NPASS Compound

Structure

NPC103292 OpenBabel07101719252D 27 28 0 0 0 0 0 0 0 0999 V2000 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 1.7321 -0.0000 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 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 2.5981 1.5000 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 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 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 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 23 2 0 0 0 0 15 24 2 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 22 1 0 0 0 0 21 22 2 0 0 0 0 21 26 1 0 0 0 0 22 25 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:	363.26
Volume:	422.538
LogP:	6.396
LogD:	4.739
LogS:	-2.897
# Rotatable Bonds:	8
TPSA:	32.86
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	2.754
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.925
MDCK Permeability:	1.789950329111889e-05
Pgp-inhibitor:	0.658
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.665
30% Bioavailability (F30%):	0.807

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	98.00948333740234%
Volume Distribution (VD):	1.464
Pgp-substrate:	1.1148713827133179%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.403
CYP2C19-inhibitor:	0.747
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.855
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.855
CYP2D6-substrate:	0.806
CYP3A4-inhibitor:	0.811
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	3.124
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.608
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.507
Skin Sensitization:	0.967
Carcinogencity:	0.025
Eye Corrosion:	0.013
Eye Irritation:	0.838
Respiratory Toxicity:	0.727

Download Data

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

Natural Product: NPC103292

Natural Product ID:	NPC103292
*Common Name:**	Aurachin D
IUPAC Name:	2-methyl-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-1H-quinolin-4-one
Synonyms:	Aurachin D
Standard InCHIKey:	JHMLNOXMSHURLQ-YEFHWUCQSA-N
Standard InCHI:	InChI=1S/C25H33NO/c1-18(2)10-8-11-19(3)12-9-13-20(4)16-17-22-21(5)26-24-15-7-6-14-23(24)25(22)27/h6-7,10,12,14-16H,8-9,11,13,17H2,1-5H3,(H,26,27)/b19-12+,20-16+
SMILES:	CC(=CCC/C(=C/CC/C(=C/Cc1c(C)[nH]c2ccccc2c1=O)/C)/C)C
Synthetic Gene Cluster:	BGC0001343;
ChEMBL Identifier:	CHEMBL573376
PubChem CID:	6124753
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33510	stigmatella sp.	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18922036]

☑ 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	4

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	1.3	ug.mL-1	PMID[486841]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.37	ug.mL-1	PMID[486841]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.25	ug.mL-1	PMID[486841]
NPT2	Others	Unspecified		IC50	=	18.0	ug.mL-1	PMID[486841]

☑ 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 NPC103292 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	432
0.1-0.2	4192
0.2-0.3	13796
0.3-0.4	16781
0.4-0.5	3564
0.5-0.6	2134
0.6-0.7	1448
0.7-0.8	317
0.8-0.85	14
0.85-0.9	4
0.9-0.95	9
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC179605
0.9912	High Similarity	NPC279385
0.9397	High Similarity	NPC112373
0.9397	High Similarity	NPC161956
0.9397	High Similarity	NPC258531
0.931	High Similarity	NPC177684
0.931	High Similarity	NPC291962
0.9237	High Similarity	NPC39818
0.8992	High Similarity	NPC257490
0.8917	High Similarity	NPC268534
0.8761	High Similarity	NPC172170
0.864	High Similarity	NPC209389
0.8571	High Similarity	NPC194562
0.8537	High Similarity	NPC254698
0.832	Intermediate Similarity	NPC192533
0.8074	Intermediate Similarity	NPC471164
0.8065	Intermediate Similarity	NPC226143
0.7899	Intermediate Similarity	NPC136002
0.7895	Intermediate Similarity	NPC316104
0.7895	Intermediate Similarity	NPC162417
0.7836	Intermediate Similarity	NPC300299
0.781	Intermediate Similarity	NPC2823
0.777	Intermediate Similarity	NPC130797
0.7681	Intermediate Similarity	NPC471574
0.7669	Intermediate Similarity	NPC316746
0.7664	Intermediate Similarity	NPC83214
0.763	Intermediate Similarity	NPC253476
0.7609	Intermediate Similarity	NPC207554
0.7594	Intermediate Similarity	NPC472245
0.7586	Intermediate Similarity	NPC295021
0.7581	Intermediate Similarity	NPC57051
0.7574	Intermediate Similarity	NPC173295
0.7557	Intermediate Similarity	NPC472244
0.7557	Intermediate Similarity	NPC470343
0.7552	Intermediate Similarity	NPC237649
0.7552	Intermediate Similarity	NPC300596
0.7397	Intermediate Similarity	NPC117032
0.7388	Intermediate Similarity	NPC122235
0.7388	Intermediate Similarity	NPC150863
0.7379	Intermediate Similarity	NPC144691
0.7353	Intermediate Similarity	NPC40364
0.7333	Intermediate Similarity	NPC477432
0.7333	Intermediate Similarity	NPC314431
0.7333	Intermediate Similarity	NPC280807
0.7313	Intermediate Similarity	NPC58827
0.7313	Intermediate Similarity	NPC72473
0.7313	Intermediate Similarity	NPC307437
0.7305	Intermediate Similarity	NPC316202
0.7305	Intermediate Similarity	NPC43477
0.7273	Intermediate Similarity	NPC38262
0.726	Intermediate Similarity	NPC13526
0.7254	Intermediate Similarity	NPC472241
0.7226	Intermediate Similarity	NPC207428
0.7218	Intermediate Similarity	NPC226794
0.7153	Intermediate Similarity	NPC470822
0.7113	Intermediate Similarity	NPC472243
0.7103	Intermediate Similarity	NPC472242
0.7083	Intermediate Similarity	NPC314287
0.7051	Intermediate Similarity	NPC472118
0.7051	Intermediate Similarity	NPC471943
0.7045	Intermediate Similarity	NPC130931
0.7013	Intermediate Similarity	NPC113056
0.7013	Intermediate Similarity	NPC138293
0.6993	Remote Similarity	NPC315051
0.6993	Remote Similarity	NPC93653
0.6993	Remote Similarity	NPC27904
0.6985	Remote Similarity	NPC322433
0.6978	Remote Similarity	NPC53044
0.6968	Remote Similarity	NPC115232
0.696	Remote Similarity	NPC79618
0.6957	Remote Similarity	NPC187231
0.6949	Remote Similarity	NPC291070
0.6949	Remote Similarity	NPC246757
0.6948	Remote Similarity	NPC293458
0.6899	Remote Similarity	NPC292265
0.6875	Remote Similarity	NPC242933
0.6875	Remote Similarity	NPC130251
0.6859	Remote Similarity	NPC299582
0.6852	Remote Similarity	NPC283810
0.6849	Remote Similarity	NPC308197
0.6839	Remote Similarity	NPC214106
0.6828	Remote Similarity	NPC301760
0.6818	Remote Similarity	NPC154478
0.6818	Remote Similarity	NPC313449
0.6803	Remote Similarity	NPC75496
0.68	Remote Similarity	NPC167336
0.6797	Remote Similarity	NPC84317
0.6792	Remote Similarity	NPC318183
0.6772	Remote Similarity	NPC302790
0.677	Remote Similarity	NPC471743
0.6769	Remote Similarity	NPC314141
0.6755	Remote Similarity	NPC314223
0.6753	Remote Similarity	NPC123241
0.6746	Remote Similarity	NPC473498
0.6735	Remote Similarity	NPC478040
0.6733	Remote Similarity	NPC242000
0.6731	Remote Similarity	NPC469741
0.6711	Remote Similarity	NPC324445
0.6709	Remote Similarity	NPC279527
0.6709	Remote Similarity	NPC214960
0.6693	Remote Similarity	NPC434
0.669	Remote Similarity	NPC469560
0.6689	Remote Similarity	NPC190945
0.6689	Remote Similarity	NPC314186
0.6689	Remote Similarity	NPC473329
0.6687	Remote Similarity	NPC49184
0.6687	Remote Similarity	NPC475094
0.6667	Remote Similarity	NPC470317
0.6667	Remote Similarity	NPC314098
0.6667	Remote Similarity	NPC151635
0.6667	Remote Similarity	NPC474926
0.6667	Remote Similarity	NPC475607
0.6646	Remote Similarity	NPC252572
0.6626	Remote Similarity	NPC284775
0.6626	Remote Similarity	NPC474081
0.6621	Remote Similarity	NPC122553
0.6619	Remote Similarity	NPC250476
0.6606	Remote Similarity	NPC472163
0.6605	Remote Similarity	NPC475594
0.66	Remote Similarity	NPC470579
0.66	Remote Similarity	NPC478039
0.6591	Remote Similarity	NPC113099
0.6582	Remote Similarity	NPC189116
0.6582	Remote Similarity	NPC204867
0.6575	Remote Similarity	NPC181527
0.6566	Remote Similarity	NPC117027
0.6562	Remote Similarity	NPC224970
0.6562	Remote Similarity	NPC167724
0.6562	Remote Similarity	NPC223595
0.656	Remote Similarity	NPC291610
0.6555	Remote Similarity	NPC78154
0.6552	Remote Similarity	NPC229477
0.6552	Remote Similarity	NPC471123
0.6549	Remote Similarity	NPC231382
0.6545	Remote Similarity	NPC85613
0.6545	Remote Similarity	NPC88110
0.6543	Remote Similarity	NPC177261
0.6541	Remote Similarity	NPC471130
0.6538	Remote Similarity	NPC76982
0.6538	Remote Similarity	NPC61013
0.6529	Remote Similarity	NPC313293
0.6525	Remote Similarity	NPC111233
0.6519	Remote Similarity	NPC88970
0.6519	Remote Similarity	NPC229353
0.6516	Remote Similarity	NPC114808
0.651	Remote Similarity	NPC469537
0.6508	Remote Similarity	NPC474430
0.6507	Remote Similarity	NPC287358
0.6503	Remote Similarity	NPC469529
0.65	Remote Similarity	NPC119326
0.65	Remote Similarity	NPC182131
0.6497	Remote Similarity	NPC36495
0.6497	Remote Similarity	NPC193410
0.649	Remote Similarity	NPC467188
0.6488	Remote Similarity	NPC476341
0.6485	Remote Similarity	NPC474041
0.6485	Remote Similarity	NPC475761
0.6471	Remote Similarity	NPC473666
0.6457	Remote Similarity	NPC275467
0.6456	Remote Similarity	NPC472102
0.6456	Remote Similarity	NPC309531
0.6456	Remote Similarity	NPC248117
0.6452	Remote Similarity	NPC251391
0.6446	Remote Similarity	NPC475685
0.6446	Remote Similarity	NPC108800
0.6446	Remote Similarity	NPC5167
0.6444	Remote Similarity	NPC192209
0.6441	Remote Similarity	NPC262295
0.6438	Remote Similarity	NPC42372
0.6434	Remote Similarity	NPC126458
0.6433	Remote Similarity	NPC324091
0.6429	Remote Similarity	NPC21429
0.6429	Remote Similarity	NPC477003
0.6423	Remote Similarity	NPC150323
0.6418	Remote Similarity	NPC288232
0.6415	Remote Similarity	NPC257763
0.6408	Remote Similarity	NPC313722
0.6407	Remote Similarity	NPC191415
0.6405	Remote Similarity	NPC105811
0.6402	Remote Similarity	NPC293216
0.64	Remote Similarity	NPC129412
0.64	Remote Similarity	NPC101130
0.64	Remote Similarity	NPC114033
0.64	Remote Similarity	NPC58268
0.6397	Remote Similarity	NPC228515
0.6391	Remote Similarity	NPC296163
0.6391	Remote Similarity	NPC133003
0.6391	Remote Similarity	NPC187036
0.6389	Remote Similarity	NPC476687
0.6389	Remote Similarity	NPC476689
0.6389	Remote Similarity	NPC476685
0.6387	Remote Similarity	NPC30445
0.6387	Remote Similarity	NPC70406
0.6382	Remote Similarity	NPC259678
0.638	Remote Similarity	NPC126676
0.638	Remote Similarity	NPC469671
0.638	Remote Similarity	NPC6982
0.638	Remote Similarity	NPC355
0.6379	Remote Similarity	NPC134825
0.6377	Remote Similarity	NPC475915

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 NPC103292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	707
0.2-0.3	926
0.3-0.4	1886
0.4-0.5	2576
0.5-0.6	2035
0.6-0.7	666
0.7-0.8	56
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8359	Intermediate Similarity	NPD486	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD6342	Discontinued
0.7955	Intermediate Similarity	NPD1541	Approved
0.7955	Intermediate Similarity	NPD441	Approved
0.7879	Intermediate Similarity	NPD1919	Approved
0.7879	Intermediate Similarity	NPD1920	Approved
0.7863	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1626	Approved
0.7724	Intermediate Similarity	NPD1175	Approved
0.7714	Intermediate Similarity	NPD6017	Discontinued
0.7704	Intermediate Similarity	NPD2331	Discontinued
0.7687	Intermediate Similarity	NPD1527	Phase 2
0.7687	Intermediate Similarity	NPD2950	Approved
0.7687	Intermediate Similarity	NPD2949	Approved
0.7622	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1625	Approved
0.7556	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4888	Discontinued
0.7534	Intermediate Similarity	NPD4045	Phase 2
0.7534	Intermediate Similarity	NPD4042	Phase 2
0.7519	Intermediate Similarity	NPD1079	Discontinued
0.7519	Intermediate Similarity	NPD1124	Approved
0.7519	Intermediate Similarity	NPD1123	Approved
0.7518	Intermediate Similarity	NPD5918	Discontinued
0.75	Intermediate Similarity	NPD6768	Approved
0.75	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1065	Approved
0.7438	Intermediate Similarity	NPD1064	Approved
0.7426	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1619	Phase 3
0.7397	Intermediate Similarity	NPD3248	Phase 1
0.7397	Intermediate Similarity	NPD1854	Approved
0.7376	Intermediate Similarity	NPD1189	Approved
0.7368	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2470	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6513	Approved
0.7254	Intermediate Similarity	NPD6512	Approved
0.723	Intermediate Similarity	NPD2790	Discontinued
0.7164	Intermediate Similarity	NPD1574	Approved
0.7154	Intermediate Similarity	NPD990	Approved
0.7154	Intermediate Similarity	NPD993	Approved
0.7143	Intermediate Similarity	NPD4645	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5227	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4549	Discontinued
0.7132	Intermediate Similarity	NPD1781	Discontinued
0.7121	Intermediate Similarity	NPD678	Discontinued
0.7111	Intermediate Similarity	NPD1593	Approved
0.7103	Intermediate Similarity	NPD5932	Phase 3
0.7103	Intermediate Similarity	NPD5931	Phase 3
0.7103	Intermediate Similarity	NPD5933	Phase 3
0.7097	Intermediate Similarity	NPD2037	Approved
0.7095	Intermediate Similarity	NPD1230	Approved
0.709	Intermediate Similarity	NPD9539	Approved
0.709	Intermediate Similarity	NPD9541	Approved
0.7075	Intermediate Similarity	NPD4942	Approved
0.7067	Intermediate Similarity	NPD7072	Phase 2
0.7063	Intermediate Similarity	NPD1222	Discontinued
0.7063	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2369	Discontinued
0.7042	Intermediate Similarity	NPD7254	Discontinued
0.7039	Intermediate Similarity	NPD4393	Approved
0.7039	Intermediate Similarity	NPD33	Approved
0.7023	Intermediate Similarity	NPD922	Approved
0.702	Intermediate Similarity	NPD2836	Approved
0.7014	Intermediate Similarity	NPD3482	Approved
0.7014	Intermediate Similarity	NPD6414	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD2999	Approved
0.7008	Intermediate Similarity	NPD3001	Approved
0.7007	Intermediate Similarity	NPD7088	Discontinued
0.6985	Remote Similarity	NPD9540	Approved
0.6972	Remote Similarity	NPD6358	Phase 2
0.6972	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD708	Approved
0.6957	Remote Similarity	NPD4329	Approved
0.6957	Remote Similarity	NPD4330	Approved
0.6944	Remote Similarity	NPD4461	Discontinued
0.6937	Remote Similarity	NPD3792	Approved
0.6918	Remote Similarity	NPD3481	Approved
0.6918	Remote Similarity	NPD4046	Approved
0.6918	Remote Similarity	NPD4043	Approved
0.6917	Remote Similarity	NPD1100	Approved
0.6917	Remote Similarity	NPD1099	Approved
0.6913	Remote Similarity	NPD5748	Phase 2
0.6908	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1208	Approved
0.6906	Remote Similarity	NPD1190	Approved
0.6899	Remote Similarity	NPD5179	Approved
0.6899	Remote Similarity	NPD5181	Approved
0.6899	Remote Similarity	NPD2431	Approved
0.6899	Remote Similarity	NPD2432	Approved
0.6899	Remote Similarity	NPD5180	Approved
0.6897	Remote Similarity	NPD6566	Discontinued
0.6894	Remote Similarity	NPD3782	Discontinued
0.6883	Remote Similarity	NPD2506	Approved
0.6879	Remote Similarity	NPD2454	Approved
0.6879	Remote Similarity	NPD2455	Approved
0.6866	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1517	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4161	Discontinued
0.6846	Remote Similarity	NPD7528	Approved
0.6846	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1228	Phase 2
0.6831	Remote Similarity	NPD1410	Phase 1
0.6829	Remote Similarity	NPD2193	Phase 2
0.6829	Remote Similarity	NPD2648	Phase 3
0.6828	Remote Similarity	NPD2010	Phase 3
0.6818	Remote Similarity	NPD7481	Approved
0.6818	Remote Similarity	NPD7480	Approved
0.6812	Remote Similarity	NPD1560	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1323	Discontinued
0.6783	Remote Similarity	NPD1207	Approved
0.6783	Remote Similarity	NPD1206	Approved
0.6776	Remote Similarity	NPD5086	Approved
0.6772	Remote Similarity	NPD1342	Approved
0.6769	Remote Similarity	NPD3387	Approved
0.6761	Remote Similarity	NPD1531	Approved
0.6746	Remote Similarity	NPD3546	Approved
0.6746	Remote Similarity	NPD3545	Approved
0.6735	Remote Similarity	NPD2820	Phase 3
0.6731	Remote Similarity	NPD1210	Approved
0.6718	Remote Similarity	NPD2319	Discontinued
0.6718	Remote Similarity	NPD853	Approved
0.6718	Remote Similarity	NPD851	Approved
0.6714	Remote Similarity	NPD5131	Approved
0.6713	Remote Similarity	NPD2791	Discontinued
0.6711	Remote Similarity	NPD1524	Phase 1
0.671	Remote Similarity	NPD2427	Approved
0.6707	Remote Similarity	NPD3470	Approved
0.6707	Remote Similarity	NPD3471	Approved
0.6694	Remote Similarity	NPD2196	Discontinued
0.6694	Remote Similarity	NPD2171	Approved
0.6694	Remote Similarity	NPD813	Approved
0.6693	Remote Similarity	NPD4115	Approved
0.6693	Remote Similarity	NPD4114	Approved
0.669	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2435	Approved
0.6688	Remote Similarity	NPD951	Approved
0.6667	Remote Similarity	NPD2404	Discontinued
0.6667	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2197	Approved
0.6667	Remote Similarity	NPD2192	Approved
0.6667	Remote Similarity	NPD1802	Approved
0.6667	Remote Similarity	NPD1801	Approved
0.6667	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD167	Phase 2
0.6667	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2365	Approved
0.6667	Remote Similarity	NPD1036	Approved
0.6667	Remote Similarity	NPD168	Phase 1
0.6644	Remote Similarity	NPD1205	Approved
0.6644	Remote Similarity	NPD1209	Approved
0.6625	Remote Similarity	NPD5186	Approved
0.6625	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5183	Approved
0.6623	Remote Similarity	NPD979	Approved
0.6622	Remote Similarity	NPD5024	Approved
0.6621	Remote Similarity	NPD2670	Approved
0.6621	Remote Similarity	NPD1532	Approved
0.6615	Remote Similarity	NPD3865	Approved
0.6601	Remote Similarity	NPD3399	Approved
0.66	Remote Similarity	NPD4041	Approved
0.6591	Remote Similarity	NPD1074	Approved
0.6591	Remote Similarity	NPD1075	Approved
0.6591	Remote Similarity	NPD1073	Approved
0.6589	Remote Similarity	NPD1107	Approved
0.6589	Remote Similarity	NPD4116	Approved
0.6589	Remote Similarity	NPD1539	Approved
0.6589	Remote Similarity	NPD1108	Approved
0.6584	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7091	Discontinued
0.6575	Remote Similarity	NPD7142	Discontinued
0.6575	Remote Similarity	NPD3170	Approved
0.6562	Remote Similarity	NPD5921	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2413	Phase 2
0.6562	Remote Similarity	NPD3468	Approved
0.656	Remote Similarity	NPD4735	Approved
0.656	Remote Similarity	NPD4734	Approved
0.6554	Remote Similarity	NPD2923	Approved
0.6549	Remote Similarity	NPD1069	Approved
0.6549	Remote Similarity	NPD1070	Approved
0.6549	Remote Similarity	NPD2754	Discontinued
0.6545	Remote Similarity	NPD2479	Phase 3
0.6545	Remote Similarity	NPD2481	Approved
0.6543	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD8241	Phase 2
0.6527	Remote Similarity	NPD4412	Phase 2
0.6525	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1360	Approved
0.6519	Remote Similarity	NPD7220	Approved
0.6513	Remote Similarity	NPD5941	Approved
0.6513	Remote Similarity	NPD5942	Approved
0.651	Remote Similarity	NPD7082	Approved
0.651	Remote Similarity	NPD4430	Phase 2
0.6507	Remote Similarity	NPD5318	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