NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	351.07
LogP:	3.02
LogD:	2.631
LogS:	-3.78
# Rotatable Bonds:	1
TPSA:	85.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	4.136
Fsp3:	0.579
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.71
MDCK Permeability:	4.0931234252639115e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.582
Plasma Protein Binding (PPB):	89.77228546142578%
Volume Distribution (VD):	0.979
Pgp-substrate:	3.9467926025390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.202
CYP1A2-substrate:	0.772
CYP2C19-inhibitor:	0.368
CYP2C19-substrate:	0.359
CYP2C9-inhibitor:	0.495
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.671
CYP2D6-substrate:	0.827
CYP3A4-inhibitor:	0.733
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	9.672
Half-life (T1/2):	0.651

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.453
AMES Toxicity:	0.213
Rat Oral Acute Toxicity:	0.619
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.201
Carcinogencity:	0.112
Eye Corrosion:	0.003
Eye Irritation:	0.103
Respiratory Toxicity:	0.3

Download Data

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

Natural Product: NPC107619

Natural Product ID:	NPC107619
*Common Name:**	P-Hydroxyphenylacetamide
IUPAC Name:	2-(4-hydroxyphenyl)acetamide
Synonyms:	2-(4-Hydroxyphenyl)Acetamide; P-Hydroxyphenylacetamide
Standard InCHIKey:	YBPAYPRLUDCSEY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H9NO2/c9-8(11)5-6-1-3-7(10)4-2-6/h1-4,10H,5H2,(H2,9,11)
SMILES:	OC(=N)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447310
PubChem CID:	86986
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002363] Phenylacetamides

*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
NPO32469	Cytophaga sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12444694]

☑ 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	6
Others	17

Activity Type	# Activity
Individual Protein	11
Others	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1144	Individual Protein	Carbonic anhydrase VB	Homo sapiens	Kinact	=	81.0	nM	PMID[507657]
NPT1143	Individual Protein	Carbonic anhydrase VA	Homo sapiens	Kinact	=	92.0	nM	PMID[507657]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Kinact	=	11.2	uM	PMID[507657]
NPT3155	Individual Protein	PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)	Mycobacterium tuberculosis	Ki	=	9120.0	nM	PMID[507658]
NPT3156	Individual Protein	Uncharacterized protein Rv1284/MT1322	Mycobacterium tuberculosis	Ki	=	850.0	nM	PMID[507658]
NPT1148	Individual Protein	Carbonic anhydrase	Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Ki	=	910.0	nM	PMID[507658]
NPT3157	Individual Protein	Carbonic anhydrase 2	Cryptococcus neoformans var. grubii	Ki	=	840.0	nM	PMID[507658]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	11200.0	nM	PMID[507658]
NPT3156	Individual Protein	Uncharacterized protein Rv1284/MT1322	Mycobacterium tuberculosis	FC	=	75.0	n.a.	PMID[507658]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Kinact	=	309.0	uM	PMID[507657]
NPT2	Others	Unspecified		Selectivity ratio	=	3358.0	n.a.	PMID[507657]
NPT2	Others	Unspecified		Selectivity ratio	=	121.0	n.a.	PMID[507657]
NPT2	Others	Unspecified		Selectivity ratio	=	3814.0	n.a.	PMID[507657]
NPT2	Others	Unspecified		Selectivity ratio	=	138.0	n.a.	PMID[507657]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	309000.0	nM	PMID[507658]
NPT2	Others	Unspecified		Ratio Ki	=	33.9	n.a.	PMID[507658]
NPT2	Others	Unspecified		Ratio Ki	=	363.5	n.a.	PMID[507658]
NPT2	Others	Unspecified		Ratio Ki	=	339.6	n.a.	PMID[507658]
NPT2	Others	Unspecified		Ratio Ki	=	367.9	n.a.	PMID[507658]
NPT2	Others	Unspecified		Ratio Ki	=	1.2	n.a.	PMID[507658]
NPT2	Others	Unspecified		Ratio Ki	=	13.2	n.a.	PMID[507658]
NPT2	Others	Unspecified		Ratio Ki	=	12.3	n.a.	PMID[507658]
NPT2	Others	Unspecified		Ratio Ki	=	13.3	n.a.	PMID[507658]

☑ 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 NPC107619 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	196
0.1-0.2	2695
0.2-0.3	9561
0.3-0.4	9558
0.4-0.5	9227
0.5-0.6	8487
0.6-0.7	2313
0.7-0.8	563
0.8-0.85	78
0.85-0.9	18
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8804	High Similarity	NPC23167
0.8791	High Similarity	NPC175313
0.8788	High Similarity	NPC178902
0.8763	High Similarity	NPC315921
0.8723	High Similarity	NPC300017
0.8713	High Similarity	NPC231705
0.871	High Similarity	NPC25493
0.871	High Similarity	NPC113460
0.8696	High Similarity	NPC197783
0.8681	High Similarity	NPC265146
0.8673	High Similarity	NPC125732
0.8641	High Similarity	NPC258056
0.8632	High Similarity	NPC45040
0.8617	High Similarity	NPC258219
0.8617	High Similarity	NPC318325
0.8617	High Similarity	NPC123273
0.8617	High Similarity	NPC280347
0.8617	High Similarity	NPC242240
0.8617	High Similarity	NPC177420
0.8587	High Similarity	NPC248817
0.8558	High Similarity	NPC474149
0.8544	High Similarity	NPC153690
0.8542	High Similarity	NPC325292
0.8542	High Similarity	NPC138117
0.8526	High Similarity	NPC55561
0.8511	High Similarity	NPC104216
0.8495	Intermediate Similarity	NPC155393
0.8478	Intermediate Similarity	NPC124436
0.8454	Intermediate Similarity	NPC128062
0.8454	Intermediate Similarity	NPC151715
0.8447	Intermediate Similarity	NPC142297
0.8438	Intermediate Similarity	NPC304541
0.8404	Intermediate Similarity	NPC184169
0.8404	Intermediate Similarity	NPC407
0.8404	Intermediate Similarity	NPC307235
0.8367	Intermediate Similarity	NPC274678
0.8367	Intermediate Similarity	NPC313650
0.8367	Intermediate Similarity	NPC26244
0.8365	Intermediate Similarity	NPC24101
0.8365	Intermediate Similarity	NPC96224
0.8333	Intermediate Similarity	NPC300478
0.8333	Intermediate Similarity	NPC151764
0.8318	Intermediate Similarity	NPC309808
0.8316	Intermediate Similarity	NPC27974
0.8286	Intermediate Similarity	NPC290566
0.8286	Intermediate Similarity	NPC145638
0.8286	Intermediate Similarity	NPC71266
0.8283	Intermediate Similarity	NPC473388
0.8265	Intermediate Similarity	NPC316301
0.8265	Intermediate Similarity	NPC27323
0.8247	Intermediate Similarity	NPC270547
0.8247	Intermediate Similarity	NPC155908
0.8247	Intermediate Similarity	NPC204210
0.8241	Intermediate Similarity	NPC118202
0.8235	Intermediate Similarity	NPC68055
0.8229	Intermediate Similarity	NPC98772
0.8218	Intermediate Similarity	NPC289381
0.8218	Intermediate Similarity	NPC29601
0.8218	Intermediate Similarity	NPC155847
0.82	Intermediate Similarity	NPC260000
0.82	Intermediate Similarity	NPC109955
0.8198	Intermediate Similarity	NPC283760
0.8191	Intermediate Similarity	NPC286904
0.8182	Intermediate Similarity	NPC8392
0.8165	Intermediate Similarity	NPC317254
0.8163	Intermediate Similarity	NPC181709
0.8144	Intermediate Similarity	NPC192
0.8132	Intermediate Similarity	NPC192623
0.8119	Intermediate Similarity	NPC280869
0.8119	Intermediate Similarity	NPC216468
0.8119	Intermediate Similarity	NPC92730
0.8119	Intermediate Similarity	NPC51333
0.8119	Intermediate Similarity	NPC80027
0.8119	Intermediate Similarity	NPC78119
0.8119	Intermediate Similarity	NPC245561
0.8119	Intermediate Similarity	NPC128723
0.8119	Intermediate Similarity	NPC132078
0.81	Intermediate Similarity	NPC216520
0.81	Intermediate Similarity	NPC132271
0.81	Intermediate Similarity	NPC82664
0.81	Intermediate Similarity	NPC202986
0.81	Intermediate Similarity	NPC292730
0.8091	Intermediate Similarity	NPC82963
0.8081	Intermediate Similarity	NPC32977
0.8081	Intermediate Similarity	NPC81010
0.8073	Intermediate Similarity	NPC142599
0.8065	Intermediate Similarity	NPC146703
0.8061	Intermediate Similarity	NPC306074
0.8056	Intermediate Similarity	NPC146422
0.8041	Intermediate Similarity	NPC70436
0.8039	Intermediate Similarity	NPC213730
0.8039	Intermediate Similarity	NPC52472
0.802	Intermediate Similarity	NPC77492
0.802	Intermediate Similarity	NPC32674
0.802	Intermediate Similarity	NPC225464
0.8018	Intermediate Similarity	NPC311737
0.8018	Intermediate Similarity	NPC38458
0.8	Intermediate Similarity	NPC286006
0.8	Intermediate Similarity	NPC150837
0.798	Intermediate Similarity	NPC147284
0.798	Intermediate Similarity	NPC306884
0.798	Intermediate Similarity	NPC162314
0.798	Intermediate Similarity	NPC271440
0.798	Intermediate Similarity	NPC94139
0.798	Intermediate Similarity	NPC210497
0.798	Intermediate Similarity	NPC55903
0.798	Intermediate Similarity	NPC3358
0.7961	Intermediate Similarity	NPC40258
0.7961	Intermediate Similarity	NPC7686
0.7961	Intermediate Similarity	NPC91461
0.7961	Intermediate Similarity	NPC110764
0.7959	Intermediate Similarity	NPC312304
0.7959	Intermediate Similarity	NPC47950
0.7941	Intermediate Similarity	NPC252821
0.7941	Intermediate Similarity	NPC122005
0.79	Intermediate Similarity	NPC245187
0.79	Intermediate Similarity	NPC152415
0.79	Intermediate Similarity	NPC76938
0.7885	Intermediate Similarity	NPC196479
0.7885	Intermediate Similarity	NPC135784
0.7885	Intermediate Similarity	NPC470202
0.7885	Intermediate Similarity	NPC168829
0.7879	Intermediate Similarity	NPC231150
0.7876	Intermediate Similarity	NPC268572
0.7864	Intermediate Similarity	NPC225506
0.7843	Intermediate Similarity	NPC474073
0.7843	Intermediate Similarity	NPC201967
0.7843	Intermediate Similarity	NPC152097
0.7838	Intermediate Similarity	NPC213
0.7838	Intermediate Similarity	NPC10286
0.7826	Intermediate Similarity	NPC27581
0.7822	Intermediate Similarity	NPC246679
0.7822	Intermediate Similarity	NPC107522
0.7822	Intermediate Similarity	NPC32714
0.7822	Intermediate Similarity	NPC144682
0.781	Intermediate Similarity	NPC12278
0.781	Intermediate Similarity	NPC288411
0.781	Intermediate Similarity	NPC120719
0.781	Intermediate Similarity	NPC119860
0.781	Intermediate Similarity	NPC8931
0.781	Intermediate Similarity	NPC471511
0.781	Intermediate Similarity	NPC261573
0.781	Intermediate Similarity	NPC120693
0.781	Intermediate Similarity	NPC30506
0.78	Intermediate Similarity	NPC29373
0.7798	Intermediate Similarity	NPC227553
0.7798	Intermediate Similarity	NPC163674
0.7798	Intermediate Similarity	NPC166837
0.7768	Intermediate Similarity	NPC188867
0.7768	Intermediate Similarity	NPC281686
0.7768	Intermediate Similarity	NPC106551
0.7767	Intermediate Similarity	NPC260775
0.7767	Intermediate Similarity	NPC131587
0.7767	Intermediate Similarity	NPC275104
0.7767	Intermediate Similarity	NPC171843
0.7767	Intermediate Similarity	NPC100870
0.7767	Intermediate Similarity	NPC130193
0.7755	Intermediate Similarity	NPC19680
0.7745	Intermediate Similarity	NPC312132
0.7745	Intermediate Similarity	NPC283711
0.7745	Intermediate Similarity	NPC259512
0.7736	Intermediate Similarity	NPC303141
0.7736	Intermediate Similarity	NPC138942
0.7736	Intermediate Similarity	NPC239291
0.7736	Intermediate Similarity	NPC474839
0.7736	Intermediate Similarity	NPC13495
0.7736	Intermediate Similarity	NPC233396
0.7736	Intermediate Similarity	NPC154899
0.7732	Intermediate Similarity	NPC198747
0.7723	Intermediate Similarity	NPC289769
0.7719	Intermediate Similarity	NPC319950
0.7699	Intermediate Similarity	NPC283468
0.7692	Intermediate Similarity	NPC48730
0.7692	Intermediate Similarity	NPC129373
0.7692	Intermediate Similarity	NPC10588
0.7692	Intermediate Similarity	NPC12931
0.7692	Intermediate Similarity	NPC174911
0.7692	Intermediate Similarity	NPC130756
0.7692	Intermediate Similarity	NPC211885
0.7692	Intermediate Similarity	NPC161571
0.7692	Intermediate Similarity	NPC248396
0.7692	Intermediate Similarity	NPC253746
0.7692	Intermediate Similarity	NPC275053
0.7692	Intermediate Similarity	NPC72729
0.7692	Intermediate Similarity	NPC130103
0.7692	Intermediate Similarity	NPC294741
0.7692	Intermediate Similarity	NPC223393
0.7692	Intermediate Similarity	NPC70677
0.7692	Intermediate Similarity	NPC248573
0.7692	Intermediate Similarity	NPC166761
0.767	Intermediate Similarity	NPC79241
0.767	Intermediate Similarity	NPC156313
0.767	Intermediate Similarity	NPC475078
0.767	Intermediate Similarity	NPC6597
0.7664	Intermediate Similarity	NPC248904
0.7664	Intermediate Similarity	NPC54765
0.7664	Intermediate Similarity	NPC477814
0.7664	Intermediate Similarity	NPC69332
0.7664	Intermediate Similarity	NPC188677
0.7664	Intermediate Similarity	NPC92623

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 NPC107619 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	986
0.2-0.3	1102
0.3-0.4	2809
0.4-0.5	2343
0.5-0.6	1260
0.6-0.7	415
0.7-0.8	72
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8763	High Similarity	NPD9273	Approved
0.8515	High Similarity	NPD9610	Approved
0.8515	High Similarity	NPD9608	Approved
0.8478	Intermediate Similarity	NPD111	Approved
0.8454	Intermediate Similarity	NPD2933	Approved
0.8454	Intermediate Similarity	NPD2934	Approved
0.8367	Intermediate Similarity	NPD2859	Approved
0.8367	Intermediate Similarity	NPD2860	Approved
0.8286	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.8265	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD3020	Approved
0.8056	Intermediate Similarity	NPD821	Approved
0.8056	Intermediate Similarity	NPD9379	Approved
0.8056	Intermediate Similarity	NPD9377	Approved
0.7961	Intermediate Similarity	NPD846	Approved
0.7961	Intermediate Similarity	NPD940	Approved
0.7909	Intermediate Similarity	NPD475	Phase 2
0.787	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD255	Approved
0.7838	Intermediate Similarity	NPD256	Approved
0.7822	Intermediate Similarity	NPD844	Approved
0.7822	Intermediate Similarity	NPD1809	Phase 2
0.78	Intermediate Similarity	NPD845	Approved
0.7768	Intermediate Similarity	NPD9568	Approved
0.7745	Intermediate Similarity	NPD288	Approved
0.7732	Intermediate Similarity	NPD9538	Approved
0.77	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD16	Approved
0.7699	Intermediate Similarity	NPD317	Approved
0.7699	Intermediate Similarity	NPD856	Approved
0.7699	Intermediate Similarity	NPD318	Approved
0.7692	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1242	Phase 1
0.7664	Intermediate Similarity	NPD1445	Approved
0.7664	Intermediate Similarity	NPD1444	Approved
0.7658	Intermediate Similarity	NPD2229	Approved
0.7658	Intermediate Similarity	NPD2228	Approved
0.7658	Intermediate Similarity	NPD2234	Approved
0.7647	Intermediate Similarity	NPD7451	Discontinued
0.7589	Intermediate Similarity	NPD9618	Approved
0.7589	Intermediate Similarity	NPD9614	Approved
0.7586	Intermediate Similarity	NPD3421	Phase 3
0.75	Intermediate Similarity	NPD9384	Approved
0.75	Intermediate Similarity	NPD9381	Approved
0.7478	Intermediate Similarity	NPD1759	Phase 1
0.7473	Intermediate Similarity	NPD9087	Approved
0.7459	Intermediate Similarity	NPD3136	Phase 2
0.7455	Intermediate Similarity	NPD3022	Approved
0.7455	Intermediate Similarity	NPD3021	Approved
0.7455	Intermediate Similarity	NPD1792	Phase 2
0.7436	Intermediate Similarity	NPD3143	Discontinued
0.7426	Intermediate Similarity	NPD530	Approved
0.7391	Intermediate Similarity	NPD1758	Phase 1
0.7391	Intermediate Similarity	NPD9613	Approved
0.7391	Intermediate Similarity	NPD9616	Approved
0.7391	Intermediate Similarity	NPD9615	Approved
0.7358	Intermediate Similarity	NPD3028	Approved
0.734	Intermediate Similarity	NPD9088	Approved
0.7328	Intermediate Similarity	NPD316	Approved
0.7321	Intermediate Similarity	NPD228	Approved
0.7311	Intermediate Similarity	NPD3070	Discontinued
0.7311	Intermediate Similarity	NPD2561	Approved
0.7311	Intermediate Similarity	NPD2562	Approved
0.7304	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD1101	Approved
0.7288	Intermediate Similarity	NPD1983	Approved
0.7288	Intermediate Similarity	NPD1981	Approved
0.7288	Intermediate Similarity	NPD1980	Approved
0.725	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD9622	Approved
0.7234	Intermediate Similarity	NPD9294	Approved
0.7203	Intermediate Similarity	NPD2286	Discontinued
0.7203	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5311	Approved
0.719	Intermediate Similarity	NPD5310	Approved
0.7182	Intermediate Similarity	NPD968	Approved
0.7179	Intermediate Similarity	NPD5303	Approved
0.7179	Intermediate Similarity	NPD5304	Approved
0.7177	Intermediate Similarity	NPD2372	Approved
0.717	Intermediate Similarity	NPD9612	Approved
0.717	Intermediate Similarity	NPD9611	Approved
0.717	Intermediate Similarity	NPD9609	Approved
0.7167	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1558	Phase 1
0.7143	Intermediate Similarity	NPD9713	Approved
0.7131	Intermediate Similarity	NPD1131	Approved
0.7131	Intermediate Similarity	NPD1135	Approved
0.7131	Intermediate Similarity	NPD3055	Approved
0.7131	Intermediate Similarity	NPD3053	Approved
0.7131	Intermediate Similarity	NPD1133	Approved
0.7131	Intermediate Similarity	NPD1134	Approved
0.7131	Intermediate Similarity	NPD1129	Approved
0.713	Intermediate Similarity	NPD1791	Approved
0.713	Intermediate Similarity	NPD1793	Approved
0.7119	Intermediate Similarity	NPD4093	Discontinued
0.7117	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9712	Approved
0.7073	Intermediate Similarity	NPD9619	Approved
0.7073	Intermediate Similarity	NPD9620	Approved
0.7073	Intermediate Similarity	NPD257	Approved
0.7073	Intermediate Similarity	NPD258	Approved
0.7073	Intermediate Similarity	NPD9621	Approved
0.7063	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2674	Phase 3
0.7063	Intermediate Similarity	NPD1423	Approved
0.7059	Intermediate Similarity	NPD1751	Approved
0.7054	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2684	Approved
0.7041	Intermediate Similarity	NPD9089	Approved
0.7018	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD9569	Approved
0.7009	Intermediate Similarity	NPD9711	Approved
0.7009	Intermediate Similarity	NPD9710	Approved
0.7	Intermediate Similarity	NPD7450	Phase 2
0.7	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4750	Phase 3
0.6977	Remote Similarity	NPD3552	Approved
0.6977	Remote Similarity	NPD3554	Approved
0.6977	Remote Similarity	NPD3555	Approved
0.6977	Remote Similarity	NPD3553	Approved
0.6975	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6582	Phase 2
0.6967	Remote Similarity	NPD6583	Phase 3
0.6967	Remote Similarity	NPD4659	Approved
0.6967	Remote Similarity	NPD1669	Approved
0.6964	Remote Similarity	NPD2342	Discontinued
0.6952	Remote Similarity	NPD1409	Phase 3
0.6947	Remote Similarity	NPD7978	Discontinued
0.6947	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9093	Approved
0.6935	Remote Similarity	NPD2195	Approved
0.6935	Remote Similarity	NPD2194	Approved
0.6929	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2667	Approved
0.6917	Remote Similarity	NPD2668	Approved
0.6911	Remote Similarity	NPD196	Phase 1
0.6909	Remote Similarity	NPD9500	Approved
0.6905	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4097	Suspended
0.6897	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1548	Phase 1
0.6891	Remote Similarity	NPD3091	Approved
0.6891	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3772	Phase 3
0.6885	Remote Similarity	NPD2235	Phase 2
0.6885	Remote Similarity	NPD2231	Phase 2
0.686	Remote Similarity	NPD3847	Discontinued
0.6857	Remote Similarity	NPD752	Approved
0.6855	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4103	Phase 2
0.685	Remote Similarity	NPD597	Approved
0.685	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.685	Remote Similarity	NPD601	Approved
0.685	Remote Similarity	NPD3144	Approved
0.685	Remote Similarity	NPD598	Approved
0.685	Remote Similarity	NPD3145	Approved
0.6847	Remote Similarity	NPD314	Approved
0.6847	Remote Similarity	NPD310	Approved
0.6847	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD315	Approved
0.6847	Remote Similarity	NPD311	Approved
0.6847	Remote Similarity	NPD309	Approved
0.6847	Remote Similarity	NPD10	Approved
0.6838	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3685	Discontinued
0.6814	Remote Similarity	NPD9532	Phase 3
0.6814	Remote Similarity	NPD290	Approved
0.6814	Remote Similarity	NPD9507	Approved
0.681	Remote Similarity	NPD7843	Approved
0.681	Remote Similarity	NPD7635	Approved
0.6803	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6584	Phase 3
0.68	Remote Similarity	NPD3691	Phase 2
0.68	Remote Similarity	NPD3690	Phase 2
0.6797	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD839	Approved
0.6797	Remote Similarity	NPD840	Approved
0.6797	Remote Similarity	NPD6407	Approved
0.6797	Remote Similarity	NPD1136	Approved
0.6797	Remote Similarity	NPD6405	Approved
0.6797	Remote Similarity	NPD1130	Approved
0.6797	Remote Similarity	NPD829	Discontinued
0.6797	Remote Similarity	NPD1132	Approved
0.6797	Remote Similarity	NPD259	Phase 1
0.6796	Remote Similarity	NPD531	Approved
0.6792	Remote Similarity	NPD719	Approved
0.6792	Remote Similarity	NPD720	Approved
0.6791	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.678	Remote Similarity	NPD709	Approved
0.678	Remote Similarity	NPD6671	Approved
0.6777	Remote Similarity	NPD2932	Approved
0.6777	Remote Similarity	NPD4059	Approved
0.6777	Remote Similarity	NPD3019	Approved
0.6772	Remote Similarity	NPD9536	Phase 1
0.6772	Remote Similarity	NPD9537	Phase 1
0.6754	Remote Similarity	NPD74	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