NPASS Compound

Structure

NPC469562 OpenBabel07101719512D 25 31 0 0 1 0 0 0 0 0999 V2000 -0.2715 -1.5299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8415 -1.2008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8816 -1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9542 0.2991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1943 -0.7296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3412 -1.2894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7423 -0.9820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0104 -0.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5336 -0.5160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5352 -0.6604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3757 0.6143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1638 -0.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0903 0.7035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7320 0.0180 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0016 -0.2845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4109 0.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8608 0.5090 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 0.6056 -0.3225 0.0000 N 0 5 0 0 0 0 0 0 0 0 0 0 1.6056 0.2005 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -0.9396 -0.5499 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -2.6135 -1.4729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4089 0.1942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8504 1.5089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9374 -1.3188 0.0000 S 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 2 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 1 0 0 0 8 18 1 0 0 0 0 8 25 1 0 0 0 0 9 4 1 6 0 0 0 9 20 1 0 0 0 0 9 25 1 0 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 23 2 0 0 0 0 17 18 1 6 0 0 0 17 24 1 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:	352.08
Volume:	320.722
LogP:	-1.587
LogD:	-0.42
LogS:	-1.352
# Rotatable Bonds:	0
TPSA:	89.89
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.649
Synthetic Accessibility Score:	7.74
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:	-5.896
MDCK Permeability:	4.141652425460052e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.604
Human Intestinal Absorption (HIA):	0.817
20% Bioavailability (F20%):	0.861
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	91.25819396972656%
Volume Distribution (VD):	1.036
Pgp-substrate:	4.483144283294678%

ADMET: Metabolism

CYP1A2-inhibitor:	0.508
CYP1A2-substrate:	0.77
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.288
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.112
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	1.164
Half-life (T1/2):	0.337

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.938
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.251
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC469562

Natural Product ID:	NPC469562
*Common Name:**	ZNHXEXDFGYAQJK-KKNACZRDSA-O
IUPAC Name:	n.a.
Synonyms:	(-)-Dihydrodiscorhabdin L
Standard InCHIKey:	ZNHXEXDFGYAQJK-KKNACZRDSA-O
Standard InCHI:	InChI=1S/C18H15N3O3S/c22-7-3-8-18-4-9(25-8)20-13-11(18)15-10-6(5-19-12(10)16(13)23)1-2-21(15)14(7)17(18)24/h3,5,7,9,14,17,22,24H,1-2,4H2,(H,19,20,23)/p+1/t7-,9+,14?,17+,18-/m1/s1
SMILES:	O[C@@H]1C=C2S[C@H]3C[C@]42[C@H](C1[N+]1CCc2c5C1=C4C(=[NH+]3)C(=O)c5[n-]c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087538
PubChem CID:	46881012
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
NPT111	Cell Line	K562	Homo sapiens	IC50	=	2500.0	nM	PMID[543163]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	192200.0	nM	PMID[543163]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	100.0	ug.mL-1	PMID[543163]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	50.0	ug.mL-1	PMID[543163]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[543163]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[543163]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	25.0	ug.mL-1	PMID[543163]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	100.0	ug.mL-1	PMID[543163]

☑ 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 NPC469562 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	311
0.1-0.2	1897
0.2-0.3	12591
0.3-0.4	20493
0.4-0.5	3954
0.5-0.6	2886
0.6-0.7	519
0.7-0.8	28
0.8-0.85	6
0.85-0.9	3
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC220594
0.9731	High Similarity	NPC469563
0.9681	High Similarity	NPC469578
0.9319	High Similarity	NPC469577
0.9319	High Similarity	NPC475410
0.9286	High Similarity	NPC477416
0.8871	High Similarity	NPC469359
0.8608	High Similarity	NPC476143
0.85	High Similarity	NPC143075
0.83	Intermediate Similarity	NPC476252
0.8155	Intermediate Similarity	NPC469544
0.7959	Intermediate Similarity	NPC477415
0.7959	Intermediate Similarity	NPC23476
0.7959	Intermediate Similarity	NPC474259
0.7761	Intermediate Similarity	NPC221726
0.7761	Intermediate Similarity	NPC225622
0.7761	Intermediate Similarity	NPC477414
0.7739	Intermediate Similarity	NPC473628
0.7612	Intermediate Similarity	NPC475874
0.7525	Intermediate Similarity	NPC268966
0.7436	Intermediate Similarity	NPC262338
0.7343	Intermediate Similarity	NPC292361
0.73	Intermediate Similarity	NPC182940
0.723	Intermediate Similarity	NPC88115
0.7217	Intermediate Similarity	NPC106757
0.7214	Intermediate Similarity	NPC79777
0.7214	Intermediate Similarity	NPC234403
0.7157	Intermediate Similarity	NPC474258
0.7087	Intermediate Similarity	NPC473946
0.7034	Intermediate Similarity	NPC477420
0.7034	Intermediate Similarity	NPC477418
0.7026	Intermediate Similarity	NPC474492
0.7009	Intermediate Similarity	NPC98864
0.699	Remote Similarity	NPC100104
0.699	Remote Similarity	NPC470680
0.6901	Remote Similarity	NPC78767
0.6901	Remote Similarity	NPC473814
0.6891	Remote Similarity	NPC473878
0.6869	Remote Similarity	NPC477041
0.6869	Remote Similarity	NPC477044
0.6866	Remote Similarity	NPC98715
0.6856	Remote Similarity	NPC217021
0.6856	Remote Similarity	NPC470679
0.6847	Remote Similarity	NPC477413
0.6822	Remote Similarity	NPC74153
0.682	Remote Similarity	NPC328596
0.682	Remote Similarity	NPC328318
0.6808	Remote Similarity	NPC93390
0.6804	Remote Similarity	NPC175602
0.6787	Remote Similarity	NPC61038
0.6774	Remote Similarity	NPC300183
0.6773	Remote Similarity	NPC46225
0.6773	Remote Similarity	NPC225821
0.6761	Remote Similarity	NPC473821
0.6759	Remote Similarity	NPC474767
0.6759	Remote Similarity	NPC477045
0.6758	Remote Similarity	NPC477043
0.675	Remote Similarity	NPC274981
0.6749	Remote Similarity	NPC302647
0.6742	Remote Similarity	NPC258062
0.6742	Remote Similarity	NPC127677
0.673	Remote Similarity	NPC103119
0.6718	Remote Similarity	NPC471655
0.6713	Remote Similarity	NPC248782
0.6701	Remote Similarity	NPC100726
0.6682	Remote Similarity	NPC473239
0.6667	Remote Similarity	NPC311282
0.6667	Remote Similarity	NPC207866
0.6653	Remote Similarity	NPC475635
0.6652	Remote Similarity	NPC317373
0.6652	Remote Similarity	NPC472285
0.6651	Remote Similarity	NPC209917
0.6651	Remote Similarity	NPC75544
0.6651	Remote Similarity	NPC294693
0.6651	Remote Similarity	NPC255909
0.6622	Remote Similarity	NPC151976
0.6622	Remote Similarity	NPC87856
0.6619	Remote Similarity	NPC207851
0.6606	Remote Similarity	NPC327592
0.6606	Remote Similarity	NPC123395
0.6602	Remote Similarity	NPC186068
0.6593	Remote Similarity	NPC267965
0.6584	Remote Similarity	NPC476446
0.6584	Remote Similarity	NPC78375
0.6584	Remote Similarity	NPC469813
0.6582	Remote Similarity	NPC102664
0.6562	Remote Similarity	NPC271862
0.655	Remote Similarity	NPC213914
0.6549	Remote Similarity	NPC110182
0.654	Remote Similarity	NPC63279
0.6535	Remote Similarity	NPC132211
0.6513	Remote Similarity	NPC297642
0.6498	Remote Similarity	NPC195239
0.6498	Remote Similarity	NPC157828
0.6476	Remote Similarity	NPC477042
0.6476	Remote Similarity	NPC471997
0.6468	Remote Similarity	NPC11445
0.6463	Remote Similarity	NPC204491
0.6463	Remote Similarity	NPC203614
0.645	Remote Similarity	NPC209362
0.645	Remote Similarity	NPC269270
0.6447	Remote Similarity	NPC317752
0.6439	Remote Similarity	NPC41717
0.6438	Remote Similarity	NPC167710
0.6429	Remote Similarity	NPC165743
0.6422	Remote Similarity	NPC14686
0.6415	Remote Similarity	NPC163055
0.6414	Remote Similarity	NPC123906
0.6413	Remote Similarity	NPC138562
0.641	Remote Similarity	NPC229893
0.6409	Remote Similarity	NPC131887
0.6407	Remote Similarity	NPC473310
0.6406	Remote Similarity	NPC216550
0.6404	Remote Similarity	NPC318299
0.6404	Remote Similarity	NPC471194
0.6404	Remote Similarity	NPC471193
0.64	Remote Similarity	NPC251391
0.6398	Remote Similarity	NPC476491
0.6395	Remote Similarity	NPC313966
0.6395	Remote Similarity	NPC2395
0.6395	Remote Similarity	NPC314254
0.6394	Remote Similarity	NPC477976
0.6391	Remote Similarity	NPC471192
0.6389	Remote Similarity	NPC154339
0.6389	Remote Similarity	NPC469489
0.6383	Remote Similarity	NPC141428
0.6381	Remote Similarity	NPC157583
0.638	Remote Similarity	NPC103361
0.6376	Remote Similarity	NPC267343
0.6359	Remote Similarity	NPC114974
0.6351	Remote Similarity	NPC252338
0.6345	Remote Similarity	NPC470730
0.6345	Remote Similarity	NPC477175
0.6329	Remote Similarity	NPC57690
0.6318	Remote Similarity	NPC475859
0.6318	Remote Similarity	NPC475969
0.6308	Remote Similarity	NPC46895
0.6293	Remote Similarity	NPC27041
0.629	Remote Similarity	NPC227582
0.6288	Remote Similarity	NPC72956
0.6288	Remote Similarity	NPC82370
0.6286	Remote Similarity	NPC139763
0.6283	Remote Similarity	NPC472065
0.6281	Remote Similarity	NPC477549
0.6278	Remote Similarity	NPC121327
0.6276	Remote Similarity	NPC477176
0.6276	Remote Similarity	NPC470729
0.6273	Remote Similarity	NPC135950
0.6273	Remote Similarity	NPC202812
0.6271	Remote Similarity	NPC147446
0.6266	Remote Similarity	NPC281049
0.6261	Remote Similarity	NPC153980
0.6261	Remote Similarity	NPC6865
0.6261	Remote Similarity	NPC111732
0.6256	Remote Similarity	NPC47190
0.625	Remote Similarity	NPC474877
0.625	Remote Similarity	NPC477177
0.6245	Remote Similarity	NPC19170
0.6245	Remote Similarity	NPC235885
0.6244	Remote Similarity	NPC61011
0.6244	Remote Similarity	NPC73994
0.6235	Remote Similarity	NPC476517
0.6234	Remote Similarity	NPC475602
0.6234	Remote Similarity	NPC297862
0.6234	Remote Similarity	NPC229348
0.6233	Remote Similarity	NPC228835
0.6228	Remote Similarity	NPC476157
0.6226	Remote Similarity	NPC248454
0.6224	Remote Similarity	NPC207686
0.6223	Remote Similarity	NPC469727
0.6223	Remote Similarity	NPC477715
0.6222	Remote Similarity	NPC57398
0.6222	Remote Similarity	NPC143977
0.6221	Remote Similarity	NPC278434
0.6221	Remote Similarity	NPC17059
0.6211	Remote Similarity	NPC472064
0.6207	Remote Similarity	NPC237740
0.6204	Remote Similarity	NPC295158
0.6203	Remote Similarity	NPC476817
0.62	Remote Similarity	NPC476516
0.6198	Remote Similarity	NPC70155
0.6197	Remote Similarity	NPC477714
0.6197	Remote Similarity	NPC126709
0.6197	Remote Similarity	NPC283219
0.6197	Remote Similarity	NPC248041
0.6195	Remote Similarity	NPC143325
0.619	Remote Similarity	NPC219087
0.6188	Remote Similarity	NPC265576
0.6186	Remote Similarity	NPC159125
0.6179	Remote Similarity	NPC150048
0.6179	Remote Similarity	NPC203754
0.6161	Remote Similarity	NPC81535
0.6161	Remote Similarity	NPC284338
0.6161	Remote Similarity	NPC50997
0.6161	Remote Similarity	NPC160127
0.616	Remote Similarity	NPC478141
0.6151	Remote Similarity	NPC267926
0.615	Remote Similarity	NPC472069
0.615	Remote Similarity	NPC472063
0.615	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 NPC469562 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	509
0.2-0.3	853
0.3-0.4	2302
0.4-0.5	3378
0.5-0.6	1768
0.6-0.7	169
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
0.6916	Remote Similarity	NPD6173	Approved
0.6916	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3178	Discontinued
0.6606	Remote Similarity	NPD8169	Discontinued
0.6507	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3394	Approved
0.6463	Remote Similarity	NPD3389	Approved
0.6463	Remote Similarity	NPD3393	Approved
0.6462	Remote Similarity	NPD1096	Discontinued
0.6435	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD8289	Discontinued
0.6384	Remote Similarity	NPD4906	Approved
0.6384	Remote Similarity	NPD4905	Approved
0.6384	Remote Similarity	NPD5901	Discontinued
0.6384	Remote Similarity	NPD4903	Approved
0.6372	Remote Similarity	NPD2509	Approved
0.6372	Remote Similarity	NPD2510	Approved
0.6372	Remote Similarity	NPD4960	Approved
0.6372	Remote Similarity	NPD4959	Approved
0.6368	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7001	Phase 3
0.6356	Remote Similarity	NPD4904	Approved
0.6339	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6044	Discontinued
0.6306	Remote Similarity	NPD6999	Discontinued
0.6306	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7666	Phase 3
0.63	Remote Similarity	NPD7665	Phase 2
0.6283	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6068	Discontinued
0.6261	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD3917	Approved
0.6261	Remote Similarity	NPD3918	Approved
0.6256	Remote Similarity	NPD6665	Discontinued
0.6256	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD4415	Approved
0.6255	Remote Similarity	NPD946	Discontinued
0.6245	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD1643	Phase 3
0.6239	Remote Similarity	NPD8114	Approved
0.6239	Remote Similarity	NPD8272	Phase 2
0.6239	Remote Similarity	NPD8115	Approved
0.6233	Remote Similarity	NPD2091	Phase 2
0.6233	Remote Similarity	NPD2096	Phase 2
0.6217	Remote Similarity	NPD3915	Approved
0.621	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD2893	Phase 3
0.6203	Remote Similarity	NPD6752	Phase 1
0.6203	Remote Similarity	NPD6753	Phase 1
0.6201	Remote Similarity	NPD3968	Approved
0.6195	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD4845	Discontinued
0.6186	Remote Similarity	NPD2092	Phase 2
0.6186	Remote Similarity	NPD2095	Phase 2
0.6186	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD2094	Phase 2
0.6184	Remote Similarity	NPD3411	Phase 2
0.6184	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD3410	Approved
0.6167	Remote Similarity	NPD5426	Phase 3
0.6161	Remote Similarity	NPD750	Phase 2
0.6157	Remote Similarity	NPD6376	Discontinued
0.6143	Remote Similarity	NPD1575	Approved
0.6143	Remote Similarity	NPD1573	Approved
0.6136	Remote Similarity	NPD2336	Approved
0.6133	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD482	Approved
0.6132	Remote Similarity	NPD5065	Approved
0.613	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3082	Discontinued
0.6127	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD4703	Approved
0.6119	Remote Similarity	NPD4702	Approved
0.6117	Remote Similarity	NPD2214	Approved
0.6117	Remote Similarity	NPD5255	Approved
0.6117	Remote Similarity	NPD2213	Approved
0.6111	Remote Similarity	NPD3353	Approved
0.6106	Remote Similarity	NPD5088	Discontinued
0.6106	Remote Similarity	NPD7817	Phase 1
0.6106	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD3947	Discontinued
0.6094	Remote Similarity	NPD3795	Approved
0.6094	Remote Similarity	NPD3794	Approved
0.6093	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD3321	Discontinued
0.6085	Remote Similarity	NPD5461	Discontinued
0.6079	Remote Similarity	NPD7187	Phase 2
0.6078	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD1996	Discontinued
0.607	Remote Similarity	NPD3967	Approved
0.6067	Remote Similarity	NPD5046	Discontinued
0.6063	Remote Similarity	NPD5077	Approved
0.6063	Remote Similarity	NPD5076	Approved
0.6063	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD5043	Discontinued
0.6062	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5510	Approved
0.6061	Remote Similarity	NPD7655	Discontinued
0.6059	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD7878	Phase 2
0.6058	Remote Similarity	NPD6164	Phase 2
0.6058	Remote Similarity	NPD6165	Phase 2
0.6054	Remote Similarity	NPD7618	Phase 3
0.6054	Remote Similarity	NPD7619	Phase 3
0.6054	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6052	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6052	Remote Similarity	NPD8093	Discontinued
0.605	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD7552	Discontinued
0.6048	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD5596	Phase 2
0.6036	Remote Similarity	NPD981	Phase 2
0.6035	Remote Similarity	NPD7727	Phase 2
0.6035	Remote Similarity	NPD5017	Discontinued
0.6028	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD7027	Phase 3
0.6027	Remote Similarity	NPD2307	Discontinued
0.6026	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6987	Phase 1
0.6025	Remote Similarity	NPD8356	Approved
0.6019	Remote Similarity	NPD9510	Approved
0.6018	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.601	Remote Similarity	NPD2511	Approved
0.6009	Remote Similarity	NPD5475	Discontinued
0.6009	Remote Similarity	NPD7564	Discontinued
0.6009	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD4417	Approved
0.6009	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD7470	Discontinued
0.6	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2720	Phase 1
0.6	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3961	Discontinued
0.6	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7010	Phase 3
0.5992	Remote Similarity	NPD8430	Approved
0.5992	Remote Similarity	NPD4086	Phase 1
0.5991	Remote Similarity	NPD484	Approved
0.5991	Remote Similarity	NPD6529	Discontinued
0.5983	Remote Similarity	NPD8072	Approved
0.5983	Remote Similarity	NPD4852	Phase 2
0.5982	Remote Similarity	NPD3395	Approved
0.5982	Remote Similarity	NPD3396	Approved
0.5982	Remote Similarity	NPD7944	Discontinued
0.5975	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD7233	Approved
0.5973	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD7234	Approved
0.5972	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD4076	Approved
0.5972	Remote Similarity	NPD4079	Approved
0.5968	Remote Similarity	NPD7677	Discontinued
0.5966	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD4051	Discontinued
0.5965	Remote Similarity	NPD4962	Approved
0.5965	Remote Similarity	NPD4963	Approved
0.5964	Remote Similarity	NPD3288	Approved
0.5962	Remote Similarity	NPD2123	Phase 3
0.5959	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD4848	Phase 1
0.5955	Remote Similarity	NPD3315	Phase 3
0.5952	Remote Similarity	NPD1631	Approved
0.5952	Remote Similarity	NPD8468	Phase 2
0.5951	Remote Similarity	NPD3006	Discontinued
0.595	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD5473	Discontinued
0.5943	Remote Similarity	NPD1659	Phase 1
0.5941	Remote Similarity	NPD6242	Discontinued
0.5939	Remote Similarity	NPD8073	Approved
0.5936	Remote Similarity	NPD7482	Phase 2
0.5936	Remote Similarity	NPD7483	Phase 2
0.5928	Remote Similarity	NPD4988	Discontinued
0.5926	Remote Similarity	NPD2144	Approved
0.5926	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3505	Approved
0.5926	Remote Similarity	NPD2753	Discontinued
0.5926	Remote Similarity	NPD3506	Approved
0.5921	Remote Similarity	NPD4961	Approved
0.592	Remote Similarity	NPD3717	Discontinued
0.5919	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD4949	Discontinued
0.5907	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD7543	Phase 2
0.5906	Remote Similarity	NPD4887	Discontinued
0.5905	Remote Similarity	NPD7562	Approved
0.5901	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7825	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