NPASS Natural Product

Natural Product: NPC229113

Natural Product ID:	NPC229113
Common Name:	Dicumarol
IUPAC Name:	4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
Synonyms:	Bishydroxycoumarin; Dicoumarol; Dicumarol
Molecular Formula:	C19H12O6
Standard InCHIKey:	DOBMPNYZJYQDGZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
Canonical SMILES:	O=c1oc2ccccc2c(c1Cc1c(=O)oc2c(c1O)cccc2)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	HerDing*
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	HerDing*
NPO20168	Melilotus albus	Species	Fabaceae	Eukaryota	HerDing*
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	HerDing*
NPO30762	Melilotus suaveolens	Species	Fabaceae	Eukaryota	HerDing*
NPO31164	Anthoxanthum sp	Species	Poaceae	Eukaryota	HerDing*
NPO9111	Gelatoporia subvermispora	Species	Coriolaceae	Eukaryota	UNPD*
NPO11940	Laurencia snyderiae	Species	Rhodomelaceae	Eukaryota	UNPD*
NPO17085	Dactylaria lutea	Species	Orbiliaceae	Eukaryota	UNPD*
NPO14160	Elaeis guineensis	Species	Arecaceae	Eukaryota	UNPD*
NPO27176	Anthoxanthum sp.	Species	Poaceae	Eukaryota	TCMID*
NPO19849.1	Melilotus officinalis subsp. suaveolens	Subspecies	Fabaceae	Eukaryota	TCMID*
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	TCMID*
NPO20168	Melilotus albus	Species	Fabaceae	Eukaryota	TCMID*
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	TCMID*
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	TCMID*
NPO12605	Butea superba	Species	Fabaceae	Eukaryota	UNPD*

Biological Activity

Activity Type	# Activity
AC50	5
EC50	2
IC50	21
Kd	1
Ki	5
MIC	8
Others	10
Potency	39

Activity Type	# Activity
Cell Line	6
Individual Protein	47
Organism	9
Others	27
Protein-Protein Interaction	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	>	100000	nM	9003523
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	>	300000	nM	9003523
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Ki	=	1900	nM	14761192
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Ki	=	600	nM	10956186
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	IC50	=	450	nM	17011189
NPT2	Others	Unspecified		IC50	=	3100	nM	17275317
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	IC50	=	5	nM	17999461
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	IC50	=	450	nM	17999461
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	7	nmol/min	17999461
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	75000	nM	17999461
NPT4885	Individual Protein	Urease	Canavalia ensiformis	IC50	=	15135.61	nM	18280742
NPT5330	Organism	Strongylocentrotus purpuratus	Strongylocentrotus purpuratus	Inhibition	=	50	%	17614164
NPT2	Others	Unspecified		Kd	=	22000	nM	17614164
NPT2	Others	Unspecified		Ki	=	50000	nM	18778048
NPT3570	Individual Protein	ATP phosphoribosyltransferase	Mycobacterium tuberculosis	Ki	=	60000	nM	18778048
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	IC50	=	2.6	nM	19877692
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	IC50	=	404	nM	19877692
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	90000	nM	19877692
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	52000	nM	19877692
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	103000	nM	19877692
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	19000	nM	19877692
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	50.1	nM	PubChem BioAssay data set
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	10000	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	6309.6	nM	PubChem BioAssay data set
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	10000	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	5011.9	nM	PubChem BioAssay data set
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	25.1	nM	PubChem BioAssay data set
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	AC50	=	25.12	nM	PubChem BioAssay data set
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	AC50	=	10000	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	5011.87	nM	PubChem BioAssay data set
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	12589.25	nM	PubChem BioAssay data set
NPT604	Individual Protein	Serum albumin	Homo sapiens	Activity	=	86.4	%	20869876
NPT604	Individual Protein	Serum albumin	Homo sapiens	Activity	=	88.8	%	20869876
NPT604	Individual Protein	Serum albumin	Homo sapiens	Activity	=	10.5	%	20869876
NPT604	Individual Protein	Serum albumin	Homo sapiens	Activity	=	19.8	%	20869876
NPT2	Others	Unspecified		IC50	=	4570	nM	21510613
NPT620	Individual Protein	Subtilisin/kexin type 7	Homo sapiens	IC50	=	1300	nM	21510613
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency		31622.8	nM	PubChem BioAssay data set
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	4093	nM	DrugMatrix in vitro pharmacology data
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	IC50	=	300	nM	DrugMatrix in vitro pharmacology data
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	IC50	=	4426	nM	DrugMatrix in vitro pharmacology data
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		8052.4	nM	PubChem BioAssay data set
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	12.27	%	23062825
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	5.48	%	23062825
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	>=	2048	ug/ml	23306152
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>=	2048	ug/ml	23306152
NPT5161	Individual Protein	Enoyl-[acyl-carrier-protein] reductase [NADH]	Francisella tularensis subsp. tularensis (strain SCHU S4 / Schu 4)	IC50	=	47000	nM	23815100
NPT1627	Individual Protein	G-protein coupled receptor 35	Homo sapiens	EC50	=	9780	nM	23888932
NPT1627	Individual Protein	G-protein coupled receptor 35	Homo sapiens	Ki	=	39	nM	23888932
NPT1627	Individual Protein	G-protein coupled receptor 35	Homo sapiens	EC50	=	1300	nM	23888932
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	19.32	%	23571415
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	33.08	%	23571415
NPT2	Others	Unspecified		Potency		13448.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		9438.4	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency		10123.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		5073.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		2037.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		638.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		11882.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		6681.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		7166.9	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		7497.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		7943.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		11358.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1678.4	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency		29847	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		5955.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		4216	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		5116.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		3228.6	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency		13332.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		2285.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		507.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		14299.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		3757.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		6007	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		7497.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		13333.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		AC50		5623.4	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 NPC229113 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	235
0.1-0.2	1131
0.2-0.3	2813
0.3-0.4	7170
0.4-0.5	5982
0.5-0.6	2986
0.6-0.7	7326
0.7-0.8	3140
0.8-0.85	93
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8908	High Similarity	NPC33717
0.8898	High Similarity	NPC2989
0.877	High Similarity	NPC31314
0.877	High Similarity	NPC474874
0.877	High Similarity	NPC193193
0.8718	High Similarity	NPC141068
0.8672	High Similarity	NPC238309
0.8651	High Similarity	NPC168259
0.8615	High Similarity	NPC307289
0.8615	High Similarity	NPC281558
0.8582	High Similarity	NPC71903
0.8527	High Similarity	NPC474289
0.8519	High Similarity	NPC170812
0.8462	Intermediate Similarity	NPC32463
0.84	Intermediate Similarity	NPC302107
0.8387	Intermediate Similarity	NPC264976
0.8346	Intermediate Similarity	NPC315807
0.8346	Intermediate Similarity	NPC131950
0.8333	Intermediate Similarity	NPC187868
0.8333	Intermediate Similarity	NPC52247
0.832	Intermediate Similarity	NPC247553
0.8319	Intermediate Similarity	NPC149545
0.8281	Intermediate Similarity	NPC89630
0.8271	Intermediate Similarity	NPC287533
0.8268	Intermediate Similarity	NPC311219
0.8258	Intermediate Similarity	NPC137264
0.8248	Intermediate Similarity	NPC310370
0.8248	Intermediate Similarity	NPC183642
0.8231	Intermediate Similarity	NPC258567
0.8231	Intermediate Similarity	NPC121740
0.8231	Intermediate Similarity	NPC224774
0.8222	Intermediate Similarity	NPC223616
0.8217	Intermediate Similarity	NPC88403
0.8211	Intermediate Similarity	NPC51345
0.8182	Intermediate Similarity	NPC115998
0.8182	Intermediate Similarity	NPC39753
0.8168	Intermediate Similarity	NPC469453
0.816	Intermediate Similarity	NPC152306
0.8156	Intermediate Similarity	NPC57470
0.8145	Intermediate Similarity	NPC128633
0.8143	Intermediate Similarity	NPC295696
0.814	Intermediate Similarity	NPC193805
0.8136	Intermediate Similarity	NPC139891
0.812	Intermediate Similarity	NPC250727
0.8106	Intermediate Similarity	NPC197425
0.8102	Intermediate Similarity	NPC37428
0.8102	Intermediate Similarity	NPC144512
0.8102	Intermediate Similarity	NPC137262
0.8102	Intermediate Similarity	NPC47040
0.8102	Intermediate Similarity	NPC278600
0.8102	Intermediate Similarity	NPC35501
0.8099	Intermediate Similarity	NPC142863
0.8099	Intermediate Similarity	NPC249942
0.8099	Intermediate Similarity	NPC180477
0.8099	Intermediate Similarity	NPC297886
0.8095	Intermediate Similarity	NPC298796
0.8092	Intermediate Similarity	NPC243688
0.8088	Intermediate Similarity	NPC246177
0.8088	Intermediate Similarity	NPC317045
0.8085	Intermediate Similarity	NPC287275
0.8077	Intermediate Similarity	NPC93219
0.8077	Intermediate Similarity	NPC4164
0.8077	Intermediate Similarity	NPC244495
0.8074	Intermediate Similarity	NPC274121
0.8074	Intermediate Similarity	NPC50898
0.8074	Intermediate Similarity	NPC78540
0.8074	Intermediate Similarity	NPC213216
0.8071	Intermediate Similarity	NPC36181
0.806	Intermediate Similarity	NPC19157
0.806	Intermediate Similarity	NPC113006
0.8045	Intermediate Similarity	NPC12694
0.8042	Intermediate Similarity	NPC161864
0.8042	Intermediate Similarity	NPC469933
0.8042	Intermediate Similarity	NPC208303
0.8033	Intermediate Similarity	NPC233238
0.803	Intermediate Similarity	NPC157212
0.803	Intermediate Similarity	NPC2401
0.8029	Intermediate Similarity	NPC47815
0.8029	Intermediate Similarity	NPC194281
0.8029	Intermediate Similarity	NPC127447
0.8029	Intermediate Similarity	NPC231772
0.8029	Intermediate Similarity	NPC473887
0.8029	Intermediate Similarity	NPC13408
0.8029	Intermediate Similarity	NPC234133
0.8029	Intermediate Similarity	NPC474886
0.8029	Intermediate Similarity	NPC29353
0.8029	Intermediate Similarity	NPC124784
0.8028	Intermediate Similarity	NPC153758
0.8028	Intermediate Similarity	NPC154217
0.8016	Intermediate Similarity	NPC96705
0.8016	Intermediate Similarity	NPC265547
0.8015	Intermediate Similarity	NPC172262
0.8015	Intermediate Similarity	NPC66705
0.8015	Intermediate Similarity	NPC61499
0.8015	Intermediate Similarity	NPC298900
0.8014	Intermediate Similarity	NPC112791
0.8014	Intermediate Similarity	NPC470216
0.8014	Intermediate Similarity	NPC470296
0.8014	Intermediate Similarity	NPC196459
0.8014	Intermediate Similarity	NPC71739
0.8014	Intermediate Similarity	NPC94794
0.8014	Intermediate Similarity	NPC188632
0.8014	Intermediate Similarity	NPC87609
0.8	Intermediate Similarity	NPC128216
0.8	Intermediate Similarity	NPC163398
0.8	Intermediate Similarity	NPC140521
0.7986	Intermediate Similarity	NPC469932
0.7986	Intermediate Similarity	NPC155552
0.7986	Intermediate Similarity	NPC254994
0.7984	Intermediate Similarity	NPC13007
0.7984	Intermediate Similarity	NPC257188
0.7972	Intermediate Similarity	NPC140120
0.7971	Intermediate Similarity	NPC266597
0.7971	Intermediate Similarity	NPC319870
0.7971	Intermediate Similarity	NPC148738
0.7971	Intermediate Similarity	NPC73078
0.7971	Intermediate Similarity	NPC250266
0.7971	Intermediate Similarity	NPC103001
0.7971	Intermediate Similarity	NPC327612
0.7969	Intermediate Similarity	NPC235190
0.7969	Intermediate Similarity	NPC180006
0.7969	Intermediate Similarity	NPC163200
0.7969	Intermediate Similarity	NPC319378
0.7967	Intermediate Similarity	NPC266116
0.7958	Intermediate Similarity	NPC178627
0.7958	Intermediate Similarity	NPC1886
0.7958	Intermediate Similarity	NPC469935
0.7958	Intermediate Similarity	NPC196137
0.7955	Intermediate Similarity	NPC95034
0.7955	Intermediate Similarity	NPC22783
0.7955	Intermediate Similarity	NPC142087
0.7953	Intermediate Similarity	NPC281356
0.7953	Intermediate Similarity	NPC295259
0.7943	Intermediate Similarity	NPC293852
0.7943	Intermediate Similarity	NPC62840
0.7943	Intermediate Similarity	NPC217083
0.7943	Intermediate Similarity	NPC59739
0.7943	Intermediate Similarity	NPC299080
0.7943	Intermediate Similarity	NPC185127
0.7943	Intermediate Similarity	NPC214236
0.7943	Intermediate Similarity	NPC78803
0.7941	Intermediate Similarity	NPC57601
0.7939	Intermediate Similarity	NPC249836
0.7939	Intermediate Similarity	NPC232692
0.7939	Intermediate Similarity	NPC202594
0.7937	Intermediate Similarity	NPC45104
0.7931	Intermediate Similarity	NPC151973
0.7929	Intermediate Similarity	NPC31081
0.7929	Intermediate Similarity	NPC245219
0.7926	Intermediate Similarity	NPC469956
0.7923	Intermediate Similarity	NPC273772
0.7923	Intermediate Similarity	NPC154176
0.7923	Intermediate Similarity	NPC290605
0.7923	Intermediate Similarity	NPC173350
0.7923	Intermediate Similarity	NPC109675
0.7923	Intermediate Similarity	NPC248786
0.792	Intermediate Similarity	NPC296526
0.7914	Intermediate Similarity	NPC201395
0.791	Intermediate Similarity	NPC113098
0.791	Intermediate Similarity	NPC327457
0.791	Intermediate Similarity	NPC86774
0.7902	Intermediate Similarity	NPC470322
0.7902	Intermediate Similarity	NPC181388
0.7899	Intermediate Similarity	NPC38874
0.7899	Intermediate Similarity	NPC116775
0.7899	Intermediate Similarity	NPC187432
0.7899	Intermediate Similarity	NPC216361
0.7899	Intermediate Similarity	NPC281917
0.7899	Intermediate Similarity	NPC471068
0.7899	Intermediate Similarity	NPC471069
0.7899	Intermediate Similarity	NPC256042
0.7895	Intermediate Similarity	NPC185066
0.7895	Intermediate Similarity	NPC167463
0.7895	Intermediate Similarity	NPC2596
0.7895	Intermediate Similarity	NPC46192
0.7891	Intermediate Similarity	NPC230951
0.7891	Intermediate Similarity	NPC168050
0.7891	Intermediate Similarity	NPC14177
0.7883	Intermediate Similarity	NPC248872
0.7874	Intermediate Similarity	NPC74821
0.7872	Intermediate Similarity	NPC14871
0.7872	Intermediate Similarity	NPC105648
0.7868	Intermediate Similarity	NPC83535
0.7868	Intermediate Similarity	NPC31849
0.7868	Intermediate Similarity	NPC205797
0.7868	Intermediate Similarity	NPC1220
0.7868	Intermediate Similarity	NPC142563
0.7868	Intermediate Similarity	NPC469952
0.7868	Intermediate Similarity	NPC291551
0.7868	Intermediate Similarity	NPC469955
0.7868	Intermediate Similarity	NPC141822
0.7868	Intermediate Similarity	NPC241165
0.7863	Intermediate Similarity	NPC107846
0.7863	Intermediate Similarity	NPC221798
0.7863	Intermediate Similarity	NPC6888
0.7863	Intermediate Similarity	NPC78446
0.7863	Intermediate Similarity	NPC27671
0.7863	Intermediate Similarity	NPC98509
0.7863	Intermediate Similarity	NPC291899
0.7863	Intermediate Similarity	NPC201667

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC229113 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	832
0.2-0.3	1427
0.3-0.4	2526
0.4-0.5	2041
0.5-0.6	1403
0.6-0.7	529
0.7-0.8	143
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3225	Approved
0.8898	High Similarity	NPD3268	Approved
0.88	High Similarity	NPD2797	Approved
0.8651	High Similarity	NPD3267	Approved
0.8651	High Similarity	NPD3266	Approved
0.8504	High Similarity	NPD1203	Approved
0.8333	Intermediate Similarity	NPD422	Phase 1
0.8268	Intermediate Similarity	NPD9717	Approved
0.8222	Intermediate Similarity	NPD4308	Phase 3
0.8188	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD9697	Approved
0.8088	Intermediate Similarity	NPD7033	Discontinued
0.7986	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD3748	Approved
0.7926	Intermediate Similarity	NPD4307	Phase 2
0.791	Intermediate Similarity	NPD2313	Discontinued
0.7899	Intermediate Similarity	NPD1551	Phase 2
0.7895	Intermediate Similarity	NPD6832	Phase 2
0.7891	Intermediate Similarity	NPD1778	Approved
0.7874	Intermediate Similarity	NPD1548	Phase 1
0.7868	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD5124	Phase 1
0.7847	Intermediate Similarity	NPD5403	Approved
0.7846	Intermediate Similarity	NPD1608	Approved
0.7832	Intermediate Similarity	NPD5401	Approved
0.7823	Intermediate Similarity	NPD5535	Approved
0.7778	Intermediate Similarity	NPD1296	Phase 2
0.7769	Intermediate Similarity	NPD1535	Discovery
0.7755	Intermediate Similarity	NPD7411	Suspended
0.7734	Intermediate Similarity	NPD1894	Discontinued
0.7714	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD1481	Phase 2
0.7708	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1549	Phase 2
0.7647	Intermediate Similarity	NPD6798	Discontinued
0.7647	Intermediate Similarity	NPD411	Approved
0.763	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3226	Approved
0.7615	Intermediate Similarity	NPD17	Approved
0.7609	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD447	Suspended
0.7609	Intermediate Similarity	NPD1933	Approved
0.7586	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1510	Phase 2
0.7557	Intermediate Similarity	NPD3496	Discontinued
0.7552	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1511	Approved
0.7517	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7483	Intermediate Similarity	NPD5402	Approved
0.7482	Intermediate Similarity	NPD4340	Discontinued
0.7481	Intermediate Similarity	NPD1019	Discontinued
0.748	Intermediate Similarity	NPD968	Approved
0.7464	Intermediate Similarity	NPD6233	Phase 2
0.7447	Intermediate Similarity	NPD2799	Discontinued
0.7442	Intermediate Similarity	NPD9493	Approved
0.7431	Intermediate Similarity	NPD4628	Phase 3
0.7424	Intermediate Similarity	NPD3847	Discontinued
0.7415	Intermediate Similarity	NPD1512	Approved
0.7413	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1240	Approved
0.7405	Intermediate Similarity	NPD5585	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7394	Intermediate Similarity	NPD2796	Approved
0.7391	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2614	Approved
0.7368	Intermediate Similarity	NPD1091	Approved
0.7368	Intermediate Similarity	NPD4288	Approved
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1652	Phase 2
0.7357	Intermediate Similarity	NPD6355	Discontinued
0.7353	Intermediate Similarity	NPD2798	Approved
0.7351	Intermediate Similarity	NPD6801	Discontinued
0.7343	Intermediate Similarity	NPD2346	Discontinued
0.7328	Intermediate Similarity	NPD9545	Approved
0.732	Intermediate Similarity	NPD7768	Phase 2
0.732	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD7095	Approved
0.731	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1607	Approved
0.7303	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7819	Suspended
0.729	Intermediate Similarity	NPD3251	Approved
0.728	Intermediate Similarity	NPD290	Approved
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD6099	Approved
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3764	Approved
0.7255	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3817	Phase 2
0.7246	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1243	Approved
0.7239	Intermediate Similarity	NPD1611	Approved
0.7219	Intermediate Similarity	NPD6599	Discontinued
0.7219	Intermediate Similarity	NPD4380	Phase 2
0.7215	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4062	Phase 3
0.7209	Intermediate Similarity	NPD1241	Discontinued
0.72	Intermediate Similarity	NPD3134	Approved
0.7194	Intermediate Similarity	NPD4625	Phase 3
0.719	Intermediate Similarity	NPD1465	Phase 2
0.719	Intermediate Similarity	NPD2801	Approved
0.7174	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4060	Phase 1
0.7162	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1358	Approved
0.7143	Intermediate Similarity	NPD9267	Approved
0.7143	Intermediate Similarity	NPD9264	Approved
0.7143	Intermediate Similarity	NPD9263	Approved
0.7133	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7097	Phase 1
0.7132	Intermediate Similarity	NPD4359	Approved
0.7132	Intermediate Similarity	NPD4749	Approved
0.7124	Intermediate Similarity	NPD1934	Approved
0.7113	Intermediate Similarity	NPD1184	Approved
0.7105	Intermediate Similarity	NPD6585	Discontinued
0.7103	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6005	Phase 3
0.7103	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2344	Approved
0.7103	Intermediate Similarity	NPD6004	Phase 3
0.7103	Intermediate Similarity	NPD6002	Phase 3
0.7099	Intermediate Similarity	NPD6671	Approved
0.7095	Intermediate Similarity	NPD7440	Discontinued
0.7095	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4626	Approved
0.7087	Intermediate Similarity	NPD9266	Approved
0.7087	Intermediate Similarity	NPD74	Approved
0.7086	Intermediate Similarity	NPD1653	Approved
0.7081	Intermediate Similarity	NPD5844	Phase 1
0.7078	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD5890	Approved
0.7059	Intermediate Similarity	NPD5889	Approved
0.705	Intermediate Similarity	NPD2861	Phase 2
0.7042	Intermediate Similarity	NPD1613	Approved
0.7042	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5909	Discontinued
0.7034	Intermediate Similarity	NPD4477	Approved
0.7034	Intermediate Similarity	NPD4476	Approved
0.7034	Intermediate Similarity	NPD6032	Approved
0.7029	Intermediate Similarity	NPD6362	Approved
0.7027	Intermediate Similarity	NPD2354	Approved
0.7021	Intermediate Similarity	NPD1048	Approved
0.702	Intermediate Similarity	NPD920	Approved
0.7007	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4618	Approved
0.6993	Remote Similarity	NPD4622	Approved
0.6993	Remote Similarity	NPD6502	Phase 2
0.6986	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6666	Approved
0.698	Remote Similarity	NPD6667	Approved
0.6968	Remote Similarity	NPD8455	Phase 2
0.6957	Remote Similarity	NPD1283	Approved
0.6954	Remote Similarity	NPD6273	Approved
0.695	Remote Similarity	NPD5163	Phase 2
0.6948	Remote Similarity	NPD2366	Approved
0.6944	Remote Similarity	NPD6653	Approved
0.6939	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7458	Discontinued
0.6918	Remote Similarity	NPD1537	Approved
0.6918	Remote Similarity	NPD1519	Approved
0.6918	Remote Similarity	NPD1538	Phase 1
0.6913	Remote Similarity	NPD2309	Approved
0.6909	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5689	Approved
0.6897	Remote Similarity	NPD5688	Approved
0.6897	Remote Similarity	NPD1536	Approved
0.6894	Remote Similarity	NPD9281	Approved
0.6892	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5691	Approved
0.6879	Remote Similarity	NPD3882	Suspended
0.6875	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7054	Approved
0.6871	Remote Similarity	NPD2353	Approved
0.6871	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5536	Phase 2
0.6857	Remote Similarity	NPD5647	Approved
0.6853	Remote Similarity	NPD8032	Phase 2
0.6842	Remote Similarity	NPD5049	Phase 3
0.6835	Remote Similarity	NPD6971	Discontinued
0.6835	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7472	Approved
0.6825	Remote Similarity	NPD9261	Approved
0.6824	Remote Similarity	NPD2424	Discontinued
0.6822	Remote Similarity	NPD2684	Approved
0.6821	Remote Similarity	NPD7837	Clinical (unspecified phase)

Structure

CID229113 OpenBabel06191716022D 25 28 0 0 0 0 0 0 0 0999 V2000 7.5255 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5255 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 -2.4138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6893 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 -2.4138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6893 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8531 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8531 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0170 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0170 0.9655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 -1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3446 -1.9310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0170 -1.9310 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 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	54676038
ChEMBL	CHEMBL1466
ZINC

Physicochemical Properties

Molecular Weight:	336.06
ALogP:	-0.3078
MLogP:	2.89
XLogP:	4.227
# Rotatable Bonds:	4
Polar Surface Area:	93.06
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	25

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