NPASS Natural Product

Natural Product: NPC85661

Natural Product ID:	NPC85661
Common Name:	Aristolochic Acid
IUPAC Name:
Synonyms:	Aristolochic Acid I
Molecular Formula:	C17H11NO7
Standard InCHIKey:	BBFQZRXNYIEMAW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)
Canonical SMILES:	COc1cccc2c1cc(N(=O)=O)c1c2c2OCOc2cc1C(=O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO31364	Aristolochia	Genus	Aristolochiaceae	Eukaryota		PMID[21141875]
NPO7356	Asarum canadense	Species	Aristolochiaceae	Eukaryota		HerDing*
NPO8034	Aristolochia kaempferi	Species	Aristolochiaceae	Eukaryota		HerDing*
NPO9269	Aristolochia tuberosa	Species	Aristolochiaceae	Eukaryota		HerDing*
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota		TM-MC*
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota		TM-MC*
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota		TM-MC*
NPO25921	Papaver nudicaule	Species	Papaveraceae	Eukaryota		UNPD*
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota		TM-MC*
NPO8725	Aristolochia indica	Species	Aristolochiaceae	Eukaryota	roots	PMID[6539809]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota		TM-MC*
NPO33321	aristolochia constricta	Species	Aristolochiaceae	Eukaryota		PMID[18570470]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota		PMID[21353775]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota		TM-MC*
NPO23841	Dysophylla verticillata	NA	NA	NA		UNPD*
NPO4659	Asiasarum heterotropoides	NA	NA	NA		TM-MC*
NPO27900	Mizuhopecten yessoensis	Species	Pectinidae	Eukaryota		UNPD*
NPO29078	Asiasarum sieboldii	NA	NA	NA		TM-MC*
NPO4533	Spatoglossum schmittii	Species	Dictyotaceae	Eukaryota		UNPD*
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota		TM-MC*
NPO10846	Aristolochia rotunda	Species	Aristolochiaceae	Eukaryota		UNPD*
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota		TM-MC*
NPO320	Coffea canephora	Species	Rubiaceae	Eukaryota		UNPD*
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota		TCMID*
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota		TCMID*
NPO267	Couepia polyandra	Species	Chrysobalanaceae	Eukaryota		UNPD*
NPO8034	Aristolochia kaempferi	Species	Aristolochiaceae	Eukaryota		TCMID*
NPO3961	Lavandula hybrida	Species	Lamiaceae	Eukaryota		UNPD*
NPO22930	Aristolochia moupinensis	Species	Aristolochiaceae	Eukaryota		TCMID*
NPO26265	Rumex alpinus	Species	Polygonaceae	Eukaryota		UNPD*
NPO23020	Aristolochia fangchi	Species	Aristolochiaceae	Eukaryota		TCMID*
NPO5606	Dimerostemma asperatum	Species	Asteraceae	Eukaryota		UNPD*
NPO7356	Asarum canadense	Species	Aristolochiaceae	Eukaryota		TCMID*
NPO11385	Chondria atropurpurea	Species	Rhodomelaceae	Eukaryota		UNPD*
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota		TCMID*
NPO10238	Erysimum rhaeticum	Species	Brassicaceae	Eukaryota		UNPD*
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota		TCMID*
NPO26653	Amomum giganteum	Species	Zingiberaceae	Eukaryota		UNPD*
NPO9269	Aristolochia tuberosa	Species	Aristolochiaceae	Eukaryota		TCMID*
NPO15018.1	Dioscorea collettii var. hypoglauca	Varieties	Dioscoreaceae	Eukaryota		UNPD*
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota		TCMID*
NPO29226	Ficus cordata	Species	Moraceae	Eukaryota		UNPD*
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota		HerDing*
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota		HerDing*
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota		HerDing*
NPO22930	Aristolochia moupinensis	Species	Aristolochiaceae	Eukaryota		HerDing*
NPO23020	Aristolochia fangchi	Species	Aristolochiaceae	Eukaryota		HerDing*
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota		HerDing*
NPO29990	Aristolochia argentina	Species	Aristolochiaceae	Eukaryota		PMID[21141875]

Biological Activity

Activity Type	# Activity
GI50	61
IC50	3
Others	6
Potency	36

Activity Type	# Activity
Cell Line	61
Individual Protein	28
Others	13
Protein-Protein Interaction	2
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT517	Cell Line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	883	nM	15743190
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	64	%	18570470
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	>	100	%	18570470
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	20000	nM	20097066
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	10000	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	1258.9	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	44668.4	nM	PubChem BioAssay data set
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	4466.8	nM	PubChem BioAssay data set
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	22334.2	nM	PubChem BioAssay data set
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	10000	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	10000	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	63.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	35481.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	>	10	ug/ml	21353775
NPT2	Others	Unspecified		Potency		32642.7	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		11582.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		14125.4	nM	PubChem BioAssay data set
NPT367	Cell Line	MDA-N	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT368	Cell Line	SN12C	Homo sapiens	GI50		74301.91	nM	PubChem BioAssay data set
NPT369	Cell Line	ACHN	Homo sapiens	GI50		41591.06	nM	PubChem BioAssay data set
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50		39445.73	nM	PubChem BioAssay data set
NPT372	Cell Line	HOP-92	Homo sapiens	GI50		77983.01	nM	PubChem BioAssay data set
NPT371	Cell Line	UO-31	Homo sapiens	GI50		40550.85	nM	PubChem BioAssay data set
NPT90	Cell Line	DU-145	Homo sapiens	GI50		30130.06	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		23067.47	nM	PubChem BioAssay data set
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50		43954.16	nM	PubChem BioAssay data set
NPT374	Cell Line	SF-539	Homo sapiens	GI50		24888.57	nM	PubChem BioAssay data set
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50		46773.51	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	GI50		33884.42	nM	PubChem BioAssay data set
NPT376	Cell Line	A498	Homo sapiens	GI50		29376.5	nM	PubChem BioAssay data set
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50		33884.42	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		26668.59	nM	PubChem BioAssay data set
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50		38106.58	nM	PubChem BioAssay data set
NPT379	Cell Line	HOP-62	Homo sapiens	GI50		23659.2	nM	PubChem BioAssay data set
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50		28707.81	nM	PubChem BioAssay data set
NPT380	Cell Line	U-251	Homo sapiens	GI50		36897.76	nM	PubChem BioAssay data set
NPT383	Cell Line	SNB-19	Homo sapiens	GI50		37497.3	nM	PubChem BioAssay data set
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50		25351.29	nM	PubChem BioAssay data set
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50		39084.09	nM	PubChem BioAssay data set
NPT384	Cell Line	TK-10	Homo sapiens	GI50		46881.34	nM	PubChem BioAssay data set
NPT385	Cell Line	SR	Homo sapiens	GI50		21727.01	nM	PubChem BioAssay data set
NPT323	Cell Line	SW-620	Homo sapiens	GI50		31988.95	nM	PubChem BioAssay data set
NPT386	Cell Line	KM12	Homo sapiens	GI50		27289.78	nM	PubChem BioAssay data set
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50		28054.34	nM	PubChem BioAssay data set
NPT387	Cell Line	M14	Homo sapiens	GI50		43853.07	nM	PubChem BioAssay data set
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50		55335.01	nM	PubChem BioAssay data set
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50		24660.39	nM	PubChem BioAssay data set
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50		31988.95	nM	PubChem BioAssay data set
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50		35481.34	nM	PubChem BioAssay data set
NPT457	Cell Line	BT-549	Homo sapiens	GI50		39445.73	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		57809.6	nM	PubChem BioAssay data set
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50		2798.98	nM	PubChem BioAssay data set
NPT81	Cell Line	A549	Homo sapiens	GI50		45919.8	nM	PubChem BioAssay data set
NPT392	Cell Line	SNB-75	Homo sapiens	GI50		30902.95	nM	PubChem BioAssay data set
NPT393	Cell Line	HCT-116	Homo sapiens	GI50		29853.83	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		18155.16	nM	PubChem BioAssay data set
NPT394	Cell Line	EKVX	Homo sapiens	GI50		43351.09	nM	PubChem BioAssay data set
NPT395	Cell Line	SF-268	Homo sapiens	GI50		33806.48	nM	PubChem BioAssay data set
NPT306	Cell Line	PC-3	Homo sapiens	GI50		46451.53	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	GI50		49431.07	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		49545.02	nM	PubChem BioAssay data set
NPT396	Cell Line	T47D	Homo sapiens	GI50		50118.72	nM	PubChem BioAssay data set
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50		27733.2	nM	PubChem BioAssay data set
NPT398	Cell Line	UACC-62	Homo sapiens	GI50		31405.09	nM	PubChem BioAssay data set
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50		27227.01	nM	PubChem BioAssay data set
NPT399	Cell Line	SF-295	Homo sapiens	GI50		32433.96	nM	PubChem BioAssay data set
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50		54827.7	nM	PubChem BioAssay data set
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50		29376.5	nM	PubChem BioAssay data set
NPT401	Cell Line	786-0	Homo sapiens	GI50		37153.52	nM	PubChem BioAssay data set
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50		52844.53	nM	PubChem BioAssay data set
NPT403	Cell Line	UACC-257	Homo sapiens	GI50		97723.72	nM	PubChem BioAssay data set
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50		20044.72	nM	PubChem BioAssay data set
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency		7943.3	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		889.2	nM	PubChem BioAssay data set
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50		33728.73	nM	PubChem BioAssay data set
NPT406	Cell Line	RXF 393	Homo sapiens	GI50		23442.29	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		41879.36	nM	PubChem BioAssay data set
NPT407	Cell Line	COLO 205	Homo sapiens	GI50		1306.17	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		4109.5	nM	PubChem BioAssay data set
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency		12589.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		3162.3	nM	PubChem BioAssay data set
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency		28183.8	nM	PubChem BioAssay data set
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency		14125.4	nM	PubChem BioAssay data set
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-16.99	%	23062825
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	22.66	%	23062825
NPT2	Others	Unspecified		Potency		18356.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		11550	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		33498.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		8176.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		29855.4	nM	PubChem BioAssay data set
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	107.62	%	23571415
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	76.91	%	23571415
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency		31622.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		891.3	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 NPC85661 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	305
0.1-0.2	1616
0.2-0.3	3367
0.3-0.4	8306
0.4-0.5	4157
0.5-0.6	7786
0.6-0.7	5195
0.7-0.8	136
0.8-0.85	9
0.85-0.9	0
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9946	High Similarity	NPC46679
0.9892	High Similarity	NPC121510
0.9892	High Similarity	NPC171882
0.9784	High Similarity	NPC38961
0.9735	High Similarity	NPC91234
0.9634	High Similarity	NPC290227
0.9583	High Similarity	NPC240684
0.9476	High Similarity	NPC61731
0.9476	High Similarity	NPC186569
0.9378	High Similarity	NPC124658
0.9378	High Similarity	NPC227361
0.9141	High Similarity	NPC256422
0.845	Intermediate Similarity	NPC90185
0.8103	Intermediate Similarity	NPC296742
0.8088	Intermediate Similarity	NPC207873
0.8088	Intermediate Similarity	NPC100573
0.8051	Intermediate Similarity	NPC224293
0.8029	Intermediate Similarity	NPC55470
0.801	Intermediate Similarity	NPC112676
0.8	Intermediate Similarity	NPC69213
0.8	Intermediate Similarity	NPC109765
0.7957	Intermediate Similarity	NPC202495
0.785	Intermediate Similarity	NPC29472
0.7835	Intermediate Similarity	NPC260118
0.7795	Intermediate Similarity	NPC192939
0.7795	Intermediate Similarity	NPC215747
0.7784	Intermediate Similarity	NPC118332
0.7784	Intermediate Similarity	NPC265383
0.7773	Intermediate Similarity	NPC298449
0.7716	Intermediate Similarity	NPC28425
0.7692	Intermediate Similarity	NPC308943
0.7692	Intermediate Similarity	NPC222561
0.7665	Intermediate Similarity	NPC119579
0.7638	Intermediate Similarity	NPC180253
0.7638	Intermediate Similarity	NPC219170
0.7626	Intermediate Similarity	NPC276060
0.7614	Intermediate Similarity	NPC311936
0.7562	Intermediate Similarity	NPC312531
0.7561	Intermediate Similarity	NPC193906
0.7561	Intermediate Similarity	NPC23080
0.7548	Intermediate Similarity	NPC159101
0.7548	Intermediate Similarity	NPC207971
0.7539	Intermediate Similarity	NPC125713
0.7536	Intermediate Similarity	NPC46990
0.7513	Intermediate Similarity	NPC116838
0.7513	Intermediate Similarity	NPC22130
0.7512	Intermediate Similarity	NPC22928
0.7475	Intermediate Similarity	NPC474904
0.7451	Intermediate Similarity	NPC254957
0.745	Intermediate Similarity	NPC249405
0.744	Intermediate Similarity	NPC5374
0.7429	Intermediate Similarity	NPC268077
0.7423	Intermediate Similarity	NPC198796
0.7396	Intermediate Similarity	NPC167098
0.7396	Intermediate Similarity	NPC296044
0.7391	Intermediate Similarity	NPC71124
0.7344	Intermediate Similarity	NPC115123
0.7344	Intermediate Similarity	NPC239113
0.734	Intermediate Similarity	NPC474009
0.733	Intermediate Similarity	NPC54179
0.7317	Intermediate Similarity	NPC294244
0.7313	Intermediate Similarity	NPC196771
0.731	Intermediate Similarity	NPC474042
0.731	Intermediate Similarity	NPC174734
0.7308	Intermediate Similarity	NPC17677
0.7306	Intermediate Similarity	NPC19600
0.7306	Intermediate Similarity	NPC143328
0.7302	Intermediate Similarity	NPC300983
0.7295	Intermediate Similarity	NPC162653
0.7255	Intermediate Similarity	NPC320088
0.7236	Intermediate Similarity	NPC117911
0.7231	Intermediate Similarity	NPC78944
0.7228	Intermediate Similarity	NPC179704
0.7219	Intermediate Similarity	NPC471305
0.7214	Intermediate Similarity	NPC190461
0.7212	Intermediate Similarity	NPC227033
0.7212	Intermediate Similarity	NPC470023
0.7209	Intermediate Similarity	NPC477825
0.7206	Intermediate Similarity	NPC18306
0.7202	Intermediate Similarity	NPC472835
0.72	Intermediate Similarity	NPC52598
0.7194	Intermediate Similarity	NPC15212
0.7186	Intermediate Similarity	NPC210296
0.7179	Intermediate Similarity	NPC68619
0.7178	Intermediate Similarity	NPC193377
0.7177	Intermediate Similarity	NPC470021
0.7176	Intermediate Similarity	NPC25961
0.7164	Intermediate Similarity	NPC114550
0.7164	Intermediate Similarity	NPC292712
0.7164	Intermediate Similarity	NPC471921
0.7164	Intermediate Similarity	NPC471922
0.7164	Intermediate Similarity	NPC129930
0.7164	Intermediate Similarity	NPC287588
0.7164	Intermediate Similarity	NPC20114
0.7164	Intermediate Similarity	NPC474075
0.7164	Intermediate Similarity	NPC471920
0.7164	Intermediate Similarity	NPC312006
0.7161	Intermediate Similarity	NPC183537
0.7158	Intermediate Similarity	NPC127827
0.7157	Intermediate Similarity	NPC276674
0.7157	Intermediate Similarity	NPC33902
0.715	Intermediate Similarity	NPC226708
0.7143	Intermediate Similarity	NPC474770
0.713	Intermediate Similarity	NPC182907
0.713	Intermediate Similarity	NPC189903
0.7129	Intermediate Similarity	NPC184624
0.7129	Intermediate Similarity	NPC33256
0.7129	Intermediate Similarity	NPC114364
0.7129	Intermediate Similarity	NPC320223
0.7123	Intermediate Similarity	NPC471489
0.712	Intermediate Similarity	NPC475722
0.712	Intermediate Similarity	NPC261322
0.712	Intermediate Similarity	NPC37220
0.7115	Intermediate Similarity	NPC78284
0.711	Intermediate Similarity	NPC477826
0.711	Intermediate Similarity	NPC477827
0.7092	Intermediate Similarity	NPC474043
0.7087	Intermediate Similarity	NPC108342
0.7085	Intermediate Similarity	NPC474301
0.7081	Intermediate Similarity	NPC469815
0.7081	Intermediate Similarity	NPC469816
0.7079	Intermediate Similarity	NPC98416
0.7079	Intermediate Similarity	NPC85613
0.7079	Intermediate Similarity	NPC5167
0.7068	Intermediate Similarity	NPC24193
0.7065	Intermediate Similarity	NPC285941
0.7056	Intermediate Similarity	NPC47623
0.705	Intermediate Similarity	NPC471923
0.7047	Intermediate Similarity	NPC302783
0.7047	Intermediate Similarity	NPC124842
0.7047	Intermediate Similarity	NPC473201
0.7044	Intermediate Similarity	NPC316539
0.7035	Intermediate Similarity	NPC247389
0.7033	Intermediate Similarity	NPC302001
0.703	Intermediate Similarity	NPC229166
0.703	Intermediate Similarity	NPC128560
0.703	Intermediate Similarity	NPC199465
0.7026	Intermediate Similarity	NPC234730
0.7024	Intermediate Similarity	NPC116284
0.7024	Intermediate Similarity	NPC248642
0.7024	Intermediate Similarity	NPC35266
0.7023	Intermediate Similarity	NPC156728
0.7023	Intermediate Similarity	NPC244606
0.7021	Intermediate Similarity	NPC86455
0.7021	Intermediate Similarity	NPC125134
0.7021	Intermediate Similarity	NPC124313
0.7021	Intermediate Similarity	NPC137920
0.7017	Intermediate Similarity	NPC77878
0.7016	Intermediate Similarity	NPC181464
0.7015	Intermediate Similarity	NPC227683
0.7015	Intermediate Similarity	NPC67978
0.7015	Intermediate Similarity	NPC311912
0.7015	Intermediate Similarity	NPC473531
0.7015	Intermediate Similarity	NPC471180
0.7015	Intermediate Similarity	NPC475453
0.7015	Intermediate Similarity	NPC303581
0.7	Intermediate Similarity	NPC22481
0.6995	Remote Similarity	NPC283810
0.699	Remote Similarity	NPC275690
0.699	Remote Similarity	NPC261484
0.699	Remote Similarity	NPC161609
0.699	Remote Similarity	NPC135772
0.699	Remote Similarity	NPC261090
0.699	Remote Similarity	NPC473900
0.699	Remote Similarity	NPC156576
0.6985	Remote Similarity	NPC476432
0.6985	Remote Similarity	NPC219341
0.6985	Remote Similarity	NPC144843
0.6985	Remote Similarity	NPC19948
0.6985	Remote Similarity	NPC24264
0.6982	Remote Similarity	NPC477828
0.698	Remote Similarity	NPC9475
0.698	Remote Similarity	NPC88557
0.6974	Remote Similarity	NPC62051
0.6967	Remote Similarity	NPC125924
0.6965	Remote Similarity	NPC320471
0.6965	Remote Similarity	NPC118162
0.6965	Remote Similarity	NPC83049
0.6961	Remote Similarity	NPC477881
0.6961	Remote Similarity	NPC199357
0.6959	Remote Similarity	NPC78505
0.6959	Remote Similarity	NPC104353
0.6957	Remote Similarity	NPC53680
0.6957	Remote Similarity	NPC208797
0.6954	Remote Similarity	NPC76458
0.6954	Remote Similarity	NPC82733
0.6953	Remote Similarity	NPC166722
0.6952	Remote Similarity	NPC205721
0.6951	Remote Similarity	NPC195120
0.695	Remote Similarity	NPC298979
0.695	Remote Similarity	NPC100420
0.6948	Remote Similarity	NPC212163
0.6947	Remote Similarity	NPC229787
0.6946	Remote Similarity	NPC308267
0.6946	Remote Similarity	NPC477558
0.6942	Remote Similarity	NPC47191
0.6939	Remote Similarity	NPC80489
0.6936	Remote Similarity	NPC207283
0.6936	Remote Similarity	NPC84164
0.6935	Remote Similarity	NPC99968

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC85661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	887
0.2-0.3	911
0.3-0.4	2330
0.4-0.5	2718
0.5-0.6	1616
0.6-0.7	414
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7534	Intermediate Similarity	NPD6723	Discontinued
0.7441	Intermediate Similarity	NPD6296	Discontinued
0.7358	Intermediate Similarity	NPD3252	Approved
0.7343	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1221	Approved
0.7231	Intermediate Similarity	NPD710	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8067	Phase 3
0.7194	Intermediate Similarity	NPD2821	Approved
0.7157	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD3251	Approved
0.7089	Intermediate Similarity	NPD5848	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD1220	Phase 1
0.7056	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7473	Discontinued
0.7037	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4859	Phase 1
0.6995	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5844	Phase 1
0.6957	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.693	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7922	Phase 1
0.6901	Remote Similarity	NPD4420	Approved
0.6893	Remote Similarity	NPD7546	Discontinued
0.689	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6625	Approved
0.6839	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD37	Approved
0.6837	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5006	Approved
0.6774	Remote Similarity	NPD5005	Approved
0.6765	Remote Similarity	NPD7177	Discontinued
0.6762	Remote Similarity	NPD3398	Discontinued
0.6762	Remote Similarity	NPD1898	Discontinued
0.6734	Remote Similarity	NPD4967	Phase 2
0.6734	Remote Similarity	NPD4965	Approved
0.6734	Remote Similarity	NPD4966	Approved
0.6728	Remote Similarity	NPD7476	Discontinued
0.6725	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6385	Approved
0.6701	Remote Similarity	NPD6386	Approved
0.6701	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5242	Approved
0.6697	Remote Similarity	NPD5950	Discontinued
0.6684	Remote Similarity	NPD7458	Discontinued
0.6682	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6652	Remote Similarity	NPD7827	Phase 1
0.6636	Remote Similarity	NPD6212	Phase 3
0.6636	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6213	Phase 3
0.6635	Remote Similarity	NPD7038	Approved
0.6635	Remote Similarity	NPD7039	Approved
0.6626	Remote Similarity	NPD8367	Approved
0.6624	Remote Similarity	NPD4846	Phase 2
0.6623	Remote Similarity	NPD5519	Discontinued
0.6621	Remote Similarity	NPD3057	Approved
0.6607	Remote Similarity	NPD683	Approved
0.6607	Remote Similarity	NPD7783	Phase 2
0.6607	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7256	Discontinued
0.6601	Remote Similarity	NPD7199	Phase 2
0.66	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3226	Approved
0.6588	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3752	Phase 2
0.6575	Remote Similarity	NPD4482	Phase 3
0.6574	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD8149	Discontinued
0.6562	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5914	Approved
0.6561	Remote Similarity	NPD7891	Discontinued
0.656	Remote Similarity	NPD6874	Approved
0.656	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5805	Approved
0.655	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2899	Discontinued
0.6549	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3533	Approved
0.6545	Remote Similarity	NPD2972	Approved
0.6544	Remote Similarity	NPD2974	Approved
0.6544	Remote Similarity	NPD2973	Approved
0.6544	Remote Similarity	NPD2975	Approved
0.654	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2672	Discontinued
0.653	Remote Similarity	NPD3290	Approved
0.653	Remote Similarity	NPD3289	Phase 3
0.6528	Remote Similarity	NPD7003	Approved
0.6526	Remote Similarity	NPD2792	Approved
0.6522	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3818	Discontinued
0.652	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.652	Remote Similarity	NPD8127	Discontinued
0.6518	Remote Similarity	NPD8151	Discontinued
0.6518	Remote Similarity	NPD8492	Approved
0.6517	Remote Similarity	NPD5977	Approved
0.6517	Remote Similarity	NPD5978	Approved
0.6514	Remote Similarity	NPD5071	Phase 2
0.6507	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2494	Approved
0.65	Remote Similarity	NPD3450	Approved
0.65	Remote Similarity	NPD2493	Approved
0.65	Remote Similarity	NPD3452	Approved
0.6498	Remote Similarity	NPD5582	Discontinued
0.6495	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5025	Approved
0.6485	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD3684	Discontinued
0.6477	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6559	Discontinued
0.6471	Remote Similarity	NPD3448	Approved
0.6471	Remote Similarity	NPD2491	Approved
0.6468	Remote Similarity	NPD7654	Discontinued
0.6468	Remote Similarity	NPD1465	Phase 2
0.6466	Remote Similarity	NPD6997	Phase 2
0.6465	Remote Similarity	NPD2488	Approved
0.6465	Remote Similarity	NPD5641	Discontinued
0.6465	Remote Similarity	NPD2490	Approved
0.6457	Remote Similarity	NPD7999	Approved
0.6457	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6776	Approved
0.6455	Remote Similarity	NPD4580	Approved
0.6455	Remote Similarity	NPD6779	Approved
0.6455	Remote Similarity	NPD6778	Approved
0.6455	Remote Similarity	NPD6777	Approved
0.6455	Remote Similarity	NPD6782	Approved
0.6455	Remote Similarity	NPD6781	Approved
0.6455	Remote Similarity	NPD6780	Approved
0.6453	Remote Similarity	NPD3453	Discontinued
0.645	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.645	Remote Similarity	NPD3437	Discontinued
0.6442	Remote Similarity	NPD7228	Approved
0.6439	Remote Similarity	NPD6457	Approved
0.6438	Remote Similarity	NPD7278	Phase 2
0.6438	Remote Similarity	NPD7279	Phase 2
0.6435	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5811	Approved
0.6429	Remote Similarity	NPD1543	Discontinued
0.6429	Remote Similarity	NPD7583	Approved
0.6429	Remote Similarity	NPD6184	Discontinued
0.6422	Remote Similarity	NPD7907	Approved
0.6422	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5928	Phase 1
0.6419	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD8313	Approved
0.6415	Remote Similarity	NPD7281	Phase 3
0.6415	Remote Similarity	NPD8312	Approved
0.6415	Remote Similarity	NPD7280	Phase 3
0.6415	Remote Similarity	NPD2968	Approved
0.6415	Remote Similarity	NPD2971	Approved
0.6413	Remote Similarity	NPD7870	Phase 2
0.6413	Remote Similarity	NPD4583	Approved
0.6413	Remote Similarity	NPD4582	Approved
0.6413	Remote Similarity	NPD7871	Phase 2
0.6411	Remote Similarity	NPD3965	Phase 1
0.6402	Remote Similarity	NPD2979	Phase 3
0.64	Remote Similarity	NPD7585	Approved
0.6396	Remote Similarity	NPD2532	Approved
0.6396	Remote Similarity	NPD7626	Approved
0.6396	Remote Similarity	NPD7627	Approved
0.6396	Remote Similarity	NPD2534	Approved
0.6396	Remote Similarity	NPD2533	Approved
0.6388	Remote Similarity	NPD5676	Approved
0.6383	Remote Similarity	NPD3764	Approved
0.6373	Remote Similarity	NPD955	Approved
0.6373	Remote Similarity	NPD2346	Discontinued
0.6368	Remote Similarity	NPD4002	Approved
0.6368	Remote Similarity	NPD1891	Discontinued
0.6368	Remote Similarity	NPD3912	Discontinued
0.6368	Remote Similarity	NPD7697	Approved
0.6368	Remote Similarity	NPD7698	Approved
0.6368	Remote Similarity	NPD7696	Phase 3
0.6368	Remote Similarity	NPD4004	Approved
0.6368	Remote Similarity	NPD2366	Approved
0.6368	Remote Similarity	NPD7435	Discontinued
0.6367	Remote Similarity	NPD5488	Discontinued
0.6364	Remote Similarity	NPD7395	Discontinued
0.6359	Remote Similarity	NPD4628	Phase 3
0.6359	Remote Similarity	NPD2247	Approved
0.6359	Remote Similarity	NPD2249	Approved
0.6356	Remote Similarity	NPD7584	Approved
0.6348	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4481	Phase 3
0.6344	Remote Similarity	NPD7874	Approved
0.6344	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7417	Discontinued
0.6336	Remote Similarity	NPD4665	Approved
0.6336	Remote Similarity	NPD4111	Phase 1
0.633	Remote Similarity	NPD4466	Phase 1
0.6329	Remote Similarity	NPD6747	Phase 1
0.6325	Remote Similarity	NPD4049	Phase 2
0.6321	Remote Similarity	NPD5637	Discontinued
0.6321	Remote Similarity	NPD7685	Pre-registration
0.6321	Remote Similarity	NPD2438	Suspended
0.6313	Remote Similarity	NPD5871	Discontinued
0.6311	Remote Similarity	NPD5494	Approved
0.6308	Remote Similarity	NPD1195	Approved

Structure

CID85661 OpenBabel06191715422D 25 28 0 0 0 0 0 0 0 0999 V2000 5.2177 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 -0.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9602 -0.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 2.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 2.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 4.8065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 3.8410 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 5.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 5.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 4.3237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 4.3237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3816 1.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3529 0.7811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 12 2 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 24 1 0 0 0 0 7 25 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	2236
ChEMBL	CHEMBL93353
ZINC

Physicochemical Properties

Molecular Weight:	341.05
ALogP:	0.0658
MLogP:	2.45
XLogP:	2.79
# Rotatable Bonds:	6
Polar Surface Area:	108.13
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	25

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