NPASS Natural Product

Natural Product: NPC36229

Natural Product ID:	NPC36229
Common Name:	Palmatine Chloride
IUPAC Name:	2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium;chloride
Synonyms:	GNF-Pf-4086
Molecular Formula:	C21H22NO4.ClH
Standard InCHIKey:	RLQYRXCUPVKSAW-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C21H22NO4.ClH/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4;/h5-6,9-12H,7-8H2,1-4H3;1H/q+1;/p-1
Canonical SMILES:	COc1cc2CC[n+]3c(c2cc1OC)cc1c(c3)c(OC)c(cc1)OC.[Cl-]
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	TM-MC*
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	TM-MC*
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	TM-MC*
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	TM-MC*
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	TM-MC*
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	PMID[17994701]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	TM-MC*
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	TM-MC*
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	TM-MC*

Biological Activity

Activity Type	# Activity
AC50	1
EC50	2
GI50	59
IC50	4
Others	22
Potency	20

Activity Type	# Activity
Cell Line	59
Individual Protein	24
Organism	18
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.281	ug/ml	3286870
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.163	ug/ml	3286870
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	900	nM	17994701
NPT2	Others	Unspecified		Inhibition	=	19	%	19716293
NPT2655	Individual Protein	Cell division control protein 42 homolog	Homo sapiens	Inhibition	=	8	%	19716293
NPT2656	Individual Protein	Ras-related C3 botulinum toxin substrate 1	Homo sapiens	Inhibition	=	15	%	19716293
NPT1229	Cell Line	Huh-7	Homo sapiens	CC50	>	100000	nM	18579783
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	766	nM	18579783
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	697	nM	18579783
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	7.9	nM	PubChem BioAssay data set
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	17740.7	nM	PubChem BioAssay data set
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	5623.4	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency		707.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		GI50	=	57430	nM	21401114
NPT2470	Cell Line	G-402	Homo sapiens	GI50	=	83140	nM	21401114
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency		165.1	nM	PubChem BioAssay data set
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency		44668.4	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency		185.3	nM	PubChem BioAssay data set
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency		89125.1	nM	PubChem BioAssay data set
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	46.89	%	22137340
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	64.78	%	22137340
NPT367	Cell Line	MDA-N	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT368	Cell Line	SN12C	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT369	Cell Line	ACHN	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT371	Cell Line	UO-31	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT372	Cell Line	HOP-92	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT374	Cell Line	SF-539	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT90	Cell Line	DU-145	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50		34833.73	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	GI50		52360.04	nM	PubChem BioAssay data set
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50		39902.49	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT379	Cell Line	HOP-62	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT380	Cell Line	U-251	Homo sapiens	GI50		27861.21	nM	PubChem BioAssay data set
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT383	Cell Line	SNB-19	Homo sapiens	GI50		15452.54	nM	PubChem BioAssay data set
NPT384	Cell Line	TK-10	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT385	Cell Line	SR	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT323	Cell Line	SW-620	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT386	Cell Line	KM12	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT387	Cell Line	M14	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT457	Cell Line	BT-549	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		97051	nM	PubChem BioAssay data set
NPT81	Cell Line	A549	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT392	Cell Line	SNB-75	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT393	Cell Line	HCT-116	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT395	Cell Line	SF-268	Homo sapiens	GI50		82413.81	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT394	Cell Line	EKVX	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT306	Cell Line	PC-3	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT396	Cell Line	T47D	Homo sapiens	GI50		83368.12	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT398	Cell Line	UACC-62	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT399	Cell Line	SF-295	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT403	Cell Line	UACC-257	Homo sapiens	GI50		48528.85	nM	PubChem BioAssay data set
NPT401	Cell Line	786-0	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT406	Cell Line	RXF 393	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT407	Cell Line	COLO 205	Homo sapiens	GI50		24434.31	nM	PubChem BioAssay data set
NPT2658	Individual Protein	Snake venom metalloproteinase Bap1	Bothrops asper	IC50	=	93300	nM	24900507
NPT2	Others	Unspecified		Potency		11220.2	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		7943.3	nM	PubChem BioAssay data set
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	72.59	%	23062825
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	7.47	%	23062825
NPT822	Organism	Lemna minor	Lemna minor	Activity	=	0	%	11055412
NPT823	Organism	Agrostis stolonifera var. palustris	Agrostis stolonifera var. palustris	Activity	=	0	%	11055412
NPT824	Organism	Ustilago maydis	Ustilago maydis	Inhibition	=	0	%	11055412
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	0	%	11055412
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	Inhibition	=	0	%	11055412
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	Inhibition	=	0	%	11055412
NPT827	Organism	Mycosphaerella graminicola	Mycosphaerella graminicola	Inhibition	=	80	%	11055412
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	0	%	11055412
NPT829	Organism	Puccinia recondita	Puccinia recondita	Activity	=	0	%	11055412
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Activity	=	0	%	11055412
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Activity	=	0	%	11055412
NPT830	Organism	Blumeria graminis f. sp. tritici	Blumeria graminis f. sp. tritici	Activity	=	0	%	11055412
NPT2	Others	Unspecified		Potency		5173.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		3264.3	nM	PubChem BioAssay data set
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency		3981.1	nM	PubChem BioAssay data set
NPT1274	Individual Protein	DNA repair protein RAD52 homolog	Homo sapiens	AC50	=	5190	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		6513.1	nM	PubChem BioAssay data set
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	110.13	%	23571415
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	97.62	%	23571415
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency		28183.8	nM	PubChem BioAssay data set

Similar Natural Products in NPASS

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

● The left chart: Distribution of similarity level between NPC36229 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	476
0.1-0.2	2208
0.2-0.3	10124
0.3-0.4	2825
0.4-0.5	10145
0.5-0.6	3176
0.6-0.7	1535
0.7-0.8	340
0.8-0.85	28
0.85-0.9	13
0.9-0.95	8
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC16452
1.0	High Similarity	NPC476581
0.9834	High Similarity	NPC31930
0.9724	High Similarity	NPC476578
0.9724	High Similarity	NPC4071
0.9724	High Similarity	NPC476582
0.9628	High Similarity	NPC112206
0.9628	High Similarity	NPC296482
0.9628	High Similarity	NPC202768
0.9628	High Similarity	NPC202605
0.9628	High Similarity	NPC53069
0.9421	High Similarity	NPC96405
0.9421	High Similarity	NPC171409
0.9392	High Similarity	NPC195268
0.9392	High Similarity	NPC133140
0.9362	High Similarity	NPC313189
0.9158	High Similarity	NPC135549
0.9115	High Similarity	NPC290689
0.9043	High Similarity	NPC477019
0.8889	High Similarity	NPC23614
0.8889	High Similarity	NPC100079
0.8842	High Similarity	NPC234197
0.875	High Similarity	NPC46451
0.8737	High Similarity	NPC235076
0.8731	High Similarity	NPC251160
0.8687	High Similarity	NPC149471
0.8687	High Similarity	NPC271215
0.8607	High Similarity	NPC473822
0.8599	High Similarity	NPC201508
0.8535	High Similarity	NPC188420
0.8522	High Similarity	NPC174049
0.85	High Similarity	NPC236668
0.8458	Intermediate Similarity	NPC146976
0.8439	Intermediate Similarity	NPC122463
0.8439	Intermediate Similarity	NPC118121
0.8429	Intermediate Similarity	NPC96584
0.8429	Intermediate Similarity	NPC255800
0.8415	Intermediate Similarity	NPC312872
0.8402	Intermediate Similarity	NPC287437
0.8284	Intermediate Similarity	NPC473513
0.8261	Intermediate Similarity	NPC210434
0.8244	Intermediate Similarity	NPC204446
0.8241	Intermediate Similarity	NPC470164
0.8241	Intermediate Similarity	NPC323345
0.8227	Intermediate Similarity	NPC162530
0.8211	Intermediate Similarity	NPC204385
0.8199	Intermediate Similarity	NPC24019
0.8178	Intermediate Similarity	NPC295228
0.8155	Intermediate Similarity	NPC173080
0.8137	Intermediate Similarity	NPC266931
0.8112	Intermediate Similarity	NPC224928
0.81	Intermediate Similarity	NPC285558
0.8079	Intermediate Similarity	NPC470020
0.8057	Intermediate Similarity	NPC214980
0.8	Intermediate Similarity	NPC22481
0.8	Intermediate Similarity	NPC114335
0.8	Intermediate Similarity	NPC280272
0.8	Intermediate Similarity	NPC206201
0.8	Intermediate Similarity	NPC141915
0.8	Intermediate Similarity	NPC280964
0.799	Intermediate Similarity	NPC167860
0.799	Intermediate Similarity	NPC123976
0.7981	Intermediate Similarity	NPC476997
0.7973	Intermediate Similarity	NPC270515
0.7963	Intermediate Similarity	NPC90875
0.7962	Intermediate Similarity	NPC322482
0.7953	Intermediate Similarity	NPC233334
0.7944	Intermediate Similarity	NPC278525
0.7944	Intermediate Similarity	NPC476998
0.7944	Intermediate Similarity	NPC469792
0.7944	Intermediate Similarity	NPC476996
0.7926	Intermediate Similarity	NPC108342
0.7921	Intermediate Similarity	NPC264166
0.7921	Intermediate Similarity	NPC274291
0.7921	Intermediate Similarity	NPC47059
0.7921	Intermediate Similarity	NPC165349
0.7921	Intermediate Similarity	NPC118832
0.7921	Intermediate Similarity	NPC329708
0.7913	Intermediate Similarity	NPC316981
0.7907	Intermediate Similarity	NPC476999
0.7897	Intermediate Similarity	NPC476994
0.789	Intermediate Similarity	NPC189903
0.789	Intermediate Similarity	NPC182907
0.788	Intermediate Similarity	NPC253675
0.7864	Intermediate Similarity	NPC119134
0.7864	Intermediate Similarity	NPC208284
0.7857	Intermediate Similarity	NPC193267
0.7857	Intermediate Similarity	NPC213530
0.7854	Intermediate Similarity	NPC166722
0.7854	Intermediate Similarity	NPC174758
0.7854	Intermediate Similarity	NPC174672
0.7814	Intermediate Similarity	NPC26850
0.7811	Intermediate Similarity	NPC11017
0.7805	Intermediate Similarity	NPC82548
0.7794	Intermediate Similarity	NPC472111
0.7784	Intermediate Similarity	NPC177404
0.7783	Intermediate Similarity	NPC475774
0.7772	Intermediate Similarity	NPC232727
0.7767	Intermediate Similarity	NPC469589
0.7766	Intermediate Similarity	NPC92111
0.7731	Intermediate Similarity	NPC246381
0.7723	Intermediate Similarity	NPC176538
0.7723	Intermediate Similarity	NPC315957
0.7718	Intermediate Similarity	NPC470931
0.7716	Intermediate Similarity	NPC76748
0.7714	Intermediate Similarity	NPC170114
0.7713	Intermediate Similarity	NPC15406
0.7703	Intermediate Similarity	NPC210296
0.7696	Intermediate Similarity	NPC469440
0.7688	Intermediate Similarity	NPC329541
0.7688	Intermediate Similarity	NPC307963
0.7679	Intermediate Similarity	NPC124313
0.7668	Intermediate Similarity	NPC84164
0.7668	Intermediate Similarity	NPC207283
0.7667	Intermediate Similarity	NPC470549
0.7665	Intermediate Similarity	NPC296527
0.7659	Intermediate Similarity	NPC137929
0.7659	Intermediate Similarity	NPC164374
0.7656	Intermediate Similarity	NPC285941
0.765	Intermediate Similarity	NPC26872
0.7647	Intermediate Similarity	NPC199277
0.7647	Intermediate Similarity	NPC135887
0.7647	Intermediate Similarity	NPC476995
0.7644	Intermediate Similarity	NPC11464
0.7641	Intermediate Similarity	NPC284559
0.7639	Intermediate Similarity	NPC200888
0.763	Intermediate Similarity	NPC274982
0.7629	Intermediate Similarity	NPC470474
0.7623	Intermediate Similarity	NPC217554
0.7621	Intermediate Similarity	NPC304183
0.7612	Intermediate Similarity	NPC473053
0.7612	Intermediate Similarity	NPC251090
0.7612	Intermediate Similarity	NPC13880
0.7606	Intermediate Similarity	NPC471178
0.7606	Intermediate Similarity	NPC17565
0.76	Intermediate Similarity	NPC284141
0.7588	Intermediate Similarity	NPC469390
0.7579	Intermediate Similarity	NPC476518
0.7574	Intermediate Similarity	NPC267928
0.7571	Intermediate Similarity	NPC264176
0.7569	Intermediate Similarity	NPC314954
0.7568	Intermediate Similarity	NPC473183
0.7564	Intermediate Similarity	NPC132385
0.7562	Intermediate Similarity	NPC131017
0.7558	Intermediate Similarity	NPC470018
0.7554	Intermediate Similarity	NPC476568
0.7549	Intermediate Similarity	NPC329747
0.7549	Intermediate Similarity	NPC329793
0.7545	Intermediate Similarity	NPC469554
0.7539	Intermediate Similarity	NPC121658
0.7539	Intermediate Similarity	NPC14651
0.7538	Intermediate Similarity	NPC190461
0.7537	Intermediate Similarity	NPC127085
0.7534	Intermediate Similarity	NPC11408
0.7527	Intermediate Similarity	NPC106295
0.7527	Intermediate Similarity	NPC51957
0.7527	Intermediate Similarity	NPC476144
0.7527	Intermediate Similarity	NPC210437
0.7527	Intermediate Similarity	NPC16107
0.7524	Intermediate Similarity	NPC162484
0.7523	Intermediate Similarity	NPC74575
0.7513	Intermediate Similarity	NPC20249
0.7512	Intermediate Similarity	NPC201697
0.7511	Intermediate Similarity	NPC183537
0.75	Intermediate Similarity	NPC193777
0.75	Intermediate Similarity	NPC216816
0.7488	Intermediate Similarity	NPC472098
0.7488	Intermediate Similarity	NPC26679
0.7486	Intermediate Similarity	NPC7467
0.7477	Intermediate Similarity	NPC473184
0.7476	Intermediate Similarity	NPC66815
0.7475	Intermediate Similarity	NPC61350
0.7467	Intermediate Similarity	NPC134637
0.7466	Intermediate Similarity	NPC49547
0.7466	Intermediate Similarity	NPC101543
0.7465	Intermediate Similarity	NPC65277
0.7464	Intermediate Similarity	NPC475910
0.7464	Intermediate Similarity	NPC287208
0.7462	Intermediate Similarity	NPC179704
0.7454	Intermediate Similarity	NPC310118
0.7453	Intermediate Similarity	NPC469592
0.7453	Intermediate Similarity	NPC471080
0.7451	Intermediate Similarity	NPC72211
0.7443	Intermediate Similarity	NPC110151
0.7442	Intermediate Similarity	NPC148409
0.744	Intermediate Similarity	NPC476138
0.744	Intermediate Similarity	NPC245816
0.7435	Intermediate Similarity	NPC77878
0.7429	Intermediate Similarity	NPC185782
0.7427	Intermediate Similarity	NPC267423
0.7421	Intermediate Similarity	NPC24954
0.7409	Intermediate Similarity	NPC111624
0.7407	Intermediate Similarity	NPC124542
0.7407	Intermediate Similarity	NPC477533
0.7407	Intermediate Similarity	NPC471177
0.7407	Intermediate Similarity	NPC59779
0.7402	Intermediate Similarity	NPC70956
0.7402	Intermediate Similarity	NPC243834
0.74	Intermediate Similarity	NPC477186
0.7395	Intermediate Similarity	NPC469594

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC36229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	692
0.2-0.3	1007
0.3-0.4	1163
0.4-0.5	2482
0.5-0.6	2285
0.6-0.7	1000
0.7-0.8	228
0.8-0.85	12
0.85-0.9	2
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9628	High Similarity	NPD3816	Phase 1
0.9628	High Similarity	NPD3815	Phase 1
0.9392	High Similarity	NPD3924	Approved
0.9392	High Similarity	NPD3922	Approved
0.9392	High Similarity	NPD3923	Approved
0.9392	High Similarity	NPD3921	Approved
0.8785	High Similarity	NPD3920	Phase 2
0.875	High Similarity	NPD3763	Approved
0.836	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6230	Discontinued
0.8281	Intermediate Similarity	NPD6569	Phase 2
0.8255	Intermediate Similarity	NPD6494	Phase 2
0.825	Intermediate Similarity	NPD5658	Approved
0.8191	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.8177	Intermediate Similarity	NPD7069	Discontinued
0.8164	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD4889	Approved
0.8021	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD4039	Approved
0.7921	Intermediate Similarity	NPD4033	Approved
0.7921	Intermediate Similarity	NPD4035	Approved
0.7921	Intermediate Similarity	NPD4795	Phase 2
0.7921	Intermediate Similarity	NPD4036	Approved
0.7921	Intermediate Similarity	NPD4122	Approved
0.7921	Intermediate Similarity	NPD4037	Approved
0.7921	Intermediate Similarity	NPD4038	Approved
0.7921	Intermediate Similarity	NPD31	Approved
0.7921	Intermediate Similarity	NPD4034	Approved
0.7921	Intermediate Similarity	NPD32	Approved
0.7919	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4418	Discontinued
0.791	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD6219	Discontinued
0.7887	Intermediate Similarity	NPD7674	Phase 3
0.7887	Intermediate Similarity	NPD7675	Phase 3
0.7887	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5530	Phase 1
0.788	Intermediate Similarity	NPD6963	Approved
0.788	Intermediate Similarity	NPD6964	Approved
0.7879	Intermediate Similarity	NPD3477	Phase 2
0.7879	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7222	Phase 2
0.7812	Intermediate Similarity	NPD3386	Phase 2
0.7811	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD8091	Phase 3
0.7807	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4551	Phase 2
0.7753	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5930	Phase 3
0.7723	Intermediate Similarity	NPD1739	Approved
0.7723	Intermediate Similarity	NPD1740	Approved
0.7721	Intermediate Similarity	NPD7426	Phase 1
0.7701	Intermediate Similarity	NPD2780	Approved
0.7701	Intermediate Similarity	NPD2782	Approved
0.7688	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1038	Approved
0.7671	Intermediate Similarity	NPD7558	Phase 2
0.7667	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD3397	Phase 2
0.7653	Intermediate Similarity	NPD4375	Approved
0.7644	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6568	Discontinued
0.7638	Intermediate Similarity	NPD4372	Phase 1
0.7632	Intermediate Similarity	NPD7859	Phase 2
0.763	Intermediate Similarity	NPD5612	Discontinued
0.7626	Intermediate Similarity	NPD4885	Approved
0.7619	Intermediate Similarity	NPD2781	Approved
0.7608	Intermediate Similarity	NPD4131	Phase 3
0.7594	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4875	Phase 3
0.7589	Intermediate Similarity	NPD4876	Phase 3
0.7588	Intermediate Similarity	NPD2334	Discontinued
0.7585	Intermediate Similarity	NPD7452	Approved
0.7585	Intermediate Similarity	NPD7453	Approved
0.7583	Intermediate Similarity	NPD5903	Approved
0.7583	Intermediate Similarity	NPD5902	Approved
0.7565	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4584	Approved
0.7512	Intermediate Similarity	NPD7719	Discontinued
0.75	Intermediate Similarity	NPD1954	Phase 1
0.75	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5601	Phase 2
0.7449	Intermediate Similarity	NPD4203	Approved
0.7449	Intermediate Similarity	NPD4204	Approved
0.7448	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6500	Approved
0.7442	Intermediate Similarity	NPD6501	Approved
0.7441	Intermediate Similarity	NPD4502	Phase 2
0.7437	Intermediate Similarity	NPD1034	Phase 3
0.7437	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4995	Approved
0.7421	Intermediate Similarity	NPD4996	Approved
0.7419	Intermediate Similarity	NPD1856	Discontinued
0.7416	Intermediate Similarity	NPD1392	Approved
0.7415	Intermediate Similarity	NPD3825	Phase 3
0.7409	Intermediate Similarity	NPD7555	Discontinued
0.7401	Intermediate Similarity	NPD7620	Phase 2
0.7396	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3396	Approved
0.7389	Intermediate Similarity	NPD6790	Phase 1
0.7389	Intermediate Similarity	NPD3395	Approved
0.7387	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD2917	Approved
0.7387	Intermediate Similarity	NPD4919	Phase 3
0.7387	Intermediate Similarity	NPD4921	Phase 3
0.7385	Intermediate Similarity	NPD1032	Phase 2
0.7381	Intermediate Similarity	NPD5529	Phase 1
0.7381	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4925	Approved
0.7374	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5147	Discontinued
0.7371	Intermediate Similarity	NPD5944	Phase 1
0.7371	Intermediate Similarity	NPD5945	Phase 1
0.7368	Intermediate Similarity	NPD2060	Approved
0.7368	Intermediate Similarity	NPD3003	Approved
0.7358	Intermediate Similarity	NPD5067	Phase 2
0.7358	Intermediate Similarity	NPD5066	Phase 2
0.7353	Intermediate Similarity	NPD2482	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7169	Suspended
0.7347	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6361	Phase 2
0.733	Intermediate Similarity	NPD3541	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6242	Discontinued
0.7323	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2952	Discontinued
0.7316	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3354	Phase 2
0.731	Intermediate Similarity	NPD2600	Approved
0.731	Intermediate Similarity	NPD2601	Approved
0.731	Intermediate Similarity	NPD2599	Approved
0.7299	Intermediate Similarity	NPD7672	Approved
0.7299	Intermediate Similarity	NPD7671	Approved
0.7297	Intermediate Similarity	NPD7567	Approved
0.7297	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4072	Approved
0.7296	Intermediate Similarity	NPD4071	Approved
0.7277	Intermediate Similarity	NPD6281	Approved
0.7277	Intermediate Similarity	NPD8063	Discontinued
0.7273	Intermediate Similarity	NPD5007	Approved
0.7273	Intermediate Similarity	NPD6991	Approved
0.7269	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD5905	Phase 1
0.7264	Intermediate Similarity	NPD4437	Phase 3
0.7263	Intermediate Similarity	NPD9705	Discontinued
0.7263	Intermediate Similarity	NPD112	Approved
0.7261	Intermediate Similarity	NPD8100	Phase 3
0.7255	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD802	Phase 2
0.7249	Intermediate Similarity	NPD2581	Approved
0.7249	Intermediate Similarity	NPD2582	Approved
0.7246	Intermediate Similarity	NPD7956	Approved
0.7246	Intermediate Similarity	NPD7955	Approved
0.7238	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4021	Phase 2
0.7225	Intermediate Similarity	NPD6975	Discontinued
0.722	Intermediate Similarity	NPD6590	Discontinued
0.722	Intermediate Similarity	NPD1602	Discontinued
0.722	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD2189	Approved
0.7217	Intermediate Similarity	NPD2187	Approved
0.721	Intermediate Similarity	NPD5008	Approved
0.7205	Intermediate Similarity	NPD5051	Phase 1
0.7202	Intermediate Similarity	NPD7194	Discontinued
0.7198	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7885	Phase 2
0.7193	Intermediate Similarity	NPD7886	Phase 2
0.719	Intermediate Similarity	NPD4044	Discontinued
0.7184	Intermediate Similarity	NPD6550	Discontinued
0.7179	Intermediate Similarity	NPD4083	Discontinued
0.7175	Intermediate Similarity	NPD5559	Phase 2
0.7175	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5429	Discontinued
0.7169	Intermediate Similarity	NPD8479	Phase 2
0.7168	Intermediate Similarity	NPD2757	Phase 2
0.7167	Intermediate Similarity	NPD8101	Phase 3
0.7167	Intermediate Similarity	NPD6244	Phase 3
0.7167	Intermediate Similarity	NPD6243	Phase 3
0.7163	Intermediate Similarity	NPD5999	Phase 2
0.7163	Intermediate Similarity	NPD4548	Discontinued
0.7157	Intermediate Similarity	NPD5100	Phase 3
0.7156	Intermediate Similarity	NPD4429	Discontinued
0.715	Intermediate Similarity	NPD6262	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7948	Phase 1
0.715	Intermediate Similarity	NPD1622	Discontinued
0.7149	Intermediate Similarity	NPD5539	Phase 2
0.7143	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7112	Discontinued
0.7137	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3324	Clinical (unspecified phase)

Structure

CID36229 OpenBabel06191715362D 27 29 0 0 0 0 0 0 0 0999 V2000 0.5000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.5000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 0.5000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6167 -3.4776 0.0000 Cl 0 5 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 22 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M CHG 2 22 1 27 -1 M END $$$$

External Identifiers

PubChem CID	73442
ChEMBL	CHEMBL274189
ZINC

Physicochemical Properties

Molecular Weight:	352.15
ALogP:	-1.3839
MLogP:	3.22
XLogP:	2.969
# Rotatable Bonds:	8
Polar Surface Area:	40.8
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	26

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