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

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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

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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