NPASS drugs

Drug Information

Drug ID:	NPD1760
Drug Name:	Capecitabine
Molecular Formula:	C15H22FN3O6
Canonical SMILES:	CCCCCOC(=Nc1nc(=O)n(cc1F)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C)O
Standard InCHI:	InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1
Standard InCHIKey:	GAGWJHPBXLXJQN-UORFTKCHSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD1760

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	49
0.1-0.2	7843
0.2-0.3	18103
0.3-0.4	4139
0.4-0.5	667
0.5-0.6	45
0.6-0.7	21
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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
Intermediate Similarity	0.7778	NPC163352
Intermediate Similarity	0.7778	NPC210456
Intermediate Similarity	0.7667	NPC43246
Intermediate Similarity	0.7667	NPC89051
Intermediate Similarity	0.764	NPC112842
Intermediate Similarity	0.764	NPC71339
Intermediate Similarity	0.7609	NPC171116
Intermediate Similarity	0.7528	NPC106780
Intermediate Similarity	0.7419	NPC315063
Intermediate Similarity	0.7312	NPC328806
Intermediate Similarity	0.7241	NPC329077
Intermediate Similarity	0.7204	NPC190334
Intermediate Similarity	0.7204	NPC62927
Intermediate Similarity	0.7159	NPC325902
Intermediate Similarity	0.7113	NPC324516
Intermediate Similarity	0.7113	NPC36985
Intermediate Similarity	0.7113	NPC17892
Intermediate Similarity	0.7113	NPC318166
Intermediate Similarity	0.7083	NPC327344
Intermediate Similarity	0.7065	NPC229249
Intermediate Similarity	0.7041	NPC317639
Intermediate Similarity	0.7041	NPC73765
Intermediate Similarity	0.7041	NPC283698
Remote Similarity	0.6979	NPC324390
Remote Similarity	0.6907	NPC320249
Remote Similarity	0.6907	NPC322594
Remote Similarity	0.6887	NPC149843
Remote Similarity	0.6887	NPC155087
Remote Similarity	0.6765	NPC328914
Remote Similarity	0.6733	NPC328779
Remote Similarity	0.6705	NPC315806
Remote Similarity	0.67	NPC226769
Remote Similarity	0.67	NPC6166
Remote Similarity	0.67	NPC280946
Remote Similarity	0.6634	NPC90240
Remote Similarity	0.6634	NPC120887
Remote Similarity	0.6632	NPC325723
Remote Similarity	0.66	NPC329384
Remote Similarity	0.6542	NPC329277
Remote Similarity	0.6489	NPC319753
Remote Similarity	0.62	NPC109188
Remote Similarity	0.6116	NPC315058
Remote Similarity	0.6083	NPC325750
Remote Similarity	0.6033	NPC284651
Remote Similarity	0.5968	NPC313962
Remote Similarity	0.5913	NPC478024
Remote Similarity	0.5897	NPC313813
Remote Similarity	0.5714	NPC92874
Remote Similarity	0.5714	NPC322449
Remote Similarity	0.5714	NPC62845
Remote Similarity	0.5714	NPC189854
Remote Similarity	0.5714	NPC166242
Remote Similarity	0.5714	NPC293551
Remote Similarity	0.5664	NPC10897
Remote Similarity	0.5664	NPC325900
Remote Similarity	0.5659	NPC318142
Remote Similarity	0.5625	NPC314398
Remote Similarity	0.5625	NPC314413
Remote Similarity	0.5625	NPC239705

Drug Structure

NPD1760 OpenBabel08211701082D 28 29 0 0 1 0 0 0 0 0999 V2000 -1.7321 7.0000 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 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 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 2.4487 -0.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 0.9706 -1.4945 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 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 F 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 -2.5981 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 2.3554 -2.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2274 -2.1637 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 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 1.7677 -3.4250 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4353 -3.1418 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 24 1 0 0 0 0 7 9 2 0 0 0 0 7 19 1 0 0 0 0 8 2 1 6 0 0 0 8 10 1 0 0 0 0 8 25 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 1 0 0 0 11 13 1 0 0 0 0 11 21 1 1 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 6 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 14 22 2 0 0 0 0 15 18 2 3 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000761
DrugBank	DB01101
ChEMBL	CHEMBL1773
IUPHAR/BPS	6799
PharmaGKB	PA448771
KEGG Drug	D01223
PubChem CID	60953
ChEBI	31348
CAS Number	154361-50-9

Drug Properties

Molecular Weight	359.15
ALogP	-2.8918
MLogP	2.01
XLogP	1.089
HDA	9
HBD	3
Rotatable Bonds	13
TPSA	124.18
RO5 Violation	0