NPASS Compound

Structure

CID258531 OpenBabel06191716062D 27 28 0 0 0 0 0 0 0 0999 V2000 -6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 3 1 0 0 0 0 2 26 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 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 18 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 20 24 2 0 0 0 0 21 22 2 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 27 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.3
Volume:	430.448
LogP:	8.461
LogD:	4.583
LogS:	-6.86
# Rotatable Bonds:	14
TPSA:	22.0
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	2.167
Fsp3:	0.64
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:	-4.861
MDCK Permeability:	8.6194140749285e-06
Pgp-inhibitor:	0.184
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.604
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	98.50736236572266%
Volume Distribution (VD):	2.932
Pgp-substrate:	0.5293500423431396%

ADMET: Metabolism

CYP1A2-inhibitor:	0.171
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.392
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.24
CYP2D6-substrate:	0.579
CYP3A4-inhibitor:	0.285
CYP3A4-substrate:	0.086

ADMET: Excretion

Clearance (CL):	4.314
Half-life (T1/2):	0.032

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.283
AMES Toxicity:	0.584
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.359
Skin Sensitization:	0.96
Carcinogencity:	0.057
Eye Corrosion:	0.016
Eye Irritation:	0.973
Respiratory Toxicity:	0.546

Download Data

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

Natural Product: NPC258531

Natural Product ID:	NPC258531
*Common Name:**	1-Methyl-2-Pentadecylquinolin-4-One
IUPAC Name:	1-methyl-2-pentadecylquinolin-4-one
Synonyms:
Standard InCHIKey:	YOXIQBPUPGISEN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H39NO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-22-21-25(27)23-19-16-17-20-24(23)26(22)2/h16-17,19-21H,3-15,18H2,1-2H3
SMILES:	CCCCCCCCCCCCCCCc1cc(=O)c2ccccc2n1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1643844
PubChem CID:	5319753
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
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO30823	Evodia rutaecarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30823	Evodia rutaecarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
MIC	1
Others	2

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	Activity	=	57.9	%	PMID[536071]
NPT171	Cell Line	MRC5	Homo sapiens	Activity	=	79.8	%	PMID[536071]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	346900.0	nM	PMID[536071]

☑ 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 NPC258531 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	434
0.1-0.2	3918
0.2-0.3	13493
0.3-0.4	16738
0.4-0.5	4020
0.5-0.6	2379
0.6-0.7	1426
0.7-0.8	261
0.8-0.85	12
0.85-0.9	2
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC112373
1.0	High Similarity	NPC161956
0.9911	High Similarity	NPC177684
0.9911	High Similarity	NPC291962
0.9565	High Similarity	NPC257490
0.9397	High Similarity	NPC103292
0.9316	High Similarity	NPC39818
0.931	High Similarity	NPC279385
0.931	High Similarity	NPC179605
0.8583	High Similarity	NPC226143
0.8374	Intermediate Similarity	NPC268534
0.8348	Intermediate Similarity	NPC172170
0.8308	Intermediate Similarity	NPC300299
0.8134	Intermediate Similarity	NPC471574
0.8125	Intermediate Similarity	NPC209389
0.8083	Intermediate Similarity	NPC57051
0.8062	Intermediate Similarity	NPC194562
0.8031	Intermediate Similarity	NPC470343
0.8031	Intermediate Similarity	NPC472244
0.8016	Intermediate Similarity	NPC254698
0.8	Intermediate Similarity	NPC471164
0.7956	Intermediate Similarity	NPC136002
0.7852	Intermediate Similarity	NPC83214
0.7846	Intermediate Similarity	NPC150863
0.782	Intermediate Similarity	NPC162417
0.782	Intermediate Similarity	NPC316104
0.7812	Intermediate Similarity	NPC192533
0.7801	Intermediate Similarity	NPC144691
0.7794	Intermediate Similarity	NPC207554
0.7786	Intermediate Similarity	NPC472245
0.7786	Intermediate Similarity	NPC314431
0.7786	Intermediate Similarity	NPC280807
0.7727	Intermediate Similarity	NPC316746
0.7669	Intermediate Similarity	NPC207428
0.7609	Intermediate Similarity	NPC2823
0.7448	Intermediate Similarity	NPC117032
0.7426	Intermediate Similarity	NPC253476
0.741	Intermediate Similarity	NPC315051
0.7407	Intermediate Similarity	NPC53044
0.7383	Intermediate Similarity	NPC27904
0.7383	Intermediate Similarity	NPC93653
0.7372	Intermediate Similarity	NPC173295
0.7324	Intermediate Similarity	NPC470822
0.7324	Intermediate Similarity	NPC130797
0.7286	Intermediate Similarity	NPC472243
0.7279	Intermediate Similarity	NPC295021
0.7273	Intermediate Similarity	NPC167336
0.7254	Intermediate Similarity	NPC308197
0.7237	Intermediate Similarity	NPC299582
0.7161	Intermediate Similarity	NPC318183
0.7133	Intermediate Similarity	NPC478040
0.7132	Intermediate Similarity	NPC187231
0.7123	Intermediate Similarity	NPC300596
0.7123	Intermediate Similarity	NPC237649
0.7123	Intermediate Similarity	NPC242000
0.7113	Intermediate Similarity	NPC43477
0.7113	Intermediate Similarity	NPC316202
0.7111	Intermediate Similarity	NPC58827
0.7111	Intermediate Similarity	NPC72473
0.7111	Intermediate Similarity	NPC307437
0.7103	Intermediate Similarity	NPC324445
0.7092	Intermediate Similarity	NPC469560
0.7083	Intermediate Similarity	NPC314186
0.708	Intermediate Similarity	NPC314098
0.7063	Intermediate Similarity	NPC472241
0.7059	Intermediate Similarity	NPC122235
0.7042	Intermediate Similarity	NPC130251
0.7037	Intermediate Similarity	NPC250476
0.7029	Intermediate Similarity	NPC40364
0.7025	Intermediate Similarity	NPC291610
0.7021	Intermediate Similarity	NPC122553
0.7014	Intermediate Similarity	NPC314287
0.7007	Intermediate Similarity	NPC477432
0.7	Intermediate Similarity	NPC75496
0.7	Intermediate Similarity	NPC313449
0.6993	Remote Similarity	NPC301760
0.6987	Remote Similarity	NPC472118
0.6986	Remote Similarity	NPC478039
0.6974	Remote Similarity	NPC154478
0.6957	Remote Similarity	NPC231382
0.6954	Remote Similarity	NPC84317
0.695	Remote Similarity	NPC471123
0.6948	Remote Similarity	NPC138293
0.6948	Remote Similarity	NPC113056
0.6948	Remote Similarity	NPC204867
0.6918	Remote Similarity	NPC472242
0.6911	Remote Similarity	NPC38262
0.6894	Remote Similarity	NPC85613
0.6889	Remote Similarity	NPC226794
0.6883	Remote Similarity	NPC293458
0.687	Remote Similarity	NPC192209
0.6855	Remote Similarity	NPC469529
0.6846	Remote Similarity	NPC288232
0.6846	Remote Similarity	NPC13526
0.6835	Remote Similarity	NPC292265
0.6822	Remote Similarity	NPC296163
0.6822	Remote Similarity	NPC187036
0.6818	Remote Similarity	NPC228515
0.6813	Remote Similarity	NPC471743
0.6813	Remote Similarity	NPC475607
0.6807	Remote Similarity	NPC256452
0.6795	Remote Similarity	NPC471130
0.679	Remote Similarity	NPC5167
0.6788	Remote Similarity	NPC322433
0.6774	Remote Similarity	NPC469741
0.6774	Remote Similarity	NPC88970
0.6772	Remote Similarity	NPC471943
0.677	Remote Similarity	NPC474081
0.6757	Remote Similarity	NPC470579
0.675	Remote Similarity	NPC475594
0.6746	Remote Similarity	NPC55529
0.673	Remote Similarity	NPC355
0.6723	Remote Similarity	NPC291070
0.6723	Remote Similarity	NPC246757
0.6716	Remote Similarity	NPC130931
0.6688	Remote Similarity	NPC123241
0.6667	Remote Similarity	NPC253667
0.6667	Remote Similarity	NPC326792
0.6667	Remote Similarity	NPC469537
0.6667	Remote Similarity	NPC35510
0.6646	Remote Similarity	NPC279527
0.6646	Remote Similarity	NPC214960
0.6643	Remote Similarity	NPC179224
0.6627	Remote Similarity	NPC476341
0.6626	Remote Similarity	NPC474041
0.6626	Remote Similarity	NPC475761
0.6626	Remote Similarity	NPC475094
0.6624	Remote Similarity	NPC265100
0.6624	Remote Similarity	NPC189116
0.6623	Remote Similarity	NPC473329
0.6614	Remote Similarity	NPC20322
0.661	Remote Similarity	NPC78154
0.6606	Remote Similarity	NPC470317
0.6604	Remote Similarity	NPC475248
0.6604	Remote Similarity	NPC63047
0.6603	Remote Similarity	NPC315368
0.6594	Remote Similarity	NPC79698
0.6593	Remote Similarity	NPC316582
0.6585	Remote Similarity	NPC475685
0.6585	Remote Similarity	NPC73994
0.6582	Remote Similarity	NPC115232
0.6581	Remote Similarity	NPC113946
0.6579	Remote Similarity	NPC314223
0.6579	Remote Similarity	NPC154602
0.6579	Remote Similarity	NPC243756
0.6564	Remote Similarity	NPC83774
0.6561	Remote Similarity	NPC242116
0.6561	Remote Similarity	NPC472117
0.6558	Remote Similarity	NPC114808
0.6543	Remote Similarity	NPC470548
0.6541	Remote Similarity	NPC114637
0.6536	Remote Similarity	NPC285381
0.6536	Remote Similarity	NPC122106
0.6531	Remote Similarity	NPC470301
0.6529	Remote Similarity	NPC1820
0.65	Remote Similarity	NPC476950
0.65	Remote Similarity	NPC167724
0.65	Remote Similarity	NPC70949
0.65	Remote Similarity	NPC223595
0.65	Remote Similarity	NPC224970
0.6486	Remote Similarity	NPC238499
0.6485	Remote Similarity	NPC283810
0.6485	Remote Similarity	NPC61011
0.6485	Remote Similarity	NPC298320
0.6484	Remote Similarity	NPC79618
0.6474	Remote Similarity	NPC61013
0.6474	Remote Similarity	NPC104345
0.6471	Remote Similarity	NPC313293
0.6471	Remote Similarity	NPC66936
0.6463	Remote Similarity	NPC284775
0.6463	Remote Similarity	NPC242933
0.6456	Remote Similarity	NPC476231
0.6456	Remote Similarity	NPC214106
0.6434	Remote Similarity	NPC164802
0.6433	Remote Similarity	NPC193410
0.6433	Remote Similarity	NPC36495
0.6429	Remote Similarity	NPC2785
0.6429	Remote Similarity	NPC285470
0.6429	Remote Similarity	NPC70406
0.6429	Remote Similarity	NPC36342
0.6429	Remote Similarity	NPC202613
0.6424	Remote Similarity	NPC467188
0.6419	Remote Similarity	NPC22082
0.6419	Remote Similarity	NPC186284
0.6415	Remote Similarity	NPC313757
0.641	Remote Similarity	NPC29285
0.6395	Remote Similarity	NPC319645
0.6392	Remote Similarity	NPC248117
0.6392	Remote Similarity	NPC472102
0.6392	Remote Similarity	NPC309531
0.6392	Remote Similarity	NPC474058
0.6391	Remote Similarity	NPC472164
0.6391	Remote Similarity	NPC113099
0.6387	Remote Similarity	NPC281094
0.6387	Remote Similarity	NPC251391
0.6387	Remote Similarity	NPC478076
0.6372	Remote Similarity	NPC300205
0.6369	Remote Similarity	NPC46895
0.6369	Remote Similarity	NPC21429
0.6364	Remote Similarity	NPC126458

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 NPC258531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	679
0.2-0.3	912
0.3-0.4	1739
0.4-0.5	2609
0.5-0.6	2064
0.6-0.7	772
0.7-0.8	99
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD486	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD441	Approved
0.8347	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD6017	Discontinued
0.8154	Intermediate Similarity	NPD2949	Approved
0.8154	Intermediate Similarity	NPD2950	Approved
0.8154	Intermediate Similarity	NPD1527	Phase 2
0.8077	Intermediate Similarity	NPD1919	Approved
0.8077	Intermediate Similarity	NPD1920	Approved
0.7949	Intermediate Similarity	NPD1065	Approved
0.7949	Intermediate Similarity	NPD1064	Approved
0.791	Intermediate Similarity	NPD6342	Discontinued
0.7879	Intermediate Similarity	NPD1541	Approved
0.7879	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD1175	Approved
0.7681	Intermediate Similarity	NPD6513	Approved
0.7681	Intermediate Similarity	NPD6512	Approved
0.7674	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5931	Phase 3
0.7518	Intermediate Similarity	NPD5933	Phase 3
0.7518	Intermediate Similarity	NPD5932	Phase 3
0.7483	Intermediate Similarity	NPD4942	Approved
0.7466	Intermediate Similarity	NPD4042	Phase 2
0.7466	Intermediate Similarity	NPD4045	Phase 2
0.7458	Intermediate Similarity	NPD708	Approved
0.7448	Intermediate Similarity	NPD3248	Phase 1
0.7447	Intermediate Similarity	NPD5918	Discontinued
0.7442	Intermediate Similarity	NPD1124	Approved
0.7442	Intermediate Similarity	NPD1123	Approved
0.7429	Intermediate Similarity	NPD6768	Approved
0.7429	Intermediate Similarity	NPD3482	Approved
0.7422	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD1100	Approved
0.7414	Intermediate Similarity	NPD1099	Approved
0.7388	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5180	Approved
0.736	Intermediate Similarity	NPD5181	Approved
0.736	Intermediate Similarity	NPD5179	Approved
0.7338	Intermediate Similarity	NPD1626	Approved
0.7324	Intermediate Similarity	NPD3481	Approved
0.7324	Intermediate Similarity	NPD4043	Approved
0.7324	Intermediate Similarity	NPD4046	Approved
0.7311	Intermediate Similarity	NPD2193	Phase 2
0.7311	Intermediate Similarity	NPD2648	Phase 3
0.7305	Intermediate Similarity	NPD6566	Discontinued
0.7279	Intermediate Similarity	NPD2790	Discontinued
0.7267	Intermediate Similarity	NPD2506	Approved
0.7246	Intermediate Similarity	NPD1410	Phase 1
0.7246	Intermediate Similarity	NPD2331	Discontinued
0.7241	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3546	Approved
0.7213	Intermediate Similarity	NPD3545	Approved
0.7192	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD4549	Discontinued
0.7167	Intermediate Similarity	NPD813	Approved
0.7167	Intermediate Similarity	NPD2196	Discontinued
0.7167	Intermediate Similarity	NPD2171	Approved
0.7154	Intermediate Similarity	NPD4115	Approved
0.7154	Intermediate Similarity	NPD4114	Approved
0.7133	Intermediate Similarity	NPD2820	Phase 3
0.7133	Intermediate Similarity	NPD1625	Approved
0.7132	Intermediate Similarity	NPD5131	Approved
0.7131	Intermediate Similarity	NPD2197	Approved
0.7131	Intermediate Similarity	NPD2192	Approved
0.7123	Intermediate Similarity	NPD4888	Discontinued
0.7122	Intermediate Similarity	NPD2791	Discontinued
0.7113	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1342	Approved
0.7092	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7254	Discontinued
0.7086	Intermediate Similarity	NPD2427	Approved
0.7078	Intermediate Similarity	NPD4645	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5227	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2365	Approved
0.7063	Intermediate Similarity	NPD6414	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1781	Discontinued
0.7045	Intermediate Similarity	NPD1079	Discontinued
0.704	Intermediate Similarity	NPD4116	Approved
0.7032	Intermediate Similarity	NPD2037	Approved
0.7025	Intermediate Similarity	NPD4735	Approved
0.7025	Intermediate Similarity	NPD4734	Approved
0.7021	Intermediate Similarity	NPD2670	Approved
0.7	Intermediate Similarity	NPD7481	Approved
0.7	Intermediate Similarity	NPD7072	Phase 2
0.7	Intermediate Similarity	NPD7480	Approved
0.6993	Remote Similarity	NPD4461	Discontinued
0.6987	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1854	Approved
0.6974	Remote Similarity	NPD33	Approved
0.6974	Remote Similarity	NPD4393	Approved
0.6972	Remote Similarity	NPD7142	Discontinued
0.6963	Remote Similarity	NPD1574	Approved
0.6957	Remote Similarity	NPD2754	Discontinued
0.6957	Remote Similarity	NPD1619	Phase 3
0.6957	Remote Similarity	NPD1190	Approved
0.6954	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1189	Approved
0.694	Remote Similarity	NPD1360	Approved
0.6939	Remote Similarity	NPD7088	Discontinued
0.6937	Remote Similarity	NPD3782	Discontinued
0.6929	Remote Similarity	NPD3001	Approved
0.6929	Remote Similarity	NPD2999	Approved
0.6917	Remote Similarity	NPD678	Discontinued
0.6912	Remote Similarity	NPD1593	Approved
0.6911	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7633	Discontinued
0.6905	Remote Similarity	NPD3548	Approved
0.6901	Remote Similarity	NPD6358	Phase 2
0.6897	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4430	Phase 2
0.6897	Remote Similarity	NPD7082	Approved
0.6894	Remote Similarity	NPD4330	Approved
0.6894	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4329	Approved
0.6889	Remote Similarity	NPD9541	Approved
0.6889	Remote Similarity	NPD9539	Approved
0.688	Remote Similarity	NPD5253	Approved
0.6879	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2369	Discontinued
0.6875	Remote Similarity	NPD1222	Discontinued
0.6875	Remote Similarity	NPD2010	Phase 3
0.6875	Remote Similarity	NPD3792	Approved
0.6871	Remote Similarity	NPD8241	Phase 2
0.6855	Remote Similarity	NPD1677	Discontinued
0.6849	Remote Similarity	NPD7487	Discontinued
0.6849	Remote Similarity	NPD7259	Approved
0.6846	Remote Similarity	NPD5748	Phase 2
0.6835	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2431	Approved
0.6835	Remote Similarity	NPD2432	Approved
0.6822	Remote Similarity	NPD2913	Approved
0.6822	Remote Similarity	NPD3387	Approved
0.6822	Remote Similarity	NPD2914	Approved
0.6821	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2455	Approved
0.6815	Remote Similarity	NPD2454	Approved
0.6813	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7295	Approved
0.6797	Remote Similarity	NPD6019	Approved
0.6797	Remote Similarity	NPD5659	Approved
0.6797	Remote Similarity	NPD5660	Approved
0.6797	Remote Similarity	NPD6018	Approved
0.6794	Remote Similarity	NPD6070	Approved
0.6794	Remote Similarity	NPD6069	Approved
0.6791	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD9540	Approved
0.6788	Remote Similarity	NPD2840	Approved
0.6783	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1524	Phase 1
0.6753	Remote Similarity	NPD6629	Discontinued
0.6746	Remote Similarity	NPD6299	Approved
0.6746	Remote Similarity	NPD6300	Approved
0.6739	Remote Similarity	NPD5993	Phase 1
0.6732	Remote Similarity	NPD2351	Discontinued
0.6732	Remote Similarity	NPD951	Approved
0.6718	Remote Similarity	NPD1323	Discontinued
0.6711	Remote Similarity	NPD7478	Approved
0.6711	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5992	Approved
0.6709	Remote Similarity	NPD2404	Discontinued
0.6694	Remote Similarity	NPD4655	Approved
0.6694	Remote Similarity	NPD4657	Approved
0.6694	Remote Similarity	NPD3357	Discontinued
0.6693	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5657	Phase 3
0.6689	Remote Similarity	NPD1230	Approved
0.6687	Remote Similarity	NPD3377	Discontinued
0.6667	Remote Similarity	NPD3865	Approved
0.6667	Remote Similarity	NPD4094	Approved
0.6667	Remote Similarity	NPD979	Approved
0.6667	Remote Similarity	NPD990	Approved
0.6667	Remote Similarity	NPD479	Approved
0.6667	Remote Similarity	NPD7528	Approved
0.6667	Remote Similarity	NPD993	Approved
0.6647	Remote Similarity	NPD4988	Discontinued
0.6646	Remote Similarity	NPD3471	Approved
0.6646	Remote Similarity	NPD3422	Phase 3
0.6646	Remote Similarity	NPD3470	Approved
0.6646	Remote Similarity	NPD3423	Phase 2
0.6644	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5631	Phase 3
0.6624	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2836	Approved
0.6621	Remote Similarity	NPD3170	Approved
0.6614	Remote Similarity	NPD1054	Approved
0.6613	Remote Similarity	NPD6024	Approved
0.6613	Remote Similarity	NPD6027	Approved
0.66	Remote Similarity	NPD1801	Approved
0.66	Remote Similarity	NPD1802	Approved
0.6596	Remote Similarity	NPD1070	Approved
0.6596	Remote Similarity	NPD1069	Approved
0.6594	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7606	Phase 3
0.6573	Remote Similarity	NPD1531	Approved
0.6569	Remote Similarity	NPD3623	Clinical (unspecified phase)

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