Bicyclo[2.2.1]heptane-2-carboxylic acid [9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-amide (S-ENBA)

ID: ALA2112181

PubChem CID: 71452673

Max Phase: Preclinical

Molecular Formula: C18H23N5O5

Molecular Weight: 389.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)[C@H]1C[C@H]2CC[C@@H]1C2

Standard InChI:  InChI=1S/C18H23N5O5/c24-5-11-13(25)14(26)18(28-11)23-7-21-12-15(19-6-20-16(12)23)22-17(27)10-4-8-1-2-9(10)3-8/h6-11,13-14,18,24-26H,1-5H2,(H,19,20,22,27)/t8-,9+,10-,11+,13+,14+,18+/m0/s1

Standard InChI Key:  AXQJNGXORVSYDU-HPMFRURESA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   10.8315   -5.7172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8315   -7.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1094   -5.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1094   -4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8315   -4.4651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4042   -8.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2919   -5.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7185   -6.7805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4436   -4.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0262   -2.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4436   -3.5410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0428   -8.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6254   -7.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2015   -2.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4436   -5.8828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7579   -4.7036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7841   -3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7579   -5.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4436   -2.1100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7841   -2.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9593   -3.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9593   -2.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9593   -3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8613   -8.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5691   -9.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5486   -2.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6254   -6.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7940   -6.7805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1950   -4.2563    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5460   -1.3960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  3  2  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  4  1  0
 10 11  1  0
 11  9  1  0
 12  6  1  0
 13  8  1  0
 14 10  1  6
 15  3  1  0
 16 18  1  0
 17 14  1  0
 18 15  2  0
 19 10  2  0
 20 14  1  0
 17 21  1  0
 22 20  1  0
 23 17  1  0
  6 24  1  6
 12 25  1  6
 26 22  1  0
 13 27  1  1
 28 27  1  0
  5  4  1  0
 13 12  1  0
 16  9  2  0
 22 21  1  0
 23 26  1  0
 17 29  1  1
 22 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2112181

   (1R,2S,4S)-N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]bicyclo[2.2.1]heptane-2-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: 389.41

Molecular Weight (Monoisotopic): 389.1699

AlogP: -0.19

#Rotatable Bonds: 4

Polar Surface Area: 142.62

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.21

CX Basic pKa: 2.34

CX LogP: -0.25

CX LogD: -0.25

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: 0.46

References

1. Ueeda M, Thompson RD, Arroyo LH, Olsson RA..  (1991)  2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor.,  34  (4): [PMID:2016707] [10.1021/jm00108a014]

Source

Source(1):

• Scientific Literature