NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	355.9
Volume:	256.62
LogP:	4.197
LogD:	3.364
LogS:	-4.429
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	2.137
Fsp3:	0.077
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.711
MDCK Permeability:	1.6654072169330902e-05
Pgp-inhibitor:	0.929
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.221
Plasma Protein Binding (PPB):	99.03510284423828%
Volume Distribution (VD):	0.941
Pgp-substrate:	1.5936758518218994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.825
CYP1A2-substrate:	0.185
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.786
CYP2C9-substrate:	0.847
CYP2D6-inhibitor:	0.96
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.348
CYP3A4-substrate:	0.517

ADMET: Excretion

Clearance (CL):	3.637
Half-life (T1/2):	0.717

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.761
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.113
Skin Sensitization:	0.9
Carcinogencity:	0.161
Eye Corrosion:	0.242
Eye Irritation:	0.983
Respiratory Toxicity:	0.08

Download Data

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

Natural Product: NPC471495

Natural Product ID:	NPC471495
*Common Name:**	3,3'-Dibromo-4,4'-Dihydroxydiphenylmethane
IUPAC Name:	2-bromo-4-[(3-bromo-4-hydroxyphenyl)methyl]phenol
Synonyms:
Standard InCHIKey:	SGQHSBDQMLESDM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10Br2O2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7,16-17H,5H2
SMILES:	C1=CC(=C(C=C1CC2=CC(=C(C=C2)O)Br)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253071
PubChem CID:	22725718
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395508]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053715]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	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
MIC	10

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[485841]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[485841]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	12.5	ug.mL-1	PMID[485841]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	25.0	ug.mL-1	PMID[485841]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	25.0	ug.mL-1	PMID[485841]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[485841]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[485841]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[485841]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[485841]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	>	100.0	ug.mL-1	PMID[485841]

☑ 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 NPC471495 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	574
0.1-0.2	3161
0.2-0.3	11368
0.3-0.4	8708
0.4-0.5	9038
0.5-0.6	7706
0.6-0.7	1752
0.7-0.8	356
0.8-0.85	24
0.85-0.9	5
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC473358
0.9515	High Similarity	NPC54543
0.9057	High Similarity	NPC471487
0.8962	High Similarity	NPC473372
0.8899	High Similarity	NPC94217
0.8839	High Similarity	NPC38483
0.8807	High Similarity	NPC471488
0.8636	High Similarity	NPC33244
0.86	High Similarity	NPC45040
0.8534	High Similarity	NPC296202
0.8522	High Similarity	NPC471486
0.8448	Intermediate Similarity	NPC7830
0.8431	Intermediate Similarity	NPC151715
0.8431	Intermediate Similarity	NPC128062
0.839	Intermediate Similarity	NPC213414
0.835	Intermediate Similarity	NPC26244
0.835	Intermediate Similarity	NPC274678
0.8319	Intermediate Similarity	NPC220311
0.8304	Intermediate Similarity	NPC59387
0.8269	Intermediate Similarity	NPC473388
0.8151	Intermediate Similarity	NPC105999
0.8113	Intermediate Similarity	NPC216468
0.8113	Intermediate Similarity	NPC92730
0.8113	Intermediate Similarity	NPC51333
0.8113	Intermediate Similarity	NPC78119
0.8113	Intermediate Similarity	NPC132078
0.8095	Intermediate Similarity	NPC82664
0.8095	Intermediate Similarity	NPC132271
0.8095	Intermediate Similarity	NPC216520
0.8095	Intermediate Similarity	NPC292730
0.807	Intermediate Similarity	NPC115803
0.8049	Intermediate Similarity	NPC474091
0.8049	Intermediate Similarity	NPC474614
0.8049	Intermediate Similarity	NPC478071
0.8039	Intermediate Similarity	NPC242240
0.8039	Intermediate Similarity	NPC258219
0.8039	Intermediate Similarity	NPC123273
0.8039	Intermediate Similarity	NPC318325
0.8037	Intermediate Similarity	NPC213730
0.8033	Intermediate Similarity	NPC78061
0.8033	Intermediate Similarity	NPC159987
0.8033	Intermediate Similarity	NPC122359
0.802	Intermediate Similarity	NPC23167
0.8019	Intermediate Similarity	NPC225464
0.8	Intermediate Similarity	NPC300678
0.8	Intermediate Similarity	NPC175313
0.7984	Intermediate Similarity	NPC473724
0.7984	Intermediate Similarity	NPC11449
0.7984	Intermediate Similarity	NPC475735
0.7981	Intermediate Similarity	NPC271440
0.7966	Intermediate Similarity	NPC180207
0.7963	Intermediate Similarity	NPC7686
0.7963	Intermediate Similarity	NPC40258
0.7963	Intermediate Similarity	NPC91461
0.7961	Intermediate Similarity	NPC300017
0.7941	Intermediate Similarity	NPC25493
0.7941	Intermediate Similarity	NPC113460
0.7921	Intermediate Similarity	NPC197783
0.7905	Intermediate Similarity	NPC76938
0.79	Intermediate Similarity	NPC265146
0.789	Intermediate Similarity	NPC135784
0.789	Intermediate Similarity	NPC168829
0.7886	Intermediate Similarity	NPC13004
0.7885	Intermediate Similarity	NPC304541
0.7881	Intermediate Similarity	NPC117759
0.7864	Intermediate Similarity	NPC280347
0.7864	Intermediate Similarity	NPC177420
0.785	Intermediate Similarity	NPC32674
0.7833	Intermediate Similarity	NPC136543
0.783	Intermediate Similarity	NPC32714
0.7826	Intermediate Similarity	NPC76400
0.7822	Intermediate Similarity	NPC248817
0.7818	Intermediate Similarity	NPC119860
0.7818	Intermediate Similarity	NPC120693
0.7818	Intermediate Similarity	NPC471511
0.7818	Intermediate Similarity	NPC30506
0.7818	Intermediate Similarity	NPC288411
0.7818	Intermediate Similarity	NPC261573
0.7818	Intermediate Similarity	NPC8931
0.781	Intermediate Similarity	NPC138117
0.781	Intermediate Similarity	NPC325292
0.7795	Intermediate Similarity	NPC244890
0.7795	Intermediate Similarity	NPC120114
0.7795	Intermediate Similarity	NPC471328
0.7795	Intermediate Similarity	NPC163560
0.7795	Intermediate Similarity	NPC71888
0.7788	Intermediate Similarity	NPC55561
0.7787	Intermediate Similarity	NPC137117
0.7778	Intermediate Similarity	NPC43613
0.7778	Intermediate Similarity	NPC79844
0.7767	Intermediate Similarity	NPC104216
0.776	Intermediate Similarity	NPC99280
0.7748	Intermediate Similarity	NPC474839
0.7748	Intermediate Similarity	NPC138942
0.7748	Intermediate Similarity	NPC233396
0.7748	Intermediate Similarity	NPC239291
0.7748	Intermediate Similarity	NPC154899
0.7745	Intermediate Similarity	NPC155393
0.7745	Intermediate Similarity	NPC252149
0.7736	Intermediate Similarity	NPC316301
0.7736	Intermediate Similarity	NPC27323
0.7734	Intermediate Similarity	NPC312155
0.7723	Intermediate Similarity	NPC124436
0.7714	Intermediate Similarity	NPC155908
0.7714	Intermediate Similarity	NPC204210
0.7706	Intermediate Similarity	NPC294741
0.7685	Intermediate Similarity	NPC201967
0.7679	Intermediate Similarity	NPC135464
0.7679	Intermediate Similarity	NPC188677
0.7679	Intermediate Similarity	NPC54765
0.7679	Intermediate Similarity	NPC92623
0.7679	Intermediate Similarity	NPC248904
0.7679	Intermediate Similarity	NPC113457
0.7674	Intermediate Similarity	NPC309667
0.767	Intermediate Similarity	NPC307235
0.767	Intermediate Similarity	NPC184169
0.767	Intermediate Similarity	NPC407
0.7664	Intermediate Similarity	NPC313650
0.7664	Intermediate Similarity	NPC8392
0.7658	Intermediate Similarity	NPC327811
0.7658	Intermediate Similarity	NPC254965
0.7636	Intermediate Similarity	NPC12221
0.7636	Intermediate Similarity	NPC143659
0.7636	Intermediate Similarity	NPC100340
0.7623	Intermediate Similarity	NPC229213
0.7619	Intermediate Similarity	NPC192
0.7619	Intermediate Similarity	NPC300478
0.7615	Intermediate Similarity	NPC128723
0.7615	Intermediate Similarity	NPC130193
0.7615	Intermediate Similarity	NPC224663
0.7615	Intermediate Similarity	NPC275104
0.76	Intermediate Similarity	NPC202776
0.7596	Intermediate Similarity	NPC27974
0.7581	Intermediate Similarity	NPC142776
0.7561	Intermediate Similarity	NPC474169
0.7561	Intermediate Similarity	NPC473572
0.7561	Intermediate Similarity	NPC84606
0.7557	Intermediate Similarity	NPC471236
0.7557	Intermediate Similarity	NPC197766
0.7557	Intermediate Similarity	NPC156356
0.7549	Intermediate Similarity	NPC319826
0.7547	Intermediate Similarity	NPC306074
0.7547	Intermediate Similarity	NPC270547
0.7545	Intermediate Similarity	NPC223393
0.7545	Intermediate Similarity	NPC248573
0.7545	Intermediate Similarity	NPC275053
0.7545	Intermediate Similarity	NPC161571
0.7544	Intermediate Similarity	NPC61885
0.7544	Intermediate Similarity	NPC262365
0.7544	Intermediate Similarity	NPC11554
0.7544	Intermediate Similarity	NPC75440
0.7544	Intermediate Similarity	NPC95344
0.7544	Intermediate Similarity	NPC63698
0.754	Intermediate Similarity	NPC150929
0.7524	Intermediate Similarity	NPC98772
0.7524	Intermediate Similarity	NPC70436
0.7523	Intermediate Similarity	NPC77492
0.7523	Intermediate Similarity	NPC107619
0.7523	Intermediate Similarity	NPC156313
0.7523	Intermediate Similarity	NPC260000
0.7523	Intermediate Similarity	NPC109955
0.7522	Intermediate Similarity	NPC70843
0.7522	Intermediate Similarity	NPC29989
0.7522	Intermediate Similarity	NPC271274
0.7522	Intermediate Similarity	NPC69332
0.7522	Intermediate Similarity	NPC95178
0.7521	Intermediate Similarity	NPC474146
0.75	Intermediate Similarity	NPC323810
0.75	Intermediate Similarity	NPC241891
0.75	Intermediate Similarity	NPC160932
0.75	Intermediate Similarity	NPC102216
0.748	Intermediate Similarity	NPC219444
0.748	Intermediate Similarity	NPC116562
0.748	Intermediate Similarity	NPC47790
0.7478	Intermediate Similarity	NPC228343
0.7478	Intermediate Similarity	NPC88141
0.7478	Intermediate Similarity	NPC62258
0.7478	Intermediate Similarity	NPC306045
0.7478	Intermediate Similarity	NPC265211
0.7478	Intermediate Similarity	NPC55617
0.7478	Intermediate Similarity	NPC254833
0.7477	Intermediate Similarity	NPC210497
0.7477	Intermediate Similarity	NPC147284
0.7477	Intermediate Similarity	NPC55903
0.7477	Intermediate Similarity	NPC94139
0.7477	Intermediate Similarity	NPC181709
0.7477	Intermediate Similarity	NPC306884
0.7477	Intermediate Similarity	NPC162314
0.7477	Intermediate Similarity	NPC3358
0.7476	Intermediate Similarity	NPC286904
0.7462	Intermediate Similarity	NPC245386
0.7455	Intermediate Similarity	NPC122005
0.7455	Intermediate Similarity	NPC280869
0.7455	Intermediate Similarity	NPC80027
0.7455	Intermediate Similarity	NPC245561
0.7455	Intermediate Similarity	NPC252821
0.7444	Intermediate Similarity	NPC474128
0.7438	Intermediate Similarity	NPC100395
0.7434	Intermediate Similarity	NPC292452
0.7434	Intermediate Similarity	NPC99557

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 NPC471495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	524
0.1-0.2	1057
0.2-0.3	1795
0.3-0.4	3061
0.4-0.5	1756
0.5-0.6	796
0.6-0.7	142
0.7-0.8	14
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.835	Intermediate Similarity	NPD2859	Approved
0.835	Intermediate Similarity	NPD2860	Approved
0.8252	Intermediate Similarity	NPD2934	Approved
0.8252	Intermediate Similarity	NPD2933	Approved
0.8113	Intermediate Similarity	NPD3020	Approved
0.7736	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD111	Approved
0.7545	Intermediate Similarity	NPD1242	Phase 1
0.75	Intermediate Similarity	NPD9244	Approved
0.7478	Intermediate Similarity	NPD3022	Approved
0.7478	Intermediate Similarity	NPD3021	Approved
0.7477	Intermediate Similarity	NPD846	Approved
0.7477	Intermediate Similarity	NPD940	Approved
0.7344	Intermediate Similarity	NPD1223	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9718	Approved
0.7339	Intermediate Similarity	NPD1809	Phase 2
0.7339	Intermediate Similarity	NPD844	Approved
0.7315	Intermediate Similarity	NPD845	Approved
0.7273	Intermediate Similarity	NPD288	Approved
0.7232	Intermediate Similarity	NPD3028	Approved
0.7232	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1169	Approved
0.7083	Intermediate Similarity	NPD2234	Approved
0.7083	Intermediate Similarity	NPD2228	Approved
0.7083	Intermediate Similarity	NPD2229	Approved
0.7069	Intermediate Similarity	NPD968	Approved
0.7043	Intermediate Similarity	NPD9608	Approved
0.7043	Intermediate Similarity	NPD9610	Approved
0.7009	Intermediate Similarity	NPD2342	Discontinued
0.6891	Remote Similarity	NPD1792	Phase 2
0.6891	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7635	Approved
0.6825	Remote Similarity	NPD2286	Discontinued
0.6825	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2296	Approved
0.68	Remote Similarity	NPD9087	Approved
0.68	Remote Similarity	NPD5303	Approved
0.68	Remote Similarity	NPD5304	Approved
0.68	Remote Similarity	NPD3091	Approved
0.68	Remote Similarity	NPD1548	Phase 1
0.678	Remote Similarity	NPD1445	Approved
0.678	Remote Similarity	NPD1444	Approved
0.6777	Remote Similarity	NPD228	Approved
0.6754	Remote Similarity	NPD9273	Approved
0.675	Remote Similarity	NPD4750	Phase 3
0.675	Remote Similarity	NPD5451	Approved
0.6746	Remote Similarity	NPD4093	Discontinued
0.6721	Remote Similarity	NPD9377	Approved
0.6721	Remote Similarity	NPD9379	Approved
0.6719	Remote Similarity	NPD1610	Phase 2
0.6699	Remote Similarity	NPD9088	Approved
0.6694	Remote Similarity	NPD255	Approved
0.6694	Remote Similarity	NPD256	Approved
0.6693	Remote Similarity	NPD2932	Approved
0.6693	Remote Similarity	NPD4589	Approved
0.6693	Remote Similarity	NPD4059	Approved
0.6693	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD2684	Approved
0.6639	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6583	Phase 3
0.6615	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD4659	Approved
0.6615	Remote Similarity	NPD6582	Phase 2
0.6602	Remote Similarity	NPD9294	Approved
0.6589	Remote Similarity	NPD1535	Discovery
0.6589	Remote Similarity	NPD3092	Approved
0.6585	Remote Similarity	NPD5535	Approved
0.6583	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4288	Approved
0.6562	Remote Similarity	NPD1751	Approved
0.656	Remote Similarity	NPD6671	Approved
0.6538	Remote Similarity	NPD2562	Approved
0.6538	Remote Similarity	NPD2561	Approved
0.6538	Remote Similarity	NPD1481	Phase 2
0.6532	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5283	Phase 1
0.6525	Remote Similarity	NPD9500	Approved
0.6515	Remote Similarity	NPD4103	Phase 2
0.6515	Remote Similarity	NPD1164	Approved
0.6515	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3847	Discontinued
0.6512	Remote Similarity	NPD3421	Phase 3
0.6508	Remote Similarity	NPD9568	Approved
0.648	Remote Similarity	NPD475	Phase 2
0.6466	Remote Similarity	NPD6584	Phase 3
0.6462	Remote Similarity	NPD1201	Approved
0.6457	Remote Similarity	NPD317	Approved
0.6457	Remote Similarity	NPD16	Approved
0.6457	Remote Similarity	NPD856	Approved
0.6457	Remote Similarity	NPD318	Approved
0.6452	Remote Similarity	NPD2496	Approved
0.6452	Remote Similarity	NPD821	Approved
0.6452	Remote Similarity	NPD2497	Approved
0.6452	Remote Similarity	NPD7843	Approved
0.6449	Remote Similarity	NPD9089	Approved
0.6439	Remote Similarity	NPD5310	Approved
0.6439	Remote Similarity	NPD5311	Approved
0.6434	Remote Similarity	NPD2668	Approved
0.6434	Remote Similarity	NPD6516	Phase 2
0.6434	Remote Similarity	NPD2667	Approved
0.6434	Remote Similarity	NPD5846	Approved
0.6434	Remote Similarity	NPD3095	Discontinued
0.6423	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2861	Phase 2
0.6406	Remote Similarity	NPD7330	Discontinued
0.6406	Remote Similarity	NPD1894	Discontinued
0.6391	Remote Similarity	NPD3094	Phase 2
0.6391	Remote Similarity	NPD3055	Approved
0.6391	Remote Similarity	NPD3053	Approved
0.6378	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.637	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.637	Remote Similarity	NPD4908	Phase 1
0.6356	Remote Similarity	NPD1616	Discontinued
0.6355	Remote Similarity	NPD9093	Approved
0.6349	Remote Similarity	NPD1791	Approved
0.6349	Remote Similarity	NPD9614	Approved
0.6349	Remote Similarity	NPD9618	Approved
0.6349	Remote Similarity	NPD497	Approved
0.6349	Remote Similarity	NPD1793	Approved
0.6343	Remote Similarity	NPD7451	Discontinued
0.6336	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD422	Phase 1
0.6336	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1237	Approved
0.6324	Remote Similarity	NPD3027	Phase 3
0.6316	Remote Similarity	NPD1283	Approved
0.6311	Remote Similarity	NPD290	Approved
0.6308	Remote Similarity	NPD9381	Approved
0.6308	Remote Similarity	NPD9384	Approved
0.6299	Remote Similarity	NPD7157	Approved
0.6299	Remote Similarity	NPD709	Approved
0.6296	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5736	Approved
0.6288	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD9545	Approved
0.6277	Remote Similarity	NPD3764	Approved
0.6277	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.627	Remote Similarity	NPD498	Approved
0.627	Remote Similarity	NPD495	Approved
0.627	Remote Similarity	NPD496	Approved
0.6269	Remote Similarity	NPD1470	Approved
0.626	Remote Similarity	NPD9266	Approved
0.626	Remote Similarity	NPD74	Approved
0.625	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4658	Approved
0.625	Remote Similarity	NPD3596	Phase 2
0.625	Remote Similarity	NPD4656	Approved
0.625	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD1669	Approved
0.6232	Remote Similarity	NPD6407	Approved
0.6232	Remote Similarity	NPD6405	Approved
0.6231	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD1651	Approved
0.6231	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD2194	Approved
0.6222	Remote Similarity	NPD2195	Approved
0.6204	Remote Similarity	NPD5156	Approved
0.6204	Remote Similarity	NPD5155	Approved
0.6202	Remote Similarity	NPD9616	Approved
0.6202	Remote Similarity	NPD9615	Approved
0.6202	Remote Similarity	NPD9613	Approved
0.6195	Remote Similarity	NPD9295	Approved
0.6187	Remote Similarity	NPD1240	Approved
0.6187	Remote Similarity	NPD943	Approved
0.6187	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD4060	Phase 1
0.6187	Remote Similarity	NPD1613	Approved
0.6183	Remote Similarity	NPD4626	Approved
0.6179	Remote Similarity	NPD9264	Approved
0.6179	Remote Similarity	NPD9263	Approved
0.6179	Remote Similarity	NPD9267	Approved
0.6176	Remote Similarity	NPD3636	Approved
0.6176	Remote Similarity	NPD3637	Approved
0.6176	Remote Similarity	NPD3635	Approved
0.6174	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4818	Approved
0.6167	Remote Similarity	NPD4817	Approved
0.6165	Remote Similarity	NPD1608	Approved
0.6165	Remote Similarity	NPD2232	Approved
0.6165	Remote Similarity	NPD2233	Approved
0.6165	Remote Similarity	NPD2230	Approved
0.6154	Remote Similarity	NPD6580	Approved
0.6154	Remote Similarity	NPD316	Approved
0.6154	Remote Similarity	NPD1759	Phase 1
0.6154	Remote Similarity	NPD6581	Approved
0.6154	Remote Similarity	NPD1182	Approved
0.6148	Remote Similarity	NPD1135	Approved
0.6148	Remote Similarity	NPD2797	Approved
0.6148	Remote Similarity	NPD1133	Approved
0.6148	Remote Similarity	NPD1134	Approved
0.6148	Remote Similarity	NPD1129	Approved
0.6148	Remote Similarity	NPD1131	Approved
0.6142	Remote Similarity	NPD1241	Discontinued
0.6136	Remote Similarity	NPD1981	Approved
0.6136	Remote Similarity	NPD1983	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