NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.96
Volume:	167.126
LogP:	2.439
LogD:	1.666
LogS:	-3.183
# Rotatable Bonds:	0
TPSA:	56.25
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.606
Synthetic Accessibility Score:	2.813
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.845
MDCK Permeability:	1.4326664313557558e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.129

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	95.92162322998047%
Volume Distribution (VD):	0.507
Pgp-substrate:	5.848208427429199%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.483
CYP2C19-inhibitor:	0.196
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.437
CYP2C9-substrate:	0.796
CYP2D6-inhibitor:	0.794
CYP2D6-substrate:	0.692
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	5.067
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.861
AMES Toxicity:	0.303
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.099
Skin Sensitization:	0.926
Carcinogencity:	0.381
Eye Corrosion:	0.187
Eye Irritation:	0.971
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC142901

Natural Product ID:	NPC142901
*Common Name:**	6-Bromo-1H-Indole-4,7-Diol
IUPAC Name:	6-bromo-1H-indole-4,7-diol
Synonyms:
Standard InCHIKey:	QLTYFQFIBAIEHN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H6BrNO2/c9-5-3-6(11)4-1-2-10-7(4)8(5)12/h1-3,10-12H
SMILES:	Brc1cc(O)c2c(c1O)[nH]cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505201
PubChem CID:	10513513
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*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
NPO25885	Drupella fragum	Species	Muricidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722496]
NPO25885	Drupella fragum	Species	Muricidae	Eukaryota	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.106	milliequivalent/kg	PMID[518953]

☑ 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 NPC142901 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	1019
0.1-0.2	14191
0.2-0.3	6575
0.3-0.4	14426
0.4-0.5	3413
0.5-0.6	2157
0.6-0.7	805
0.7-0.8	107
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8995	High Similarity	NPC246518
0.8763	High Similarity	NPC222018
0.8488	Intermediate Similarity	NPC128084
0.803	Intermediate Similarity	NPC46580
0.8009	Intermediate Similarity	NPC477610
0.799	Intermediate Similarity	NPC184964
0.799	Intermediate Similarity	NPC96890
0.797	Intermediate Similarity	NPC326634
0.7944	Intermediate Similarity	NPC477609
0.7905	Intermediate Similarity	NPC80596
0.7839	Intermediate Similarity	NPC314002
0.7828	Intermediate Similarity	NPC220765
0.7789	Intermediate Similarity	NPC204717
0.7767	Intermediate Similarity	NPC192315
0.7766	Intermediate Similarity	NPC42979
0.7762	Intermediate Similarity	NPC476121
0.7756	Intermediate Similarity	NPC242209
0.7755	Intermediate Similarity	NPC224764
0.7729	Intermediate Similarity	NPC476167
0.7711	Intermediate Similarity	NPC171171
0.7703	Intermediate Similarity	NPC477608
0.7703	Intermediate Similarity	NPC477607
0.7682	Intermediate Similarity	NPC167908
0.7647	Intermediate Similarity	NPC245348
0.7641	Intermediate Similarity	NPC473764
0.7641	Intermediate Similarity	NPC314940
0.761	Intermediate Similarity	NPC99666
0.7594	Intermediate Similarity	NPC476124
0.7573	Intermediate Similarity	NPC106937
0.7548	Intermediate Similarity	NPC156704
0.7534	Intermediate Similarity	NPC60006
0.7513	Intermediate Similarity	NPC252590
0.75	Intermediate Similarity	NPC292958
0.7475	Intermediate Similarity	NPC474409
0.7464	Intermediate Similarity	NPC77555
0.7441	Intermediate Similarity	NPC315491
0.7441	Intermediate Similarity	NPC213308
0.7441	Intermediate Similarity	NPC45459
0.7416	Intermediate Similarity	NPC251090
0.7399	Intermediate Similarity	NPC470501
0.738	Intermediate Similarity	NPC97902
0.7373	Intermediate Similarity	NPC5145
0.7364	Intermediate Similarity	NPC470799
0.7364	Intermediate Similarity	NPC8022
0.7361	Intermediate Similarity	NPC18348
0.7354	Intermediate Similarity	NPC470502
0.7342	Intermediate Similarity	NPC255110
0.7333	Intermediate Similarity	NPC475746
0.7333	Intermediate Similarity	NPC13880
0.7327	Intermediate Similarity	NPC72980
0.7321	Intermediate Similarity	NPC307963
0.7306	Intermediate Similarity	NPC316981
0.7289	Intermediate Similarity	NPC470503
0.7285	Intermediate Similarity	NPC477110
0.7245	Intermediate Similarity	NPC131718
0.7235	Intermediate Similarity	NPC183777
0.7235	Intermediate Similarity	NPC88008
0.722	Intermediate Similarity	NPC212535
0.7214	Intermediate Similarity	NPC247980
0.7212	Intermediate Similarity	NPC211416
0.7212	Intermediate Similarity	NPC32771
0.7212	Intermediate Similarity	NPC296527
0.7196	Intermediate Similarity	NPC205254
0.7196	Intermediate Similarity	NPC303820
0.7196	Intermediate Similarity	NPC106771
0.7196	Intermediate Similarity	NPC23420
0.7196	Intermediate Similarity	NPC121772
0.719	Intermediate Similarity	NPC304187
0.719	Intermediate Similarity	NPC473342
0.719	Intermediate Similarity	NPC477166
0.719	Intermediate Similarity	NPC477167
0.7189	Intermediate Similarity	NPC477113
0.7177	Intermediate Similarity	NPC76748
0.7172	Intermediate Similarity	NPC102423
0.7163	Intermediate Similarity	NPC475935
0.7163	Intermediate Similarity	NPC94211
0.7163	Intermediate Similarity	NPC52909
0.715	Intermediate Similarity	NPC94943
0.7143	Intermediate Similarity	NPC475070
0.7143	Intermediate Similarity	NPC92111
0.7136	Intermediate Similarity	NPC153042
0.7136	Intermediate Similarity	NPC11464
0.713	Intermediate Similarity	NPC473761
0.7123	Intermediate Similarity	NPC171787
0.7123	Intermediate Similarity	NPC477111
0.7118	Intermediate Similarity	NPC473185
0.7101	Intermediate Similarity	NPC190007
0.7097	Intermediate Similarity	NPC476138
0.7097	Intermediate Similarity	NPC245816
0.7091	Intermediate Similarity	NPC185782
0.709	Intermediate Similarity	NPC216369
0.7075	Intermediate Similarity	NPC88315
0.7073	Intermediate Similarity	NPC88363
0.7072	Intermediate Similarity	NPC219087
0.7072	Intermediate Similarity	NPC207020
0.707	Intermediate Similarity	NPC128823
0.7068	Intermediate Similarity	NPC117980
0.7067	Intermediate Similarity	NPC264285
0.7064	Intermediate Similarity	NPC470505
0.7064	Intermediate Similarity	NPC470500
0.7042	Intermediate Similarity	NPC276517
0.7034	Intermediate Similarity	NPC477861
0.7028	Intermediate Similarity	NPC324149
0.7026	Intermediate Similarity	NPC476451
0.702	Intermediate Similarity	NPC230869
0.7014	Intermediate Similarity	NPC209769
0.6996	Remote Similarity	NPC26679
0.6974	Remote Similarity	NPC310118
0.6972	Remote Similarity	NPC470678
0.6967	Remote Similarity	NPC246700
0.6967	Remote Similarity	NPC128751
0.6964	Remote Similarity	NPC266931
0.6961	Remote Similarity	NPC313791
0.696	Remote Similarity	NPC213530
0.696	Remote Similarity	NPC473179
0.696	Remote Similarity	NPC193267
0.6959	Remote Similarity	NPC19872
0.6957	Remote Similarity	NPC478032
0.6947	Remote Similarity	NPC477114
0.6944	Remote Similarity	NPC306376
0.6941	Remote Similarity	NPC475774
0.6941	Remote Similarity	NPC476098
0.6941	Remote Similarity	NPC200836
0.6934	Remote Similarity	NPC469497
0.6934	Remote Similarity	NPC106833
0.6927	Remote Similarity	NPC232727
0.6904	Remote Similarity	NPC141926
0.6903	Remote Similarity	NPC288349
0.6903	Remote Similarity	NPC170114
0.69	Remote Similarity	NPC279918
0.6898	Remote Similarity	NPC243834
0.6898	Remote Similarity	NPC70956
0.689	Remote Similarity	NPC48938
0.6889	Remote Similarity	NPC476287
0.6886	Remote Similarity	NPC74360
0.6881	Remote Similarity	NPC176538
0.6881	Remote Similarity	NPC249040
0.6878	Remote Similarity	NPC473183
0.6878	Remote Similarity	NPC82053
0.6875	Remote Similarity	NPC294375
0.6875	Remote Similarity	NPC478023
0.687	Remote Similarity	NPC16352
0.6866	Remote Similarity	NPC282231
0.6864	Remote Similarity	NPC245055
0.6858	Remote Similarity	NPC470549
0.6856	Remote Similarity	NPC132642
0.6852	Remote Similarity	NPC179701
0.6849	Remote Similarity	NPC98685
0.6847	Remote Similarity	NPC193777
0.6847	Remote Similarity	NPC283117
0.6842	Remote Similarity	NPC475736
0.6834	Remote Similarity	NPC141353
0.6833	Remote Similarity	NPC285558
0.6828	Remote Similarity	NPC74969
0.6827	Remote Similarity	NPC276540
0.6827	Remote Similarity	NPC233050
0.6825	Remote Similarity	NPC42591
0.6824	Remote Similarity	NPC110151
0.682	Remote Similarity	NPC262898
0.682	Remote Similarity	NPC37152
0.6818	Remote Similarity	NPC135887
0.6818	Remote Similarity	NPC199277
0.6816	Remote Similarity	NPC324203
0.6816	Remote Similarity	NPC322976
0.6816	Remote Similarity	NPC63338
0.6808	Remote Similarity	NPC242928
0.6806	Remote Similarity	NPC131017
0.6804	Remote Similarity	NPC315957
0.6798	Remote Similarity	NPC304926
0.6798	Remote Similarity	NPC476041
0.6796	Remote Similarity	NPC314603
0.6793	Remote Similarity	NPC473184
0.679	Remote Similarity	NPC471891
0.6787	Remote Similarity	NPC53144
0.6786	Remote Similarity	NPC325297
0.6784	Remote Similarity	NPC118228
0.6783	Remote Similarity	NPC276657
0.678	Remote Similarity	NPC63031
0.678	Remote Similarity	NPC200553
0.678	Remote Similarity	NPC469554
0.6777	Remote Similarity	NPC84478
0.6777	Remote Similarity	NPC470504
0.6769	Remote Similarity	NPC173080
0.6765	Remote Similarity	NPC49954
0.6765	Remote Similarity	NPC474561
0.6765	Remote Similarity	NPC54988
0.6765	Remote Similarity	NPC160105
0.6763	Remote Similarity	NPC473312
0.6762	Remote Similarity	NPC275292
0.6762	Remote Similarity	NPC243381
0.6753	Remote Similarity	NPC60621
0.6752	Remote Similarity	NPC6215
0.6745	Remote Similarity	NPC188387
0.6745	Remote Similarity	NPC163421
0.6742	Remote Similarity	NPC211813
0.6742	Remote Similarity	NPC475085
0.6742	Remote Similarity	NPC291535
0.6742	Remote Similarity	NPC475112
0.674	Remote Similarity	NPC162530
0.6738	Remote Similarity	NPC179287

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 NPC142901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	440
0.1-0.2	1010
0.2-0.3	786
0.3-0.4	2695
0.4-0.5	2609
0.5-0.6	1390
0.6-0.7	209
0.7-0.8	11
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
0.7573	Intermediate Similarity	NPD802	Phase 2
0.7488	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD484	Approved
0.7437	Intermediate Similarity	NPD9690	Approved
0.7395	Intermediate Similarity	NPD1392	Approved
0.7333	Intermediate Similarity	NPD9705	Discontinued
0.7333	Intermediate Similarity	NPD112	Approved
0.7321	Intermediate Similarity	NPD1038	Approved
0.7299	Intermediate Similarity	NPD7948	Phase 1
0.7225	Intermediate Similarity	NPD7603	Discontinued
0.7156	Intermediate Similarity	NPD9695	Approved
0.7075	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1768	Approved
0.7054	Intermediate Similarity	NPD5612	Discontinued
0.6991	Remote Similarity	NPD2177	Approved
0.6991	Remote Similarity	NPD2175	Phase 3
0.6991	Remote Similarity	NPD2176	Approved
0.6964	Remote Similarity	NPD2616	Phase 3
0.6964	Remote Similarity	NPD2615	Phase 3
0.6948	Remote Similarity	NPD9689	Approved
0.6903	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4890	Phase 2
0.6878	Remote Similarity	NPD3003	Approved
0.685	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7558	Phase 2
0.6816	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1740	Approved
0.6804	Remote Similarity	NPD1739	Approved
0.6802	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6290	Phase 2
0.6769	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5065	Approved
0.6758	Remote Similarity	NPD9688	Approved
0.6758	Remote Similarity	NPD9687	Approved
0.6745	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5067	Phase 2
0.6726	Remote Similarity	NPD5939	Approved
0.6726	Remote Similarity	NPD5936	Approved
0.6726	Remote Similarity	NPD5066	Phase 2
0.6725	Remote Similarity	NPD5164	Discontinued
0.6696	Remote Similarity	NPD3330	Phase 1
0.6682	Remote Similarity	NPD3825	Phase 3
0.6682	Remote Similarity	NPD4795	Phase 2
0.6667	Remote Similarity	NPD2187	Approved
0.6667	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2189	Approved
0.6652	Remote Similarity	NPD4502	Phase 2
0.6638	Remote Similarity	NPD5902	Approved
0.6638	Remote Similarity	NPD5903	Approved
0.6634	Remote Similarity	NPD9383	Approved
0.6634	Remote Similarity	NPD9382	Approved
0.6618	Remote Similarity	NPD1326	Approved
0.6618	Remote Similarity	NPD1325	Approved
0.6603	Remote Similarity	NPD482	Approved
0.6602	Remote Similarity	NPD424	Approved
0.6602	Remote Similarity	NPD425	Approved
0.6599	Remote Similarity	NPD3986	Discontinued
0.6593	Remote Similarity	NPD2916	Discontinued
0.6591	Remote Similarity	NPD1229	Phase 2
0.658	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4511	Phase 1
0.654	Remote Similarity	NPD6159	Phase 2
0.652	Remote Similarity	NPD5658	Approved
0.6518	Remote Similarity	NPD3928	Approved
0.6518	Remote Similarity	NPD3931	Approved
0.6495	Remote Similarity	NPD2094	Phase 2
0.6495	Remote Similarity	NPD2095	Phase 2
0.6495	Remote Similarity	NPD2092	Phase 2
0.6488	Remote Similarity	NPD4454	Phase 2
0.6481	Remote Similarity	NPD6985	Discontinued
0.6479	Remote Similarity	NPD6595	Phase 3
0.6475	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD2096	Phase 2
0.6465	Remote Similarity	NPD2091	Phase 2
0.6457	Remote Similarity	NPD3814	Phase 1
0.6453	Remote Similarity	NPD537	Phase 2
0.6453	Remote Similarity	NPD7194	Discontinued
0.6453	Remote Similarity	NPD534	Phase 2
0.6438	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD6242	Discontinued
0.6422	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5632	Approved
0.6406	Remote Similarity	NPD706	Phase 1
0.6393	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7628	Phase 3
0.6393	Remote Similarity	NPD1213	Phase 3
0.6393	Remote Similarity	NPD7630	Phase 3
0.6388	Remote Similarity	NPD5901	Discontinued
0.6384	Remote Similarity	NPD8396	Approved
0.6384	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD8395	Approved
0.6376	Remote Similarity	NPD2383	Phase 1
0.6375	Remote Similarity	NPD5559	Phase 2
0.6372	Remote Similarity	NPD6975	Discontinued
0.6364	Remote Similarity	NPD1592	Phase 3
0.6356	Remote Similarity	NPD5051	Phase 1
0.6348	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD863	Approved
0.6346	Remote Similarity	NPD5140	Approved
0.6346	Remote Similarity	NPD5138	Approved
0.6346	Remote Similarity	NPD862	Approved
0.6346	Remote Similarity	NPD861	Approved
0.6344	Remote Similarity	NPD6991	Approved
0.6337	Remote Similarity	NPD6494	Phase 2
0.6337	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5482	Discontinued
0.6335	Remote Similarity	NPD3404	Approved
0.6333	Remote Similarity	NPD4845	Discontinued
0.6332	Remote Similarity	NPD7222	Phase 2
0.6332	Remote Similarity	NPD7453	Approved
0.6332	Remote Similarity	NPD7452	Approved
0.6325	Remote Similarity	NPD2763	Phase 2
0.6325	Remote Similarity	NPD7112	Discontinued
0.6321	Remote Similarity	NPD750	Phase 2
0.6316	Remote Similarity	NPD4035	Approved
0.6316	Remote Similarity	NPD31	Approved
0.6316	Remote Similarity	NPD4039	Approved
0.6316	Remote Similarity	NPD4036	Approved
0.6316	Remote Similarity	NPD4034	Approved
0.6316	Remote Similarity	NPD4038	Approved
0.6316	Remote Similarity	NPD926	Approved
0.6316	Remote Similarity	NPD32	Approved
0.6316	Remote Similarity	NPD4122	Approved
0.6316	Remote Similarity	NPD4033	Approved
0.6316	Remote Similarity	NPD925	Approved
0.6316	Remote Similarity	NPD4037	Approved
0.6311	Remote Similarity	NPD5999	Phase 2
0.6308	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD8431	Approved
0.6301	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD2952	Discontinued
0.6294	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8284	Discontinued
0.6293	Remote Similarity	NPD949	Phase 1
0.6286	Remote Similarity	NPD3006	Discontinued
0.6284	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD408	Approved
0.6271	Remote Similarity	NPD4429	Discontinued
0.6267	Remote Similarity	NPD712	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD7067	Approved
0.6265	Remote Similarity	NPD7068	Approved
0.6261	Remote Similarity	NPD7726	Phase 1
0.6256	Remote Similarity	NPD5256	Discontinued
0.6245	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.624	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD7672	Approved
0.6234	Remote Similarity	NPD7671	Approved
0.6234	Remote Similarity	NPD1856	Discontinued
0.6233	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD2144	Approved
0.6223	Remote Similarity	NPD4131	Phase 3
0.6223	Remote Similarity	NPD7470	Discontinued
0.6223	Remote Similarity	NPD3570	Phase 2
0.6221	Remote Similarity	NPD3178	Discontinued
0.6217	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8512	Phase 3
0.6204	Remote Similarity	NPD4079	Approved
0.6204	Remote Similarity	NPD4076	Approved
0.6202	Remote Similarity	NPD5255	Approved
0.6197	Remote Similarity	NPD3816	Phase 1
0.6197	Remote Similarity	NPD3815	Phase 1
0.6197	Remote Similarity	NPD8093	Discontinued
0.6193	Remote Similarity	NPD5596	Phase 2
0.619	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6189	Remote Similarity	NPD1505	Phase 2
0.6187	Remote Similarity	NPD5050	Approved
0.6186	Remote Similarity	NPD5100	Phase 3
0.6186	Remote Similarity	NPD5287	Discontinued
0.6181	Remote Similarity	NPD786	Approved
0.618	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3013	Phase 3
0.6179	Remote Similarity	NPD2781	Approved
0.6179	Remote Similarity	NPD2951	Discontinued
0.6176	Remote Similarity	NPD3402	Phase 1
0.6176	Remote Similarity	NPD3875	Discontinued
0.6175	Remote Similarity	NPD9510	Approved
0.6173	Remote Similarity	NPD7555	Discontinued
0.617	Remote Similarity	NPD5945	Phase 1
0.617	Remote Similarity	NPD5944	Phase 1
0.6169	Remote Similarity	NPD3343	Phase 3
0.6167	Remote Similarity	NPD4548	Discontinued
0.6167	Remote Similarity	NPD1954	Phase 1
0.6164	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD2782	Approved
0.6161	Remote Similarity	NPD2780	Approved
0.616	Remote Similarity	NPD5409	Clinical (unspecified phase)

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