NPASS Compound

Structure

NPC469563 OpenBabel07101719512D 24 30 0 0 1 0 0 0 0 0999 V2000 0.6681 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0981 -0.6509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0581 -0.9410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0788 1.0589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8938 0.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1339 -0.1797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2808 -0.7395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7923 0.5679 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8027 -0.4320 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9292 -0.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4732 0.0340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4749 -0.1105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3154 1.1642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1035 0.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0299 1.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9380 0.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3505 0.6818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9396 0.5499 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5452 0.2274 0.0000 N 0 5 0 0 0 0 0 0 0 0 0 0 2.5452 0.7504 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -1.6739 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3485 0.7441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8770 -0.7689 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 7 1 0 0 0 0 2 21 1 0 0 0 0 3 9 1 0 0 0 0 3 10 2 0 0 0 0 4 8 1 0 0 0 0 5 18 1 0 0 0 0 6 7 2 0 0 0 0 6 19 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 1 0 0 0 10 18 1 0 0 0 0 10 24 1 0 0 0 0 11 5 1 6 0 0 0 11 20 1 0 0 0 0 11 24 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 18 4 1 6 0 0 0 M CHG 3 19 -1 20 1 21 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.08
Volume:	311.932
LogP:	-1.456
LogD:	0.082
LogS:	-2.283
# Rotatable Bonds:	0
TPSA:	69.66
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	7.715
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.735
MDCK Permeability:	1.0178320735576563e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.303
Human Intestinal Absorption (HIA):	0.83
20% Bioavailability (F20%):	0.805
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.787
Plasma Protein Binding (PPB):	94.7561264038086%
Volume Distribution (VD):	0.74
Pgp-substrate:	2.7247719764709473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.498
CYP1A2-substrate:	0.739
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.321
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.122
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.51

ADMET: Excretion

Clearance (CL):	1.207
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.913
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.252
Carcinogencity:	0.505
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC469563

Natural Product ID:	NPC469563
*Common Name:**	UASAUPLJUYBGRK-AUXFETMMSA-O
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UASAUPLJUYBGRK-AUXFETMMSA-O
Standard InCHI:	InChI=1S/C18H15N3O2S/c22-9-3-10-18-4-8(9)21-2-1-7-6-19-14-12(7)16(21)13(18)15(17(14)23)20-11(5-18)24-10/h3,6,8-9,11,22H,1-2,4-5H2,(H,19,20,23)/p+1/t8?,9-,11+,18+/m1/s1
SMILES:	O[C@@H]1C=C2S[C@H]3C[C@]42CC1[N+]1CCc2c5C1=C4C(=[NH+]3)C(=O)c5[n-]c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087539
PubChem CID:	46881013
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO33184	sceptrella sp.	Species	Latrunculiidae	Eukaryota	n.a.	Korean	n.a.	PMID[20055495]

☑ 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
MIC	6

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	75700.0	nM	PMID[450961]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	2100.0	nM	PMID[450961]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	100.0	ug.mL-1	PMID[450961]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	50.0	ug.mL-1	PMID[450961]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[450961]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[450961]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	25.0	ug.mL-1	PMID[450961]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[450961]

☑ 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 NPC469563 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	294
0.1-0.2	1872
0.2-0.3	13629
0.3-0.4	19769
0.4-0.5	3699
0.5-0.6	2797
0.6-0.7	586
0.7-0.8	32
0.8-0.85	4
0.85-0.9	4
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9731	High Similarity	NPC220594
0.9731	High Similarity	NPC469562
0.9519	High Similarity	NPC469578
0.9158	High Similarity	NPC475410
0.9158	High Similarity	NPC469577
0.9128	High Similarity	NPC477416
0.9116	High Similarity	NPC469359
0.8836	High Similarity	NPC476143
0.8718	High Similarity	NPC143075
0.8513	High Similarity	NPC476252
0.8168	Intermediate Similarity	NPC477415
0.8168	Intermediate Similarity	NPC23476
0.8168	Intermediate Similarity	NPC474259
0.7959	Intermediate Similarity	NPC477414
0.7959	Intermediate Similarity	NPC221726
0.7959	Intermediate Similarity	NPC225622
0.7938	Intermediate Similarity	NPC473628
0.7913	Intermediate Similarity	NPC469544
0.7806	Intermediate Similarity	NPC475874
0.7716	Intermediate Similarity	NPC268966
0.7632	Intermediate Similarity	NPC262338
0.7487	Intermediate Similarity	NPC182940
0.7404	Intermediate Similarity	NPC88115
0.7398	Intermediate Similarity	NPC79777
0.7398	Intermediate Similarity	NPC234403
0.7391	Intermediate Similarity	NPC106757
0.7353	Intermediate Similarity	NPC292361
0.7337	Intermediate Similarity	NPC474258
0.7264	Intermediate Similarity	NPC473946
0.7211	Intermediate Similarity	NPC474492
0.7173	Intermediate Similarity	NPC100104
0.7173	Intermediate Similarity	NPC470680
0.7112	Intermediate Similarity	NPC477420
0.7112	Intermediate Similarity	NPC477418
0.7095	Intermediate Similarity	NPC98864
0.7074	Intermediate Similarity	NPC473878
0.7037	Intermediate Similarity	NPC217021
0.7037	Intermediate Similarity	NPC470679
0.7033	Intermediate Similarity	NPC477041
0.7033	Intermediate Similarity	NPC477044
0.7005	Intermediate Similarity	NPC477413
0.6986	Remote Similarity	NPC473814
0.6986	Remote Similarity	NPC78767
0.6923	Remote Similarity	NPC274981
0.6919	Remote Similarity	NPC477045
0.6905	Remote Similarity	NPC74153
0.6901	Remote Similarity	NPC328596
0.6901	Remote Similarity	NPC328318
0.6895	Remote Similarity	NPC471655
0.6893	Remote Similarity	NPC103119
0.689	Remote Similarity	NPC93390
0.6884	Remote Similarity	NPC175602
0.6878	Remote Similarity	NPC100726
0.6869	Remote Similarity	NPC98715
0.6866	Remote Similarity	NPC61038
0.6854	Remote Similarity	NPC300183
0.6842	Remote Similarity	NPC473821
0.6837	Remote Similarity	NPC477043
0.6812	Remote Similarity	NPC255909
0.6792	Remote Similarity	NPC248782
0.6774	Remote Similarity	NPC46225
0.6774	Remote Similarity	NPC225821
0.6766	Remote Similarity	NPC186068
0.6761	Remote Similarity	NPC474767
0.6759	Remote Similarity	NPC473239
0.6754	Remote Similarity	NPC102664
0.675	Remote Similarity	NPC302647
0.6743	Remote Similarity	NPC258062
0.6743	Remote Similarity	NPC127677
0.6742	Remote Similarity	NPC207866
0.6731	Remote Similarity	NPC209917
0.673	Remote Similarity	NPC294693
0.6728	Remote Similarity	NPC317373
0.6724	Remote Similarity	NPC475635
0.6718	Remote Similarity	NPC213914
0.6699	Remote Similarity	NPC207851
0.6682	Remote Similarity	NPC327592
0.6682	Remote Similarity	NPC123395
0.6667	Remote Similarity	NPC476446
0.6667	Remote Similarity	NPC311282
0.6667	Remote Similarity	NPC78375
0.6667	Remote Similarity	NPC469813
0.6636	Remote Similarity	NPC271862
0.6634	Remote Similarity	NPC477042
0.6622	Remote Similarity	NPC151976
0.6622	Remote Similarity	NPC87856
0.6622	Remote Similarity	NPC110182
0.6615	Remote Similarity	NPC209362
0.6592	Remote Similarity	NPC267965
0.6589	Remote Similarity	NPC167710
0.658	Remote Similarity	NPC123906
0.6578	Remote Similarity	NPC472285
0.6573	Remote Similarity	NPC195239
0.6573	Remote Similarity	NPC157828
0.6571	Remote Similarity	NPC75544
0.6564	Remote Similarity	NPC251391
0.656	Remote Similarity	NPC138562
0.6557	Remote Similarity	NPC216550
0.6547	Remote Similarity	NPC471193
0.6547	Remote Similarity	NPC471194
0.6542	Remote Similarity	NPC11445
0.6538	Remote Similarity	NPC63279
0.6537	Remote Similarity	NPC157583
0.6533	Remote Similarity	NPC471192
0.6533	Remote Similarity	NPC132211
0.652	Remote Similarity	NPC269270
0.6518	Remote Similarity	NPC317752
0.6517	Remote Similarity	NPC41717
0.6511	Remote Similarity	NPC297642
0.6491	Remote Similarity	NPC14686
0.649	Remote Similarity	NPC163055
0.6478	Remote Similarity	NPC229893
0.6476	Remote Similarity	NPC473310
0.6473	Remote Similarity	NPC318299
0.6471	Remote Similarity	NPC477976
0.646	Remote Similarity	NPC203614
0.646	Remote Similarity	NPC204491
0.6429	Remote Similarity	NPC72956
0.6426	Remote Similarity	NPC165743
0.6422	Remote Similarity	NPC252338
0.6419	Remote Similarity	NPC202812
0.6406	Remote Similarity	NPC131887
0.64	Remote Similarity	NPC6865
0.64	Remote Similarity	NPC153980
0.6394	Remote Similarity	NPC471997
0.6391	Remote Similarity	NPC2395
0.6385	Remote Similarity	NPC469489
0.6385	Remote Similarity	NPC154339
0.6381	Remote Similarity	NPC228835
0.6381	Remote Similarity	NPC46895
0.6379	Remote Similarity	NPC19170
0.6377	Remote Similarity	NPC248454
0.6376	Remote Similarity	NPC103361
0.6372	Remote Similarity	NPC267343
0.6368	Remote Similarity	NPC17059
0.6368	Remote Similarity	NPC297862
0.6359	Remote Similarity	NPC139763
0.6359	Remote Similarity	NPC227582
0.6356	Remote Similarity	NPC82370
0.6351	Remote Similarity	NPC472065
0.6346	Remote Similarity	NPC248041
0.6346	Remote Similarity	NPC126709
0.6346	Remote Similarity	NPC283219
0.634	Remote Similarity	NPC477175
0.634	Remote Similarity	NPC470730
0.6336	Remote Similarity	NPC476817
0.6333	Remote Similarity	NPC159125
0.6326	Remote Similarity	NPC47190
0.6325	Remote Similarity	NPC476491
0.6316	Remote Similarity	NPC73994
0.6316	Remote Similarity	NPC61011
0.6314	Remote Similarity	NPC475859
0.6314	Remote Similarity	NPC475969
0.63	Remote Similarity	NPC475602
0.6294	Remote Similarity	NPC313889
0.629	Remote Similarity	NPC57398
0.629	Remote Similarity	NPC143977
0.6288	Remote Similarity	NPC477715
0.6284	Remote Similarity	NPC272483
0.628	Remote Similarity	NPC110500
0.628	Remote Similarity	NPC149155
0.628	Remote Similarity	NPC203468
0.6279	Remote Similarity	NPC114974
0.6278	Remote Similarity	NPC472064
0.6276	Remote Similarity	NPC105811
0.6274	Remote Similarity	NPC295158
0.6273	Remote Similarity	NPC121327
0.6272	Remote Similarity	NPC237740
0.6271	Remote Similarity	NPC477176
0.6271	Remote Similarity	NPC470729
0.6268	Remote Similarity	NPC11126
0.6267	Remote Similarity	NPC135950
0.6263	Remote Similarity	NPC70406
0.6261	Remote Similarity	NPC477714
0.6256	Remote Similarity	NPC265576
0.6256	Remote Similarity	NPC34837
0.6256	Remote Similarity	NPC467188
0.625	Remote Similarity	NPC267885
0.6245	Remote Similarity	NPC470731
0.6245	Remote Similarity	NPC477177
0.6245	Remote Similarity	NPC474877
0.6239	Remote Similarity	NPC235885
0.6239	Remote Similarity	NPC141428
0.6227	Remote Similarity	NPC284338
0.6226	Remote Similarity	NPC467063
0.6226	Remote Similarity	NPC477003
0.6222	Remote Similarity	NPC476157
0.6221	Remote Similarity	NPC474177
0.6221	Remote Similarity	NPC326422
0.622	Remote Similarity	NPC14113
0.622	Remote Similarity	NPC145885
0.622	Remote Similarity	NPC84827
0.622	Remote Similarity	NPC284775
0.622	Remote Similarity	NPC83774
0.622	Remote Similarity	NPC237188
0.6217	Remote Similarity	NPC469727
0.6217	Remote Similarity	NPC27041
0.6216	Remote Similarity	NPC472069
0.6216	Remote Similarity	NPC260900
0.6216	Remote Similarity	NPC472062

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 NPC469563 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	510
0.2-0.3	841
0.3-0.4	2327
0.4-0.5	3260
0.5-0.6	1843
0.6-0.7	201
0.7-0.8	1
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
0.692	Remote Similarity	NPD6173	Approved
0.6919	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3178	Discontinued
0.6682	Remote Similarity	NPD8169	Discontinued
0.6651	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.652	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6044	Discontinued
0.646	Remote Similarity	NPD3394	Approved
0.646	Remote Similarity	NPD3393	Approved
0.646	Remote Similarity	NPD3389	Approved
0.6455	Remote Similarity	NPD5901	Discontinued
0.6441	Remote Similarity	NPD4960	Approved
0.6441	Remote Similarity	NPD4959	Approved
0.6422	Remote Similarity	NPD8289	Discontinued
0.6415	Remote Similarity	NPD6068	Discontinued
0.6396	Remote Similarity	NPD4415	Approved
0.6384	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD1096	Discontinued
0.638	Remote Similarity	NPD4905	Approved
0.638	Remote Similarity	NPD4903	Approved
0.638	Remote Similarity	NPD8272	Phase 2
0.638	Remote Similarity	NPD4906	Approved
0.638	Remote Similarity	NPD8114	Approved
0.638	Remote Similarity	NPD8115	Approved
0.6368	Remote Similarity	NPD2510	Approved
0.6368	Remote Similarity	NPD2509	Approved
0.6351	Remote Similarity	NPD7001	Phase 3
0.6351	Remote Similarity	NPD4904	Approved
0.6335	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2893	Phase 3
0.6333	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD750	Phase 2
0.6301	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6999	Discontinued
0.6295	Remote Similarity	NPD7666	Phase 3
0.6295	Remote Similarity	NPD7665	Phase 2
0.6286	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.628	Remote Similarity	NPD482	Approved
0.6279	Remote Similarity	NPD2336	Approved
0.6278	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD2214	Approved
0.6269	Remote Similarity	NPD2213	Approved
0.6266	Remote Similarity	NPD6752	Phase 1
0.6266	Remote Similarity	NPD6753	Phase 1
0.625	Remote Similarity	NPD276	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6665	Discontinued
0.625	Remote Similarity	NPD946	Discontinued
0.6244	Remote Similarity	NPD7817	Phase 1
0.6244	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD2096	Phase 2
0.6226	Remote Similarity	NPD2091	Phase 2
0.6222	Remote Similarity	NPD6376	Discontinued
0.6216	Remote Similarity	NPD7187	Phase 2
0.6206	Remote Similarity	NPD5461	Discontinued
0.6204	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD5065	Approved
0.6199	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD5043	Discontinued
0.6197	Remote Similarity	NPD3082	Discontinued
0.6195	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD3968	Approved
0.6193	Remote Similarity	NPD7618	Phase 3
0.6193	Remote Similarity	NPD7619	Phase 3
0.619	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD3917	Approved
0.6184	Remote Similarity	NPD3918	Approved
0.6184	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD2092	Phase 2
0.6179	Remote Similarity	NPD2095	Phase 2
0.6179	Remote Similarity	NPD2094	Phase 2
0.6178	Remote Similarity	NPD3410	Approved
0.6178	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD3411	Phase 2
0.6176	Remote Similarity	NPD5088	Discontinued
0.6172	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD5017	Discontinued
0.6171	Remote Similarity	NPD7727	Phase 2
0.6164	Remote Similarity	NPD7027	Phase 3
0.6164	Remote Similarity	NPD2307	Discontinued
0.6164	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3947	Discontinued
0.6161	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD1643	Phase 3
0.6161	Remote Similarity	NPD5426	Phase 3
0.6157	Remote Similarity	NPD3321	Discontinued
0.615	Remote Similarity	NPD7564	Discontinued
0.615	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD2720	Phase 1
0.614	Remote Similarity	NPD3915	Approved
0.614	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3961	Discontinued
0.6137	Remote Similarity	NPD1996	Discontinued
0.6135	Remote Similarity	NPD1573	Approved
0.6135	Remote Similarity	NPD1575	Approved
0.613	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6128	Remote Similarity	NPD5046	Discontinued
0.6126	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6123	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6123	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD8072	Approved
0.6111	Remote Similarity	NPD4703	Approved
0.6111	Remote Similarity	NPD4702	Approved
0.6111	Remote Similarity	NPD7233	Approved
0.6111	Remote Similarity	NPD7234	Approved
0.6109	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD7552	Discontinued
0.6108	Remote Similarity	NPD5255	Approved
0.6104	Remote Similarity	NPD3353	Approved
0.6101	Remote Similarity	NPD981	Phase 2
0.61	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD4051	Discontinued
0.6091	Remote Similarity	NPD4848	Phase 1
0.6087	Remote Similarity	NPD3794	Approved
0.6087	Remote Similarity	NPD3795	Approved
0.6085	Remote Similarity	NPD5473	Discontinued
0.6081	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD2511	Approved
0.6075	Remote Similarity	NPD7483	Phase 2
0.6075	Remote Similarity	NPD7482	Phase 2
0.6071	Remote Similarity	NPD8073	Approved
0.607	Remote Similarity	NPD180	Clinical (unspecified phase)
0.607	Remote Similarity	NPD7470	Discontinued
0.607	Remote Similarity	NPD5475	Discontinued
0.607	Remote Similarity	NPD4417	Approved
0.6066	Remote Similarity	NPD2753	Discontinued
0.6066	Remote Similarity	NPD2144	Approved
0.6065	Remote Similarity	NPD4988	Discontinued
0.6062	Remote Similarity	NPD7010	Phase 3
0.6062	Remote Similarity	NPD3967	Approved
0.6055	Remote Similarity	NPD4949	Discontinued
0.6055	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5076	Approved
0.6055	Remote Similarity	NPD5077	Approved
0.6053	Remote Similarity	NPD5510	Approved
0.605	Remote Similarity	NPD6165	Phase 2
0.605	Remote Similarity	NPD4845	Discontinued
0.605	Remote Similarity	NPD6164	Phase 2
0.6048	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD3396	Approved
0.6045	Remote Similarity	NPD3395	Approved
0.6045	Remote Similarity	NPD7944	Discontinued
0.6043	Remote Similarity	NPD8093	Discontinued
0.6038	Remote Similarity	NPD4076	Approved
0.6038	Remote Similarity	NPD4079	Approved
0.6037	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.603	Remote Similarity	NPD1270	Approved
0.6029	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD5596	Phase 2
0.6027	Remote Similarity	NPD3288	Approved
0.6027	Remote Similarity	NPD4962	Approved
0.6027	Remote Similarity	NPD4963	Approved
0.6026	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD7677	Discontinued
0.6021	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3315	Phase 3
0.6019	Remote Similarity	NPD3238	Discontinued
0.6019	Remote Similarity	NPD1631	Approved
0.6018	Remote Similarity	NPD6987	Phase 1
0.6018	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5888	Phase 2
0.601	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD7308	Discontinued
0.6009	Remote Similarity	NPD3425	Discontinued
0.6009	Remote Similarity	NPD2479	Phase 3
0.6009	Remote Similarity	NPD2481	Approved
0.6009	Remote Similarity	NPD9510	Approved
0.6009	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6178	Phase 3
0.5992	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD7655	Discontinued
0.5991	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD8122	Approved
0.5991	Remote Similarity	NPD3506	Approved
0.5991	Remote Similarity	NPD3505	Approved
0.5991	Remote Similarity	NPD8123	Approved
0.5982	Remote Similarity	NPD4961	Approved
0.5982	Remote Similarity	NPD6479	Discontinued
0.5982	Remote Similarity	NPD484	Approved
0.5981	Remote Similarity	NPD3038	Discontinued
0.5974	Remote Similarity	NPD4852	Phase 2

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