(E)-5-(naphthalen-2-yl)-N'-(3-nitrobenzylidene)-1H-pyrazole-3-carbohydrazide

ID: ALA4866324

PubChem CID: 9565050

Max Phase: Preclinical

Molecular Formula: C21H15N5O3

Molecular Weight: 385.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/c1cccc([N+](=O)[O-])c1)c1cc(-c2ccc3ccccc3c2)[nH]n1

Standard InChI:  InChI=1S/C21H15N5O3/c27-21(25-22-13-14-4-3-7-18(10-14)26(28)29)20-12-19(23-24-20)17-9-8-15-5-1-2-6-16(15)11-17/h1-13H,(H,23,24)(H,25,27)/b22-13+

Standard InChI Key:  GSRZNGDNNSEOTR-LPYMAVHISA-N

Molfile:  

 
     RDKit          2D

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   28.9871  -31.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.6933  -30.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4020  -31.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4027  -31.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1113  -32.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8195  -31.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8148  -31.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1057  -30.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5191  -30.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2677  -30.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8108  -30.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3979  -29.6394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5996  -29.8143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.6240  -30.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9609  -31.1696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1003  -29.7611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9135  -29.8416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3898  -29.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2030  -29.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5377  -30.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3501  -30.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8273  -29.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4862  -28.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6748  -28.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9576  -28.0054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.7711  -28.0830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6180  -27.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  5  4  2  0
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  9 10  2  0
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  9 11  1  0
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 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  1  0
 27 29  2  0
 25 27  1  0
M  CHG  2  27   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4866324

   3-naphthalen-2-yl-N-[(E)-(3-nitrophenyl)methylideneamino]-1H-pyrazole-5-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 385.38

Molecular Weight (Monoisotopic): 385.1175

AlogP: 3.90

#Rotatable Bonds: 5

Polar Surface Area: 113.28

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.06

CX Basic pKa: 1.64

CX LogP: 4.15

CX LogD: 4.14

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: -1.95

References

1. Butler KJ, Castro AA, Dwyer TS, Hardwick LM, Iacino MC, Manore SG, Mays KM, McGlade CA, Hair LN, Parker EW, Smith MR, Turnow MT, Wilson MR, Woodson SR, Cotham WE, Walla MD, Hurlbert JC, Christian Grattan T..  (2021)  Design, synthesis and analysis of novel sphingosine kinase-1 inhibitors to improve oral bioavailability.,  50  [PMID:34418572] [10.1016/j.bmcl.2021.128329]

Source

Source(1):

• Scientific Literature