N-(1-(3,4-Dichlorobenzyl)-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: ALA3126782

PubChem CID: 76314645

Max Phase: Preclinical

Molecular Formula: C25H28Cl2N4O2

Molecular Weight: 487.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C(=O)NCc1cn(Cc2ccc(Cl)c(Cl)c2)nn1)[C@@H]1CC[C@H](C)[C@@H]2CC(=O)C(C)=C2C1

Standard InChI:  InChI=1S/C25H28Cl2N4O2/c1-14-4-6-18(9-21-16(3)24(32)10-20(14)21)15(2)25(33)28-11-19-13-31(30-29-19)12-17-5-7-22(26)23(27)8-17/h5,7-8,13-14,18,20H,2,4,6,9-12H2,1,3H3,(H,28,33)/t14-,18+,20-/m0/s1

Standard InChI Key:  AVNBZTPJXJNIGR-QMIHWGKISA-N

Molfile:  

     RDKit          2D

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   26.2343  -26.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6033  -26.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2589  -27.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.7721  -28.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6974  -26.9428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7867  -25.6784    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.4242  -25.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.1605  -29.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9611  -30.5661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6577  -31.0079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2922  -30.4826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9894  -29.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0018  -30.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9922  -31.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2741  -32.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2642  -32.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9743  -33.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6959  -32.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7023  -32.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9658  -34.2006    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.4070  -33.3854    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 28 29  1  0
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 30 31  1  0
 31 32  2  0
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 30 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3126782

   2-[(5R,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]-N-[[1-[(3,4-dichlorophenyl)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: 487.43

Molecular Weight (Monoisotopic): 486.1589

AlogP: 5.15

#Rotatable Bonds: 6

Polar Surface Area: 76.88

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.28

CX LogP: 5.19

CX LogD: 5.19

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.57

Np Likeness Score: -0.30

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