Symyx   11300911332D 1   1.00000     0.00000     0

 19 21  0     0  0            999 V2000
    3.1663   -8.6582    0.0000 O   0  0  0  0  0  0           0  0  0
    3.7386   -8.0648    0.0000 C   0  0  0  0  0  0           0  0  0
    4.5306   -8.3062    0.0000 C   0  0  2  0  0  0           0  0  0
    4.7966   -9.0834    0.0000 C   0  0  1  0  0  0           0  0  0
    4.3294   -9.7593    0.0000 O   0  0  0  0  0  0           0  0  0
    5.6213   -9.0679    0.0000 C   0  0  0  0  0  0           0  0  0
    5.8669   -8.2801    0.0000 C   0  0  1  0  0  0           0  0  0
    5.1868   -7.8047    0.0000 O   0  0  0  0  0  0           0  0  0
    6.6442   -8.0100    0.0000 N   0  0  3  0  0  0           0  0  0
    7.3243   -8.4812    0.0000 C   0  0  0  0  0  0           0  0  0
    7.9763   -7.9840    0.0000 N   0  0  0  0  0  0           0  0  0
    7.7104   -7.2066    0.0000 C   0  0  0  0  0  0           0  0  0
    8.1084   -6.4826    0.0000 C   0  0  0  0  0  0           0  0  0
    8.9332   -6.4671    0.0000 N   0  0  0  0  0  0           0  0  0
    7.6816   -5.7742    0.0000 N   0  0  0  0  0  0           0  0  0
    6.8568   -5.7897    0.0000 C   0  0  0  0  0  0           0  0  0
    6.4588   -6.5137    0.0000 N   0  0  0  0  0  0           0  0  0
    6.8856   -7.2221    0.0000 C   0  0  0  0  0  0           0  0  0
    6.4301   -5.0853    0.0000 Cl  0  0  0  0  0  0           0  0  0
  1  2  1  0     0  0
  3  2  1  1     0  0
  3  4  1  0     0  0
  4  5  1  6     0  0
  4  6  1  0     0  0
  6  7  1  0     0  0
  7  8  1  0     0  0
  3  8  1  0     0  0
  7  9  1  1     0  0
  9 10  1  0     0  0
 10 11  2  0     0  0
 11 12  1  0     0  0
 12 13  1  0     0  0
 13 14  1  0     0  0
 13 15  2  0     0  0
 15 16  1  0     0  0
 16 17  2  0     0  0
 17 18  1  0     0  0
 12 18  2  0     0  0
  9 18  1  0     0  0
 16 19  1  0     0  0
M  END
> <ID>
CHEBI:567361

> <NAME>
cladribine

> <DEFINITION>
2'-Deoxyadenosine in which the hydrogen at position 2 on the purine ring has been substituted by chlorine. It inhibits the synthesis and repair of DNA, particularly in  lymphocytes and monocytes, and is used as an antimetabolite antineoplastic drug for the treatment of lymphoid malignancies including  hairy-cell leukaemia and chronic lymphocytic leukaemia.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:568373; CHEBI:31407

> <SYNONYM>
CldAdo; Cladribine; 2ClAdo; 2-chlorodeoxyadenosine; 2-chloro-deoxyadenosine; 2-chloro-6-amino-9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine; 2-chloro-2'-deoxy-beta-adenosine; 2-CdA; (2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

> <IUPAC_NAME>
2-chloro-2'-deoxyadenosine

> <INN>
cladribinum; cladribine; cladribina

> <FORMULA>
C10H12ClN5O3

> <MASS>
285.68700

> <MONOISOTOPIC_MASS>
285.06287

> <CHARGE>
0

> <SMILES>
Nc1nc(Cl)nc2n(cnc12)[C@H]1C[C@H](O)[C@@H](CO)O1

> <INCHI>
InChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1

> <INCHIKEY>
PTOAARAWEBMLNO-KVQBGUIXSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
624220

> <CAS_REGISTRY_NUMBER>
4291-63-8

> <CHEMIDPLUS>
4291-63-8

> <DRUGBANK_ACCESSION>
DB00242

> <KEGG_DRUG_ACCESSION>
D01370

> <LINCS_ACCESSION>
LSM-5976

> <WIKIPEDIA_ACCESSION>
Cladribine

> <PUBMED_CITATION>
17526755; 26024233; 18570408

$$$$