(5R,7S,8R)-2-(benzo[d]thiazol-5-yl)-7-hydroxy-4,5,6,7,8,9-hexahydro-5,8-methanopyrazolo[1,5-a][1,3]diazocine-3-carboxamide

ID: ALA4583311

PubChem CID: 155566265

Max Phase: Preclinical

Molecular Formula: C17H17N5O2S

Molecular Weight: 355.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(-c2ccc3scnc3c2)nn2c1N[C@@H]1C[C@H](C2)[C@@H](O)C1

Standard InChI:  InChI=1S/C17H17N5O2S/c18-16(24)14-15(8-1-2-13-11(4-8)19-7-25-13)21-22-6-9-3-10(5-12(9)23)20-17(14)22/h1-2,4,7,9-10,12,20,23H,3,5-6H2,(H2,18,24)/t9-,10-,12+/m1/s1

Standard InChI Key:  KCCBHMDLTMFMBQ-FOGDFJRCSA-N

Molfile:  

 
     RDKit          2D

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   23.6649  -23.8676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4245  -23.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6247  -23.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1560  -22.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4839  -21.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3552  -22.5316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8906  -22.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6874  -22.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0363  -21.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5695  -21.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8382  -21.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1602  -21.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9603  -21.8213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1331  -21.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4383  -20.6277    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.1410  -25.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6705  -25.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8905  -25.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0137  -24.3317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3707  -23.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5906  -23.9886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1244  -24.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2474  -25.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2127  -24.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9922  -26.4819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.3312  -24.5580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.7000  -26.6727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  0
  1  2  2  0
  2  3  1  0
  3 20  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  7  8  2  0
  8 12  1  0
 11  9  1  0
  9 10  2  0
 10  7  1  0
  2  7  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 16 17  1  0
 17 18  1  0
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 20 21  1  0
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 22 23  1  0
 23 18  1  0
 22 24  1  0
 17 24  1  0
 17 25  1  1
 22 26  1  1
 18 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4583311

   ---

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: 355.42

Molecular Weight (Monoisotopic): 355.1103

AlogP: 1.82

#Rotatable Bonds: 2

Polar Surface Area: 106.06

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.77

CX Basic pKa: 2.72

CX LogP: 1.02

CX LogD: 1.02

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: -0.68

References

1. Haffner CD, Charnley AK, Aquino CJ, Casillas L, Convery MA, Cox JA, Elban MA, Goodwin NC, Gough PJ, Haile PA, Hughes TV, Knapp-Reed B, Kreatsoulas C, Lakdawala AS, Li H, Lian Y, Lipshutz D, Mehlmann JF, Ouellette M, Romano J, Shewchuk L, Shu A, Votta BJ, Zhou H, Bertin J, Marquis RW..  (2019)  Discovery of Pyrazolocarboxamides as Potent and Selective Receptor Interacting Protein 2 (RIP2) Kinase Inhibitors.,  10  (11): [PMID:31749904] [10.1021/acsmedchemlett.9b00141]

Source

Source(1):

• Scientific Literature