NPASS Compound

Structure

NPC469544 OpenBabel07101719242D 26 31 0 0 1 0 0 0 0 0999 V2000 2.9136 -1.2206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0476 -1.7206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5962 -0.9155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4387 0.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6568 0.4486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9136 -0.2206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1745 -1.3511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5185 -0.3142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3514 1.0924 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0476 0.2794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6466 0.3918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2555 1.2576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7918 1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4290 -1.2930 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.1816 -0.2206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5078 1.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0968 -0.7498 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2500 1.3621 0.0000 N 0 5 0 0 0 0 0 0 0 0 0 0 0.1962 1.4174 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 1.1816 -1.2206 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -0.5200 -2.2895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3565 0.2315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1843 1.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4630 2.5762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0459 -1.0647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 6 1 0 0 0 0 2 21 1 0 0 0 0 3 7 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 19 1 0 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 7 22 1 6 0 0 0 8 18 1 0 0 0 0 8 23 2 0 0 0 0 9 20 1 0 0 0 0 9 24 1 1 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 21 1 0 0 0 0 16 25 2 0 0 0 0 17 18 1 6 0 0 0 17 26 1 0 0 0 0 18 4 1 1 0 0 0 M CHG 3 19 -1 20 1 21 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.11
Volume:	328.35
LogP:	-2.009
LogD:	-0.714
LogS:	-1.049
# Rotatable Bonds:	0
TPSA:	127.19
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	7.26
Fsp3:	0.5
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:	-5.874
MDCK Permeability:	3.3405797239538515e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.731
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176
Plasma Protein Binding (PPB):	58.69731903076172%
Volume Distribution (VD):	0.761
Pgp-substrate:	42.30118179321289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.205
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.377

ADMET: Excretion

Clearance (CL):	1.557
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.72
AMES Toxicity:	0.894
Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.212
Carcinogencity:	0.188
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.452

Download Data

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

Natural Product: NPC469544

Natural Product ID:	NPC469544
*Common Name:**	CUHRPNQIGJRXJO-XZXJIDFESA-O
IUPAC Name:	n.a.
Synonyms:	(-)-Discorhabdin Z
Standard InCHIKey:	CUHRPNQIGJRXJO-XZXJIDFESA-O
Standard InCHI:	InChI=1S/C18H17N3O5/c22-7-3-8(23)18-4-9(24)20-13-11(18)15-10-6(5-19-12(10)16(13)25)1-2-21(15)14(7)17(18)26/h5,7,9,14,17,22,24,26H,1-4H2,(H,19,20,25)/p+1/t7-,9-,14?,17+,18-/m1/s1
SMILES:	O[C@H]1[NH+]=C2C(=O)c3[n-]cc4c3C3=C2[C@@]2(C1)C(=O)C[C@H](C([C@@H]2O)[N+]3CC4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086901
PubChem CID:	46881028
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
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	6500.0	nM	PMID[481445]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	2200.0	nM	PMID[481445]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	Selectivity ratio	=	10.0	n.a.	PMID[481445]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	100.0	ug.mL-1	PMID[481445]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[481445]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[481445]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[481445]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[481445]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[481445]

☑ 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 NPC469544 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	350
0.1-0.2	1719
0.2-0.3	9326
0.3-0.4	20871
0.4-0.5	6680
0.5-0.6	2876
0.6-0.7	849
0.7-0.8	20
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8325	Intermediate Similarity	NPC469578
0.8155	Intermediate Similarity	NPC220594
0.8155	Intermediate Similarity	NPC469562
0.8095	Intermediate Similarity	NPC477416
0.801	Intermediate Similarity	NPC469577
0.801	Intermediate Similarity	NPC475410
0.7913	Intermediate Similarity	NPC469563
0.7524	Intermediate Similarity	NPC292361
0.7389	Intermediate Similarity	NPC469359
0.7286	Intermediate Similarity	NPC476143
0.715	Intermediate Similarity	NPC473628
0.71	Intermediate Similarity	NPC262338
0.7064	Intermediate Similarity	NPC143075
0.7037	Intermediate Similarity	NPC476252
0.7033	Intermediate Similarity	NPC475874
0.6982	Remote Similarity	NPC267965
0.6976	Remote Similarity	NPC182940
0.6943	Remote Similarity	NPC267926
0.693	Remote Similarity	NPC266192
0.692	Remote Similarity	NPC132211
0.6893	Remote Similarity	NPC234403
0.6893	Remote Similarity	NPC79777
0.6884	Remote Similarity	NPC477044
0.6884	Remote Similarity	NPC477041
0.6861	Remote Similarity	NPC87856
0.6861	Remote Similarity	NPC151976
0.6852	Remote Similarity	NPC474767
0.6835	Remote Similarity	NPC328596
0.6835	Remote Similarity	NPC328318
0.6826	Remote Similarity	NPC141428
0.6784	Remote Similarity	NPC474492
0.6774	Remote Similarity	NPC477045
0.6773	Remote Similarity	NPC477043
0.677	Remote Similarity	NPC204491
0.677	Remote Similarity	NPC203614
0.6767	Remote Similarity	NPC57690
0.675	Remote Similarity	NPC470680
0.675	Remote Similarity	NPC100104
0.6745	Remote Similarity	NPC75544
0.6726	Remote Similarity	NPC271862
0.6714	Remote Similarity	NPC268966
0.6698	Remote Similarity	NPC474259
0.6698	Remote Similarity	NPC23476
0.6698	Remote Similarity	NPC477415
0.6695	Remote Similarity	NPC70155
0.6682	Remote Similarity	NPC473814
0.6682	Remote Similarity	NPC78767
0.6667	Remote Similarity	NPC317373
0.6652	Remote Similarity	NPC98715
0.665	Remote Similarity	NPC473878
0.6638	Remote Similarity	NPC147446
0.6637	Remote Similarity	NPC225821
0.6637	Remote Similarity	NPC46225
0.6623	Remote Similarity	NPC2395
0.6622	Remote Similarity	NPC327592
0.6621	Remote Similarity	NPC123395
0.6616	Remote Similarity	NPC470679
0.6616	Remote Similarity	NPC217021
0.661	Remote Similarity	NPC290529
0.6608	Remote Similarity	NPC472291
0.6607	Remote Similarity	NPC127677
0.6607	Remote Similarity	NPC258062
0.6606	Remote Similarity	NPC74153
0.6604	Remote Similarity	NPC474258
0.6602	Remote Similarity	NPC302647
0.6601	Remote Similarity	NPC274981
0.6597	Remote Similarity	NPC475426
0.6594	Remote Similarity	NPC472285
0.659	Remote Similarity	NPC93390
0.6571	Remote Similarity	NPC471997
0.6557	Remote Similarity	NPC207851
0.655	Remote Similarity	NPC30570
0.6549	Remote Similarity	NPC234999
0.6544	Remote Similarity	NPC225622
0.6544	Remote Similarity	NPC221726
0.6544	Remote Similarity	NPC477414
0.6542	Remote Similarity	NPC473946
0.6538	Remote Similarity	NPC235885
0.6535	Remote Similarity	NPC317752
0.6527	Remote Similarity	NPC170751
0.6527	Remote Similarity	NPC35208
0.6514	Remote Similarity	NPC195239
0.6514	Remote Similarity	NPC157828
0.65	Remote Similarity	NPC149708
0.6494	Remote Similarity	NPC281049
0.6491	Remote Similarity	NPC318299
0.6491	Remote Similarity	NPC292517
0.6491	Remote Similarity	NPC111732
0.649	Remote Similarity	NPC477976
0.6488	Remote Similarity	NPC253482
0.6486	Remote Similarity	NPC155792
0.6484	Remote Similarity	NPC11445
0.6483	Remote Similarity	NPC124029
0.6482	Remote Similarity	NPC471655
0.6481	Remote Similarity	NPC154339
0.6478	Remote Similarity	NPC471192
0.6475	Remote Similarity	NPC475648
0.6473	Remote Similarity	NPC88115
0.6471	Remote Similarity	NPC477906
0.6471	Remote Similarity	NPC103361
0.6468	Remote Similarity	NPC267343
0.6468	Remote Similarity	NPC473821
0.6465	Remote Similarity	NPC100726
0.6463	Remote Similarity	NPC229348
0.6459	Remote Similarity	NPC139763
0.6449	Remote Similarity	NPC311282
0.6444	Remote Similarity	NPC175602
0.6444	Remote Similarity	NPC472064
0.6439	Remote Similarity	NPC469813
0.6439	Remote Similarity	NPC476446
0.6439	Remote Similarity	NPC78375
0.6435	Remote Similarity	NPC209917
0.6432	Remote Similarity	NPC102664
0.6432	Remote Similarity	NPC61038
0.6422	Remote Similarity	NPC216550
0.6419	Remote Similarity	NPC477413
0.6419	Remote Similarity	NPC471193
0.6419	Remote Similarity	NPC475778
0.6419	Remote Similarity	NPC471194
0.6414	Remote Similarity	NPC211920
0.6413	Remote Similarity	NPC300183
0.641	Remote Similarity	NPC253314
0.6404	Remote Similarity	NPC213914
0.6402	Remote Similarity	NPC475969
0.6402	Remote Similarity	NPC475859
0.6398	Remote Similarity	NPC477902
0.6398	Remote Similarity	NPC475498
0.6398	Remote Similarity	NPC475137
0.6387	Remote Similarity	NPC475644
0.6387	Remote Similarity	NPC471977
0.6387	Remote Similarity	NPC471190
0.6387	Remote Similarity	NPC470486
0.6384	Remote Similarity	NPC106757
0.6382	Remote Similarity	NPC476517
0.638	Remote Similarity	NPC167710
0.6379	Remote Similarity	NPC162812
0.6379	Remote Similarity	NPC477715
0.6376	Remote Similarity	NPC72956
0.6375	Remote Similarity	NPC469748
0.6375	Remote Similarity	NPC30456
0.6372	Remote Similarity	NPC472065
0.6368	Remote Similarity	NPC252338
0.636	Remote Similarity	NPC470730
0.636	Remote Similarity	NPC477175
0.636	Remote Similarity	NPC472070
0.6356	Remote Similarity	NPC76565
0.6355	Remote Similarity	NPC159125
0.6352	Remote Similarity	NPC477714
0.6348	Remote Similarity	NPC153980
0.6348	Remote Similarity	NPC6865
0.6345	Remote Similarity	NPC475600
0.6345	Remote Similarity	NPC87152
0.6345	Remote Similarity	NPC244536
0.6345	Remote Similarity	NPC476516
0.6345	Remote Similarity	NPC475631
0.6345	Remote Similarity	NPC476110
0.6338	Remote Similarity	NPC477042
0.6333	Remote Similarity	NPC475303
0.6333	Remote Similarity	NPC96801
0.6333	Remote Similarity	NPC150698
0.6333	Remote Similarity	NPC474877
0.6333	Remote Similarity	NPC475596
0.633	Remote Similarity	NPC469489
0.6329	Remote Similarity	NPC473850
0.6329	Remote Similarity	NPC476818
0.6329	Remote Similarity	NPC26881
0.6327	Remote Similarity	NPC475847
0.6327	Remote Similarity	NPC185742
0.6323	Remote Similarity	NPC160127
0.6323	Remote Similarity	NPC50997
0.6322	Remote Similarity	NPC327769
0.6321	Remote Similarity	NPC157583
0.632	Remote Similarity	NPC475602
0.632	Remote Similarity	NPC207866
0.6318	Remote Similarity	NPC475362
0.6316	Remote Similarity	NPC63041
0.6311	Remote Similarity	NPC472062
0.6311	Remote Similarity	NPC472063
0.6311	Remote Similarity	NPC472069
0.6311	Remote Similarity	NPC260900
0.6311	Remote Similarity	NPC476874
0.6307	Remote Similarity	NPC165743
0.6306	Remote Similarity	NPC227582
0.6306	Remote Similarity	NPC469736
0.6305	Remote Similarity	NPC209362
0.6303	Remote Similarity	NPC473506
0.6303	Remote Similarity	NPC472762
0.6303	Remote Similarity	NPC186068
0.6298	Remote Similarity	NPC477901
0.6295	Remote Similarity	NPC470497
0.6293	Remote Similarity	NPC264674
0.6292	Remote Similarity	NPC477176
0.6292	Remote Similarity	NPC470729
0.6291	Remote Similarity	NPC283219
0.629	Remote Similarity	NPC135950
0.629	Remote Similarity	NPC477420
0.629	Remote Similarity	NPC20593
0.629	Remote Similarity	NPC477418
0.629	Remote Similarity	NPC202812
0.6287	Remote Similarity	NPC250807

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 NPC469544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	483
0.2-0.3	849
0.3-0.4	2550
0.4-0.5	3212
0.5-0.6	1660
0.6-0.7	214
0.7-0.8	0
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
0.6538	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6173	Approved
0.6479	Remote Similarity	NPD2096	Phase 2
0.6479	Remote Similarity	NPD2091	Phase 2
0.6441	Remote Similarity	NPD8289	Discontinued
0.6432	Remote Similarity	NPD2092	Phase 2
0.6432	Remote Similarity	NPD2095	Phase 2
0.6432	Remote Similarity	NPD2094	Phase 2
0.6432	Remote Similarity	NPD3968	Approved
0.6422	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD3411	Phase 2
0.6416	Remote Similarity	NPD3410	Approved
0.6404	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD1096	Discontinued
0.64	Remote Similarity	NPD8115	Approved
0.64	Remote Similarity	NPD8114	Approved
0.6385	Remote Similarity	NPD3178	Discontinued
0.6376	Remote Similarity	NPD2336	Approved
0.6355	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD7878	Phase 2
0.6347	Remote Similarity	NPD6665	Discontinued
0.6345	Remote Similarity	NPD4086	Phase 1
0.6327	Remote Similarity	NPD5426	Phase 3
0.6327	Remote Similarity	NPD5901	Discontinued
0.6308	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3967	Approved
0.6288	Remote Similarity	NPD5510	Approved
0.6287	Remote Similarity	NPD6753	Phase 1
0.6287	Remote Similarity	NPD6752	Phase 1
0.6284	Remote Similarity	NPD6068	Discontinued
0.6267	Remote Similarity	NPD7817	Phase 1
0.6266	Remote Similarity	NPD3389	Approved
0.6266	Remote Similarity	NPD3393	Approved
0.6266	Remote Similarity	NPD3394	Approved
0.6262	Remote Similarity	NPD9510	Approved
0.6261	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD2307	Discontinued
0.6256	Remote Similarity	NPD8169	Discontinued
0.6239	Remote Similarity	NPD8325	Phase 3
0.6239	Remote Similarity	NPD8326	Phase 3
0.6239	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD3915	Approved
0.6228	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7001	Phase 3
0.6222	Remote Similarity	NPD4601	Approved
0.6222	Remote Similarity	NPD4600	Approved
0.6217	Remote Similarity	NPD6529	Discontinued
0.6215	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3918	Approved
0.6207	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3917	Approved
0.6204	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD3353	Approved
0.6195	Remote Similarity	NPD7727	Phase 2
0.6186	Remote Similarity	NPD1643	Phase 3
0.6184	Remote Similarity	NPD3947	Discontinued
0.6184	Remote Similarity	NPD6987	Phase 1
0.6184	Remote Similarity	NPD2511	Approved
0.6179	Remote Similarity	NPD750	Phase 2
0.6178	Remote Similarity	NPD6999	Discontinued
0.6178	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7665	Phase 2
0.6174	Remote Similarity	NPD7666	Phase 3
0.6167	Remote Similarity	NPD7187	Phase 2
0.6164	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.616	Remote Similarity	NPD8468	Phase 2
0.6157	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD7957	Phase 1
0.615	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.615	Remote Similarity	NPD482	Approved
0.6146	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD7944	Discontinued
0.614	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4703	Approved
0.6139	Remote Similarity	NPD4702	Approved
0.6136	Remote Similarity	NPD7234	Approved
0.6136	Remote Similarity	NPD7233	Approved
0.6135	Remote Similarity	NPD2213	Approved
0.6135	Remote Similarity	NPD2214	Approved
0.6132	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6123	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD3321	Discontinued
0.6104	Remote Similarity	NPD2509	Approved
0.6104	Remote Similarity	NPD2510	Approved
0.6102	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD9364	Phase 2
0.6091	Remote Similarity	NPD9363	Approved
0.6085	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD9362	Approved
0.6075	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5017	Discontinued
0.6047	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD3795	Approved
0.6043	Remote Similarity	NPD3794	Approved
0.6043	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD7483	Phase 2
0.6027	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD7564	Discontinued
0.6027	Remote Similarity	NPD7482	Phase 2
0.6026	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD1659	Phase 1
0.6019	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD3961	Discontinued
0.6017	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD4500	Approved
0.6009	Remote Similarity	NPD4501	Approved
0.6008	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD4845	Discontinued
0.6	Remote Similarity	NPD7619	Phase 3
0.6	Remote Similarity	NPD7618	Phase 3
0.6	Remote Similarity	NPD4427	Phase 2
0.6	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4602	Approved
0.5991	Remote Similarity	NPD53	Approved
0.5991	Remote Similarity	NPD7778	Approved
0.5991	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD4079	Approved
0.5991	Remote Similarity	NPD4076	Approved
0.5991	Remote Similarity	NPD7777	Approved
0.599	Remote Similarity	NPD751	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7781	Approved
0.5984	Remote Similarity	NPD7780	Approved
0.5983	Remote Similarity	NPD4051	Discontinued
0.5974	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD510	Phase 1
0.5968	Remote Similarity	NPD3006	Discontinued
0.5966	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6376	Discontinued
0.5966	Remote Similarity	NPD7191	Phase 2
0.5964	Remote Similarity	NPD4499	Approved
0.5963	Remote Similarity	NPD2481	Approved
0.5963	Remote Similarity	NPD2479	Phase 3
0.5962	Remote Similarity	NPD6026	Approved
0.5961	Remote Similarity	NPD5482	Discontinued
0.5958	Remote Similarity	NPD1996	Discontinued
0.5957	Remote Similarity	NPD7470	Discontinued
0.5948	Remote Similarity	NPD7010	Phase 3
0.5946	Remote Similarity	NPD8021	Approved
0.5946	Remote Similarity	NPD8020	Approved
0.5945	Remote Similarity	NPD3506	Approved
0.5945	Remote Similarity	NPD6641	Approved
0.5945	Remote Similarity	NPD8122	Approved
0.5945	Remote Similarity	NPD8123	Approved
0.5945	Remote Similarity	NPD6642	Approved
0.5945	Remote Similarity	NPD3505	Approved
0.5944	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6165	Phase 2
0.5943	Remote Similarity	NPD6164	Phase 2
0.5939	Remote Similarity	NPD5043	Discontinued
0.5935	Remote Similarity	NPD1575	Approved
0.5935	Remote Similarity	NPD1573	Approved
0.5932	Remote Similarity	NPD4852	Phase 2
0.5924	Remote Similarity	NPD7543	Phase 2
0.5917	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6770	Approved
0.5913	Remote Similarity	NPD8412	Phase 1
0.5911	Remote Similarity	NPD7031	Phase 1
0.5911	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8356	Approved
0.5907	Remote Similarity	NPD5888	Phase 2
0.5905	Remote Similarity	NPD5255	Approved
0.5905	Remote Similarity	NPD3379	Phase 2
0.5905	Remote Similarity	NPD3380	Phase 3
0.5903	Remote Similarity	NPD4848	Phase 1
0.59	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7232	Discontinued
0.5897	Remote Similarity	NPD6486	Approved
0.5897	Remote Similarity	NPD6487	Approved
0.5896	Remote Similarity	NPD5088	Discontinued
0.5895	Remote Similarity	NPD3425	Discontinued
0.5895	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD7824	Approved
0.5892	Remote Similarity	NPD6242	Discontinued
0.589	Remote Similarity	NPD5475	Discontinued
0.589	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.589	Remote Similarity	NPD5473	Discontinued
0.589	Remote Similarity	NPD5898	Approved
0.589	Remote Similarity	NPD5899	Approved
0.589	Remote Similarity	NPD5897	Approved
0.5888	Remote Similarity	NPD5862	Discovery
0.5887	Remote Similarity	NPD7952	Approved
0.5887	Remote Similarity	NPD7791	Approved
0.5887	Remote Similarity	NPD7951	Approved
0.5887	Remote Similarity	NPD4924	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