NPASS Compound

Structure

NPC37152 OpenBabel07101718202D 25 28 0 0 0 0 0 0 0 0999 V2000 4.0575 2.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 1.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6562 3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6508 3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2386 4.0962 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 Br 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 1.0739 2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 1 0 0 0 0 3 11 2 0 0 0 0 4 22 2 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 24 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	521.82
Volume:	356.719
LogP:	5.498
LogD:	3.117
LogS:	-5.792
# Rotatable Bonds:	2
TPSA:	65.98
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	2.638
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.214
MDCK Permeability:	1.3615069292427506e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.483
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	99.89199829101562%
Volume Distribution (VD):	0.563
Pgp-substrate:	1.2746012210845947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.698
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.6
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.693
CYP2D6-substrate:	0.559
CYP3A4-inhibitor:	0.244
CYP3A4-substrate:	0.086

ADMET: Excretion

Clearance (CL):	0.526
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.162
Carcinogencity:	0.629
Eye Corrosion:	0.004
Eye Irritation:	0.585
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC37152

Natural Product ID:	NPC37152
*Common Name:**	Eudistomin Y7
IUPAC Name:	(7-bromo-9H-pyrido[3,4-b]indol-1-yl)-(3,5-dibromo-4-hydroxyphenyl)methanone
Synonyms:	Eudistomin Y7
Standard InCHIKey:	JIBBXIBLZPCSSH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H9Br3N2O2/c19-9-1-2-10-11-3-4-22-16(15(11)23-14(10)7-9)17(24)8-5-12(20)18(25)13(21)6-8/h1-7,23,25H
SMILES:	Brc1ccc2c(c1)[nH]c1c2ccnc1C(=O)c1cc(Br)c(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048340
PubChem CID:	24800708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22652254]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23145909]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23747224]

☑ 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	10
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	LC50	=	59000.0	nM	PMID[491404]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	190500.0	nM	PMID[491404]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.125	ug.mL-1	PMID[491404]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.78	ug.mL-1	PMID[491404]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	1.56	ug.mL-1	PMID[491404]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	0.78	ug.mL-1	PMID[491404]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	0.78	ug.mL-1	PMID[491404]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	50.0	ug.mL-1	PMID[491404]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[491404]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[491404]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[491404]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[491404]
NPT2	Others	Unspecified		IC50	=	11300.0	nM	PMID[491404]

☑ 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 NPC37152 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	754
0.1-0.2	5654
0.2-0.3	11971
0.3-0.4	14761
0.4-0.5	5810
0.5-0.6	2317
0.6-0.7	1267
0.7-0.8	148
0.8-0.85	7
0.85-0.9	2
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.981	High Similarity	NPC174489
0.9718	High Similarity	NPC26641
0.9623	High Similarity	NPC200553
0.9579	High Similarity	NPC162002
0.9439	High Similarity	NPC279189
0.9009	High Similarity	NPC27041
0.8661	High Similarity	NPC97902
0.8333	Intermediate Similarity	NPC470502
0.8326	Intermediate Similarity	NPC207686
0.8259	Intermediate Similarity	NPC470503
0.819	Intermediate Similarity	NPC322064
0.8169	Intermediate Similarity	NPC237414
0.8133	Intermediate Similarity	NPC470501
0.796	Intermediate Similarity	NPC77101
0.791	Intermediate Similarity	NPC216369
0.7887	Intermediate Similarity	NPC324149
0.786	Intermediate Similarity	NPC229893
0.7807	Intermediate Similarity	NPC276657
0.7801	Intermediate Similarity	NPC63971
0.7801	Intermediate Similarity	NPC91868
0.7797	Intermediate Similarity	NPC235685
0.7787	Intermediate Similarity	NPC182222
0.7783	Intermediate Similarity	NPC122436
0.7764	Intermediate Similarity	NPC101350
0.7706	Intermediate Similarity	NPC474916
0.7658	Intermediate Similarity	NPC470505
0.7652	Intermediate Similarity	NPC323969
0.7645	Intermediate Similarity	NPC178858
0.7604	Intermediate Similarity	NPC326422
0.7578	Intermediate Similarity	NPC470500
0.7577	Intermediate Similarity	NPC110182
0.7547	Intermediate Similarity	NPC191415
0.7545	Intermediate Similarity	NPC82053
0.7545	Intermediate Similarity	NPC175602
0.7545	Intermediate Similarity	NPC476121
0.7544	Intermediate Similarity	NPC470703
0.7511	Intermediate Similarity	NPC260434
0.75	Intermediate Similarity	NPC473218
0.75	Intermediate Similarity	NPC470702
0.75	Intermediate Similarity	NPC472259
0.75	Intermediate Similarity	NPC219087
0.75	Intermediate Similarity	NPC74153
0.7478	Intermediate Similarity	NPC266249
0.7478	Intermediate Similarity	NPC171787
0.7467	Intermediate Similarity	NPC477610
0.7459	Intermediate Similarity	NPC470504
0.7458	Intermediate Similarity	NPC477549
0.7445	Intermediate Similarity	NPC61038
0.7443	Intermediate Similarity	NPC473821
0.744	Intermediate Similarity	NPC63109
0.7436	Intermediate Similarity	NPC220851
0.7434	Intermediate Similarity	NPC183777
0.7432	Intermediate Similarity	NPC477004
0.7415	Intermediate Similarity	NPC60006
0.7412	Intermediate Similarity	NPC123839
0.7389	Intermediate Similarity	NPC476124
0.7378	Intermediate Similarity	NPC317701
0.7376	Intermediate Similarity	NPC222018
0.7373	Intermediate Similarity	NPC245348
0.7371	Intermediate Similarity	NPC258048
0.7366	Intermediate Similarity	NPC471944
0.7362	Intermediate Similarity	NPC175150
0.7362	Intermediate Similarity	NPC243633
0.7349	Intermediate Similarity	NPC102755
0.7349	Intermediate Similarity	NPC471536
0.7345	Intermediate Similarity	NPC475070
0.7344	Intermediate Similarity	NPC33064
0.7344	Intermediate Similarity	NPC475635
0.7344	Intermediate Similarity	NPC245055
0.7341	Intermediate Similarity	NPC74619
0.7339	Intermediate Similarity	NPC264285
0.7339	Intermediate Similarity	NPC477609
0.7316	Intermediate Similarity	NPC207866
0.7308	Intermediate Similarity	NPC269270
0.7303	Intermediate Similarity	NPC474357
0.7294	Intermediate Similarity	NPC278434
0.7281	Intermediate Similarity	NPC270918
0.7277	Intermediate Similarity	NPC14686
0.7273	Intermediate Similarity	NPC207020
0.7265	Intermediate Similarity	NPC78767
0.7265	Intermediate Similarity	NPC473814
0.7261	Intermediate Similarity	NPC5145
0.7261	Intermediate Similarity	NPC267078
0.7261	Intermediate Similarity	NPC935
0.7257	Intermediate Similarity	NPC57398
0.7257	Intermediate Similarity	NPC473761
0.7235	Intermediate Similarity	NPC110158
0.7234	Intermediate Similarity	NPC74360
0.7233	Intermediate Similarity	NPC475746
0.7231	Intermediate Similarity	NPC284888
0.7227	Intermediate Similarity	NPC324091
0.7225	Intermediate Similarity	NPC53144
0.721	Intermediate Similarity	NPC237740
0.7208	Intermediate Similarity	NPC477607
0.7208	Intermediate Similarity	NPC477608
0.72	Intermediate Similarity	NPC81535
0.7198	Intermediate Similarity	NPC118940
0.7195	Intermediate Similarity	NPC148889
0.7188	Intermediate Similarity	NPC141454
0.7175	Intermediate Similarity	NPC93390
0.7173	Intermediate Similarity	NPC60621
0.7163	Intermediate Similarity	NPC284775
0.7162	Intermediate Similarity	NPC99666
0.7161	Intermediate Similarity	NPC213530
0.7161	Intermediate Similarity	NPC193267
0.7156	Intermediate Similarity	NPC192315
0.7155	Intermediate Similarity	NPC82370
0.7149	Intermediate Similarity	NPC469727
0.7149	Intermediate Similarity	NPC470323
0.7143	Intermediate Similarity	NPC16352
0.7137	Intermediate Similarity	NPC52909
0.7137	Intermediate Similarity	NPC475935
0.7137	Intermediate Similarity	NPC94211
0.7126	Intermediate Similarity	NPC53534
0.7125	Intermediate Similarity	NPC214142
0.7124	Intermediate Similarity	NPC128084
0.7124	Intermediate Similarity	NPC476167
0.7115	Intermediate Similarity	NPC117980
0.7109	Intermediate Similarity	NPC274229
0.7106	Intermediate Similarity	NPC74969
0.7105	Intermediate Similarity	NPC211813
0.7103	Intermediate Similarity	NPC181081
0.7095	Intermediate Similarity	NPC261251
0.7095	Intermediate Similarity	NPC124920
0.7095	Intermediate Similarity	NPC34580
0.7095	Intermediate Similarity	NPC118559
0.7095	Intermediate Similarity	NPC304307
0.7093	Intermediate Similarity	NPC45459
0.7093	Intermediate Similarity	NPC77241
0.7093	Intermediate Similarity	NPC166209
0.7093	Intermediate Similarity	NPC13456
0.7093	Intermediate Similarity	NPC205254
0.7093	Intermediate Similarity	NPC303820
0.7093	Intermediate Similarity	NPC269203
0.7093	Intermediate Similarity	NPC23420
0.7093	Intermediate Similarity	NPC315491
0.7093	Intermediate Similarity	NPC106771
0.7074	Intermediate Similarity	NPC200836
0.7074	Intermediate Similarity	NPC165599
0.7073	Intermediate Similarity	NPC15801
0.7072	Intermediate Similarity	NPC154339
0.7066	Intermediate Similarity	NPC156003
0.7066	Intermediate Similarity	NPC100547
0.7054	Intermediate Similarity	NPC24370
0.7054	Intermediate Similarity	NPC319232
0.7048	Intermediate Similarity	NPC220797
0.7048	Intermediate Similarity	NPC474318
0.7048	Intermediate Similarity	NPC475914
0.7048	Intermediate Similarity	NPC268744
0.7048	Intermediate Similarity	NPC153123
0.7048	Intermediate Similarity	NPC201266
0.7043	Intermediate Similarity	NPC132539
0.7042	Intermediate Similarity	NPC167908
0.704	Intermediate Similarity	NPC476460
0.7039	Intermediate Similarity	NPC85273
0.7039	Intermediate Similarity	NPC309845
0.7037	Intermediate Similarity	NPC322135
0.7037	Intermediate Similarity	NPC223409
0.7037	Intermediate Similarity	NPC326363
0.7037	Intermediate Similarity	NPC151635
0.7037	Intermediate Similarity	NPC95240
0.7035	Intermediate Similarity	NPC227582
0.7035	Intermediate Similarity	NPC90229
0.7035	Intermediate Similarity	NPC167710
0.7034	Intermediate Similarity	NPC67658
0.7032	Intermediate Similarity	NPC48938
0.7022	Intermediate Similarity	NPC202812
0.7018	Intermediate Similarity	NPC213308
0.7017	Intermediate Similarity	NPC168209
0.7014	Intermediate Similarity	NPC62749
0.7008	Intermediate Similarity	NPC14288
0.7004	Intermediate Similarity	NPC476041
0.7004	Intermediate Similarity	NPC131887
0.7004	Intermediate Similarity	NPC304926
0.6992	Remote Similarity	NPC325976
0.6991	Remote Similarity	NPC179701
0.6991	Remote Similarity	NPC79356
0.6991	Remote Similarity	NPC102592
0.6983	Remote Similarity	NPC244741
0.6982	Remote Similarity	NPC46580
0.698	Remote Similarity	NPC54803
0.698	Remote Similarity	NPC321592
0.6978	Remote Similarity	NPC267343
0.6978	Remote Similarity	NPC88315
0.6978	Remote Similarity	NPC304203
0.6977	Remote Similarity	NPC82331
0.6976	Remote Similarity	NPC41679
0.6968	Remote Similarity	NPC295158
0.6966	Remote Similarity	NPC123976
0.6966	Remote Similarity	NPC167860
0.6964	Remote Similarity	NPC138370
0.6962	Remote Similarity	NPC152620
0.696	Remote Similarity	NPC262898
0.6959	Remote Similarity	NPC474958
0.6953	Remote Similarity	NPC116555
0.6946	Remote Similarity	NPC292958
0.6944	Remote Similarity	NPC252572
0.6943	Remote Similarity	NPC252338
0.6939	Remote Similarity	NPC477112
0.6936	Remote Similarity	NPC246518

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 NPC37152 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	733
0.2-0.3	886
0.3-0.4	2452
0.4-0.5	2423
0.5-0.6	1894
0.6-0.7	363
0.7-0.8	8
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
0.7339	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD4845	Discontinued
0.7303	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD8106	Phase 2
0.7203	Intermediate Similarity	NPD1996	Discontinued
0.7197	Intermediate Similarity	NPD7603	Discontinued
0.7188	Intermediate Similarity	NPD7948	Phase 1
0.7118	Intermediate Similarity	NPD5901	Discontinued
0.7108	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD484	Approved
0.7034	Intermediate Similarity	NPD3389	Approved
0.7034	Intermediate Similarity	NPD3394	Approved
0.7034	Intermediate Similarity	NPD3393	Approved
0.7016	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5482	Discontinued
0.6991	Remote Similarity	NPD5065	Approved
0.6987	Remote Similarity	NPD6242	Discontinued
0.6983	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6376	Discontinued
0.6953	Remote Similarity	NPD2510	Approved
0.6953	Remote Similarity	NPD2509	Approved
0.6905	Remote Similarity	NPD3959	Phase 2
0.6905	Remote Similarity	NPD3962	Phase 2
0.6867	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6458	Discontinued
0.6846	Remote Similarity	NPD6530	Approved
0.6846	Remote Similarity	NPD6531	Approved
0.6834	Remote Similarity	NPD5050	Approved
0.6833	Remote Similarity	NPD4429	Discontinued
0.6831	Remote Similarity	NPD2803	Discontinued
0.6829	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4558	Phase 2
0.6757	Remote Similarity	NPD3178	Discontinued
0.6756	Remote Similarity	NPD4948	Discontinued
0.6748	Remote Similarity	NPD7994	Phase 2
0.6736	Remote Similarity	NPD3794	Approved
0.6736	Remote Similarity	NPD3795	Approved
0.6726	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5475	Discontinued
0.6708	Remote Similarity	NPD5827	Discontinued
0.6695	Remote Similarity	NPD8093	Discontinued
0.6694	Remote Similarity	NPD5022	Discontinued
0.6681	Remote Similarity	NPD5426	Phase 3
0.6681	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6999	Discontinued
0.668	Remote Similarity	NPD6164	Phase 2
0.668	Remote Similarity	NPD6165	Phase 2
0.6679	Remote Similarity	NPD5450	Discontinued
0.6667	Remote Similarity	NPD3243	Approved
0.6654	Remote Similarity	NPD6790	Phase 1
0.6653	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8091	Phase 3
0.664	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.664	Remote Similarity	NPD8289	Discontinued
0.6637	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5891	Approved
0.6627	Remote Similarity	NPD7853	Phase 2
0.6622	Remote Similarity	NPD6178	Phase 3
0.6612	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6987	Phase 1
0.6609	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD460	Discontinued
0.6606	Remote Similarity	NPD482	Approved
0.6602	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8094	Discontinued
0.6597	Remote Similarity	NPD7665	Phase 2
0.6597	Remote Similarity	NPD7666	Phase 3
0.6594	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2951	Discontinued
0.6584	Remote Similarity	NPD4989	Phase 2
0.6583	Remote Similarity	NPD5416	Discontinued
0.6582	Remote Similarity	NPD2008	Discontinued
0.658	Remote Similarity	NPD7619	Phase 3
0.658	Remote Similarity	NPD7618	Phase 3
0.6578	Remote Similarity	NPD2095	Phase 2
0.6578	Remote Similarity	NPD2092	Phase 2
0.6578	Remote Similarity	NPD2094	Phase 2
0.6577	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD4922	Phase 2
0.6561	Remote Similarity	NPD3006	Discontinued
0.656	Remote Similarity	NPD5479	Discontinued
0.6556	Remote Similarity	NPD2411	Approved
0.6556	Remote Similarity	NPD3330	Phase 1
0.6552	Remote Similarity	NPD2290	Phase 3
0.6552	Remote Similarity	NPD2289	Phase 3
0.6549	Remote Similarity	NPD2091	Phase 2
0.6549	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2096	Phase 2
0.6548	Remote Similarity	NPD4850	Phase 1
0.6543	Remote Similarity	NPD5612	Discontinued
0.6542	Remote Similarity	NPD4051	Discontinued
0.654	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7404	Approved
0.6531	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.653	Remote Similarity	NPD424	Approved
0.653	Remote Similarity	NPD425	Approved
0.6525	Remote Similarity	NPD7187	Phase 2
0.6525	Remote Similarity	NPD6975	Discontinued
0.6522	Remote Similarity	NPD2336	Approved
0.6516	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3280	Approved
0.6502	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1600	Suspended
0.6496	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7689	Approved
0.6492	Remote Similarity	NPD6173	Approved
0.6492	Remote Similarity	NPD3222	Phase 2
0.6489	Remote Similarity	NPD2479	Phase 3
0.6489	Remote Similarity	NPD2481	Approved
0.6483	Remote Similarity	NPD4511	Phase 1
0.6483	Remote Similarity	NPD5017	Discontinued
0.6481	Remote Similarity	NPD4848	Phase 1
0.6475	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3947	Discontinued
0.6466	Remote Similarity	NPD1038	Approved
0.6463	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4883	Approved
0.6452	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8356	Approved
0.645	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7470	Discontinued
0.6443	Remote Similarity	NPD3746	Discontinued
0.6434	Remote Similarity	NPD5293	Phase 2
0.6429	Remote Similarity	NPD6991	Approved
0.6426	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD6752	Phase 1
0.6426	Remote Similarity	NPD6753	Phase 1
0.6425	Remote Similarity	NPD2781	Approved
0.6423	Remote Similarity	NPD7878	Phase 2
0.6422	Remote Similarity	NPD4376	Phase 3
0.642	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7558	Phase 2
0.6417	Remote Similarity	NPD7415	Suspended
0.6416	Remote Similarity	NPD5473	Discontinued
0.6414	Remote Similarity	NPD3259	Approved
0.6414	Remote Similarity	NPD8430	Approved
0.641	Remote Similarity	NPD2307	Discontinued
0.6409	Remote Similarity	NPD2782	Approved
0.6409	Remote Similarity	NPD2780	Approved
0.6404	Remote Similarity	NPD1096	Discontinued
0.6402	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6153	Approved
0.64	Remote Similarity	NPD4890	Phase 2
0.6395	Remote Similarity	NPD802	Phase 2
0.639	Remote Similarity	NPD2916	Discontinued
0.639	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7924	Phase 2
0.6384	Remote Similarity	NPD7925	Phase 2
0.6383	Remote Similarity	NPD8349	Phase 1
0.6378	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7001	Phase 3
0.6372	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5850	Phase 3
0.6364	Remote Similarity	NPD4520	Approved
0.636	Remote Similarity	NPD4886	Phase 2
0.636	Remote Similarity	NPD6176	Phase 1
0.6356	Remote Similarity	NPD7395	Discontinued
0.6353	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4373	Phase 2
0.6352	Remote Similarity	NPD3404	Approved
0.6349	Remote Similarity	NPD3905	Phase 3
0.6349	Remote Similarity	NPD1506	Discontinued
0.6344	Remote Similarity	NPD6595	Phase 3
0.6344	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.634	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD750	Phase 2
0.6335	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7564	Discontinued
0.6329	Remote Similarity	NPD3814	Phase 1
0.6329	Remote Similarity	NPD3825	Phase 3
0.6327	Remote Similarity	NPD6159	Phase 2
0.6325	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7672	Approved
0.6322	Remote Similarity	NPD7671	Approved
0.6322	Remote Similarity	NPD2442	Approved
0.6322	Remote Similarity	NPD2443	Approved
0.6318	Remote Similarity	NPD3931	Approved
0.6318	Remote Similarity	NPD3928	Approved

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