NPASS Compound

Structure

CID279385 OpenBabel06191716082D 22 23 0 0 0 0 0 0 0 0999 V2000 -4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 13 1 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 19 2 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.22
Volume:	343.968
LogP:	6.411
LogD:	4.366
LogS:	-4.175
# Rotatable Bonds:	10
TPSA:	32.86
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	2.035
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.898
MDCK Permeability:	1.1550710951269139e-05
Pgp-inhibitor:	0.924
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.747
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	98.64769744873047%
Volume Distribution (VD):	3.051
Pgp-substrate:	1.1581614017486572%

ADMET: Metabolism

CYP1A2-inhibitor:	0.661
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.648
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.313
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.553
CYP2D6-substrate:	0.641
CYP3A4-inhibitor:	0.43
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	3.407
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.342
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.243
AMES Toxicity:	0.142
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.497
Skin Sensitization:	0.955
Carcinogencity:	0.094
Eye Corrosion:	0.066
Eye Irritation:	0.981
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC279385

Natural Product ID:	NPC279385
*Common Name:**	2-Undecyl-1H-Quinolin-4-One
IUPAC Name:	2-undecyl-1H-quinolin-4-one
Synonyms:
Standard InCHIKey:	KKSIGOUTTVXAKQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H29NO/c1-2-3-4-5-6-7-8-9-10-13-17-16-20(22)18-14-11-12-15-19(18)21-17/h11-12,14-16H,2-10,13H2,1H3,(H,21,22)
SMILES:	CCCCCCCCCCCc1cc(=O)c2ccccc2[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2042447
PubChem CID:	10063343
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO30823	Evodia rutaecarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30823	Evodia rutaecarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
IC50	2
Others	1

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT469	Individual Protein	Cathepsin L	Homo sapiens	IC50	=	2900.0	nM	PMID[470677]
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	IC50	=	9900.0	nM	PMID[470677]
NPT2	Others	Unspecified		Ratio IC50	=	0.3	n.a.	PMID[470677]

☑ 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 NPC279385 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	441
0.1-0.2	4553
0.2-0.3	13594
0.3-0.4	16676
0.4-0.5	3496
0.5-0.6	2117
0.6-0.7	1455
0.7-0.8	328
0.8-0.85	17
0.85-0.9	4
0.9-0.95	10
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC179605
0.9912	High Similarity	NPC103292
0.9391	High Similarity	NPC291962
0.9391	High Similarity	NPC177684
0.931	High Similarity	NPC161956
0.931	High Similarity	NPC258531
0.931	High Similarity	NPC112373
0.9153	High Similarity	NPC39818
0.9068	High Similarity	NPC257490
0.8992	High Similarity	NPC268534
0.8839	High Similarity	NPC172170
0.871	High Similarity	NPC209389
0.864	High Similarity	NPC194562
0.8607	High Similarity	NPC254698
0.8387	Intermediate Similarity	NPC192533
0.8134	Intermediate Similarity	NPC471164
0.813	Intermediate Similarity	NPC226143
0.7956	Intermediate Similarity	NPC136002
0.7955	Intermediate Similarity	NPC316104
0.7955	Intermediate Similarity	NPC162417
0.7895	Intermediate Similarity	NPC300299
0.7868	Intermediate Similarity	NPC2823
0.7826	Intermediate Similarity	NPC130797
0.7737	Intermediate Similarity	NPC471574
0.7727	Intermediate Similarity	NPC316746
0.7721	Intermediate Similarity	NPC83214
0.7687	Intermediate Similarity	NPC253476
0.7664	Intermediate Similarity	NPC207554
0.7652	Intermediate Similarity	NPC472245
0.7642	Intermediate Similarity	NPC57051
0.7639	Intermediate Similarity	NPC295021
0.763	Intermediate Similarity	NPC173295
0.7615	Intermediate Similarity	NPC470343
0.7615	Intermediate Similarity	NPC472244
0.7606	Intermediate Similarity	NPC237649
0.7606	Intermediate Similarity	NPC300596
0.7448	Intermediate Similarity	NPC117032
0.7444	Intermediate Similarity	NPC150863
0.7444	Intermediate Similarity	NPC122235
0.7431	Intermediate Similarity	NPC144691
0.7407	Intermediate Similarity	NPC40364
0.7388	Intermediate Similarity	NPC280807
0.7388	Intermediate Similarity	NPC477432
0.7388	Intermediate Similarity	NPC314431
0.7368	Intermediate Similarity	NPC72473
0.7368	Intermediate Similarity	NPC58827
0.7368	Intermediate Similarity	NPC307437
0.7357	Intermediate Similarity	NPC43477
0.7333	Intermediate Similarity	NPC38262
0.731	Intermediate Similarity	NPC13526
0.7305	Intermediate Similarity	NPC472241
0.7279	Intermediate Similarity	NPC207428
0.7273	Intermediate Similarity	NPC226794
0.7234	Intermediate Similarity	NPC316202
0.7203	Intermediate Similarity	NPC470822
0.7163	Intermediate Similarity	NPC472243
0.7153	Intermediate Similarity	NPC472242
0.7099	Intermediate Similarity	NPC130931
0.7097	Intermediate Similarity	NPC472118
0.7097	Intermediate Similarity	NPC471943
0.7059	Intermediate Similarity	NPC113056
0.7059	Intermediate Similarity	NPC138293
0.7042	Intermediate Similarity	NPC315051
0.7039	Intermediate Similarity	NPC93653
0.7039	Intermediate Similarity	NPC27904
0.7037	Intermediate Similarity	NPC322433
0.7016	Intermediate Similarity	NPC79618
0.7014	Intermediate Similarity	NPC314287
0.7013	Intermediate Similarity	NPC115232
0.7009	Intermediate Similarity	NPC291070
0.7009	Intermediate Similarity	NPC246757
0.7007	Intermediate Similarity	NPC187231
0.6993	Remote Similarity	NPC293458
0.6943	Remote Similarity	NPC292265
0.6923	Remote Similarity	NPC130251
0.6923	Remote Similarity	NPC242933
0.6906	Remote Similarity	NPC53044
0.6903	Remote Similarity	NPC299582
0.6897	Remote Similarity	NPC308197
0.6894	Remote Similarity	NPC283810
0.6883	Remote Similarity	NPC214106
0.6875	Remote Similarity	NPC301760
0.6863	Remote Similarity	NPC154478
0.686	Remote Similarity	NPC75496
0.6855	Remote Similarity	NPC167336
0.6842	Remote Similarity	NPC84317
0.6835	Remote Similarity	NPC318183
0.6825	Remote Similarity	NPC302790
0.6822	Remote Similarity	NPC314141
0.6813	Remote Similarity	NPC471743
0.68	Remote Similarity	NPC314223
0.68	Remote Similarity	NPC473498
0.6797	Remote Similarity	NPC123241
0.6781	Remote Similarity	NPC478040
0.6779	Remote Similarity	NPC242000
0.6757	Remote Similarity	NPC324445
0.6752	Remote Similarity	NPC214960
0.6752	Remote Similarity	NPC279527
0.6746	Remote Similarity	NPC434
0.6742	Remote Similarity	NPC313449
0.6736	Remote Similarity	NPC469560
0.6735	Remote Similarity	NPC190945
0.6735	Remote Similarity	NPC314186
0.6733	Remote Similarity	NPC473329
0.6728	Remote Similarity	NPC475094
0.6727	Remote Similarity	NPC49184
0.6715	Remote Similarity	NPC474926
0.6714	Remote Similarity	NPC314098
0.6708	Remote Similarity	NPC475607
0.6708	Remote Similarity	NPC151635
0.6707	Remote Similarity	NPC470317
0.6687	Remote Similarity	NPC252572
0.6667	Remote Similarity	NPC122553
0.6667	Remote Similarity	NPC250476
0.6667	Remote Similarity	NPC284775
0.6667	Remote Similarity	NPC469741
0.6667	Remote Similarity	NPC474081
0.6646	Remote Similarity	NPC475594
0.6646	Remote Similarity	NPC472163
0.6644	Remote Similarity	NPC478039
0.6644	Remote Similarity	NPC470579
0.6641	Remote Similarity	NPC113099
0.6624	Remote Similarity	NPC204867
0.6621	Remote Similarity	NPC181527
0.6613	Remote Similarity	NPC291610
0.661	Remote Similarity	NPC78154
0.6609	Remote Similarity	NPC229477
0.6606	Remote Similarity	NPC117027
0.6604	Remote Similarity	NPC223595
0.6604	Remote Similarity	NPC167724
0.6604	Remote Similarity	NPC224970
0.6597	Remote Similarity	NPC471123
0.6596	Remote Similarity	NPC231382
0.6585	Remote Similarity	NPC85613
0.6585	Remote Similarity	NPC88110
0.6584	Remote Similarity	NPC177261
0.6582	Remote Similarity	NPC471130
0.6581	Remote Similarity	NPC111233
0.6581	Remote Similarity	NPC61013
0.6581	Remote Similarity	NPC76982
0.6567	Remote Similarity	NPC229353
0.6561	Remote Similarity	NPC88970
0.6554	Remote Similarity	NPC469537
0.6552	Remote Similarity	NPC287358
0.6543	Remote Similarity	NPC469529
0.6541	Remote Similarity	NPC182131
0.6538	Remote Similarity	NPC36495
0.6538	Remote Similarity	NPC193410
0.6533	Remote Similarity	NPC467188
0.6524	Remote Similarity	NPC474041
0.6524	Remote Similarity	NPC475761
0.6519	Remote Similarity	NPC189116
0.6509	Remote Similarity	NPC473666
0.6508	Remote Similarity	NPC275467
0.65	Remote Similarity	NPC108800
0.6497	Remote Similarity	NPC309531
0.6497	Remote Similarity	NPC248117
0.6497	Remote Similarity	NPC472102
0.6496	Remote Similarity	NPC262295
0.6494	Remote Similarity	NPC251391
0.6493	Remote Similarity	NPC192209
0.6485	Remote Similarity	NPC5167
0.6485	Remote Similarity	NPC475685
0.6478	Remote Similarity	NPC42372
0.6471	Remote Similarity	NPC313293
0.6471	Remote Similarity	NPC150323
0.6471	Remote Similarity	NPC324091
0.6467	Remote Similarity	NPC477003
0.6467	Remote Similarity	NPC21429
0.6466	Remote Similarity	NPC288232
0.6456	Remote Similarity	NPC257763
0.6454	Remote Similarity	NPC313722
0.6452	Remote Similarity	NPC114808
0.6447	Remote Similarity	NPC105811
0.6446	Remote Similarity	NPC191415
0.6444	Remote Similarity	NPC228515
0.6442	Remote Similarity	NPC293216
0.6441	Remote Similarity	NPC30445
0.6439	Remote Similarity	NPC187036
0.6439	Remote Similarity	NPC296163
0.6435	Remote Similarity	NPC134825
0.6434	Remote Similarity	NPC476687
0.6434	Remote Similarity	NPC476689
0.6434	Remote Similarity	NPC476685
0.6429	Remote Similarity	NPC70406
0.6429	Remote Similarity	NPC2785
0.6429	Remote Similarity	NPC133003
0.6429	Remote Similarity	NPC285470
0.6429	Remote Similarity	NPC474430
0.6429	Remote Similarity	NPC476341
0.6429	Remote Similarity	NPC36342
0.6429	Remote Similarity	NPC119326
0.6424	Remote Similarity	NPC259678
0.6423	Remote Similarity	NPC475915
0.642	Remote Similarity	NPC355
0.642	Remote Similarity	NPC6982
0.6415	Remote Similarity	NPC265100
0.6412	Remote Similarity	NPC275410
0.64	Remote Similarity	NPC326792
0.6395	Remote Similarity	NPC319645

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 NPC279385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	744
0.2-0.3	890
0.3-0.4	1858
0.4-0.5	2558
0.5-0.6	2040
0.6-0.7	687
0.7-0.8	70
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8425	Intermediate Similarity	NPD486	Clinical (unspecified phase)
0.824	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1541	Approved
0.8015	Intermediate Similarity	NPD441	Approved
0.7939	Intermediate Similarity	NPD1919	Approved
0.7939	Intermediate Similarity	NPD1920	Approved
0.7923	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6342	Discontinued
0.7903	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1626	Approved
0.7787	Intermediate Similarity	NPD1175	Approved
0.777	Intermediate Similarity	NPD6017	Discontinued
0.7761	Intermediate Similarity	NPD2331	Discontinued
0.7744	Intermediate Similarity	NPD1527	Phase 2
0.7744	Intermediate Similarity	NPD2949	Approved
0.7744	Intermediate Similarity	NPD2950	Approved
0.7676	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1625	Approved
0.7612	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4888	Discontinued
0.7586	Intermediate Similarity	NPD4045	Phase 2
0.7586	Intermediate Similarity	NPD4042	Phase 2
0.7578	Intermediate Similarity	NPD1124	Approved
0.7578	Intermediate Similarity	NPD1079	Discontinued
0.7578	Intermediate Similarity	NPD1123	Approved
0.7571	Intermediate Similarity	NPD5918	Discontinued
0.7559	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6768	Approved
0.75	Intermediate Similarity	NPD1065	Approved
0.75	Intermediate Similarity	NPD1064	Approved
0.7481	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1619	Phase 3
0.7448	Intermediate Similarity	NPD1854	Approved
0.7448	Intermediate Similarity	NPD3248	Phase 1
0.7429	Intermediate Similarity	NPD1189	Approved
0.7424	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2470	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6513	Approved
0.7305	Intermediate Similarity	NPD6512	Approved
0.7279	Intermediate Similarity	NPD2790	Discontinued
0.7252	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1574	Approved
0.7213	Intermediate Similarity	NPD990	Approved
0.7213	Intermediate Similarity	NPD993	Approved
0.7194	Intermediate Similarity	NPD5227	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4645	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1781	Discontinued
0.7185	Intermediate Similarity	NPD4549	Discontinued
0.7176	Intermediate Similarity	NPD678	Discontinued
0.7164	Intermediate Similarity	NPD1593	Approved
0.7153	Intermediate Similarity	NPD5933	Phase 3
0.7153	Intermediate Similarity	NPD5932	Phase 3
0.7153	Intermediate Similarity	NPD5931	Phase 3
0.7143	Intermediate Similarity	NPD2037	Approved
0.7143	Intermediate Similarity	NPD9541	Approved
0.7143	Intermediate Similarity	NPD1230	Approved
0.7143	Intermediate Similarity	NPD9539	Approved
0.7123	Intermediate Similarity	NPD4942	Approved
0.7113	Intermediate Similarity	NPD1222	Discontinued
0.7113	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2369	Discontinued
0.7086	Intermediate Similarity	NPD33	Approved
0.7086	Intermediate Similarity	NPD4393	Approved
0.7077	Intermediate Similarity	NPD922	Approved
0.7067	Intermediate Similarity	NPD2836	Approved
0.7063	Intermediate Similarity	NPD3001	Approved
0.7063	Intermediate Similarity	NPD3482	Approved
0.7063	Intermediate Similarity	NPD2999	Approved
0.7037	Intermediate Similarity	NPD9540	Approved
0.7025	Intermediate Similarity	NPD708	Approved
0.7021	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4330	Approved
0.7	Intermediate Similarity	NPD4329	Approved
0.7	Intermediate Similarity	NPD7072	Phase 2
0.6993	Remote Similarity	NPD4461	Discontinued
0.6981	Remote Similarity	NPD3792	Approved
0.6975	Remote Similarity	NPD1099	Approved
0.6975	Remote Similarity	NPD1100	Approved
0.6972	Remote Similarity	NPD7254	Discontinued
0.6966	Remote Similarity	NPD3481	Approved
0.6966	Remote Similarity	NPD4046	Approved
0.6966	Remote Similarity	NPD4043	Approved
0.6957	Remote Similarity	NPD1190	Approved
0.6954	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1208	Approved
0.6953	Remote Similarity	NPD5180	Approved
0.6953	Remote Similarity	NPD5179	Approved
0.6953	Remote Similarity	NPD5181	Approved
0.6944	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6566	Discontinued
0.6943	Remote Similarity	NPD2432	Approved
0.6943	Remote Similarity	NPD2431	Approved
0.6939	Remote Similarity	NPD7088	Discontinued
0.6937	Remote Similarity	NPD3782	Discontinued
0.6928	Remote Similarity	NPD2506	Approved
0.6923	Remote Similarity	NPD2455	Approved
0.6923	Remote Similarity	NPD2454	Approved
0.6917	Remote Similarity	NPD1517	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6358	Phase 2
0.6897	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4161	Discontinued
0.6892	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2648	Phase 3
0.6885	Remote Similarity	NPD2193	Phase 2
0.6879	Remote Similarity	NPD1410	Phase 1
0.6879	Remote Similarity	NPD1228	Phase 2
0.6875	Remote Similarity	NPD2010	Phase 3
0.6861	Remote Similarity	NPD1560	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1323	Discontinued
0.6846	Remote Similarity	NPD5748	Phase 2
0.6831	Remote Similarity	NPD1206	Approved
0.6831	Remote Similarity	NPD1207	Approved
0.6825	Remote Similarity	NPD1342	Approved
0.6822	Remote Similarity	NPD3387	Approved
0.6821	Remote Similarity	NPD5086	Approved
0.6809	Remote Similarity	NPD1531	Approved
0.68	Remote Similarity	NPD3545	Approved
0.68	Remote Similarity	NPD3546	Approved
0.6781	Remote Similarity	NPD2820	Phase 3
0.6779	Remote Similarity	NPD7528	Approved
0.6774	Remote Similarity	NPD1210	Approved
0.6769	Remote Similarity	NPD853	Approved
0.6769	Remote Similarity	NPD2319	Discontinued
0.6769	Remote Similarity	NPD851	Approved
0.6763	Remote Similarity	NPD5131	Approved
0.6761	Remote Similarity	NPD2791	Discontinued
0.6757	Remote Similarity	NPD1524	Phase 1
0.6753	Remote Similarity	NPD2427	Approved
0.6748	Remote Similarity	NPD813	Approved
0.6748	Remote Similarity	NPD3471	Approved
0.6748	Remote Similarity	NPD2171	Approved
0.6748	Remote Similarity	NPD3470	Approved
0.6748	Remote Similarity	NPD2196	Discontinued
0.6746	Remote Similarity	NPD4115	Approved
0.6746	Remote Similarity	NPD4114	Approved
0.6742	Remote Similarity	NPD7481	Approved
0.6742	Remote Similarity	NPD7480	Approved
0.6735	Remote Similarity	NPD2435	Approved
0.6732	Remote Similarity	NPD951	Approved
0.672	Remote Similarity	NPD2197	Approved
0.672	Remote Similarity	NPD2192	Approved
0.6715	Remote Similarity	NPD1036	Approved
0.6714	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD168	Phase 1
0.6712	Remote Similarity	NPD2365	Approved
0.6712	Remote Similarity	NPD167	Phase 2
0.6711	Remote Similarity	NPD1802	Approved
0.6711	Remote Similarity	NPD1801	Approved
0.6709	Remote Similarity	NPD2404	Discontinued
0.6708	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1209	Approved
0.669	Remote Similarity	NPD1205	Approved
0.6667	Remote Similarity	NPD5024	Approved
0.6667	Remote Similarity	NPD5186	Approved
0.6667	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD979	Approved
0.6667	Remote Similarity	NPD3865	Approved
0.6667	Remote Similarity	NPD1532	Approved
0.6667	Remote Similarity	NPD5183	Approved
0.6667	Remote Similarity	NPD2670	Approved
0.6645	Remote Similarity	NPD3399	Approved
0.6644	Remote Similarity	NPD4041	Approved
0.6641	Remote Similarity	NPD1073	Approved
0.6641	Remote Similarity	NPD1539	Approved
0.6641	Remote Similarity	NPD1107	Approved
0.6641	Remote Similarity	NPD1108	Approved
0.6641	Remote Similarity	NPD1075	Approved
0.6641	Remote Similarity	NPD4116	Approved
0.6641	Remote Similarity	NPD1074	Approved
0.6621	Remote Similarity	NPD3170	Approved
0.6621	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4734	Approved
0.6613	Remote Similarity	NPD4735	Approved
0.6604	Remote Similarity	NPD2413	Phase 2
0.6604	Remote Similarity	NPD3468	Approved
0.6604	Remote Similarity	NPD5921	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2923	Approved
0.6596	Remote Similarity	NPD1070	Approved
0.6596	Remote Similarity	NPD2754	Discontinued
0.6596	Remote Similarity	NPD1069	Approved
0.6585	Remote Similarity	NPD2481	Approved
0.6585	Remote Similarity	NPD2479	Phase 3
0.6571	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1360	Approved
0.6566	Remote Similarity	NPD4412	Phase 2
0.6556	Remote Similarity	NPD5941	Approved
0.6556	Remote Similarity	NPD5942	Approved
0.6554	Remote Similarity	NPD4430	Phase 2
0.6547	Remote Similarity	NPD552	Approved
0.6547	Remote Similarity	NPD9567	Approved
0.6547	Remote Similarity	NPD553	Approved
0.6543	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2039	Approved
0.6538	Remote Similarity	NPD2038	Approved
0.6533	Remote Similarity	NPD4607	Approved
0.6531	Remote Similarity	NPD3625	Discontinued

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