NPASS drugs

Drug Information

Drug ID:	NPD2249
Drug Name:	Proparacaine
Molecular Formula:	C16H26N2O3
Canonical SMILES:	CCCOc1ccc(cc1N)C(=O)OCCN(CC)CC
Standard InCHI:	InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3
Standard InCHIKey:	KCLANYCVBBTKTO-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2249

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	191
0.1-0.2	1355
0.2-0.3	4859
0.3-0.4	7493
0.4-0.5	4409
0.5-0.6	11114
0.6-0.7	1437
0.7-0.8	31
0.8-0.85	1
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	0.8129	NPC315631
Intermediate Similarity	0.7956	NPC108847
Intermediate Similarity	0.7929	NPC314861
Intermediate Similarity	0.7848	NPC314252
Intermediate Similarity	0.7785	NPC319645
Intermediate Similarity	0.7636	NPC214239
Intermediate Similarity	0.7543	NPC73280
Intermediate Similarity	0.7486	NPC472163
Intermediate Similarity	0.7384	NPC231862
Intermediate Similarity	0.7374	NPC474815
Intermediate Similarity	0.7349	NPC17760
Intermediate Similarity	0.7277	NPC214368
Intermediate Similarity	0.7253	NPC314659
Intermediate Similarity	0.7244	NPC221798
Intermediate Similarity	0.7241	NPC57105
Intermediate Similarity	0.7213	NPC469829
Intermediate Similarity	0.7198	NPC197335
Intermediate Similarity	0.7135	NPC87391
Intermediate Similarity	0.7115	NPC291189
Intermediate Similarity	0.7115	NPC69403
Intermediate Similarity	0.7107	NPC122235
Intermediate Similarity	0.7104	NPC288305
Intermediate Similarity	0.7099	NPC266425
Intermediate Similarity	0.7091	NPC181526
Intermediate Similarity	0.7081	NPC235194
Intermediate Similarity	0.7062	NPC299582
Intermediate Similarity	0.7049	NPC98416
Intermediate Similarity	0.7048	NPC314113
Intermediate Similarity	0.7039	NPC220540
Intermediate Similarity	0.7033	NPC9475
Intermediate Similarity	0.7029	NPC301163
Intermediate Similarity	0.7	NPC471825
Remote Similarity	0.6989	NPC93653
Remote Similarity	0.6979	NPC314948
Remote Similarity	0.6978	NPC8467
Remote Similarity	0.6975	NPC313466
Remote Similarity	0.6973	NPC469831
Remote Similarity	0.6962	NPC226794
Remote Similarity	0.6949	NPC257763
Remote Similarity	0.6937	NPC475236
Remote Similarity	0.6933	NPC470392
Remote Similarity	0.6927	NPC471652
Remote Similarity	0.6919	NPC270301
Remote Similarity	0.6901	NPC154922
Remote Similarity	0.6898	NPC313886
Remote Similarity	0.6898	NPC473007
Remote Similarity	0.6895	NPC1820
Remote Similarity	0.6894	NPC37512
Remote Similarity	0.6891	NPC478049
Remote Similarity	0.6886	NPC160747
Remote Similarity	0.6875	NPC165556
Remote Similarity	0.6869	NPC246140
Remote Similarity	0.6869	NPC195787
Remote Similarity	0.6867	NPC316574
Remote Similarity	0.6859	NPC61779
Remote Similarity	0.6856	NPC234933
Remote Similarity	0.6853	NPC207971
Remote Similarity	0.6852	NPC2596
Remote Similarity	0.6848	NPC173295
Remote Similarity	0.6848	NPC329992
Remote Similarity	0.6829	NPC77777
Remote Similarity	0.6828	NPC309692
Remote Similarity	0.6828	NPC28368
Remote Similarity	0.6825	NPC469830
Remote Similarity	0.6821	NPC241263
Remote Similarity	0.6818	NPC36836
Remote Similarity	0.6818	NPC473422
Remote Similarity	0.6818	NPC87714
Remote Similarity	0.6818	NPC63370
Remote Similarity	0.6816	NPC26353
Remote Similarity	0.6813	NPC471648
Remote Similarity	0.6807	NPC196708
Remote Similarity	0.6796	NPC35345
Remote Similarity	0.6795	NPC229353
Remote Similarity	0.6774	NPC85613
Remote Similarity	0.6774	NPC470860
Remote Similarity	0.677	NPC124776
Remote Similarity	0.6768	NPC41216
Remote Similarity	0.6763	NPC476069
Remote Similarity	0.676	NPC199737
Remote Similarity	0.6754	NPC473008
Remote Similarity	0.6753	NPC252004
Remote Similarity	0.675	NPC198160
Remote Similarity	0.6743	NPC113455
Remote Similarity	0.674	NPC127362
Remote Similarity	0.6734	NPC268077
Remote Similarity	0.6725	NPC323798
Remote Similarity	0.6724	NPC241392
Remote Similarity	0.6722	NPC158900
Remote Similarity	0.6719	NPC22476
Remote Similarity	0.6716	NPC30749
Remote Similarity	0.6699	NPC195636
Remote Similarity	0.6698	NPC160113
Remote Similarity	0.6698	NPC476220
Remote Similarity	0.6688	NPC94298
Remote Similarity	0.6688	NPC27633
Remote Similarity	0.6688	NPC293424
Remote Similarity	0.6685	NPC204179
Remote Similarity	0.6684	NPC262725
Remote Similarity	0.6684	NPC283810
Remote Similarity	0.6684	NPC112937
Remote Similarity	0.6684	NPC5167
Remote Similarity	0.6667	NPC282230
Remote Similarity	0.6667	NPC474858
Remote Similarity	0.6667	NPC469437
Remote Similarity	0.6667	NPC473562
Remote Similarity	0.6667	NPC327457
Remote Similarity	0.6667	NPC183348
Remote Similarity	0.6667	NPC86774
Remote Similarity	0.6652	NPC120239
Remote Similarity	0.6646	NPC2401
Remote Similarity	0.6634	NPC268223
Remote Similarity	0.6633	NPC15987
Remote Similarity	0.6627	NPC470977
Remote Similarity	0.6627	NPC196979
Remote Similarity	0.6627	NPC471316
Remote Similarity	0.6627	NPC104854
Remote Similarity	0.6627	NPC15083
Remote Similarity	0.6627	NPC470976
Remote Similarity	0.6627	NPC208022
Remote Similarity	0.6613	NPC227683
Remote Similarity	0.6613	NPC472894
Remote Similarity	0.6609	NPC315829
Remote Similarity	0.6608	NPC476462
Remote Similarity	0.6607	NPC311339
Remote Similarity	0.6606	NPC170546
Remote Similarity	0.6606	NPC66246
Remote Similarity	0.6605	NPC139373
Remote Similarity	0.6599	NPC100863
Remote Similarity	0.6599	NPC71124
Remote Similarity	0.6598	NPC114039
Remote Similarity	0.6598	NPC206109
Remote Similarity	0.6596	NPC35680
Remote Similarity	0.6589	NPC223242
Remote Similarity	0.6587	NPC195120
Remote Similarity	0.6587	NPC132308
Remote Similarity	0.6587	NPC87560
Remote Similarity	0.6585	NPC116178
Remote Similarity	0.6585	NPC121104
Remote Similarity	0.6585	NPC305542
Remote Similarity	0.6584	NPC212123
Remote Similarity	0.6584	NPC478075
Remote Similarity	0.6584	NPC257266
Remote Similarity	0.6581	NPC26524
Remote Similarity	0.658	NPC141440
Remote Similarity	0.6576	NPC471778
Remote Similarity	0.6575	NPC476258
Remote Similarity	0.6575	NPC304837
Remote Similarity	0.657	NPC234772
Remote Similarity	0.6568	NPC307682
Remote Similarity	0.6568	NPC43218
Remote Similarity	0.6566	NPC109778
Remote Similarity	0.6564	NPC94499
Remote Similarity	0.6564	NPC49938
Remote Similarity	0.6561	NPC131192
Remote Similarity	0.6561	NPC329816
Remote Similarity	0.656	NPC314702
Remote Similarity	0.6558	NPC57879
Remote Similarity	0.6558	NPC23332
Remote Similarity	0.6557	NPC231924
Remote Similarity	0.6553	NPC321166
Remote Similarity	0.6553	NPC217903
Remote Similarity	0.6552	NPC329567
Remote Similarity	0.6552	NPC330683
Remote Similarity	0.6552	NPC257728
Remote Similarity	0.655	NPC253616
Remote Similarity	0.655	NPC288759
Remote Similarity	0.6548	NPC66158
Remote Similarity	0.6546	NPC70340
Remote Similarity	0.6545	NPC477391
Remote Similarity	0.6545	NPC132751
Remote Similarity	0.6541	NPC112336
Remote Similarity	0.6541	NPC284842
Remote Similarity	0.6541	NPC474814
Remote Similarity	0.654	NPC251071
Remote Similarity	0.6537	NPC61731
Remote Similarity	0.6537	NPC186569
Remote Similarity	0.6536	NPC470708
Remote Similarity	0.6535	NPC477161
Remote Similarity	0.6532	NPC260601
Remote Similarity	0.6532	NPC184053
Remote Similarity	0.6531	NPC230313
Remote Similarity	0.6531	NPC243626
Remote Similarity	0.6529	NPC476475
Remote Similarity	0.6529	NPC238412
Remote Similarity	0.6524	NPC154275
Remote Similarity	0.6524	NPC129578
Remote Similarity	0.6524	NPC110211
Remote Similarity	0.6524	NPC254053
Remote Similarity	0.6524	NPC204579
Remote Similarity	0.6522	NPC189661
Remote Similarity	0.6522	NPC470971
Remote Similarity	0.652	NPC153365
Remote Similarity	0.652	NPC477160
Remote Similarity	0.652	NPC475133
Remote Similarity	0.6519	NPC469954
Remote Similarity	0.6519	NPC306366
Remote Similarity	0.6517	NPC119669
Remote Similarity	0.6513	NPC157473
Remote Similarity	0.6513	NPC151530

Drug Structure

NPD2249 OpenBabel08211701392D 23 23 0 0 0 0 0 0 0 0999 V2000 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 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 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 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 6.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 4 10 1 0 0 0 0 5 18 1 0 0 0 0 6 18 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 16 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000513
DrugBank	DB00807
ChEMBL	CHEMBL1196
IUPHAR/BPS	7283
PharmaGKB	PA164776849
KEGG Drug	D08448
PubChem CID	4935
ChEBI	8485
CAS Number	499-67-2

Drug Properties

Molecular Weight	294.19
ALogP	-0.4784
MLogP	2.67
XLogP	2.36
HDA	4
HBD	1
Rotatable Bonds	14
TPSA	64.79
RO5 Violation	0