(1S,2R,3S,4R,5S)-4-(2-chloro-6-(methoxyamino)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

ID: ALA402607

PubChem CID: 44448978

Max Phase: Preclinical

Molecular Formula: C14H17ClN6O4

Molecular Weight: 368.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NOC)nc(Cl)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C14H17ClN6O4/c1-16-12(24)14-3-5(14)7(8(22)9(14)23)21-4-17-6-10(20-25-2)18-13(15)19-11(6)21/h4-5,7-9,22-23H,3H2,1-2H3,(H,16,24)(H,18,19,20)/t5-,7-,8+,9+,14+/m1/s1

Standard InChI Key:  IDFINWOKYJJUJZ-RGUAOFKASA-N

Molfile:  

     RDKit          2D

 26 29  0  0  1  0  0  0  0  0999 V2000
   -7.4921  -10.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6671  -10.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4072   -9.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4397  -10.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1699   -9.7319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4094  -10.9443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8700  -10.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6177   -9.4273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9730  -11.1343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1762  -11.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5434   -8.6412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3685   -8.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2875   -9.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9559   -9.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8706  -10.7279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174  -11.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487  -10.5754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5374   -9.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8711   -9.2719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7396   -9.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0765   -9.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8278   -8.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4528   -8.6638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166   -9.6058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304  -11.8846    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0284  -10.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12  8  1  0
  2  3  1  0
  4  6  2  0
 13 14  2  0
  3 21  1  0
 14 15  1  0
  5  7  1  0
 15 16  2  0
 20  1  1  0
 16 17  1  0
  3  8  1  1
 17 18  2  0
 18 13  1  0
  1  2  1  0
 18 19  1  0
 21 20  1  0
 22 21  1  0
 20 22  1  0
  1  9  1  6
 20  4  1  1
  2 10  1  6
  8 14  1  0
 21 23  1  1
 19 24  1  0
  4  5  1  0
 16 25  1  0
 13 11  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA402607

   (1S,2R,3S,4R,5S)-4-[2-chloro-6-(methoxyamino)purin-9-yl]-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

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: 368.78

Molecular Weight (Monoisotopic): 368.1000

AlogP: -0.52

#Rotatable Bonds: 4

Polar Surface Area: 134.42

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: 0.73

CX LogP: -0.67

CX LogD: -0.67

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.42

Np Likeness Score: 0.17

References

1. Melman A, Gao ZG, Kumar D, Wan TC, Gizewski E, Auchampach JA, Jacobson KA..  (2008)  Design of (N)-methanocarba adenosine 5'-uronamides as species-independent A3 receptor-selective agonists.,  18  (9): [PMID:18424135] [10.1016/j.bmcl.2008.04.001]

Source

Source(1):

• Scientific Literature