NPASS drugs

Drug Information

Drug ID:	NPD4993
Drug Name:	XR-1853
Molecular Formula:	C22H23N3O3
Canonical SMILES:	CN(CCOc1ccc(cc1)/C=c/1 c(O)/c(=C/c2ccccc2)/nc1O)C
Standard InCHI:	InChI=1S/C22H23N3O3/c1-25(2)12-13-28-18-10-8-17(9-11-18)15-20-22(27)23-19(21(26)24-20)14-16-6-4-3-5-7-16/h3-11,14-15H,12-13H2,1-2H3,(H,23,27)(H,24,26)/b19-14-,20-15-
Standard InCHIKey:	SKAOOZAHHYQXKN-SGAFJUGLSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4993

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	110
0.1-0.2	1060
0.2-0.3	4855
0.3-0.4	8093
0.4-0.5	4035
0.5-0.6	9224
0.6-0.7	3321
0.7-0.8	171
0.8-0.85	16
0.85-0.9	5
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
High Similarity	0.8934	NPC256369
High Similarity	0.8843	NPC258992
High Similarity	0.8626	NPC471953
High Similarity	0.8607	NPC303370
High Similarity	0.856	NPC263835
Intermediate Similarity	0.8358	NPC29650
Intermediate Similarity	0.8346	NPC274732
Intermediate Similarity	0.8321	NPC189724
Intermediate Similarity	0.8321	NPC212850
Intermediate Similarity	0.8321	NPC83289
Intermediate Similarity	0.832	NPC323948
Intermediate Similarity	0.8296	NPC138365
Intermediate Similarity	0.8268	NPC41801
Intermediate Similarity	0.8227	NPC245974
Intermediate Similarity	0.8214	NPC247298
Intermediate Similarity	0.8203	NPC83279
Intermediate Similarity	0.8156	NPC9373
Intermediate Similarity	0.8154	NPC211218
Intermediate Similarity	0.813	NPC166837
Intermediate Similarity	0.8047	NPC43275
Intermediate Similarity	0.8015	NPC255253
Intermediate Similarity	0.7955	NPC62101
Intermediate Similarity	0.7955	NPC95733
Intermediate Similarity	0.7895	NPC29477
Intermediate Similarity	0.7886	NPC146530
Intermediate Similarity	0.7769	NPC192596
Intermediate Similarity	0.7734	NPC37302
Intermediate Similarity	0.7686	NPC51633
Intermediate Similarity	0.7647	NPC186898
Intermediate Similarity	0.7583	NPC313918
Intermediate Similarity	0.7574	NPC301713
Intermediate Similarity	0.7554	NPC97870
Intermediate Similarity	0.7554	NPC247018
Intermediate Similarity	0.7554	NPC307123
Intermediate Similarity	0.7538	NPC82963
Intermediate Similarity	0.7518	NPC251571
Intermediate Similarity	0.7517	NPC135349
Intermediate Similarity	0.75	NPC320242
Intermediate Similarity	0.75	NPC470393
Intermediate Similarity	0.7481	NPC38458
Intermediate Similarity	0.7481	NPC311737
Intermediate Similarity	0.7464	NPC155838
Intermediate Similarity	0.746	NPC309982
Intermediate Similarity	0.7447	NPC303993
Intermediate Similarity	0.7444	NPC321133
Intermediate Similarity	0.744	NPC113457
Intermediate Similarity	0.7432	NPC277857
Intermediate Similarity	0.7432	NPC115144
Intermediate Similarity	0.7429	NPC470392
Intermediate Similarity	0.7422	NPC266932
Intermediate Similarity	0.7419	NPC38079
Intermediate Similarity	0.7419	NPC108875
Intermediate Similarity	0.741	NPC52029
Intermediate Similarity	0.741	NPC195749
Intermediate Similarity	0.741	NPC35961
Intermediate Similarity	0.7397	NPC78530
Intermediate Similarity	0.7397	NPC63628
Intermediate Similarity	0.7397	NPC178466
Intermediate Similarity	0.7394	NPC237227
Intermediate Similarity	0.7379	NPC195814
Intermediate Similarity	0.7377	NPC471576
Intermediate Similarity	0.7372	NPC476249
Intermediate Similarity	0.7361	NPC299583
Intermediate Similarity	0.7353	NPC328267
Intermediate Similarity	0.7344	NPC95977
Intermediate Similarity	0.7323	NPC96224
Intermediate Similarity	0.7323	NPC24101
Intermediate Similarity	0.7323	NPC201959
Intermediate Similarity	0.7319	NPC218323
Intermediate Similarity	0.7308	NPC254700
Intermediate Similarity	0.7308	NPC26524
Intermediate Similarity	0.7305	NPC214869
Intermediate Similarity	0.7292	NPC213471
Intermediate Similarity	0.7292	NPC14600
Intermediate Similarity	0.7292	NPC160607
Intermediate Similarity	0.7292	NPC204848
Intermediate Similarity	0.7292	NPC193528
Intermediate Similarity	0.7292	NPC41473
Intermediate Similarity	0.7292	NPC312770
Intermediate Similarity	0.7286	NPC470706
Intermediate Similarity	0.7285	NPC47672
Intermediate Similarity	0.728	NPC474603
Intermediate Similarity	0.728	NPC12987
Intermediate Similarity	0.7279	NPC471315
Intermediate Similarity	0.7279	NPC471314
Intermediate Similarity	0.7267	NPC76412
Intermediate Similarity	0.7266	NPC474272
Intermediate Similarity	0.7255	NPC233926
Intermediate Similarity	0.7255	NPC56635
Intermediate Similarity	0.7252	NPC118202
Intermediate Similarity	0.7248	NPC132771
Intermediate Similarity	0.7246	NPC207541
Intermediate Similarity	0.7246	NPC71105
Intermediate Similarity	0.7246	NPC246133
Intermediate Similarity	0.7246	NPC136112
Intermediate Similarity	0.7246	NPC170583
Intermediate Similarity	0.7246	NPC141739
Intermediate Similarity	0.7246	NPC152186
Intermediate Similarity	0.7246	NPC182147
Intermediate Similarity	0.7239	NPC163036
Intermediate Similarity	0.7239	NPC295259
Intermediate Similarity	0.7234	NPC114102
Intermediate Similarity	0.7231	NPC165646
Intermediate Similarity	0.7222	NPC8302
Intermediate Similarity	0.7219	NPC258222
Intermediate Similarity	0.7209	NPC46844
Intermediate Similarity	0.7203	NPC284855
Intermediate Similarity	0.7203	NPC282477
Intermediate Similarity	0.7194	NPC251466
Intermediate Similarity	0.7194	NPC156944
Intermediate Similarity	0.7192	NPC477838
Intermediate Similarity	0.7192	NPC477837
Intermediate Similarity	0.7188	NPC75440
Intermediate Similarity	0.7183	NPC118419
Intermediate Similarity	0.7181	NPC313414
Intermediate Similarity	0.7177	NPC316797
Intermediate Similarity	0.7174	NPC300955
Intermediate Similarity	0.7172	NPC318591
Intermediate Similarity	0.7172	NPC231163
Intermediate Similarity	0.7165	NPC326801
Intermediate Similarity	0.7164	NPC74821
Intermediate Similarity	0.7164	NPC5932
Intermediate Similarity	0.7154	NPC55300
Intermediate Similarity	0.7153	NPC36016
Intermediate Similarity	0.7153	NPC100099
Intermediate Similarity	0.7152	NPC471032
Intermediate Similarity	0.7152	NPC470935
Intermediate Similarity	0.7143	NPC99798
Intermediate Similarity	0.7143	NPC41331
Intermediate Similarity	0.7143	NPC291449
Intermediate Similarity	0.7143	NPC153990
Intermediate Similarity	0.7143	NPC157740
Intermediate Similarity	0.7133	NPC169766
Intermediate Similarity	0.7132	NPC318357
Intermediate Similarity	0.7132	NPC306045
Intermediate Similarity	0.7132	NPC265211
Intermediate Similarity	0.7121	NPC161696
Intermediate Similarity	0.7115	NPC231862
Intermediate Similarity	0.7109	NPC157473
Intermediate Similarity	0.7109	NPC151530
Intermediate Similarity	0.7109	NPC142297
Intermediate Similarity	0.7105	NPC114659
Intermediate Similarity	0.7105	NPC139699
Intermediate Similarity	0.7105	NPC182119
Intermediate Similarity	0.7101	NPC38761
Intermediate Similarity	0.7101	NPC76465
Intermediate Similarity	0.7101	NPC307020
Intermediate Similarity	0.7097	NPC100870
Intermediate Similarity	0.7095	NPC222039
Intermediate Similarity	0.7095	NPC100478
Intermediate Similarity	0.7092	NPC246974
Intermediate Similarity	0.7092	NPC147247
Intermediate Similarity	0.7087	NPC473855
Intermediate Similarity	0.708	NPC54972
Intermediate Similarity	0.7075	NPC314113
Intermediate Similarity	0.7063	NPC305205
Intermediate Similarity	0.7059	NPC289330
Intermediate Similarity	0.7059	NPC17388
Intermediate Similarity	0.7059	NPC53596
Intermediate Similarity	0.7059	NPC252817
Intermediate Similarity	0.7059	NPC160120
Intermediate Similarity	0.7059	NPC471308
Intermediate Similarity	0.7054	NPC153690
Intermediate Similarity	0.705	NPC106914
Intermediate Similarity	0.705	NPC134195
Intermediate Similarity	0.705	NPC86502
Intermediate Similarity	0.705	NPC246648
Intermediate Similarity	0.705	NPC270030
Intermediate Similarity	0.705	NPC197351
Intermediate Similarity	0.7049	NPC471581
Intermediate Similarity	0.7045	NPC141003
Intermediate Similarity	0.7045	NPC35344
Intermediate Similarity	0.7044	NPC314861
Intermediate Similarity	0.7034	NPC11147
Intermediate Similarity	0.7031	NPC176971
Intermediate Similarity	0.7031	NPC231705
Intermediate Similarity	0.7031	NPC92623
Intermediate Similarity	0.7031	NPC135464
Intermediate Similarity	0.7029	NPC150026
Intermediate Similarity	0.7027	NPC474128
Intermediate Similarity	0.7021	NPC149796
Intermediate Similarity	0.7008	NPC283546
Intermediate Similarity	0.7007	NPC296898
Intermediate Similarity	0.7	NPC99886
Intermediate Similarity	0.7	NPC102540
Intermediate Similarity	0.7	NPC188022
Intermediate Similarity	0.7	NPC103420
Intermediate Similarity	0.7	NPC177844
Intermediate Similarity	0.7	NPC259134
Intermediate Similarity	0.7	NPC8002
Intermediate Similarity	0.7	NPC285040
Intermediate Similarity	0.7	NPC17809
Remote Similarity	0.6992	NPC180508
Remote Similarity	0.6992	NPC228287
Remote Similarity	0.6985	NPC59561
Remote Similarity	0.6985	NPC172253
Remote Similarity	0.6984	NPC300166
Remote Similarity	0.6977	NPC258171
Remote Similarity	0.6972	NPC283079
Remote Similarity	0.6972	NPC469977

Drug Structure

NPD4993 OpenBabel08211706322D 30 32 0 0 0 0 0 0 0 0999 V2000 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 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 3.4641 -1.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 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 -3.4641 -1.0000 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 -4.3301 -1.5000 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 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 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 -3.4641 0.0000 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 -0.0000 -1.0000 0.0000 C 0 0 0 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 -0.8660 -1.5000 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 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 17 2 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB003899
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	377.17
ALogP	-0.0343
MLogP	3.22
XLogP	5.662
HDA	5
HBD	2
Rotatable Bonds	10
TPSA	77.65
RO5 Violation	1