NPASS drugs

Drug Information

Drug ID:	NPD185
Drug Name:	Cladribine
Molecular Formula:	C10H12ClN5O3
Canonical SMILES:	OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1nc(Cl)nc2N
Standard 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"
Standard InCHIKey:	PTOAARAWEBMLNO-KVQBGUIXSA-N
Max Developmental Stage:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD185

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	140744
0.1-0.2	69990
0.2-0.3	682
0.3-0.4	253
0.4-0.5	48
0.5-0.6	11
0.6-0.7	8
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC574902
High Similarity	1.0	NPC599876
Intermediate Similarity	0.7069	NPC269827
Intermediate Similarity	0.7069	NPC602648
Remote Similarity	0.6724	NPC209525
Remote Similarity	0.6724	NPC236015
Remote Similarity	0.6724	NPC161659
Remote Similarity	0.6724	NPC137784
Remote Similarity	0.6724	NPC567109
Remote Similarity	0.6724	NPC602314
Remote Similarity	0.65	NPC538546
Remote Similarity	0.6393	NPC474526
Remote Similarity	0.5882	NPC472816
Remote Similarity	0.5882	NPC517016
Remote Similarity	0.5882	NPC574893
Remote Similarity	0.5882	NPC581344
Remote Similarity	0.5882	NPC600171
Remote Similarity	0.5455	NPC561547
Remote Similarity	0.5395	NPC518550
Remote Similarity	0.5395	NPC572845
Remote Similarity	0.5395	NPC611003
Remote Similarity	0.5238	NPC52238
Remote Similarity	0.5217	NPC316865

Drug Structure

NPD185 OpenBabel08201723122D 23 25 0 0 1 0 0 0 0 0999 V2000 2.1280 -0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2440 -2.0371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 -0.6522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3305 -1.6303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7213 -1.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0530 -1.4493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7917 0.0909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4644 -2.1303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9666 -1.8560 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7698 -0.1170 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 17 1 0 0 0 0 3 13 2 0 0 0 0 3 16 1 0 0 0 0 4 5 1 0 0 0 0 4 18 1 6 0 0 0 5 2 1 1 0 0 0 5 19 1 0 0 0 0 6 1 1 1 0 0 0 6 16 1 0 0 0 0 6 19 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000565
DrugBank	DB00242
ChEMBL	CHEMBL1619
IUPHAR/BPS	4799
PharmaGKB	PA449027
KEGG Drug	D01370
PubChem CID	20279
ChEBI	567361
CAS Number	4291-63-8

Drug Properties

Molecular Weight	285.06
ALogP	-1.7568
MLogP	1.57
XLogP	-0.692
HDA	8
HBD	3
Rotatable Bonds	6
TPSA	119.31
RO5 Violation	0