3-(3-{4-[2-(5-Nitro-2,3-dioxo-2,3-dihydro-indol-1-yl)-acetyl]-piperazine-1-carbonyl}-ureido)-benzoic acid ethyl ester

ID: ALA315217

PubChem CID: 44318178

Max Phase: Preclinical

Molecular Formula: C25H24N6O9

Molecular Weight: 552.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cccc(NC(=O)NC(=O)N2CCN(C(=O)CN3C(=O)C(=O)c4cc([N+](=O)[O-])ccc43)CC2)c1

Standard InChI:  InChI=1S/C25H24N6O9/c1-2-40-23(35)15-4-3-5-16(12-15)26-24(36)27-25(37)29-10-8-28(9-11-29)20(32)14-30-19-7-6-17(31(38)39)13-18(19)21(33)22(30)34/h3-7,12-13H,2,8-11,14H2,1H3,(H2,26,27,36,37)

Standard InChI Key:  JUPAIAVKUFMZNR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.4917   -9.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9667   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  2  1  0
  5  1  1  0
  6 12  1  0
  7 15  1  0
  8  6  1  0
  9  1  1  0
 10  8  1  0
 11  9  1  0
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 13 11  1  0
 14  3  2  0
 15 31  2  0
 16 19  1  0
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 19 32  2  0
 20  7  1  0
 21  2  2  0
 22  7  2  0
 23  4  2  0
 24  6  2  0
 25 27  1  0
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 27 13  1  0
 28 13  1  0
 29 10  2  0
 30 11  2  0
 31 17  1  0
 32 33  1  0
 33 18  1  0
 34 16  2  0
 35 16  1  0
 36 37  2  0
 37 38  1  0
 38 33  2  0
 39 35  1  0
 40 39  1  0
  3  4  1  0
 14 15  1  0
 25 12  1  0
 19 36  1  0
M  CHG  2   7   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA315217

   Ethyl 3-[[4-[2-(5-nitro-2,3-dioxoindol-1-yl)acetyl]piperazine-1-carbonyl]carbamoylamino]benzoate

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: 552.50

Molecular Weight (Monoisotopic): 552.1605

AlogP: 1.39

#Rotatable Bonds: 6

Polar Surface Area: 188.57

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 15

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.09

CX Basic pKa: ┄

CX LogP: 0.87

CX LogD: 0.87

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.23

Np Likeness Score: -1.59

References

1. Shuttleworth SJ, Nasturica D, Gervais C, Siddiqui MA, Rando RF, Lee N..  (2000)  Parallel synthesis of isatin-based serine protease inhibitors.,  10  (22): [PMID:11086715] [10.1016/s0960-894x(00)00523-0]

Source

Source(1):

• Scientific Literature