NPASS drugs

Drug Information

Drug ID:	NPD3968
Drug Name:	Methotrexate
Molecular Formula:	C20H22N8O5
Canonical SMILES:	CN(c1ccc(cc1)C(=O)N[C@H](C(=O)O)CCC(=O)O)Cc1cnc2c(n1)c(N)[nH]c(=N)n2
Standard InCHI:	InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1
Standard InCHIKey:	FBOZXECLQNJBKD-ZDUSSCGKSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3968

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	282
0.1-0.2	3027
0.2-0.3	11956
0.3-0.4	11339
0.4-0.5	1679
0.5-0.6	1853
0.6-0.7	724
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
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
High Similarity	0.9381	NPC147983
High Similarity	0.9381	NPC177996
Intermediate Similarity	0.7958	NPC14849
Intermediate Similarity	0.7853	NPC328611
Intermediate Similarity	0.7853	NPC248862
Intermediate Similarity	0.7824	NPC131450
Intermediate Similarity	0.7824	NPC182057
Intermediate Similarity	0.7824	NPC147298
Intermediate Similarity	0.7512	NPC471194
Intermediate Similarity	0.7512	NPC153980
Intermediate Similarity	0.7512	NPC471193
Intermediate Similarity	0.7512	NPC6865
Intermediate Similarity	0.7465	NPC72956
Intermediate Similarity	0.7346	NPC473376
Intermediate Similarity	0.7337	NPC40530
Intermediate Similarity	0.7337	NPC314281
Intermediate Similarity	0.7327	NPC471192
Intermediate Similarity	0.7313	NPC228835
Intermediate Similarity	0.7268	NPC210123
Intermediate Similarity	0.72	NPC11126
Intermediate Similarity	0.7182	NPC281049
Intermediate Similarity	0.7175	NPC64216
Intermediate Similarity	0.7143	NPC54981
Intermediate Similarity	0.7122	NPC17059
Intermediate Similarity	0.708	NPC476491
Intermediate Similarity	0.7078	NPC54744
Intermediate Similarity	0.7056	NPC317701
Intermediate Similarity	0.7047	NPC84317
Intermediate Similarity	0.7031	NPC89987
Intermediate Similarity	0.7005	NPC71238
Remote Similarity	0.699	NPC94752
Remote Similarity	0.6976	NPC477003
Remote Similarity	0.6974	NPC154478
Remote Similarity	0.6972	NPC472070
Remote Similarity	0.6943	NPC69843
Remote Similarity	0.693	NPC57398
Remote Similarity	0.6927	NPC270834
Remote Similarity	0.6912	NPC471191
Remote Similarity	0.6912	NPC73994
Remote Similarity	0.6909	NPC320968
Remote Similarity	0.6908	NPC62749
Remote Similarity	0.6906	NPC238945
Remote Similarity	0.6893	NPC21429
Remote Similarity	0.6893	NPC285923
Remote Similarity	0.6869	NPC293917
Remote Similarity	0.686	NPC99939
Remote Similarity	0.686	NPC308931
Remote Similarity	0.686	NPC133003
Remote Similarity	0.6856	NPC251391
Remote Similarity	0.6849	NPC476524
Remote Similarity	0.684	NPC202812
Remote Similarity	0.6832	NPC477976
Remote Similarity	0.6829	NPC61011
Remote Similarity	0.6829	NPC91179
Remote Similarity	0.6822	NPC171317
Remote Similarity	0.6818	NPC478158
Remote Similarity	0.6812	NPC46895
Remote Similarity	0.681	NPC324091
Remote Similarity	0.6808	NPC102592
Remote Similarity	0.6808	NPC79356
Remote Similarity	0.6806	NPC471944
Remote Similarity	0.68	NPC41717
Remote Similarity	0.6798	NPC469529
Remote Similarity	0.6798	NPC469938
Remote Similarity	0.6798	NPC229893
Remote Similarity	0.6798	NPC476817
Remote Similarity	0.6783	NPC323244
Remote Similarity	0.678	NPC126709
Remote Similarity	0.678	NPC283219
Remote Similarity	0.678	NPC248041
Remote Similarity	0.6777	NPC473763
Remote Similarity	0.6777	NPC117244
Remote Similarity	0.6774	NPC472062
Remote Similarity	0.6774	NPC472063
Remote Similarity	0.6774	NPC472069
Remote Similarity	0.6773	NPC116555
Remote Similarity	0.6762	NPC213629
Remote Similarity	0.6761	NPC294693
Remote Similarity	0.6758	NPC472064
Remote Similarity	0.6748	NPC16659
Remote Similarity	0.6745	NPC216550
Remote Similarity	0.6741	NPC478157
Remote Similarity	0.6732	NPC14113
Remote Similarity	0.6732	NPC145885
Remote Similarity	0.6732	NPC83774
Remote Similarity	0.6732	NPC84827
Remote Similarity	0.6727	NPC54420
Remote Similarity	0.6726	NPC75634
Remote Similarity	0.6724	NPC116622
Remote Similarity	0.6723	NPC171393
Remote Similarity	0.6723	NPC295452
Remote Similarity	0.6713	NPC284338
Remote Similarity	0.6708	NPC477420
Remote Similarity	0.6708	NPC477418
Remote Similarity	0.6707	NPC74619
Remote Similarity	0.6701	NPC123906
Remote Similarity	0.67	NPC138293
Remote Similarity	0.67	NPC113056
Remote Similarity	0.67	NPC478182
Remote Similarity	0.6699	NPC265710
Remote Similarity	0.6699	NPC219336
Remote Similarity	0.6699	NPC311282
Remote Similarity	0.6698	NPC78767
Remote Similarity	0.6698	NPC476460
Remote Similarity	0.6698	NPC473814
Remote Similarity	0.6697	NPC476525
Remote Similarity	0.6683	NPC267885
Remote Similarity	0.6682	NPC121327
Remote Similarity	0.6682	NPC93390
Remote Similarity	0.6667	NPC213914
Remote Similarity	0.6667	NPC328924
Remote Similarity	0.6667	NPC476527
Remote Similarity	0.6667	NPC474916
Remote Similarity	0.6667	NPC162860
Remote Similarity	0.6667	NPC477979
Remote Similarity	0.6667	NPC235684
Remote Similarity	0.6652	NPC118940
Remote Similarity	0.6652	NPC477714
Remote Similarity	0.6651	NPC469489
Remote Similarity	0.6651	NPC472293
Remote Similarity	0.665	NPC240088
Remote Similarity	0.665	NPC15573
Remote Similarity	0.665	NPC183662
Remote Similarity	0.665	NPC473380
Remote Similarity	0.665	NPC217372
Remote Similarity	0.665	NPC157583
Remote Similarity	0.665	NPC209362
Remote Similarity	0.6638	NPC186351
Remote Similarity	0.6636	NPC103361
Remote Similarity	0.6636	NPC326422
Remote Similarity	0.6636	NPC100321
Remote Similarity	0.6635	NPC191415
Remote Similarity	0.6634	NPC110500
Remote Similarity	0.6634	NPC56233
Remote Similarity	0.6634	NPC149155
Remote Similarity	0.6634	NPC203468
Remote Similarity	0.6633	NPC472260
Remote Similarity	0.6632	NPC478039
Remote Similarity	0.6621	NPC143977
Remote Similarity	0.662	NPC167710
Remote Similarity	0.662	NPC106824
Remote Similarity	0.6618	NPC248462
Remote Similarity	0.6617	NPC478184
Remote Similarity	0.6612	NPC314882
Remote Similarity	0.6609	NPC327095
Remote Similarity	0.6609	NPC155444
Remote Similarity	0.6609	NPC312942
Remote Similarity	0.6609	NPC191382
Remote Similarity	0.6609	NPC56109
Remote Similarity	0.6608	NPC267811
Remote Similarity	0.6608	NPC477715
Remote Similarity	0.6606	NPC472065
Remote Similarity	0.6605	NPC19692
Remote Similarity	0.6605	NPC220151
Remote Similarity	0.6604	NPC321708
Remote Similarity	0.6603	NPC470205
Remote Similarity	0.6589	NPC472292
Remote Similarity	0.6585	NPC161861
Remote Similarity	0.6582	NPC313889
Remote Similarity	0.658	NPC40455
Remote Similarity	0.6577	NPC243850
Remote Similarity	0.6573	NPC83111
Remote Similarity	0.6571	NPC207851
Remote Similarity	0.6571	NPC165495
Remote Similarity	0.657	NPC111275
Remote Similarity	0.6564	NPC470731
Remote Similarity	0.6564	NPC470732
Remote Similarity	0.6564	NPC105811
Remote Similarity	0.656	NPC472296
Remote Similarity	0.656	NPC313421
Remote Similarity	0.656	NPC477004
Remote Similarity	0.656	NPC472297
Remote Similarity	0.656	NPC474767
Remote Similarity	0.656	NPC81535
Remote Similarity	0.6552	NPC19170
Remote Similarity	0.655	NPC293487
Remote Similarity	0.655	NPC315804
Remote Similarity	0.655	NPC313804
Remote Similarity	0.6549	NPC221100
Remote Similarity	0.6549	NPC282247
Remote Similarity	0.6549	NPC234078
Remote Similarity	0.6548	NPC70406
Remote Similarity	0.6547	NPC266249
Remote Similarity	0.6546	NPC467188
Remote Similarity	0.6545	NPC476874
Remote Similarity	0.6544	NPC74153
Remote Similarity	0.6544	NPC141454
Remote Similarity	0.6537	NPC478141
Remote Similarity	0.6528	NPC135950
Remote Similarity	0.6524	NPC102755
Remote Similarity	0.6524	NPC243058
Remote Similarity	0.6522	NPC272174
Remote Similarity	0.652	NPC70949
Remote Similarity	0.6514	NPC473640
Remote Similarity	0.6514	NPC470499
Remote Similarity	0.6509	NPC135601
Remote Similarity	0.6509	NPC141612
Remote Similarity	0.6509	NPC17273
Remote Similarity	0.6509	NPC478077
Remote Similarity	0.6507	NPC469896

Drug Structure

NPD3968 OpenBabel08211704332D 40 42 0 0 1 0 0 0 0 0999 V2000 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 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 -0.0000 -2.0000 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 -0.0000 -3.0000 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 1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 2.5981 2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 12 2 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 23 2 0 0 0 0 9 11 1 0 0 0 0 9 28 1 0 0 0 0 10 18 1 0 0 0 0 11 24 2 0 0 0 0 12 28 1 0 0 0 0 13 6 1 1 0 0 0 13 19 1 0 0 0 0 13 25 1 0 0 0 0 14 29 2 0 0 0 0 14 30 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 17 27 2 0 0 0 0 18 25 1 0 0 0 0 18 31 2 0 0 0 0 19 32 2 0 0 0 0 19 33 1 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 21 34 1 0 0 0 0 21 35 1 0 0 0 0 22 36 1 0 0 0 0 25 37 1 0 0 0 0 26 38 1 0 0 0 0 30 39 1 0 0 0 0 33 40 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000681; DNC000933
DrugBank	DB00563
ChEMBL	CHEMBL34259
IUPHAR/BPS	4815
PharmaGKB	PA450428
KEGG Drug	D00142
PubChem CID	11557063
ChEBI	44185
CAS Number	59-05-2

Drug Properties

Molecular Weight	454.17
ALogP	-3.1982
MLogP	2.23
XLogP	-1.911
HDA	13
HBD	6
Rotatable Bonds	14
TPSA	206.98
RO5 Violation	2