery study on thienodiazepine derivatives as inhibitors of T cell proliferation induced by CD28 co-stimulation leads to the discovery of a first bromodomain inhibitor.,  26  (5): [PMID:26869194] [10.1016/j.bmcl.2016.01.084]

Source

Source(1):

• Scientific Literature