N-(1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl 2-((5R,8S,8aS)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylamide

ID: ALA3126779

PubChem CID: 76325545

Max Phase: Preclinical

Molecular Formula: C25H29ClN4O2

Molecular Weight: 452.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C(=O)NCc1cn(Cc2ccc(Cl)cc2)nn1)[C@@H]1CC[C@H](C)[C@@H]2CC(=O)C(C)=C2C1

Standard InChI:  InChI=1S/C25H29ClN4O2/c1-15-4-7-19(10-23-17(3)24(31)11-22(15)23)16(2)25(32)27-12-21-14-30(29-28-21)13-18-5-8-20(26)9-6-18/h5-6,8-9,14-15,19,22H,2,4,7,10-13H2,1,3H3,(H,27,32)/t15-,19+,22-/m0/s1

Standard InChI Key:  NXQMBJCTCYVIKF-LYLBAIIYSA-N

Molfile:  

     RDKit          2D

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    4.2308  -13.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5998  -14.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2554  -15.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4543  -15.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000  -14.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7903  -14.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9986  -13.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189  -14.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143  -15.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7686  -15.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6939  -14.4557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7833  -13.1912    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4208  -12.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4976  -15.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9148  -16.5764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9053  -15.1475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7398  -16.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1570  -17.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9576  -18.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6543  -18.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2887  -17.9954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9859  -17.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9983  -18.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9887  -19.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2706  -19.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2607  -20.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9708  -20.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6924  -20.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6988  -19.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9623  -21.7134    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  7  1  1  0
  3  4  1  0
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  6  5  1  0
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  7  8  1  0
  8  9  1  0
  9 10  1  0
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 10 11  1  0
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  7 13  1  6
  1 14  1  1
  4 15  1  1
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 18 20  1  0
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 24 25  1  0
 25 21  2  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3126779

   2-[(5R,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]-N-[[1-[(4-chlorophenyl)methyl]triazol-4-yl]methyl]prop-2-enamide

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: 452.99

Molecular Weight (Monoisotopic): 452.1979

AlogP: 4.49

#Rotatable Bonds: 6

Polar Surface Area: 76.88

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.28

CX LogP: 4.59

CX LogD: 4.59

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.65

Np Likeness Score: -0.18

References

1. He YW, Dong CZ, Zhao JY, Ma LL, Li YH, Aisa HA..  (2014)  1,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses.,  76  [PMID:24583605] [10.1016/j.ejmech.2014.02.029]

Source

Source(1):

• Scientific Literature