NPASS Natural Product

Natural Product: NPC228922

Natural Product ID:	NPC228922
Common Name:	4-Methoxy-3,3',5-Trihydroxybibenzyl
IUPAC Name:	5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]benzene-1,3-diol
Synonyms:
Molecular Formula:	C15H16O4
Standard InCHIKey:	XYWLGCOVGGWHHO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h4-9,16-18H,2-3H2,1H3
Canonical SMILES:	COc1ccc(cc1O)CCc1cc(O)cc(c1)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	Rhizomes			PMID[10714491]

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Organism	1
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	49000	nM	15050621
NPT548	Tissue	Ileum	Cavia porcellus	IC50	=	700	nM	PubChem BioAssay data set
NPT548	Tissue	Ileum	Cavia porcellus	Ratio IC50	=	5.99		15104478

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 NPC228922 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	1167
0.2-0.3	3005
0.3-0.4	9020
0.4-0.5	4026
0.5-0.6	2717
0.6-0.7	4932
0.7-0.8	4347
0.8-0.85	768
0.85-0.9	469
0.9-0.95	139
0.95-1	64

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC197757
0.9914	High Similarity	NPC41562
0.9831	High Similarity	NPC57490
0.9831	High Similarity	NPC251855
0.9831	High Similarity	NPC472093
0.9831	High Similarity	NPC116907
0.9831	High Similarity	NPC117214
0.9831	High Similarity	NPC193544
0.9831	High Similarity	NPC298757
0.9831	High Similarity	NPC475169
0.9831	High Similarity	NPC221077
0.9831	High Similarity	NPC17943
0.9831	High Similarity	NPC233410
0.9831	High Similarity	NPC208950
0.9831	High Similarity	NPC203133
0.9667	High Similarity	NPC293054
0.9667	High Similarity	NPC324112
0.9667	High Similarity	NPC74817
0.9667	High Similarity	NPC82679
0.9667	High Similarity	NPC159968
0.9667	High Similarity	NPC169474
0.9667	High Similarity	NPC236791
0.9667	High Similarity	NPC246620
0.9667	High Similarity	NPC282000
0.9667	High Similarity	NPC127587
0.9667	High Similarity	NPC124452
0.9661	High Similarity	NPC136319
0.9661	High Similarity	NPC233526
0.9661	High Similarity	NPC282496
0.9661	High Similarity	NPC121115
0.9655	High Similarity	NPC61516
0.9655	High Similarity	NPC247364
0.9655	High Similarity	NPC232084
0.9655	High Similarity	NPC10932
0.9587	High Similarity	NPC206615
0.9587	High Similarity	NPC98631
0.9587	High Similarity	NPC470213
0.9587	High Similarity	NPC186843
0.9587	High Similarity	NPC154866
0.9583	High Similarity	NPC78974
0.9583	High Similarity	NPC223136
0.9583	High Similarity	NPC214406
0.9583	High Similarity	NPC103823
0.9583	High Similarity	NPC18924
0.9583	High Similarity	NPC76451
0.9583	High Similarity	NPC28730
0.9583	High Similarity	NPC44748
0.958	High Similarity	NPC5796
0.958	High Similarity	NPC206487
0.9576	High Similarity	NPC473411
0.9576	High Similarity	NPC71579
0.9576	High Similarity	NPC262253
0.9508	High Similarity	NPC476968
0.9508	High Similarity	NPC212015
0.9508	High Similarity	NPC170844
0.9504	High Similarity	NPC252131
0.9504	High Similarity	NPC266555
0.9504	High Similarity	NPC210355
0.95	High Similarity	NPC60885
0.95	High Similarity	NPC82483
0.95	High Similarity	NPC105925
0.95	High Similarity	NPC234400
0.95	High Similarity	NPC299584
0.95	High Similarity	NPC265483
0.9496	High Similarity	NPC84086
0.9487	High Similarity	NPC474565
0.9431	High Similarity	NPC299221
0.9431	High Similarity	NPC234488
0.9431	High Similarity	NPC51840
0.9431	High Similarity	NPC311680
0.9431	High Similarity	NPC126836
0.9426	High Similarity	NPC28765
0.9421	High Similarity	NPC223953
0.9407	High Similarity	NPC166759
0.9402	High Similarity	NPC20674
0.9402	High Similarity	NPC226629
0.9397	High Similarity	NPC293619
0.9355	High Similarity	NPC232275
0.9355	High Similarity	NPC474017
0.935	High Similarity	NPC10225
0.935	High Similarity	NPC58164
0.9344	High Similarity	NPC470699
0.9344	High Similarity	NPC236760
0.9333	High Similarity	NPC95168
0.9328	High Similarity	NPC49341
0.9316	High Similarity	NPC470626
0.928	High Similarity	NPC6451
0.928	High Similarity	NPC253105
0.928	High Similarity	NPC201587
0.9274	High Similarity	NPC472338
0.9268	High Similarity	NPC266691
0.9262	High Similarity	NPC181361
0.9256	High Similarity	NPC228972
0.9256	High Similarity	NPC122792
0.9237	High Similarity	NPC475961
0.9237	High Similarity	NPC254625
0.9231	High Similarity	NPC259638
0.9206	High Similarity	NPC32778
0.9206	High Similarity	NPC158331
0.9206	High Similarity	NPC475840
0.92	High Similarity	NPC12275
0.92	High Similarity	NPC45715
0.92	High Similarity	NPC474356
0.92	High Similarity	NPC472597
0.92	High Similarity	NPC470096
0.92	High Similarity	NPC470095
0.9174	High Similarity	NPC471693
0.9174	High Similarity	NPC165375
0.9174	High Similarity	NPC220598
0.9167	High Similarity	NPC473853
0.9167	High Similarity	NPC262156
0.9167	High Similarity	NPC343720
0.9167	High Similarity	NPC113865
0.9167	High Similarity	NPC75713
0.9167	High Similarity	NPC312675
0.9167	High Similarity	NPC184651
0.9167	High Similarity	NPC324571
0.9167	High Similarity	NPC54872
0.9167	High Similarity	NPC145780
0.9167	High Similarity	NPC470212
0.916	High Similarity	NPC227217
0.916	High Similarity	NPC56214
0.916	High Similarity	NPC117780
0.916	High Similarity	NPC95614
0.916	High Similarity	NPC242885
0.916	High Similarity	NPC165133
0.916	High Similarity	NPC229401
0.916	High Similarity	NPC232316
0.9145	High Similarity	NPC141090
0.9145	High Similarity	NPC193067
0.9134	High Similarity	NPC287745
0.9134	High Similarity	NPC317380
0.9127	High Similarity	NPC14224
0.9127	High Similarity	NPC175067
0.9127	High Similarity	NPC86655
0.9127	High Similarity	NPC204215
0.9127	High Similarity	NPC35932
0.9127	High Similarity	NPC161958
0.9127	High Similarity	NPC160991
0.9127	High Similarity	NPC202762
0.9127	High Similarity	NPC16208
0.9127	High Similarity	NPC470752
0.9127	High Similarity	NPC127624
0.9127	High Similarity	NPC7903
0.9127	High Similarity	NPC184447
0.912	High Similarity	NPC224157
0.912	High Similarity	NPC63574
0.912	High Similarity	NPC192687
0.9098	High Similarity	NPC183446
0.9083	High Similarity	NPC207613
0.9076	High Similarity	NPC281298
0.9076	High Similarity	NPC310338
0.9076	High Similarity	NPC15805
0.9068	High Similarity	NPC474933
0.9062	High Similarity	NPC200557
0.9062	High Similarity	NPC470356
0.9062	High Similarity	NPC94750
0.9062	High Similarity	NPC126409
0.9062	High Similarity	NPC474206
0.9062	High Similarity	NPC294884
0.9062	High Similarity	NPC112246
0.9062	High Similarity	NPC108198
0.9062	High Similarity	NPC99572
0.9062	High Similarity	NPC158142
0.9062	High Similarity	NPC121812
0.9062	High Similarity	NPC69029
0.9062	High Similarity	NPC256262
0.9062	High Similarity	NPC313081
0.9062	High Similarity	NPC112939
0.9062	High Similarity	NPC10314
0.9055	High Similarity	NPC471391
0.9055	High Similarity	NPC471390
0.9055	High Similarity	NPC168059
0.9055	High Similarity	NPC229442
0.9048	High Similarity	NPC15543
0.9048	High Similarity	NPC309787
0.904	High Similarity	NPC218856
0.904	High Similarity	NPC469963
0.904	High Similarity	NPC45824
0.904	High Similarity	NPC470633
0.904	High Similarity	NPC469951
0.904	High Similarity	NPC202582
0.904	High Similarity	NPC226788
0.904	High Similarity	NPC190144
0.904	High Similarity	NPC190629
0.904	High Similarity	NPC470258
0.904	High Similarity	NPC285339
0.904	High Similarity	NPC3439
0.904	High Similarity	NPC210623
0.904	High Similarity	NPC222004
0.904	High Similarity	NPC273295
0.904	High Similarity	NPC228769
0.9032	High Similarity	NPC474119
0.9032	High Similarity	NPC242032
0.9032	High Similarity	NPC5428
0.9032	High Similarity	NPC165045
0.9032	High Similarity	NPC118533
0.9024	High Similarity	NPC148627
0.9016	High Similarity	NPC280704
0.9008	High Similarity	NPC476343

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC228922 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	916
0.2-0.3	1545
0.3-0.4	2684
0.4-0.5	1876
0.5-0.6	1000
0.6-0.7	695
0.7-0.8	180
0.8-0.85	9
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9508	High Similarity	NPD3027	Phase 3
0.896	High Similarity	NPD1529	Clinical (unspecified phase)
0.888	High Similarity	NPD1530	Clinical (unspecified phase)
0.8879	High Similarity	NPD228	Approved
0.8828	High Similarity	NPD1613	Approved
0.8828	High Similarity	NPD1612	Clinical (unspecified phase)
0.8571	High Similarity	NPD5283	Phase 1
0.856	High Similarity	NPD2982	Phase 2
0.856	High Similarity	NPD2983	Phase 2
0.848	Intermediate Similarity	NPD2981	Phase 2
0.8438	Intermediate Similarity	NPD3018	Phase 2
0.8413	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3021	Approved
0.8235	Intermediate Similarity	NPD3022	Approved
0.811	Intermediate Similarity	NPD1610	Phase 2
0.8092	Intermediate Similarity	NPD4908	Phase 1
0.808	Intermediate Similarity	NPD1548	Phase 1
0.8017	Intermediate Similarity	NPD1242	Phase 1
0.7985	Intermediate Similarity	NPD1558	Phase 1
0.797	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1934	Approved
0.7857	Intermediate Similarity	NPD5536	Phase 2
0.7852	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3620	Phase 2
0.7823	Intermediate Similarity	NPD2801	Approved
0.7797	Intermediate Similarity	NPD940	Approved
0.7797	Intermediate Similarity	NPD846	Approved
0.777	Intermediate Similarity	NPD3540	Phase 1
0.7761	Intermediate Similarity	NPD4625	Phase 3
0.7734	Intermediate Similarity	NPD1357	Approved
0.7718	Intermediate Similarity	NPD3882	Suspended
0.771	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD4749	Approved
0.7705	Intermediate Similarity	NPD2684	Approved
0.7703	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3539	Phase 1
0.7692	Intermediate Similarity	NPD4357	Discontinued
0.7692	Intermediate Similarity	NPD1511	Approved
0.7676	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3060	Approved
0.7647	Intermediate Similarity	NPD2674	Phase 3
0.7622	Intermediate Similarity	NPD7124	Phase 2
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.7603	Intermediate Similarity	NPD1653	Approved
0.76	Intermediate Similarity	NPD7843	Approved
0.7591	Intermediate Similarity	NPD4060	Phase 1
0.7586	Intermediate Similarity	NPD9296	Approved
0.7586	Intermediate Similarity	NPD1512	Approved
0.7559	Intermediate Similarity	NPD7157	Approved
0.7557	Intermediate Similarity	NPD3705	Approved
0.7557	Intermediate Similarity	NPD422	Phase 1
0.7551	Intermediate Similarity	NPD4005	Discontinued
0.7537	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD2860	Approved
0.7521	Intermediate Similarity	NPD2859	Approved
0.7517	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD4675	Approved
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2861	Phase 2
0.7481	Intermediate Similarity	NPD9494	Approved
0.7479	Intermediate Similarity	NPD3020	Approved
0.7464	Intermediate Similarity	NPD1240	Approved
0.7464	Intermediate Similarity	NPD943	Approved
0.7448	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD5111	Phase 2
0.7445	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD5109	Approved
0.7445	Intermediate Similarity	NPD3144	Approved
0.7445	Intermediate Similarity	NPD3145	Approved
0.7445	Intermediate Similarity	NPD5110	Phase 2
0.7436	Intermediate Similarity	NPD2933	Approved
0.7436	Intermediate Similarity	NPD2934	Approved
0.7431	Intermediate Similarity	NPD2219	Phase 1
0.7429	Intermediate Similarity	NPD6111	Discontinued
0.7422	Intermediate Similarity	NPD6671	Approved
0.7415	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD230	Phase 1
0.7407	Intermediate Similarity	NPD6584	Phase 3
0.7398	Intermediate Similarity	NPD968	Approved
0.7394	Intermediate Similarity	NPD7266	Discontinued
0.7376	Intermediate Similarity	NPD1510	Phase 2
0.7372	Intermediate Similarity	NPD7095	Approved
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4965	Approved
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.736	Intermediate Similarity	NPD5451	Approved
0.7357	Intermediate Similarity	NPD1607	Approved
0.7355	Intermediate Similarity	NPD6232	Discontinued
0.7339	Intermediate Similarity	NPD290	Approved
0.732	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4536	Approved
0.7305	Intermediate Similarity	NPD4538	Approved
0.7303	Intermediate Similarity	NPD3817	Phase 2
0.7299	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7074	Phase 3
0.7293	Intermediate Similarity	NPD1091	Approved
0.7292	Intermediate Similarity	NPD4236	Phase 3
0.7292	Intermediate Similarity	NPD4237	Approved
0.7292	Intermediate Similarity	NPD5177	Phase 3
0.729	Intermediate Similarity	NPD7199	Phase 2
0.7278	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD3818	Discontinued
0.7273	Intermediate Similarity	NPD6516	Phase 2
0.7273	Intermediate Similarity	NPD5846	Approved
0.7259	Intermediate Similarity	NPD2922	Phase 1
0.7237	Intermediate Similarity	NPD2977	Approved
0.7237	Intermediate Similarity	NPD2978	Approved
0.7237	Intermediate Similarity	NPD1465	Phase 2
0.7233	Intermediate Similarity	NPD7054	Approved
0.7218	Intermediate Similarity	NPD3847	Discontinued
0.7215	Intermediate Similarity	NPD7473	Discontinued
0.7214	Intermediate Similarity	NPD2238	Phase 2
0.7213	Intermediate Similarity	NPD291	Approved
0.7208	Intermediate Similarity	NPD4055	Discovery
0.7203	Intermediate Similarity	NPD2935	Discontinued
0.72	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1651	Approved
0.7194	Intermediate Similarity	NPD5718	Phase 2
0.719	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5535	Approved
0.7188	Intermediate Similarity	NPD7472	Approved
0.7185	Intermediate Similarity	NPD6582	Phase 2
0.7185	Intermediate Similarity	NPD1669	Approved
0.7185	Intermediate Similarity	NPD6583	Phase 3
0.7183	Intermediate Similarity	NPD6896	Approved
0.7183	Intermediate Similarity	NPD6895	Approved
0.7172	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4162	Approved
0.7165	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4123	Phase 3
0.7162	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7447	Phase 1
0.7153	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1375	Discontinued
0.7153	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2667	Approved
0.7143	Intermediate Similarity	NPD2668	Approved
0.7143	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5588	Approved
0.7133	Intermediate Similarity	NPD5960	Phase 3
0.7132	Intermediate Similarity	NPD8651	Approved
0.7132	Intermediate Similarity	NPD1283	Approved
0.7123	Intermediate Similarity	NPD6331	Phase 2
0.7123	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4110	Phase 3
0.7114	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2232	Approved
0.7111	Intermediate Similarity	NPD1608	Approved
0.7111	Intermediate Similarity	NPD2233	Approved
0.7111	Intermediate Similarity	NPD2230	Approved
0.7103	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1549	Phase 2
0.7095	Intermediate Similarity	NPD7212	Phase 2
0.7095	Intermediate Similarity	NPD7213	Phase 3
0.7086	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD844	Approved
0.7083	Intermediate Similarity	NPD6100	Approved
0.7083	Intermediate Similarity	NPD6099	Approved
0.7075	Intermediate Similarity	NPD6190	Approved
0.7075	Intermediate Similarity	NPD5241	Discontinued
0.7073	Intermediate Similarity	NPD8053	Approved
0.7073	Intermediate Similarity	NPD8054	Approved
0.7071	Intermediate Similarity	NPD6798	Discontinued
0.7069	Intermediate Similarity	NPD9094	Approved
0.7063	Intermediate Similarity	NPD1358	Approved
0.7055	Intermediate Similarity	NPD1652	Phase 2
0.7055	Intermediate Similarity	NPD6674	Discontinued
0.7054	Intermediate Similarity	NPD821	Approved
0.7054	Intermediate Similarity	NPD9377	Approved
0.7054	Intermediate Similarity	NPD9379	Approved
0.7042	Intermediate Similarity	NPD6355	Discontinued
0.7042	Intermediate Similarity	NPD3657	Discovery
0.7042	Intermediate Similarity	NPD5735	Approved
0.7037	Intermediate Similarity	NPD6797	Phase 2
0.7029	Intermediate Similarity	NPD4624	Approved
0.7023	Intermediate Similarity	NPD709	Approved
0.7021	Intermediate Similarity	NPD6233	Phase 2
0.7019	Intermediate Similarity	NPD5844	Phase 1
0.7015	Intermediate Similarity	NPD9381	Approved
0.7015	Intermediate Similarity	NPD9384	Approved
0.7014	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4628	Phase 3
0.7007	Intermediate Similarity	NPD3892	Phase 2
0.7007	Intermediate Similarity	NPD3750	Approved
0.6994	Remote Similarity	NPD7251	Discontinued
0.6993	Remote Similarity	NPD4097	Suspended

Structure

External Identifiers

PubChem CID	11459623
ChEMBL	CHEMBL110154
ZINC

Physicochemical Properties

Molecular Weight:	260.10
ALogP:	-1.3079
MLogP:	2.67
XLogP:	2.565
# Rotatable Bonds:	8
Polar Surface Area:	69.92
# H-Bond Aceptor:	0
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	19

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