8-CHLOROADENOSINE

ID: ALA4594396

Cas Number: 34408-14-5

PubChem CID: 147569

Product Number: C287342, Order Now?

Max Phase: Phase

Molecular Formula: C10H12ClN5O4

Molecular Weight: 301.69

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 8-chloroadenosine | NSC-354258 | 8-Chloroadenosine|34408-14-5|Adenosine, 8-chloro-|8-Cl-Ado|PA05MFH3I7|(2R,3R,4S,5R)-2-(6-amino-8-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol|NSC-354258|8-Chloro-adenosine|UNII-PA05MFH3I7|(2R,3R,4S,5R)-2-(6-amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol|Adenosine,8-chloro|SCHEMBL987728|CHEMBL4594396|MHDPPLULTMGBSI-UUOKFMHZSA-N|MFCD01076457|AKOS024284395|NSC 354258|(2R,3R,4S,5R)-2-(6-amino-8-chloro-purin-9-yl)-5-(hydroxymethyl)tetraShow More⌵

Canonical SMILES:  Nc1ncnc2c1nc(Cl)n2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H12ClN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1

Standard InChI Key:  MHDPPLULTMGBSI-UUOKFMHZSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  1  0  0  0  0  0999 V2000
    4.1159   -6.9718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7238   -6.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931   -6.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7175   -7.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074   -8.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -7.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0026   -8.2159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8279   -6.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1819   -6.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6237   -6.5293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2719   -7.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9584   -6.5826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7361   -5.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1766   -5.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0007   -5.1266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7928   -4.3630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9687   -4.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5242   -5.0295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9079   -5.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2388   -7.8677    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  6
  6  8  1  0
  9  8  1  0
  3  9  1  0
  8 10  1  1
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 13 19  2  0
 10 19  1  0
 11 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4594396

   8-Chloroadenosine

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 301.69

Molecular Weight (Monoisotopic): 301.0578

AlogP: -1.33

#Rotatable Bonds: 2

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 2.78

CX LogP: -1.18

CX LogD: -1.18

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.50

Np Likeness Score: 0.78

References

1. Unpublished dataset, 

2. Patel BA, D'Amico TL, Blagg BSJ..  (2020)  Natural products and other inhibitors of F₁F_O ATP synthase.,  207  [PMID:32942072] [10.1016/j.ejmech.2020.112779]

Source

Source(2):

• Scientific Literature
• Clinical Candidates