NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	548.62
Volume:	267.426
LogP:	5.677
LogD:	3.107
LogS:	-6.319
# Rotatable Bonds:	1
TPSA:	36.02
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	3.127
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.928
MDCK Permeability:	1.393836282659322e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.938
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.387

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	101.5119400024414%
Volume Distribution (VD):	4.73
Pgp-substrate:	3.370800495147705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.638
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.562
CYP2D6-inhibitor:	0.421
CYP2D6-substrate:	0.658
CYP3A4-inhibitor:	0.202
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	0.981
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.223
Drug-inuced Liver Injury (DILI):	0.757
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.775
Carcinogencity:	0.189
Eye Corrosion:	0.631
Eye Irritation:	0.973
Respiratory Toxicity:	0.959

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC247980

Natural Product ID:	NPC247980
*Common Name:**	Pentabromopseudilin
IUPAC Name:	2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol
Synonyms:	Pentabromopseudilin
Standard InCHIKey:	LXMNWKJHYOZUQL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H4Br5NO/c11-3-1-4(9(17)5(12)2-3)8-6(13)7(14)10(15)16-8/h1-2,16-17H
SMILES:	Brc1cc(Br)c(c(c1)c1[nH]c(c(c1Br)Br)Br)O
Synthetic Gene Cluster:	BGC0000890;BGC0000891;
ChEMBL Identifier:	CHEMBL1235156
PubChem CID:	324093
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002334] Phenylpyrroles

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30945	Pseudoalteromonas	Genus	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20973551]
NPO31196	Chromobacterium	Genus	Chromobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20973551]
NPO31297	Pseudoalteromonas bromoutilis	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20973551]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20973551]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Organism	1
Others	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5423	Individual Protein	Myosin-Va	Gallus gallus	IC50	=	1200.0	nM	PMID[473647]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	67.0	%	PMID[473648]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LED	=	1.0	uM	PMID[473648]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	100.0	nM	PMID[473646]
NPT2	Others	Unspecified		IC50	=	24400.0	nM	PMID[473647]
NPT2	Others	Unspecified		Activity	=	103.9	%	PMID[473648]
NPT25122	SINGLE PROTEIN	Myosin light chain kinase 2, skeletal/cardiac muscle	Oryctolagus cuniculus	IC50	=	5100.0	nM	PMID[473648]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC247980 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	747
0.1-0.2	9281
0.2-0.3	9088
0.3-0.4	15504
0.4-0.5	5544
0.5-0.6	2152
0.6-0.7	369
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7714	Intermediate Similarity	NPC474409
0.7634	Intermediate Similarity	NPC222018
0.7617	Intermediate Similarity	NPC80596
0.7525	Intermediate Similarity	NPC223189
0.7418	Intermediate Similarity	NPC212535
0.7377	Intermediate Similarity	NPC190007
0.736	Intermediate Similarity	NPC246518
0.7348	Intermediate Similarity	NPC72980
0.7337	Intermediate Similarity	NPC94943
0.7293	Intermediate Similarity	NPC96890
0.7291	Intermediate Similarity	NPC470502
0.7236	Intermediate Similarity	NPC128084
0.722	Intermediate Similarity	NPC470503
0.7214	Intermediate Similarity	NPC142901
0.7198	Intermediate Similarity	NPC184964
0.7158	Intermediate Similarity	NPC88363
0.7143	Intermediate Similarity	NPC60553
0.7095	Intermediate Similarity	NPC109447
0.7087	Intermediate Similarity	NPC470501
0.7074	Intermediate Similarity	NPC46580
0.7043	Intermediate Similarity	NPC220765
0.7037	Intermediate Similarity	NPC128751
0.7037	Intermediate Similarity	NPC246700
0.7005	Intermediate Similarity	NPC204717
0.7	Intermediate Similarity	NPC106833
0.7	Intermediate Similarity	NPC469497
0.6995	Remote Similarity	NPC242209
0.6989	Remote Similarity	NPC141353
0.6973	Remote Similarity	NPC42979
0.6968	Remote Similarity	NPC314002
0.6966	Remote Similarity	NPC131718
0.6959	Remote Similarity	NPC153042
0.6959	Remote Similarity	NPC70956
0.6959	Remote Similarity	NPC243834
0.6957	Remote Similarity	NPC224764
0.6931	Remote Similarity	NPC171171
0.6893	Remote Similarity	NPC477609
0.6889	Remote Similarity	NPC102423
0.6878	Remote Similarity	NPC74969
0.6863	Remote Similarity	NPC477610
0.6856	Remote Similarity	NPC326634
0.6848	Remote Similarity	NPC64055
0.6845	Remote Similarity	NPC249662
0.6837	Remote Similarity	NPC174489
0.6837	Remote Similarity	NPC33064
0.6818	Remote Similarity	NPC98685
0.681	Remote Similarity	NPC167908
0.68	Remote Similarity	NPC470505
0.6784	Remote Similarity	NPC475112
0.6784	Remote Similarity	NPC475085
0.6784	Remote Similarity	NPC291535
0.6779	Remote Similarity	NPC255110
0.6774	Remote Similarity	NPC26641
0.6769	Remote Similarity	NPC276517
0.6765	Remote Similarity	NPC471596
0.6753	Remote Similarity	NPC99666
0.6753	Remote Similarity	NPC324149
0.6751	Remote Similarity	NPC306376
0.6737	Remote Similarity	NPC84478
0.673	Remote Similarity	NPC211416
0.6725	Remote Similarity	NPC280853
0.6718	Remote Similarity	NPC106937
0.6712	Remote Similarity	NPC37152
0.6686	Remote Similarity	NPC245657
0.6686	Remote Similarity	NPC316069
0.6686	Remote Similarity	NPC161292
0.6686	Remote Similarity	NPC285016
0.6685	Remote Similarity	NPC26872
0.6683	Remote Similarity	NPC476121
0.6683	Remote Similarity	NPC476124
0.6682	Remote Similarity	NPC477607
0.6682	Remote Similarity	NPC477608
0.6667	Remote Similarity	NPC313791
0.6667	Remote Similarity	NPC200553
0.6651	Remote Similarity	NPC162002
0.665	Remote Similarity	NPC193777
0.6635	Remote Similarity	NPC67658
0.6633	Remote Similarity	NPC18487
0.6632	Remote Similarity	NPC474798
0.662	Remote Similarity	NPC245348
0.6618	Remote Similarity	NPC210828
0.6618	Remote Similarity	NPC86834
0.6617	Remote Similarity	NPC199277
0.6617	Remote Similarity	NPC135887
0.6616	Remote Similarity	NPC156704
0.6616	Remote Similarity	NPC77555
0.6612	Remote Similarity	NPC476118
0.6601	Remote Similarity	NPC476106
0.66	Remote Similarity	NPC249040
0.6599	Remote Similarity	NPC43787
0.6599	Remote Similarity	NPC131017
0.6599	Remote Similarity	NPC205934
0.6597	Remote Similarity	NPC176127
0.6596	Remote Similarity	NPC288943
0.6595	Remote Similarity	NPC44161
0.6589	Remote Similarity	NPC60006
0.6589	Remote Similarity	NPC214142
0.6585	Remote Similarity	NPC209769
0.6584	Remote Similarity	NPC134848
0.6583	Remote Similarity	NPC192315
0.6579	Remote Similarity	NPC478023
0.6578	Remote Similarity	NPC288074
0.6575	Remote Similarity	NPC26850
0.6571	Remote Similarity	NPC471598
0.657	Remote Similarity	NPC471594
0.6566	Remote Similarity	NPC13880
0.6566	Remote Similarity	NPC70259
0.6561	Remote Similarity	NPC283152
0.6559	Remote Similarity	NPC314940
0.6559	Remote Similarity	NPC473764
0.6558	Remote Similarity	NPC124920
0.6558	Remote Similarity	NPC34580
0.6558	Remote Similarity	NPC304307
0.6558	Remote Similarity	NPC261251
0.6558	Remote Similarity	NPC118559
0.6557	Remote Similarity	NPC177404
0.6553	Remote Similarity	NPC11464
0.6553	Remote Similarity	NPC303951
0.655	Remote Similarity	NPC476167
0.6545	Remote Similarity	NPC314394
0.6536	Remote Similarity	NPC153769
0.653	Remote Similarity	NPC245055
0.6528	Remote Similarity	NPC476319
0.6528	Remote Similarity	NPC100547
0.6524	Remote Similarity	NPC252590
0.6522	Remote Similarity	NPC23294
0.6517	Remote Similarity	NPC315491
0.6517	Remote Similarity	NPC161550
0.6517	Remote Similarity	NPC45459
0.6517	Remote Similarity	NPC213308
0.6514	Remote Similarity	NPC279189
0.6508	Remote Similarity	NPC225857
0.65	Remote Similarity	NPC72211
0.65	Remote Similarity	NPC232798
0.6498	Remote Similarity	NPC322135
0.6498	Remote Similarity	NPC223409
0.6498	Remote Similarity	NPC95240
0.649	Remote Similarity	NPC48353
0.6489	Remote Similarity	NPC34508
0.6482	Remote Similarity	NPC251090
0.6477	Remote Similarity	NPC242556
0.6471	Remote Similarity	NPC470500
0.6468	Remote Similarity	NPC14288
0.6468	Remote Similarity	NPC128823
0.6467	Remote Similarity	NPC224632
0.6467	Remote Similarity	NPC124542
0.6467	Remote Similarity	NPC59779
0.6467	Remote Similarity	NPC471177
0.6465	Remote Similarity	NPC307963
0.6464	Remote Similarity	NPC34844
0.6463	Remote Similarity	NPC41174
0.6462	Remote Similarity	NPC238242
0.6456	Remote Similarity	NPC39679
0.6448	Remote Similarity	NPC230869
0.6444	Remote Similarity	NPC470504
0.6441	Remote Similarity	NPC159856
0.644	Remote Similarity	NPC94174
0.6438	Remote Similarity	NPC54803
0.6438	Remote Similarity	NPC321592
0.6436	Remote Similarity	NPC121772
0.6429	Remote Similarity	NPC296527
0.6429	Remote Similarity	NPC242928
0.6425	Remote Similarity	NPC288445
0.6425	Remote Similarity	NPC187951
0.6425	Remote Similarity	NPC37548
0.6425	Remote Similarity	NPC325297
0.6425	Remote Similarity	NPC48938
0.6425	Remote Similarity	NPC2272
0.6422	Remote Similarity	NPC223427
0.6422	Remote Similarity	NPC476098
0.6417	Remote Similarity	NPC278874
0.6409	Remote Similarity	NPC25008
0.6409	Remote Similarity	NPC73952
0.6409	Remote Similarity	NPC284888
0.6409	Remote Similarity	NPC469760
0.6409	Remote Similarity	NPC259644
0.6409	Remote Similarity	NPC469765
0.6409	Remote Similarity	NPC469786
0.6409	Remote Similarity	NPC469763
0.6408	Remote Similarity	NPC183777
0.6404	Remote Similarity	NPC267423
0.6404	Remote Similarity	NPC476044
0.6404	Remote Similarity	NPC129042
0.6402	Remote Similarity	NPC208060
0.6398	Remote Similarity	NPC183407
0.6398	Remote Similarity	NPC3207
0.6398	Remote Similarity	NPC471178
0.6396	Remote Similarity	NPC76748
0.6393	Remote Similarity	NPC475870
0.6392	Remote Similarity	NPC62069
0.639	Remote Similarity	NPC475070
0.6387	Remote Similarity	NPC293472
0.6385	Remote Similarity	NPC292958
0.638	Remote Similarity	NPC97902
0.6378	Remote Similarity	NPC47298
0.6378	Remote Similarity	NPC315214
0.6374	Remote Similarity	NPC80597
0.6374	Remote Similarity	NPC212376
0.6374	Remote Similarity	NPC75540
0.6374	Remote Similarity	NPC207726

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC247980 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	904
0.2-0.3	696
0.3-0.4	2458
0.4-0.5	3610
0.5-0.6	952
0.6-0.7	75
0.7-0.8	2
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
0.7317	Intermediate Similarity	NPD1169	Approved
0.7041	Intermediate Similarity	NPD1592	Phase 3
0.6739	Remote Similarity	NPD1161	Approved
0.6718	Remote Similarity	NPD802	Phase 2
0.6718	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD1325	Approved
0.6649	Remote Similarity	NPD1326	Approved
0.6633	Remote Similarity	NPD1768	Approved
0.6616	Remote Similarity	NPD7948	Phase 1
0.6612	Remote Similarity	NPD5138	Approved
0.6612	Remote Similarity	NPD5140	Approved
0.655	Remote Similarity	NPD8395	Approved
0.655	Remote Similarity	NPD3814	Phase 1
0.655	Remote Similarity	NPD8396	Approved
0.6543	Remote Similarity	NPD5065	Approved
0.6538	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD484	Approved
0.6502	Remote Similarity	NPD6991	Approved
0.6486	Remote Similarity	NPD1168	Approved
0.6485	Remote Similarity	NPD4511	Phase 1
0.6474	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD1038	Approved
0.6455	Remote Similarity	NPD9690	Approved
0.6444	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD2762	Phase 2
0.6439	Remote Similarity	NPD3003	Approved
0.6408	Remote Similarity	NPD1392	Approved
0.64	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6159	Phase 2
0.6378	Remote Similarity	NPD1685	Approved
0.6378	Remote Similarity	NPD1684	Approved
0.6377	Remote Similarity	NPD7672	Approved
0.6377	Remote Similarity	NPD7671	Approved
0.6354	Remote Similarity	NPD2882	Phase 1
0.633	Remote Similarity	NPD1921	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD3525	Discontinued
0.6324	Remote Similarity	NPD112	Approved
0.6324	Remote Similarity	NPD9705	Discontinued
0.6321	Remote Similarity	NPD5287	Discontinued
0.63	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD4463	Approved
0.6298	Remote Similarity	NPD2916	Discontinued
0.6298	Remote Similarity	NPD4462	Approved
0.6294	Remote Similarity	NPD2383	Phase 1
0.6291	Remote Similarity	NPD5164	Discontinued
0.6269	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6158	Phase 2
0.6256	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5596	Phase 2
0.6243	Remote Similarity	NPD2844	Phase 3
0.6216	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3931	Approved
0.6214	Remote Similarity	NPD3928	Approved
0.6212	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3833	Phase 3
0.6209	Remote Similarity	NPD5066	Phase 2
0.6209	Remote Similarity	NPD3835	Phase 3
0.6209	Remote Similarity	NPD5067	Phase 2
0.6207	Remote Similarity	NPD1218	Approved
0.6207	Remote Similarity	NPD1219	Approved
0.6202	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD5902	Approved
0.6197	Remote Similarity	NPD5903	Approved
0.619	Remote Similarity	NPD424	Approved
0.619	Remote Similarity	NPD1411	Approved
0.619	Remote Similarity	NPD425	Approved
0.6179	Remote Similarity	NPD2794	Discontinued
0.6179	Remote Similarity	NPD3330	Phase 1
0.6172	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD2763	Phase 2
0.6164	Remote Similarity	NPD4890	Phase 2
0.615	Remote Similarity	NPD2565	Phase 2
0.615	Remote Similarity	NPD2564	Approved
0.6146	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD926	Approved
0.6138	Remote Similarity	NPD925	Approved
0.6135	Remote Similarity	NPD6975	Discontinued
0.6134	Remote Similarity	NPD1170	Approved
0.6111	Remote Similarity	NPD6985	Discontinued
0.6103	Remote Similarity	NPD6202	Discontinued
0.6102	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.61	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.61	Remote Similarity	NPD408	Approved
0.6099	Remote Similarity	NPD8106	Phase 2
0.6096	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD5612	Discontinued
0.6093	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD863	Approved
0.6085	Remote Similarity	NPD862	Approved
0.6085	Remote Similarity	NPD861	Approved
0.6083	Remote Similarity	NPD7194	Discontinued
0.6082	Remote Similarity	NPD2382	Approved
0.6082	Remote Similarity	NPD2380	Approved
0.6082	Remote Similarity	NPD2381	Approved
0.608	Remote Similarity	NPD706	Phase 1
0.6077	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD2177	Approved
0.6068	Remote Similarity	NPD2175	Phase 3
0.6068	Remote Similarity	NPD2176	Approved
0.6068	Remote Similarity	NPD3825	Phase 3
0.6066	Remote Similarity	NPD5658	Approved
0.6066	Remote Similarity	NPD1183	Approved
0.6065	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD1273	Discontinued
0.6062	Remote Similarity	NPD3224	Phase 2
0.6058	Remote Similarity	NPD5495	Phase 2
0.6051	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8403	Phase 1
0.6042	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD4204	Approved
0.6041	Remote Similarity	NPD4203	Approved
0.604	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD6492	Phase 2
0.6029	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD3336	Discovery
0.6023	Remote Similarity	NPD4880	Discontinued
0.6021	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD2727	Phase 2
0.601	Remote Similarity	NPD9689	Approved
0.6	Remote Similarity	NPD444	Approved
0.6	Remote Similarity	NPD4847	Phase 1
0.6	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6376	Discontinued
0.5991	Remote Similarity	NPD7603	Discontinued
0.599	Remote Similarity	NPD2781	Approved
0.599	Remote Similarity	NPD1043	Phase 3
0.5989	Remote Similarity	NPD198	Clinical (unspecified phase)
0.598	Remote Similarity	NPD9695	Approved
0.5973	Remote Similarity	NPD983	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD5003	Discontinued
0.597	Remote Similarity	NPD4948	Discontinued
0.5969	Remote Similarity	NPD2782	Approved
0.5969	Remote Similarity	NPD2780	Approved
0.5963	Remote Similarity	NPD5632	Approved
0.5957	Remote Similarity	NPD9382	Approved
0.5957	Remote Similarity	NPD9383	Approved
0.5955	Remote Similarity	NPD1262	Discovery
0.5954	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD482	Approved
0.5939	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD3404	Approved
0.5926	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD2616	Phase 3
0.5926	Remote Similarity	NPD2615	Phase 3
0.5926	Remote Similarity	NPD5255	Approved
0.5924	Remote Similarity	NPD4702	Approved
0.5924	Remote Similarity	NPD4703	Approved
0.592	Remote Similarity	NPD5256	Discontinued
0.5918	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD2187	Approved
0.5915	Remote Similarity	NPD2189	Approved
0.5911	Remote Similarity	NPD1213	Phase 3
0.5909	Remote Similarity	NPD6452	Discontinued
0.5907	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD6220	Phase 3
0.5907	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD7558	Phase 2
0.5897	Remote Similarity	NPD7418	Discontinued
0.5894	Remote Similarity	NPD2952	Discontinued
0.5891	Remote Similarity	NPD2749	Discontinued
0.5889	Remote Similarity	NPD786	Approved
0.5889	Remote Similarity	NPD680	Discontinued
0.5885	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5913	Phase 3
0.5882	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7474	Suspended
0.5874	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD4401	Phase 2
0.5874	Remote Similarity	NPD4403	Phase 3
0.5869	Remote Similarity	NPD7222	Phase 2
0.5869	Remote Similarity	NPD7453	Approved
0.5869	Remote Similarity	NPD6290	Phase 2
0.5869	Remote Similarity	NPD7452	Approved
0.5865	Remote Similarity	NPD712	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8386	Phase 2
0.5859	Remote Similarity	NPD3417	Phase 1
0.5857	Remote Similarity	NPD6145	Phase 1
0.5856	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.585	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD3813	Approved
0.5845	Remote Similarity	NPD6594	Discontinued
0.5845	Remote Similarity	NPD5512	Phase 3
0.5838	Remote Similarity	NPD5100	Phase 3
0.5837	Remote Similarity	NPD9687	Approved
0.5837	Remote Similarity	NPD9688	Approved
0.5833	Remote Similarity	NPD5939	Approved
0.5833	Remote Similarity	NPD5936	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data