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:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD9554

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	54
0.1-0.2	9867
0.2-0.3	18017
0.3-0.4	2468
0.4-0.5	410
0.5-0.6	33
0.6-0.7	21
0.7-0.8	8
0.8-0.85	8
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	0.9506	NPC229249
High Similarity	0.9167	NPC190334
High Similarity	0.9167	NPC62927
High Similarity	0.8556	NPC329384
Intermediate Similarity	0.8462	NPC280946
Intermediate Similarity	0.8462	NPC226769
Intermediate Similarity	0.8462	NPC6166
Intermediate Similarity	0.837	NPC90240
Intermediate Similarity	0.837	NPC120887
Intermediate Similarity	0.828	NPC328779
Intermediate Similarity	0.8202	NPC328806
Intermediate Similarity	0.8105	NPC328914
Intermediate Similarity	0.764	NPC106780
Intermediate Similarity	0.7391	NPC89051
Intermediate Similarity	0.7391	NPC43246
Intermediate Similarity	0.7158	NPC315063
Intermediate Similarity	0.7083	NPC324390
Intermediate Similarity	0.7011	NPC315806
Intermediate Similarity	0.701	NPC322594
Intermediate Similarity	0.701	NPC320249
Remote Similarity	0.6869	NPC36985
Remote Similarity	0.6869	NPC17892
Remote Similarity	0.6854	NPC469972
Remote Similarity	0.6809	NPC112842
Remote Similarity	0.6809	NPC71339
Remote Similarity	0.68	NPC283698
Remote Similarity	0.68	NPC73765
Remote Similarity	0.6696	NPC313813
Remote Similarity	0.6598	NPC163352
Remote Similarity	0.6598	NPC210456
Remote Similarity	0.6465	NPC171116
Remote Similarity	0.6413	NPC329077
Remote Similarity	0.6344	NPC325902
Remote Similarity	0.6337	NPC327344
Remote Similarity	0.6214	NPC318166
Remote Similarity	0.6214	NPC324516
Remote Similarity	0.6182	NPC329277
Remote Similarity	0.6154	NPC317639
Remote Similarity	0.6111	NPC318142
Remote Similarity	0.6071	NPC149843
Remote Similarity	0.6071	NPC155087
Remote Similarity	0.5918	NPC319753
Remote Similarity	0.59	NPC325723
Remote Similarity	0.5868	NPC245534

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