NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.07
Volume:	235.634
LogP:	1.965
LogD:	1.915
LogS:	-1.736
# Rotatable Bonds:	2
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.598
Synthetic Accessibility Score:	2.022
Fsp3:	0.077
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.834
MDCK Permeability:	1.1653549336188007e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.48
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	95.0753402709961%
Volume Distribution (VD):	0.617
Pgp-substrate:	3.3624894618988037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.536
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.234
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.64
CYP2C9-substrate:	0.758
CYP2D6-inhibitor:	0.519
CYP2D6-substrate:	0.708
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	21.012
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.557
AMES Toxicity:	0.755
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.953
Carcinogencity:	0.494
Eye Corrosion:	0.073
Eye Irritation:	0.969
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC471511

Natural Product ID:	NPC471511
*Common Name:**	4,4'-Methylenedibenzene-1,2-Diol
IUPAC Name:	4-[(3,4-dihydroxyphenyl)methyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	GGOBECRWBXYXEY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H12O4/c14-10-3-1-8(6-12(10)16)5-9-2-4-11(15)13(17)7-9/h1-4,6-7,14-17H,5H2
SMILES:	C1=CC(=C(C=C1CC2=CC(=C(C=C2)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253691
PubChem CID:	10059806
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
Ki	4
MIC	10
Others	1

Activity Type	# Activity
Individual Protein	5
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	9.27	%	PMID[550461]
NPT1063	Individual Protein	Carbonic anhydrase VI	Homo sapiens	Ki	=	13692.0	nM	PMID[550462]
NPT1062	Individual Protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	7640.0	nM	PMID[550462]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	5636.0	nM	PMID[550462]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	>	100.0	ug.mL-1	PMID[550460]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	18356.0	nM	PMID[550462]

☑ 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 NPC471511 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	473
0.1-0.2	2137
0.2-0.3	7141
0.3-0.4	12352
0.4-0.5	4928
0.5-0.6	8741
0.6-0.7	4977
0.7-0.8	1663
0.8-0.85	204
0.85-0.9	56
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9694	High Similarity	NPC239291
0.9688	High Similarity	NPC223393
0.9505	High Similarity	NPC254833
0.9505	High Similarity	NPC228343
0.9479	High Similarity	NPC109955
0.9412	High Similarity	NPC226401
0.9412	High Similarity	NPC120982
0.9412	High Similarity	NPC147634
0.9412	High Similarity	NPC174096
0.9412	High Similarity	NPC79793
0.932	High Similarity	NPC187583
0.932	High Similarity	NPC179002
0.932	High Similarity	NPC257430
0.932	High Similarity	NPC268032
0.9314	High Similarity	NPC55617
0.9314	High Similarity	NPC62258
0.9271	High Similarity	NPC274678
0.9216	High Similarity	NPC233835
0.92	High Similarity	NPC120719
0.9192	High Similarity	NPC110764
0.9143	High Similarity	NPC471485
0.9135	High Similarity	NPC297657
0.91	High Similarity	NPC196479
0.9072	High Similarity	NPC107522
0.9057	High Similarity	NPC120280
0.9029	High Similarity	NPC34864
0.9029	High Similarity	NPC114392
0.9029	High Similarity	NPC105727
0.9029	High Similarity	NPC58427
0.902	High Similarity	NPC477814
0.901	High Similarity	NPC12278
0.899	High Similarity	NPC131587
0.8958	High Similarity	NPC45040
0.8932	High Similarity	NPC176527
0.8824	High Similarity	NPC52087
0.8807	High Similarity	NPC175799
0.8807	High Similarity	NPC200988
0.8807	High Similarity	NPC145023
0.8807	High Similarity	NPC293619
0.8807	High Similarity	NPC610
0.8796	High Similarity	NPC472893
0.8776	High Similarity	NPC76938
0.8776	High Similarity	NPC151715
0.8776	High Similarity	NPC128062
0.8727	High Similarity	NPC144343
0.8727	High Similarity	NPC470626
0.8727	High Similarity	NPC86198
0.8725	High Similarity	NPC477801
0.8725	High Similarity	NPC477802
0.8716	High Similarity	NPC61062
0.8716	High Similarity	NPC277394
0.8716	High Similarity	NPC299252
0.87	High Similarity	NPC32674
0.8692	High Similarity	NPC51698
0.8687	High Similarity	NPC26244
0.8687	High Similarity	NPC32714
0.8679	High Similarity	NPC222084
0.8654	High Similarity	NPC1075
0.8654	High Similarity	NPC294902
0.8654	High Similarity	NPC1786
0.8649	High Similarity	NPC470214
0.8649	High Similarity	NPC109371
0.8649	High Similarity	NPC470215
0.8649	High Similarity	NPC70084
0.8641	High Similarity	NPC30506
0.8641	High Similarity	NPC79672
0.8636	High Similarity	NPC277588
0.8636	High Similarity	NPC278652
0.8614	High Similarity	NPC92730
0.86	High Similarity	NPC132271
0.86	High Similarity	NPC216520
0.86	High Similarity	NPC292730
0.86	High Similarity	NPC473388
0.86	High Similarity	NPC82664
0.8571	High Similarity	NPC117780
0.8571	High Similarity	NPC165133
0.8571	High Similarity	NPC227217
0.8571	High Similarity	NPC265454
0.8571	High Similarity	NPC95614
0.8571	High Similarity	NPC56214
0.8571	High Similarity	NPC34634
0.8571	High Similarity	NPC242885
0.8571	High Similarity	NPC472071
0.8571	High Similarity	NPC232316
0.8571	High Similarity	NPC475245
0.8529	High Similarity	NPC294741
0.8519	High Similarity	NPC471179
0.8515	High Similarity	NPC225464
0.8496	Intermediate Similarity	NPC24125
0.8496	Intermediate Similarity	NPC207613
0.8496	Intermediate Similarity	NPC470414
0.8496	Intermediate Similarity	NPC98305
0.8482	Intermediate Similarity	NPC310338
0.8482	Intermediate Similarity	NPC217174
0.8482	Intermediate Similarity	NPC263386
0.8482	Intermediate Similarity	NPC281298
0.8482	Intermediate Similarity	NPC141791
0.8482	Intermediate Similarity	NPC268572
0.8482	Intermediate Similarity	NPC176893
0.8482	Intermediate Similarity	NPC191866
0.8482	Intermediate Similarity	NPC38483
0.8476	Intermediate Similarity	NPC19149
0.8476	Intermediate Similarity	NPC54765
0.8469	Intermediate Similarity	NPC192
0.8468	Intermediate Similarity	NPC86947
0.8462	Intermediate Similarity	NPC323810
0.8462	Intermediate Similarity	NPC327811
0.8462	Intermediate Similarity	NPC254965
0.8454	Intermediate Similarity	NPC27974
0.8447	Intermediate Similarity	NPC91461
0.8447	Intermediate Similarity	NPC12221
0.8447	Intermediate Similarity	NPC100340
0.8447	Intermediate Similarity	NPC143659
0.8447	Intermediate Similarity	NPC7686
0.8447	Intermediate Similarity	NPC40258
0.844	Intermediate Similarity	NPC148969
0.844	Intermediate Similarity	NPC264558
0.8431	Intermediate Similarity	NPC51333
0.8431	Intermediate Similarity	NPC132078
0.8431	Intermediate Similarity	NPC216468
0.8431	Intermediate Similarity	NPC78119
0.8426	Intermediate Similarity	NPC173746
0.8426	Intermediate Similarity	NPC156840
0.8426	Intermediate Similarity	NPC8547
0.8426	Intermediate Similarity	NPC257124
0.8421	Intermediate Similarity	NPC54872
0.8421	Intermediate Similarity	NPC312675
0.8421	Intermediate Similarity	NPC473853
0.8421	Intermediate Similarity	NPC262156
0.8421	Intermediate Similarity	NPC184651
0.8421	Intermediate Similarity	NPC38996
0.8421	Intermediate Similarity	NPC237667
0.8421	Intermediate Similarity	NPC113865
0.8421	Intermediate Similarity	NPC343720
0.8421	Intermediate Similarity	NPC470212
0.8421	Intermediate Similarity	NPC160380
0.8421	Intermediate Similarity	NPC324571
0.8393	Intermediate Similarity	NPC122009
0.8393	Intermediate Similarity	NPC275519
0.8384	Intermediate Similarity	NPC304541
0.8381	Intermediate Similarity	NPC292452
0.8367	Intermediate Similarity	NPC242240
0.8367	Intermediate Similarity	NPC318325
0.8367	Intermediate Similarity	NPC258219
0.8367	Intermediate Similarity	NPC123273
0.8365	Intermediate Similarity	NPC168829
0.8351	Intermediate Similarity	NPC23167
0.835	Intermediate Similarity	NPC161571
0.835	Intermediate Similarity	NPC275053
0.835	Intermediate Similarity	NPC213730
0.835	Intermediate Similarity	NPC248573
0.8349	Intermediate Similarity	NPC146422
0.8349	Intermediate Similarity	NPC131530
0.8348	Intermediate Similarity	NPC86900
0.8348	Intermediate Similarity	NPC85488
0.8333	Intermediate Similarity	NPC44732
0.8333	Intermediate Similarity	NPC175313
0.8333	Intermediate Similarity	NPC156313
0.8333	Intermediate Similarity	NPC470849
0.8333	Intermediate Similarity	NPC284078
0.8333	Intermediate Similarity	NPC236520
0.8333	Intermediate Similarity	NPC294361
0.8333	Intermediate Similarity	NPC470848
0.8318	Intermediate Similarity	NPC95344
0.8318	Intermediate Similarity	NPC11554
0.8318	Intermediate Similarity	NPC75440
0.8304	Intermediate Similarity	NPC16030
0.8304	Intermediate Similarity	NPC283468
0.8302	Intermediate Similarity	NPC470700
0.8302	Intermediate Similarity	NPC109691
0.8302	Intermediate Similarity	NPC302681
0.8302	Intermediate Similarity	NPC39664
0.8302	Intermediate Similarity	NPC39097
0.8302	Intermediate Similarity	NPC118286
0.83	Intermediate Similarity	NPC94139
0.83	Intermediate Similarity	NPC55903
0.83	Intermediate Similarity	NPC306884
0.83	Intermediate Similarity	NPC147284
0.83	Intermediate Similarity	NPC162314
0.83	Intermediate Similarity	NPC271440
0.83	Intermediate Similarity	NPC3358
0.83	Intermediate Similarity	NPC210497
0.8288	Intermediate Similarity	NPC4665
0.8286	Intermediate Similarity	NPC102216
0.8286	Intermediate Similarity	NPC288411
0.8286	Intermediate Similarity	NPC241891
0.8283	Intermediate Similarity	NPC300017
0.8276	Intermediate Similarity	NPC84086
0.8276	Intermediate Similarity	NPC317769
0.8276	Intermediate Similarity	NPC31344
0.8276	Intermediate Similarity	NPC280704
0.8276	Intermediate Similarity	NPC228922
0.8276	Intermediate Similarity	NPC471693
0.8276	Intermediate Similarity	NPC473451
0.8276	Intermediate Similarity	NPC136319
0.8276	Intermediate Similarity	NPC197757
0.8276	Intermediate Similarity	NPC53567
0.8265	Intermediate Similarity	NPC113460
0.8265	Intermediate Similarity	NPC25493
0.8261	Intermediate Similarity	NPC472271

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 NPC471511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	444
0.1-0.2	1025
0.2-0.3	1485
0.3-0.4	2958
0.4-0.5	1749
0.5-0.6	1052
0.6-0.7	359
0.7-0.8	65
0.8-0.85	6
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9505	High Similarity	NPD3022	Approved
0.9505	High Similarity	NPD3021	Approved
0.8687	High Similarity	NPD2860	Approved
0.8687	High Similarity	NPD2859	Approved
0.8614	High Similarity	NPD3020	Approved
0.8586	High Similarity	NPD2934	Approved
0.8586	High Similarity	NPD2933	Approved
0.8426	Intermediate Similarity	NPD228	Approved
0.835	Intermediate Similarity	NPD1242	Phase 1
0.8349	Intermediate Similarity	NPD9379	Approved
0.8349	Intermediate Similarity	NPD9377	Approved
0.8218	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD844	Approved
0.8058	Intermediate Similarity	NPD288	Approved
0.8041	Intermediate Similarity	NPD111	Approved
0.8	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD5283	Phase 1
0.7934	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD5310	Approved
0.7899	Intermediate Similarity	NPD5311	Approved
0.7869	Intermediate Similarity	NPD3027	Phase 3
0.7851	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD3053	Approved
0.7833	Intermediate Similarity	NPD3055	Approved
0.7815	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9381	Approved
0.7778	Intermediate Similarity	NPD9384	Approved
0.7757	Intermediate Similarity	NPD846	Approved
0.7757	Intermediate Similarity	NPD940	Approved
0.7731	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2342	Discontinued
0.768	Intermediate Similarity	NPD1613	Approved
0.768	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD943	Approved
0.7664	Intermediate Similarity	NPD3028	Approved
0.7661	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD258	Approved
0.7623	Intermediate Similarity	NPD257	Approved
0.7619	Intermediate Similarity	NPD1809	Phase 2
0.7603	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD845	Approved
0.7589	Intermediate Similarity	NPD1792	Phase 2
0.7544	Intermediate Similarity	NPD7635	Approved
0.754	Intermediate Similarity	NPD3061	Approved
0.754	Intermediate Similarity	NPD3059	Approved
0.754	Intermediate Similarity	NPD3062	Approved
0.7521	Intermediate Similarity	NPD9622	Approved
0.75	Intermediate Similarity	NPD3092	Approved
0.7479	Intermediate Similarity	NPD2286	Discontinued
0.7478	Intermediate Similarity	NPD2228	Approved
0.7478	Intermediate Similarity	NPD2229	Approved
0.7478	Intermediate Similarity	NPD2234	Approved
0.7477	Intermediate Similarity	NPD1444	Approved
0.7477	Intermediate Similarity	NPD1445	Approved
0.7458	Intermediate Similarity	NPD3091	Approved
0.7434	Intermediate Similarity	NPD4750	Phase 3
0.7422	Intermediate Similarity	NPD5314	Approved
0.7419	Intermediate Similarity	NPD9569	Approved
0.7402	Intermediate Similarity	NPD1558	Phase 1
0.7398	Intermediate Similarity	NPD3094	Phase 2
0.7395	Intermediate Similarity	NPD4093	Discontinued
0.7385	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD9619	Approved
0.7339	Intermediate Similarity	NPD9621	Approved
0.7339	Intermediate Similarity	NPD9620	Approved
0.7333	Intermediate Similarity	NPD4059	Approved
0.7333	Intermediate Similarity	NPD3019	Approved
0.7333	Intermediate Similarity	NPD2932	Approved
0.7321	Intermediate Similarity	NPD968	Approved
0.7297	Intermediate Similarity	NPD9608	Approved
0.7297	Intermediate Similarity	NPD9610	Approved
0.7282	Intermediate Similarity	NPD9094	Approved
0.7266	Intermediate Similarity	NPD3620	Phase 2
0.7266	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD825	Approved
0.7266	Intermediate Similarity	NPD826	Approved
0.7258	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5536	Phase 2
0.7209	Intermediate Similarity	NPD275	Approved
0.7209	Intermediate Similarity	NPD274	Approved
0.7207	Intermediate Similarity	NPD9500	Approved
0.7203	Intermediate Similarity	NPD6671	Approved
0.7197	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7266	Discontinued
0.7193	Intermediate Similarity	NPD2684	Approved
0.719	Intermediate Similarity	NPD1751	Approved
0.719	Intermediate Similarity	NPD3095	Discontinued
0.7188	Intermediate Similarity	NPD259	Phase 1
0.7165	Intermediate Similarity	NPD9536	Phase 1
0.7165	Intermediate Similarity	NPD9537	Phase 1
0.7154	Intermediate Similarity	NPD9269	Phase 2
0.7154	Intermediate Similarity	NPD823	Approved
0.7154	Intermediate Similarity	NPD817	Approved
0.7132	Intermediate Similarity	NPD4060	Phase 1
0.713	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD497	Approved
0.7109	Intermediate Similarity	NPD601	Approved
0.7109	Intermediate Similarity	NPD597	Approved
0.7109	Intermediate Similarity	NPD598	Approved
0.7107	Intermediate Similarity	NPD1357	Approved
0.7094	Intermediate Similarity	NPD7843	Approved
0.7083	Intermediate Similarity	NPD9087	Approved
0.7077	Intermediate Similarity	NPD555	Phase 2
0.7073	Intermediate Similarity	NPD1610	Phase 2
0.7073	Intermediate Similarity	NPD1201	Approved
0.7063	Intermediate Similarity	NPD6584	Phase 3
0.7059	Intermediate Similarity	NPD7157	Approved
0.7054	Intermediate Similarity	NPD1136	Approved
0.7054	Intermediate Similarity	NPD1132	Approved
0.7054	Intermediate Similarity	NPD1130	Approved
0.7054	Intermediate Similarity	NPD2674	Phase 3
0.7049	Intermediate Similarity	NPD4589	Approved
0.7049	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD9296	Approved
0.7037	Intermediate Similarity	NPD8166	Discontinued
0.7034	Intermediate Similarity	NPD496	Approved
0.7034	Intermediate Similarity	NPD498	Approved
0.7034	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD495	Approved
0.7031	Intermediate Similarity	NPD7095	Approved
0.7025	Intermediate Similarity	NPD5303	Approved
0.7025	Intermediate Similarity	NPD1548	Phase 1
0.7025	Intermediate Similarity	NPD5304	Approved
0.7009	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD2861	Phase 2
0.7008	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD9273	Approved
0.6984	Remote Similarity	NPD1470	Approved
0.6983	Remote Similarity	NPD5451	Approved
0.6975	Remote Similarity	NPD9614	Approved
0.6975	Remote Similarity	NPD1793	Approved
0.6975	Remote Similarity	NPD1791	Approved
0.6975	Remote Similarity	NPD9618	Approved
0.6975	Remote Similarity	NPD475	Phase 2
0.697	Remote Similarity	NPD9088	Approved
0.696	Remote Similarity	NPD2982	Phase 2
0.696	Remote Similarity	NPD2983	Phase 2
0.6949	Remote Similarity	NPD5535	Approved
0.6935	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1535	Discovery
0.6935	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3845	Phase 1
0.6934	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD255	Approved
0.6917	Remote Similarity	NPD709	Approved
0.6917	Remote Similarity	NPD256	Approved
0.6911	Remote Similarity	NPD6516	Phase 2
0.6911	Remote Similarity	NPD5846	Approved
0.6905	Remote Similarity	NPD1283	Approved
0.6891	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2421	Approved
0.6884	Remote Similarity	NPD2420	Approved
0.6884	Remote Similarity	NPD1511	Approved
0.688	Remote Similarity	NPD2981	Phase 2
0.688	Remote Similarity	NPD1481	Phase 2
0.6875	Remote Similarity	NPD5736	Approved
0.6875	Remote Similarity	NPD3018	Phase 2
0.6869	Remote Similarity	NPD9294	Approved
0.6866	Remote Similarity	NPD9570	Approved
0.6861	Remote Similarity	NPD6190	Approved
0.686	Remote Similarity	NPD405	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3847	Discontinued
0.6855	Remote Similarity	NPD3023	Approved
0.6855	Remote Similarity	NPD3026	Approved
0.685	Remote Similarity	NPD1164	Approved
0.6846	Remote Similarity	NPD5110	Phase 2
0.6846	Remote Similarity	NPD3145	Approved
0.6846	Remote Similarity	NPD3144	Approved
0.6846	Remote Similarity	NPD5109	Approved
0.6846	Remote Similarity	NPD5111	Phase 2
0.6838	Remote Similarity	NPD3060	Approved
0.6829	Remote Similarity	NPD9268	Approved
0.6829	Remote Similarity	NPD1651	Approved
0.6829	Remote Similarity	NPD3025	Approved
0.6829	Remote Similarity	NPD3024	Approved
0.6825	Remote Similarity	NPD6582	Phase 2
0.6825	Remote Similarity	NPD1669	Approved
0.6825	Remote Similarity	NPD6583	Phase 3
0.6825	Remote Similarity	NPD4659	Approved
0.6822	Remote Similarity	NPD4908	Phase 1
0.6818	Remote Similarity	NPD230	Phase 1
0.681	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.681	Remote Similarity	NPD290	Approved
0.6803	Remote Similarity	NPD9616	Approved
0.6803	Remote Similarity	NPD9613	Approved
0.6803	Remote Similarity	NPD9615	Approved
0.6797	Remote Similarity	NPD2195	Approved
0.6797	Remote Similarity	NPD2194	Approved
0.6786	Remote Similarity	NPD1512	Approved
0.6774	Remote Similarity	NPD2667	Approved
0.6774	Remote Similarity	NPD2668	Approved
0.6774	Remote Similarity	NPD4626	Approved
0.6769	Remote Similarity	NPD5156	Approved
0.6769	Remote Similarity	NPD5155	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