NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	135.07
Volume:	147.609
LogP:	1.517
LogD:	1.179
LogS:	-1.715
# Rotatable Bonds:	1
TPSA:	43.09
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	1.646
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.434
MDCK Permeability:	5.090069316793233e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.884
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	60.41502380371094%
Volume Distribution (VD):	1.121
Pgp-substrate:	66.04037475585938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.643
CYP2C19-inhibitor:	0.608
CYP2C19-substrate:	0.514
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.337
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.785
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	6.865
Half-life (T1/2):	0.592

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.435
AMES Toxicity:	0.319
Rat Oral Acute Toxicity:	0.251
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.528
Carcinogencity:	0.303
Eye Corrosion:	0.494
Eye Irritation:	0.994
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC172170

Natural Product ID:	NPC172170
*Common Name:**	2-Aminoacetophenone
IUPAC Name:	1-(2-aminophenyl)ethanone
Synonyms:
Standard InCHIKey:	GTDQGKWDWVUKTI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H9NO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,9H2,1H3
SMILES:	CC(=O)c1ccccc1N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2251601
PubChem CID:	11086
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO14821	Sus scrofa domesticus	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-012-0441-5]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10556916]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19406895]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19917748]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20932054]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25043228]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25960261]
NPO14821	Sus scrofa domesticus	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26804051]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32603106]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	Antarctic	n.a.	PMID[8882433]
NPO14821	Sus scrofa domesticus	Species	Suidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO14821	Sus scrofa domesticus	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14821	Sus scrofa domesticus	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO14821	Sus scrofa domesticus	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
EC50	1
Others	3

Activity Type	# Activity
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1280	Organism	Thrips tabaci	Thrips tabaci	Ratio	=	6.0	n.a.	PMID[537757]
NPT1281	Organism	Thrips obscuratus	Thrips obscuratus	Ratio	=	26.7	n.a.	PMID[537757]
NPT1281	Organism	Thrips obscuratus	Thrips obscuratus	Ratio	=	20.7	n.a.	PMID[537757]
NPT2	Others	Unspecified		EC50	=	46000.0	nM	PMID[537758]

☑ 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 NPC172170 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	274
0.1-0.2	4057
0.2-0.3	11838
0.3-0.4	15700
0.4-0.5	9083
0.5-0.6	1462
0.6-0.7	232
0.7-0.8	41
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8839	High Similarity	NPC279385
0.8839	High Similarity	NPC179605
0.8761	High Similarity	NPC103292
0.8522	High Similarity	NPC268534
0.8421	Intermediate Similarity	NPC291962
0.8421	Intermediate Similarity	NPC177684
0.8348	Intermediate Similarity	NPC161956
0.8348	Intermediate Similarity	NPC112373
0.8348	Intermediate Similarity	NPC258531
0.8291	Intermediate Similarity	NPC254698
0.8276	Intermediate Similarity	NPC257490
0.8224	Intermediate Similarity	NPC38262
0.8205	Intermediate Similarity	NPC39818
0.8182	Intermediate Similarity	NPC477432
0.8167	Intermediate Similarity	NPC58827
0.8167	Intermediate Similarity	NPC307437
0.8167	Intermediate Similarity	NPC72473
0.8099	Intermediate Similarity	NPC209389
0.8067	Intermediate Similarity	NPC226794
0.7951	Intermediate Similarity	NPC122235
0.7886	Intermediate Similarity	NPC194562
0.7885	Intermediate Similarity	NPC291070
0.7885	Intermediate Similarity	NPC246757
0.7881	Intermediate Similarity	NPC130931
0.7769	Intermediate Similarity	NPC192533
0.768	Intermediate Similarity	NPC316746
0.7647	Intermediate Similarity	NPC226143
0.7619	Intermediate Similarity	NPC40364
0.7586	Intermediate Similarity	NPC57051
0.7557	Intermediate Similarity	NPC316202
0.75	Intermediate Similarity	NPC316104
0.75	Intermediate Similarity	NPC253476
0.75	Intermediate Similarity	NPC162417
0.7442	Intermediate Similarity	NPC173295
0.7424	Intermediate Similarity	NPC471164
0.7404	Intermediate Similarity	NPC111233
0.7323	Intermediate Similarity	NPC472245
0.7313	Intermediate Similarity	NPC314287
0.7308	Intermediate Similarity	NPC262295
0.728	Intermediate Similarity	NPC470343
0.728	Intermediate Similarity	NPC472244
0.7273	Intermediate Similarity	NPC2785
0.7273	Intermediate Similarity	NPC285470
0.7273	Intermediate Similarity	NPC181527
0.7273	Intermediate Similarity	NPC36342
0.7273	Intermediate Similarity	NPC229353
0.7264	Intermediate Similarity	NPC78154
0.7238	Intermediate Similarity	NPC30445
0.72	Intermediate Similarity	NPC300205
0.7176	Intermediate Similarity	NPC300299
0.7172	Intermediate Similarity	NPC245966
0.7164	Intermediate Similarity	NPC2823
0.7154	Intermediate Similarity	NPC150323
0.7132	Intermediate Similarity	NPC130797
0.7132	Intermediate Similarity	NPC136002
0.713	Intermediate Similarity	NPC108800
0.7129	Intermediate Similarity	NPC164086
0.7129	Intermediate Similarity	NPC190567
0.7109	Intermediate Similarity	NPC150863
0.709	Intermediate Similarity	NPC207554
0.7087	Intermediate Similarity	NPC322433
0.7077	Intermediate Similarity	NPC207428
0.7059	Intermediate Similarity	NPC145053
0.7054	Intermediate Similarity	NPC314431
0.7054	Intermediate Similarity	NPC280807
0.705	Intermediate Similarity	NPC237649
0.705	Intermediate Similarity	NPC300596
0.7037	Intermediate Similarity	NPC471574
0.7037	Intermediate Similarity	NPC43477
0.7009	Intermediate Similarity	NPC176858
0.7007	Intermediate Similarity	NPC470822
0.6961	Remote Similarity	NPC71664
0.6944	Remote Similarity	NPC191444
0.694	Remote Similarity	NPC159722
0.6906	Remote Similarity	NPC259678
0.6893	Remote Similarity	NPC273033
0.6893	Remote Similarity	NPC12936
0.6889	Remote Similarity	NPC83214
0.6875	Remote Similarity	NPC205946
0.6861	Remote Similarity	NPC472241
0.6853	Remote Similarity	NPC295021
0.6852	Remote Similarity	NPC173991
0.6838	Remote Similarity	NPC472243
0.6815	Remote Similarity	NPC122553
0.6794	Remote Similarity	NPC187231
0.6786	Remote Similarity	NPC470579
0.6768	Remote Similarity	NPC285679
0.6767	Remote Similarity	NPC130655
0.6762	Remote Similarity	NPC273758
0.6761	Remote Similarity	NPC144691
0.6761	Remote Similarity	NPC241392
0.6752	Remote Similarity	NPC167336
0.6744	Remote Similarity	NPC474926
0.6731	Remote Similarity	NPC73978
0.6729	Remote Similarity	NPC307
0.6729	Remote Similarity	NPC160339
0.6714	Remote Similarity	NPC472242
0.6691	Remote Similarity	NPC43218
0.6667	Remote Similarity	NPC113099
0.6667	Remote Similarity	NPC74458
0.6667	Remote Similarity	NPC43945
0.6667	Remote Similarity	NPC69057
0.6643	Remote Similarity	NPC13526
0.6642	Remote Similarity	NPC319645
0.6617	Remote Similarity	NPC314098
0.6609	Remote Similarity	NPC75496
0.6606	Remote Similarity	NPC157778
0.6604	Remote Similarity	NPC215008
0.6604	Remote Similarity	NPC197581
0.6604	Remote Similarity	NPC39600
0.6604	Remote Similarity	NPC324624
0.66	Remote Similarity	NPC115232
0.6591	Remote Similarity	NPC313722
0.6579	Remote Similarity	NPC472788
0.6577	Remote Similarity	NPC214106
0.6575	Remote Similarity	NPC114808
0.6571	Remote Similarity	NPC100039
0.6566	Remote Similarity	NPC271732
0.6552	Remote Similarity	NPC117032
0.6549	Remote Similarity	NPC324445
0.6538	Remote Similarity	NPC151405
0.6538	Remote Similarity	NPC139901
0.6533	Remote Similarity	NPC113056
0.6533	Remote Similarity	NPC138293
0.6505	Remote Similarity	NPC98269
0.6505	Remote Similarity	NPC325662
0.65	Remote Similarity	NPC55529
0.65	Remote Similarity	NPC37584
0.6486	Remote Similarity	NPC277277
0.6486	Remote Similarity	NPC173413
0.6481	Remote Similarity	NPC252067
0.6476	Remote Similarity	NPC95868
0.6476	Remote Similarity	NPC17408
0.6476	Remote Similarity	NPC285716
0.6475	Remote Similarity	NPC315051
0.6475	Remote Similarity	NPC242933
0.6471	Remote Similarity	NPC472118
0.6471	Remote Similarity	NPC301874
0.6465	Remote Similarity	NPC98880
0.6462	Remote Similarity	NPC2982
0.6455	Remote Similarity	NPC473345
0.6455	Remote Similarity	NPC267262
0.6454	Remote Similarity	NPC478040
0.6449	Remote Similarity	NPC316574
0.6443	Remote Similarity	NPC154478
0.6442	Remote Similarity	NPC137847
0.6442	Remote Similarity	NPC76455
0.6441	Remote Similarity	NPC202613
0.6441	Remote Similarity	NPC178681
0.6439	Remote Similarity	NPC314278
0.6429	Remote Similarity	NPC284475
0.6429	Remote Similarity	NPC133461
0.6424	Remote Similarity	NPC189116
0.6419	Remote Similarity	NPC84317
0.6415	Remote Similarity	NPC307456
0.6412	Remote Similarity	NPC317758
0.6408	Remote Similarity	NPC190945
0.6408	Remote Similarity	NPC78500
0.6408	Remote Similarity	NPC314186
0.64	Remote Similarity	NPC93653
0.64	Remote Similarity	NPC95289
0.6396	Remote Similarity	NPC113307
0.6396	Remote Similarity	NPC418308
0.6372	Remote Similarity	NPC155232
0.6372	Remote Similarity	NPC59677
0.6372	Remote Similarity	NPC153885
0.6372	Remote Similarity	NPC1682
0.6372	Remote Similarity	NPC188844
0.637	Remote Similarity	NPC314223
0.6364	Remote Similarity	NPC471943
0.6364	Remote Similarity	NPC79618
0.6364	Remote Similarity	NPC311343
0.6357	Remote Similarity	NPC314252
0.6357	Remote Similarity	NPC181526
0.6346	Remote Similarity	NPC329318
0.6339	Remote Similarity	NPC92689
0.6339	Remote Similarity	NPC19256
0.6325	Remote Similarity	NPC323726
0.6319	Remote Similarity	NPC478039
0.6316	Remote Similarity	NPC289883
0.6316	Remote Similarity	NPC204867
0.6316	Remote Similarity	NPC238219
0.6311	Remote Similarity	NPC302790
0.6306	Remote Similarity	NPC153308
0.6306	Remote Similarity	NPC151635
0.6303	Remote Similarity	NPC471317
0.6296	Remote Similarity	NPC15839
0.6296	Remote Similarity	NPC149263
0.6293	Remote Similarity	NPC122493
0.6293	Remote Similarity	NPC10781
0.6293	Remote Similarity	NPC293628
0.6291	Remote Similarity	NPC27904
0.629	Remote Similarity	NPC275410
0.6286	Remote Similarity	NPC103488
0.6282	Remote Similarity	NPC252572
0.6281	Remote Similarity	NPC473498
0.6275	Remote Similarity	NPC299582
0.627	Remote Similarity	NPC470550
0.627	Remote Similarity	NPC205652
0.6268	Remote Similarity	NPC301702

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 NPC172170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1057
0.2-0.3	832
0.3-0.4	2678
0.4-0.5	3223
0.5-0.6	931
0.6-0.7	186
0.7-0.8	32
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
0.7984	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD486	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD1574	Approved
0.7787	Intermediate Similarity	NPD1593	Approved
0.7698	Intermediate Similarity	NPD1541	Approved
0.7623	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD441	Approved
0.754	Intermediate Similarity	NPD1190	Approved
0.7521	Intermediate Similarity	NPD1124	Approved
0.7521	Intermediate Similarity	NPD1079	Discontinued
0.7521	Intermediate Similarity	NPD1123	Approved
0.75	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1175	Approved
0.7422	Intermediate Similarity	NPD1527	Phase 2
0.7405	Intermediate Similarity	NPD1626	Approved
0.7368	Intermediate Similarity	NPD167	Phase 2
0.7368	Intermediate Similarity	NPD168	Phase 1
0.7364	Intermediate Similarity	NPD1531	Approved
0.7222	Intermediate Similarity	NPD9567	Approved
0.7222	Intermediate Similarity	NPD552	Approved
0.7222	Intermediate Similarity	NPD553	Approved
0.7209	Intermediate Similarity	NPD1919	Approved
0.7209	Intermediate Similarity	NPD1920	Approved
0.72	Intermediate Similarity	NPD9539	Approved
0.72	Intermediate Similarity	NPD9541	Approved
0.7197	Intermediate Similarity	NPD6342	Discontinued
0.7197	Intermediate Similarity	NPD1532	Approved
0.7188	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1625	Approved
0.7182	Intermediate Similarity	NPD1099	Approved
0.7182	Intermediate Similarity	NPD1100	Approved
0.7176	Intermediate Similarity	NPD2331	Discontinued
0.7154	Intermediate Similarity	NPD2949	Approved
0.7154	Intermediate Similarity	NPD9272	Approved
0.7154	Intermediate Similarity	NPD2950	Approved
0.7131	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1065	Approved
0.713	Intermediate Similarity	NPD1064	Approved
0.7122	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1781	Discontinued
0.7087	Intermediate Similarity	NPD9540	Approved
0.7059	Intermediate Similarity	NPD181	Approved
0.7	Intermediate Similarity	NPD1619	Phase 3
0.6985	Remote Similarity	NPD1189	Approved
0.6977	Remote Similarity	NPD4549	Discontinued
0.6957	Remote Similarity	NPD6017	Discontinued
0.6929	Remote Similarity	NPD4888	Discontinued
0.6923	Remote Similarity	NPD4042	Phase 2
0.6923	Remote Similarity	NPD4045	Phase 2
0.6912	Remote Similarity	NPD4461	Discontinued
0.6901	Remote Similarity	NPD1854	Approved
0.6894	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD942	Approved
0.6884	Remote Similarity	NPD5918	Discontinued
0.6866	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD476	Approved
0.6861	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6768	Approved
0.6788	Remote Similarity	NPD1222	Discontinued
0.6783	Remote Similarity	NPD2196	Discontinued
0.6783	Remote Similarity	NPD813	Approved
0.6783	Remote Similarity	NPD2648	Phase 3
0.6783	Remote Similarity	NPD2193	Phase 2
0.6765	Remote Similarity	NPD7254	Discontinued
0.6759	Remote Similarity	NPD2672	Discontinued
0.6752	Remote Similarity	NPD2197	Approved
0.6752	Remote Similarity	NPD2192	Approved
0.6744	Remote Similarity	NPD1036	Approved
0.6739	Remote Similarity	NPD6513	Approved
0.6739	Remote Similarity	NPD6512	Approved
0.6738	Remote Similarity	NPD7088	Discontinued
0.672	Remote Similarity	NPD922	Approved
0.6716	Remote Similarity	NPD1588	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1518	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1230	Approved
0.6693	Remote Similarity	NPD1517	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4942	Approved
0.6667	Remote Similarity	NPD853	Approved
0.6667	Remote Similarity	NPD1075	Approved
0.6667	Remote Similarity	NPD1108	Approved
0.6667	Remote Similarity	NPD650	Approved
0.6667	Remote Similarity	NPD1107	Approved
0.6667	Remote Similarity	NPD1073	Approved
0.6667	Remote Similarity	NPD1074	Approved
0.6667	Remote Similarity	NPD9477	Approved
0.6667	Remote Similarity	NPD2010	Phase 3
0.6667	Remote Similarity	NPD851	Approved
0.6667	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1109	Approved
0.6642	Remote Similarity	NPD3170	Approved
0.6642	Remote Similarity	NPD1110	Approved
0.6641	Remote Similarity	NPD1560	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD2171	Approved
0.6621	Remote Similarity	NPD2790	Discontinued
0.6613	Remote Similarity	NPD1323	Discontinued
0.661	Remote Similarity	NPD563	Approved
0.661	Remote Similarity	NPD564	Approved
0.661	Remote Similarity	NPD1677	Discontinued
0.6596	Remote Similarity	NPD5932	Phase 3
0.6596	Remote Similarity	NPD5931	Phase 3
0.6596	Remote Similarity	NPD5933	Phase 3
0.6562	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD678	Discontinued
0.6556	Remote Similarity	NPD4645	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3248	Phase 1
0.6549	Remote Similarity	NPD1524	Phase 1
0.6544	Remote Similarity	NPD1410	Phase 1
0.6531	Remote Similarity	NPD951	Approved
0.6531	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1208	Approved
0.6528	Remote Similarity	NPD1890	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD997	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3482	Approved
0.65	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2369	Discontinued
0.6458	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD979	Approved
0.6449	Remote Similarity	NPD9279	Approved
0.6446	Remote Similarity	NPD1342	Approved
0.6443	Remote Similarity	NPD33	Approved
0.6443	Remote Similarity	NPD4393	Approved
0.6429	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7609	Phase 3
0.6423	Remote Similarity	NPD9508	Approved
0.6423	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD1228	Phase 2
0.6419	Remote Similarity	NPD2836	Approved
0.6417	Remote Similarity	NPD990	Approved
0.6417	Remote Similarity	NPD993	Approved
0.6408	Remote Similarity	NPD2435	Approved
0.6408	Remote Similarity	NPD4043	Approved
0.6408	Remote Similarity	NPD4046	Approved
0.6408	Remote Similarity	NPD3481	Approved
0.6403	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2319	Discontinued
0.64	Remote Similarity	NPD1023	Approved
0.64	Remote Similarity	NPD1021	Approved
0.64	Remote Similarity	NPD1022	Approved
0.64	Remote Similarity	NPD1020	Approved
0.6387	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6566	Discontinued
0.6377	Remote Similarity	NPD1207	Approved
0.6377	Remote Similarity	NPD1206	Approved
0.6372	Remote Similarity	NPD7631	Approved
0.6364	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1210	Approved
0.6356	Remote Similarity	NPD1419	Approved
0.6356	Remote Similarity	NPD1417	Approved
0.6356	Remote Similarity	NPD708	Approved
0.6351	Remote Similarity	NPD7072	Phase 2
0.635	Remote Similarity	NPD5182	Approved
0.635	Remote Similarity	NPD5184	Approved
0.635	Remote Similarity	NPD5185	Approved
0.6349	Remote Similarity	NPD1025	Discontinued
0.6337	Remote Similarity	NPD294	Approved
0.6337	Remote Similarity	NPD292	Approved
0.6331	Remote Similarity	NPD2670	Approved
0.6327	Remote Similarity	NPD3399	Approved
0.6324	Remote Similarity	NPD9471	Clinical (unspecified phase)
0.632	Remote Similarity	NPD1680	Approved
0.632	Remote Similarity	NPD1681	Approved
0.632	Remote Similarity	NPD5181	Approved
0.632	Remote Similarity	NPD14	Approved
0.632	Remote Similarity	NPD731	Approved
0.632	Remote Similarity	NPD5179	Approved
0.632	Remote Similarity	NPD5180	Approved
0.632	Remote Similarity	NPD1682	Approved
0.6319	Remote Similarity	NPD4041	Approved
0.6312	Remote Similarity	NPD9274	Approved
0.6312	Remote Similarity	NPD9275	Approved
0.6312	Remote Similarity	NPD9276	Approved
0.6312	Remote Similarity	NPD9278	Suspended
0.6308	Remote Similarity	NPD9692	Approved
0.6308	Remote Similarity	NPD9693	Approved
0.6303	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2037	Approved
0.6293	Remote Similarity	NPD9566	Approved
0.6293	Remote Similarity	NPD4657	Approved
0.6293	Remote Similarity	NPD4655	Approved
0.629	Remote Similarity	NPD3001	Approved
0.629	Remote Similarity	NPD2038	Approved
0.629	Remote Similarity	NPD2999	Approved
0.629	Remote Similarity	NPD2039	Approved
0.6286	Remote Similarity	NPD7142	Discontinued
0.6284	Remote Similarity	NPD2360	Approved
0.6279	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD1801	Approved
0.6276	Remote Similarity	NPD1802	Approved
0.6268	Remote Similarity	NPD2365	Approved
0.6268	Remote Similarity	NPD2923	Approved
0.6268	Remote Similarity	NPD75	Approved
0.6268	Remote Similarity	NPD9277	Approved
0.6261	Remote Similarity	NPD4094	Approved
0.626	Remote Similarity	NPD1539	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