NPASS drugs

Drug Information

Drug ID:	NPD9554
Drug Name:	Gemcitabine
Molecular Formula:	C9H11F2N3O4
Canonical SMILES:	OC[C@H]1O[C@H](C([C@@H]1O)(F)F)n1ccc(=N)nc1O
Standard InCHI:	"InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1"
Standard InCHIKey:	SDUQYLNIPVEERB-QPPQHZFASA-N
Max Developmental Stage:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD9554

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	116505
0.1-0.2	94415
0.2-0.3	776
0.3-0.4	22
0.4-0.5	15
0.5-0.6	3
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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	NPC480848
Remote Similarity	0.6275	NPC62927
Remote Similarity	0.6154	NPC229249
Remote Similarity	0.6154	NPC140420
Remote Similarity	0.566	NPC487916
Remote Similarity	0.5424	NPC280946
Remote Similarity	0.5167	NPC6166

Drug Structure

NPD9554 OpenBabel08211713452D 22 23 0 0 1 0 0 0 0 0999 V2000 1.7321 0.0000 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 -3.4432 0.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 0.8364 0.0000 C 0 0 2 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 -1.9487 1.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 -0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0076 1.7024 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -0.6615 2.4456 0.0000 F 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 0.8660 -1.5000 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 -4.0310 1.5409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3554 2.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 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 -3.6243 2.4544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7677 3.4250 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 5 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 3 1 6 0 0 0 4 6 1 0 0 0 0 4 18 1 0 0 0 0 5 12 2 0 0 0 0 5 13 1 0 0 0 0 6 9 1 0 0 0 0 6 16 1 1 0 0 0 7 9 1 0 0 0 0 7 14 1 6 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 12 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001246
DrugBank	DB00441
ChEMBL	CHEMBL888
IUPHAR/BPS	4793
PharmaGKB	PA449748
KEGG Drug	D02368
PubChem CID	60750
ChEBI	175901
CAS Number	95058-81-4

Drug Properties

Molecular Weight	263.07
ALogP	-1.386
MLogP	1.46
XLogP	0.518
HDA	7
HBD	4
Rotatable Bonds	7
TPSA	109.37
RO5 Violation	0