NPASS Natural Product

Natural Product: NPC163524

Natural Product ID:	NPC163524
Common Name:	Axillarin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxychromen-4-one
Synonyms:	Axillarin
Molecular Formula:	C17H14O8
Standard InCHIKey:	KIGVXRGRNLQNNI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O8/c1-23-16-10(20)6-11-12(13(16)21)14(22)17(24-2)15(25-11)7-3-4-8(18)9(19)5-7/h3-6,18-21H,1-2H3
Canonical SMILES:	COc1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(c(c1)O)O)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO28772	Polygonum mite	Species	Polygonaceae	Eukaryota	UNPD*
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	UNPD*
NPO21330	Ilex integra	Species	Aquifoliaceae	Eukaryota	UNPD*
NPO19665	Salvia aerea	Species	Lamiaceae	Eukaryota	UNPD*
NPO26677	Garcinia pseudoguttifera	Species	Clusiaceae	Eukaryota	UNPD*
NPO20180	Rabdosia loxothyrsa	Species	Lamiaceae	Eukaryota	UNPD*
NPO18555	Vernonia chinensis	Species	Asteraceae	Eukaryota	UNPD*
NPO13840	Streptomyces incarnatus	Species	Streptomycetaceae	Bacteria	UNPD*
NPO19126	Lycopodium sieboldii	Species	Lycopodiaceae	Eukaryota	UNPD*
NPO21594	Sporobolus cynosuroides	Species	Poaceae	Eukaryota	UNPD*
NPO19748	Aspergillus phoenicis	Species	Aspergillaceae	Eukaryota	UNPD*
NPO13328	Bridelia balansae	Species	Phyllanthaceae	Eukaryota	UNPD*
NPO11665	Kloeckera brevis	NA	NA	NA	UNPD*
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	UNPD*
NPO19045	Solenopsis geminata	Species	Formicidae	Eukaryota	UNPD*
NPO26975	Aloe vulgaris	Species	Asphodelaceae	Eukaryota	UNPD*
NPO16644	Ormosia jamaicensis	Species	Limoniidae	Eukaryota	UNPD*
NPO16284	Scutellaria galericulata	Species	Lamiaceae	Eukaryota	UNPD*
NPO20185	Lachnanthes tinctoria	Species	Haemodoraceae	Eukaryota	UNPD*
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	UNPD*
NPO17664	Mucor plumbeus	Species	Mucoraceae	Eukaryota	UNPD*
NPO24834	Cystoseira jabukae	Species	Sargassaceae	Eukaryota	UNPD*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	HerDing*
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	UNPD*
NPO24447	Thalictrum cultratum	Species	Ranunculaceae	Eukaryota	UNPD*
NPO22785	Nicotiana debneyi	Species	Solanaceae	Eukaryota	UNPD*
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	TCM_Taiwan*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota	TCM_Taiwan*
NPO26744	Heliotropium eichwaldii	Species	Heliotropiaceae	Eukaryota	UNPD*
NPO21018	Macrozamia riedlei	Species	Zamiaceae	Eukaryota	UNPD*
NPO18369	Stizolophus balsamita	Species	Asteraceae	Eukaryota	UNPD*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota	HerDing*
NPO19875	Ceratocystis ips	Species	Ceratocystidaceae	Eukaryota	UNPD*
NPO10541	Dioscorea spongiosa	Species	Dioscoreaceae	Eukaryota	UNPD*
NPO26312	Cirsium tanakae	Species	Asteraceae	Eukaryota	UNPD*
NPO29083	Matricaria chamomilla	Species	Asteraceae	Eukaryota	TCM_Taiwan*
NPO20442	Croton stellatopilosus	Species	Euphorbiaceae	Eukaryota	UNPD*
NPO24510	Turricula parryi	Species	Namaceae	Eukaryota	UNPD*
NPO13918	Sinularia rigida	Species	Alcyoniidae	Eukaryota	UNPD*
NPO29083	Matricaria chamomilla	Species	Asteraceae	Eukaryota	HerDing*
NPO26889	Chaetomium subaffine	Species	Chaetomiaceae	Eukaryota	UNPD*
NPO26483	Chrysosplenium echinus	Species	Saxifragaceae	Eukaryota	UNPD*
NPO24324	Halobacterium salinarum	Species	Halobacteriaceae	Archaea	UNPD*
NPO31478	Artemisia sp	Species	Asteraceae	Eukaryota	HerDing*
NPO28927	Gutierrezia microcephala	Species	Asteraceae	Eukaryota	UNPD*
NPO25402	Kuehneromyces mutabilis	Species	Strophariaceae	Eukaryota	UNPD*
NPO20253	Eucalyptus decorticans	Species	Myrtaceae	Eukaryota	UNPD*
NPO4347	Artemisia chinensis	Species	Asteraceae	Eukaryota	PMID[24689280]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	UNPD*
NPO21702	Decachaeta thieleana	NA	NA	NA	UNPD*
NPO25772	Lippia mexicana	Species	Verbenaceae	Eukaryota	UNPD*
NPO21477	Euryops rupestris	Species	Asteraceae	Eukaryota	UNPD*
NPO25324	Phorbas amaranthus	Species	Hymedesmiidae	Eukaryota	UNPD*
NPO10235	Castanopsis eyrei	Species	Fagaceae	Eukaryota	UNPD*
NPO20602	Trichomanes reniforme	Species	Hymenophyllaceae	Eukaryota	UNPD*
NPO26916	Thermopsis alpina	Species	Fabaceae	Eukaryota	UNPD*
NPO26848	Ligularia lamarum	Species	Asteraceae	Eukaryota	UNPD*
NPO26786	Berkheya zeyheri	Species	Asteraceae	Eukaryota	UNPD*
NPO25093	Ericameria diffusa	Species	Asteraceae	Eukaryota	UNPD*
NPO20071	Dracaena cinnabari	Species	Asparagaceae	Eukaryota	UNPD*
NPO4239	Betula neoalaskana	Species	Betulaceae	Eukaryota	UNPD*
NPO18359	Canella winterana	Species	Canellaceae	Eukaryota	UNPD*
NPO26945	Crangon vulgaris	Species	Crangonidae	Eukaryota	UNPD*
NPO25474	Ocotea pulchella	Species	Lauraceae	Eukaryota	UNPD*
NPO26645	Beilschmiedia volckii	Species	Lauraceae	Eukaryota	UNPD*
NPO13536	Odontoschisma denudatum	Species	Cephaloziaceae	Eukaryota	UNPD*
NPO26115	Asterogyne martiana	Species	Arecaceae	Eukaryota	UNPD*
NPO20052	Flemingia chappar	Species	Fabaceae	Eukaryota	UNPD*
NPO26525	Eriostemon thryptomenoides	Species	Rutaceae	Eukaryota	UNPD*
NPO24653	Calonectria cylindrospora	Species	Nectriaceae	Eukaryota	UNPD*
NPO10023	Francoeuria undulata	Species	Asteraceae	Eukaryota	UNPD*
NPO21204	Achillea holosericea	Species	Asteraceae	Eukaryota	UNPD*
NPO26709	Phyllanthus discoideus	Species	Leiothrichidae	Eukaryota	UNPD*
NPO17203	Impatiens siculifer	Species	Balsaminaceae	Eukaryota	UNPD*
NPO11489	Primula viscosa	Species	Primulaceae	Eukaryota	UNPD*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota	TCMSP*
NPO26819	Xanthium pungens	Species	Asteraceae	Eukaryota	UNPD*
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	UNPD*
NPO12907	Hypericum carinatum	Species	Hypericaceae	Eukaryota	UNPD*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	TCMID*
NPO32995	pulicaria crispa	Species	Asteraceae	Eukaryota	PMID[3404160]
NPO25520	Uncaria laevigata	Species	Rubiaceae	Eukaryota	UNPD*
NPO12656	Holarrhena febrifuga	Species	Apocynaceae	Eukaryota	UNPD*
NPO29083	Matricaria chamomilla	Species	Asteraceae	Eukaryota	TCMID*
NPO8004	Hexaplex trunculus	Species	Muricidae	Eukaryota	UNPD*
NPO17051	Bursaphelenchus xylophilus	Species	Aphelenchoididae	Eukaryota	UNPD*
NPO26457	Alpinia allughas	Species	Staphylinidae	Eukaryota	UNPD*
NPO25910	Trichoderma polysporum	Species	Hypocreaceae	Eukaryota	UNPD*
NPO6879	Laetia corymbulosa	Species	Salicaceae	Eukaryota	UNPD*
NPO26049	Salvia digitaloides	Species	Lamiaceae	Eukaryota	UNPD*
NPO26853	Baccharis magellanica	Species	Asteraceae	Eukaryota	UNPD*
NPO20628	Magnolia kachirachirai	Species	Magnoliaceae	Eukaryota	UNPD*
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	UNPD*
NPO24630	Sophora exigua	Species	Fabaceae	Eukaryota	UNPD*
NPO26210	Eupatorium birmanicum	Species	Asteraceae	Eukaryota	UNPD*
NPO17743	Solanum aculeatum	Species	Solanaceae	Eukaryota	UNPD*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota	TCMID*
NPO26001	Carlina acaulis	Species	Asteraceae	Eukaryota	UNPD*
NPO10241	Afrocarpus falcatus	Species	Podocarpaceae	Eukaryota	UNPD*
NPO26083	Eumorphia sericea	Species	Asteraceae	Eukaryota	UNPD*
NPO18695	Citrus limetta	Species	Rutaceae	Eukaryota	UNPD*
NPO23684	Narcissus obesus	Species	Amaryllidaceae	Eukaryota	UNPD*
NPO19225	Artemisia sp.	Species	Asteraceae	Eukaryota	TCMID*
NPO25643	Streptomyces chattanoogensis	Species	Streptomycetaceae	Bacteria	UNPD*
NPO8912	Daphne giraldii	Species	Thymelaeaceae	Eukaryota	UNPD*
NPO17172	Euphorbia hermentiana	Species	Euphorbiaceae	Eukaryota	UNPD*
NPO24736	Acacia pycnantha	Species	Fabaceae	Eukaryota	UNPD*

Biological Activity

Activity Type	# Activity
IC50	4
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	61.3	%	3404160
NPT1	Others	Radical scavenging activity		IC50	=	12.4	ug/ml	10650074
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2.9	ug/ml	10650074
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	36000	nM	10425142
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	27.99	nM	18585047

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 NPC163524 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	340
0.1-0.2	1333
0.2-0.3	3205
0.3-0.4	7232
0.4-0.5	5298
0.5-0.6	2595
0.6-0.7	3681
0.7-0.8	3945
0.8-0.85	1698
0.85-0.9	947
0.9-0.95	455
0.95-1	160

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC176665
1.0	High Similarity	NPC305663
1.0	High Similarity	NPC287979
0.9933	High Similarity	NPC7846
0.9933	High Similarity	NPC25495
0.9933	High Similarity	NPC204854
0.9933	High Similarity	NPC266960
0.9933	High Similarity	NPC245546
0.9933	High Similarity	NPC191459
0.9933	High Similarity	NPC9609
0.9933	High Similarity	NPC261004
0.9933	High Similarity	NPC152166
0.9933	High Similarity	NPC22472
0.9933	High Similarity	NPC98661
0.9933	High Similarity	NPC143828
0.9933	High Similarity	NPC288669
0.9933	High Similarity	NPC105242
0.9933	High Similarity	NPC115798
0.9933	High Similarity	NPC247017
0.9933	High Similarity	NPC18607
0.9933	High Similarity	NPC18772
0.9933	High Similarity	NPC130894
0.9933	High Similarity	NPC4481
0.9933	High Similarity	NPC43243
0.9933	High Similarity	NPC300943
0.9933	High Similarity	NPC176300
0.9933	High Similarity	NPC253634
0.9933	High Similarity	NPC19687
0.9867	High Similarity	NPC110070
0.9867	High Similarity	NPC472438
0.9867	High Similarity	NPC29841
0.9867	High Similarity	NPC227192
0.9867	High Similarity	NPC7973
0.9867	High Similarity	NPC203891
0.9867	High Similarity	NPC75215
0.9867	High Similarity	NPC224137
0.9867	High Similarity	NPC78302
0.9867	High Similarity	NPC101830
0.9867	High Similarity	NPC189179
0.9867	High Similarity	NPC93376
0.9867	High Similarity	NPC235215
0.9866	High Similarity	NPC44079
0.9866	High Similarity	NPC214138
0.9866	High Similarity	NPC201451
0.9866	High Similarity	NPC26227
0.9801	High Similarity	NPC193842
0.98	High Similarity	NPC100916
0.98	High Similarity	NPC292107
0.98	High Similarity	NPC474520
0.98	High Similarity	NPC49824
0.98	High Similarity	NPC55619
0.98	High Similarity	NPC268161
0.98	High Similarity	NPC200388
0.98	High Similarity	NPC178854
0.9733	High Similarity	NPC201136
0.9733	High Similarity	NPC50715
0.9733	High Similarity	NPC167815
0.9733	High Similarity	NPC146165
0.9733	High Similarity	NPC2476
0.9733	High Similarity	NPC280339
0.9733	High Similarity	NPC189960
0.9733	High Similarity	NPC163780
0.9733	High Similarity	NPC128863
0.9733	High Similarity	NPC227325
0.9733	High Similarity	NPC32557
0.9733	High Similarity	NPC92659
0.9733	High Similarity	NPC183597
0.9733	High Similarity	NPC4455
0.9733	High Similarity	NPC196439
0.9733	High Similarity	NPC138360
0.9732	High Similarity	NPC156222
0.9732	High Similarity	NPC27208
0.9732	High Similarity	NPC100887
0.9732	High Similarity	NPC198826
0.9732	High Similarity	NPC256283
0.9732	High Similarity	NPC57030
0.9732	High Similarity	NPC82325
0.9732	High Similarity	NPC120163
0.9732	High Similarity	NPC212678
0.9732	High Similarity	NPC275836
0.9732	High Similarity	NPC275722
0.9732	High Similarity	NPC142540
0.9732	High Similarity	NPC25270
0.9732	High Similarity	NPC279989
0.9732	High Similarity	NPC162313
0.9732	High Similarity	NPC239128
0.9732	High Similarity	NPC241498
0.9732	High Similarity	NPC222830
0.9732	High Similarity	NPC71334
0.9732	High Similarity	NPC301123
0.9732	High Similarity	NPC83508
0.9732	High Similarity	NPC131624
0.9732	High Similarity	NPC187498
0.9732	High Similarity	NPC301323
0.9732	High Similarity	NPC188203
0.9732	High Similarity	NPC293183
0.9732	High Similarity	NPC123886
0.9669	High Similarity	NPC265511
0.9667	High Similarity	NPC270620
0.9667	High Similarity	NPC69394
0.9667	High Similarity	NPC162351
0.9667	High Similarity	NPC276409
0.9667	High Similarity	NPC183878
0.9667	High Similarity	NPC236223
0.9667	High Similarity	NPC255350
0.9667	High Similarity	NPC179126
0.9667	High Similarity	NPC145379
0.9667	High Similarity	NPC78326
0.9667	High Similarity	NPC22519
0.9667	High Similarity	NPC176775
0.9667	High Similarity	NPC231018
0.9667	High Similarity	NPC47781
0.9667	High Similarity	NPC160951
0.9667	High Similarity	NPC75279
0.9667	High Similarity	NPC274327
0.9667	High Similarity	NPC86485
0.9667	High Similarity	NPC250822
0.9667	High Similarity	NPC246204
0.9667	High Similarity	NPC58382
0.9664	High Similarity	NPC54394
0.9664	High Similarity	NPC28274
0.9664	High Similarity	NPC125062
0.9664	High Similarity	NPC133953
0.9664	High Similarity	NPC200740
0.9664	High Similarity	NPC252933
0.9664	High Similarity	NPC50403
0.9664	High Similarity	NPC225731
0.9608	High Similarity	NPC246478
0.9603	High Similarity	NPC256612
0.9603	High Similarity	NPC20830
0.9603	High Similarity	NPC208197
0.9603	High Similarity	NPC213622
0.96	High Similarity	NPC55205
0.96	High Similarity	NPC134677
0.9597	High Similarity	NPC188871
0.9597	High Similarity	NPC77858
0.9597	High Similarity	NPC286342
0.9597	High Similarity	NPC184136
0.9597	High Similarity	NPC306821
0.9597	High Similarity	NPC149127
0.9548	High Similarity	NPC470459
0.9542	High Similarity	NPC195832
0.9533	High Similarity	NPC236769
0.9533	High Similarity	NPC226973
0.9533	High Similarity	NPC76376
0.9533	High Similarity	NPC208043
0.9533	High Similarity	NPC260895
0.953	High Similarity	NPC296197
0.953	High Similarity	NPC287101
0.953	High Similarity	NPC137062
0.953	High Similarity	NPC17286
0.953	High Similarity	NPC195351
0.953	High Similarity	NPC87125
0.953	High Similarity	NPC270465
0.953	High Similarity	NPC259713
0.953	High Similarity	NPC223579
0.953	High Similarity	NPC159103
0.953	High Similarity	NPC183950
0.953	High Similarity	NPC52005
0.953	High Similarity	NPC216318
0.949	High Similarity	NPC76482
0.9487	High Similarity	NPC470457
0.9481	High Similarity	NPC263449
0.9477	High Similarity	NPC470402
0.9477	High Similarity	NPC174908
0.9474	High Similarity	NPC2928
0.947	High Similarity	NPC39732
0.947	High Similarity	NPC180234
0.947	High Similarity	NPC60972
0.947	High Similarity	NPC199100
0.947	High Similarity	NPC120537
0.9467	High Similarity	NPC259058
0.9467	High Similarity	NPC201547
0.9467	High Similarity	NPC45873
0.9467	High Similarity	NPC50728
0.9467	High Similarity	NPC166753
0.9467	High Similarity	NPC219330
0.9463	High Similarity	NPC120464
0.943	High Similarity	NPC280493
0.9427	High Similarity	NPC470462
0.9419	High Similarity	NPC308992
0.9416	High Similarity	NPC152904
0.9412	High Similarity	NPC235165
0.9412	High Similarity	NPC472916
0.9412	High Similarity	NPC255106
0.9408	High Similarity	NPC206238
0.9408	High Similarity	NPC167091
0.9408	High Similarity	NPC88645
0.9408	High Similarity	NPC292214
0.9408	High Similarity	NPC271779
0.9404	High Similarity	NPC117579
0.9404	High Similarity	NPC308451
0.94	High Similarity	NPC181250
0.94	High Similarity	NPC48479
0.94	High Similarity	NPC69752
0.94	High Similarity	NPC328119
0.94	High Similarity	NPC177298
0.9396	High Similarity	NPC108406
0.9396	High Similarity	NPC275772
0.9396	High Similarity	NPC55557

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC163524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	906
0.2-0.3	1807
0.3-0.4	2683
0.4-0.5	1773
0.5-0.6	1011
0.6-0.7	453
0.7-0.8	126
0.8-0.85	28
0.85-0.9	11
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9667	High Similarity	NPD2801	Approved
0.9329	High Similarity	NPD1512	Approved
0.9286	High Similarity	NPD3882	Suspended
0.9221	High Similarity	NPD3817	Phase 2
0.9216	High Similarity	NPD1934	Approved
0.9195	High Similarity	NPD1511	Approved
0.908	High Similarity	NPD4338	Clinical (unspecified phase)
0.9	High Similarity	NPD6166	Phase 2
0.9	High Similarity	NPD6168	Clinical (unspecified phase)
0.9	High Similarity	NPD6167	Clinical (unspecified phase)
0.891	High Similarity	NPD2393	Clinical (unspecified phase)
0.8841	High Similarity	NPD6797	Phase 2
0.8788	High Similarity	NPD7251	Discontinued
0.8773	High Similarity	NPD3818	Discontinued
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8735	High Similarity	NPD7808	Phase 3
0.872	High Similarity	NPD7054	Approved
0.8667	High Similarity	NPD7472	Approved
0.8616	High Similarity	NPD5402	Approved
0.8554	High Similarity	NPD7074	Phase 3
0.8509	High Similarity	NPD7075	Discontinued
0.8466	Intermediate Similarity	NPD1247	Approved
0.8452	Intermediate Similarity	NPD6799	Approved
0.8447	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD5494	Approved
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8365	Intermediate Similarity	NPD4380	Phase 2
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6232	Discontinued
0.8301	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8282	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.8247	Intermediate Similarity	NPD1549	Phase 2
0.821	Intermediate Similarity	NPD1465	Phase 2
0.8176	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5401	Approved
0.8146	Intermediate Similarity	NPD1240	Approved
0.8146	Intermediate Similarity	NPD943	Approved
0.8144	Intermediate Similarity	NPD3926	Phase 2
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8121	Intermediate Similarity	NPD919	Approved
0.8117	Intermediate Similarity	NPD2796	Approved
0.8039	Intermediate Similarity	NPD1607	Approved
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7953	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7411	Suspended
0.7862	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD447	Suspended
0.7857	Intermediate Similarity	NPD230	Phase 1
0.7815	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6959	Discontinued
0.7799	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1613	Approved
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7736	Intermediate Similarity	NPD2800	Approved
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6559	Discontinued
0.7683	Intermediate Similarity	NPD1653	Approved
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.7633	Intermediate Similarity	NPD3749	Approved
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3027	Phase 3
0.7582	Intermediate Similarity	NPD9494	Approved
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3226	Approved
0.7516	Intermediate Similarity	NPD1933	Approved
0.7515	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7484	Intermediate Similarity	NPD3748	Approved
0.7471	Intermediate Similarity	NPD7768	Phase 2
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1243	Approved
0.7407	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6233	Phase 2
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4628	Phase 3
0.736	Intermediate Similarity	NPD5953	Discontinued
0.7358	Intermediate Similarity	NPD6651	Approved
0.7338	Intermediate Similarity	NPD1203	Approved
0.7329	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD6100	Approved
0.7318	Intermediate Similarity	NPD7685	Pre-registration
0.7317	Intermediate Similarity	NPD2309	Approved
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7294	Intermediate Similarity	NPD37	Approved
0.7284	Intermediate Similarity	NPD2346	Discontinued
0.7278	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2403	Approved
0.7267	Intermediate Similarity	NPD4965	Approved
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD2799	Discontinued
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7247	Intermediate Similarity	NPD7286	Phase 2
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7215	Intermediate Similarity	NPD6798	Discontinued
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7193	Intermediate Similarity	NPD6844	Discontinued
0.7191	Intermediate Similarity	NPD7228	Approved
0.719	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9717	Approved
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.712	Intermediate Similarity	NPD8150	Discontinued
0.7119	Intermediate Similarity	NPD5242	Approved
0.7108	Intermediate Similarity	NPD2354	Approved
0.7107	Intermediate Similarity	NPD3268	Approved
0.7089	Intermediate Similarity	NPD4908	Phase 1
0.7083	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7078	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1610	Phase 2
0.7073	Intermediate Similarity	NPD1471	Phase 3
0.707	Intermediate Similarity	NPD2798	Approved
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7051	Intermediate Similarity	NPD3225	Approved
0.7049	Intermediate Similarity	NPD8312	Approved
0.7049	Intermediate Similarity	NPD8313	Approved
0.7048	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD7697	Approved
0.7035	Intermediate Similarity	NPD6386	Approved
0.7035	Intermediate Similarity	NPD6385	Approved
0.7032	Intermediate Similarity	NPD1608	Approved
0.7024	Intermediate Similarity	NPD4357	Discontinued
0.7019	Intermediate Similarity	NPD4060	Phase 1
0.7011	Intermediate Similarity	NPD5353	Approved
0.701	Intermediate Similarity	NPD7870	Phase 2
0.701	Intermediate Similarity	NPD7871	Phase 2
0.7006	Intermediate Similarity	NPD2797	Approved
0.7005	Intermediate Similarity	NPD7874	Approved
0.7005	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2163	Approved
0.7	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9268	Approved
0.699	Remote Similarity	NPD7701	Phase 2
0.6988	Remote Similarity	NPD2654	Approved
0.6987	Remote Similarity	NPD2983	Phase 2
0.6987	Remote Similarity	NPD2982	Phase 2
0.6984	Remote Similarity	NPD4363	Phase 3
0.6984	Remote Similarity	NPD6534	Approved
0.6984	Remote Similarity	NPD4360	Phase 2
0.6984	Remote Similarity	NPD6535	Approved
0.6974	Remote Similarity	NPD5536	Phase 2
0.6966	Remote Similarity	NPD5710	Approved
0.6966	Remote Similarity	NPD5711	Approved
0.6941	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7584	Approved
0.6937	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD2981	Phase 2
0.6923	Remote Similarity	NPD1481	Phase 2
0.6918	Remote Similarity	NPD2861	Phase 2
0.6914	Remote Similarity	NPD4288	Approved
0.6913	Remote Similarity	NPD228	Approved
0.6912	Remote Similarity	NPD7907	Approved
0.6902	Remote Similarity	NPD7549	Discontinued
0.6899	Remote Similarity	NPD3267	Approved
0.6899	Remote Similarity	NPD3266	Approved
0.6899	Remote Similarity	NPD1470	Approved

Structure

CID163524 OpenBabel06191715532D 25 27 0 0 0 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 24 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 17 2 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281603
ChEMBL	CHEMBL487810
ZINC

Physicochemical Properties

Molecular Weight:	346.07
ALogP:	-2.7885
MLogP:	2.45
XLogP:	0.829
# Rotatable Bonds:	9
Polar Surface Area:	125.68
# H-Bond Aceptor:	2
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	25

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