NPASS Compound

Structure

NPC476013 OpenBabel07101719252D 31 34 0 0 1 0 0 0 0 0999 V2000 4.8363 -2.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4661 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6001 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8646 -1.0086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4661 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6063 -4.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8680 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7341 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8680 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0610 -1.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4661 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3880 -1.1034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7681 -2.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4661 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4221 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5523 -3.7758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7926 -3.1053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0951 -1.8105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6001 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6001 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.7341 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2297 -2.6865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3387 -2.2325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2820 -3.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7341 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.6001 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.2863 -1.2339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.7772 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4433 -4.2298 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2479 -3.9440 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 3.1633 -2.3282 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 31 1 0 0 0 0 16 28 2 0 0 0 0 16 29 1 0 0 0 0 17 30 2 0 0 0 0 17 31 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 2 0 0 0 0 24 30 1 0 0 0 0 M CHG 1 30 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.33
Volume:	464.51
LogP:	3.875
LogD:	4.687
LogS:	-2.677
# Rotatable Bonds:	5
TPSA:	61.34
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.505
Synthetic Accessibility Score:	5.046
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.247
MDCK Permeability:	3.2782220387161942e-06
Pgp-inhibitor:	0.428
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.938
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.462
Plasma Protein Binding (PPB):	74.86510467529297%
Volume Distribution (VD):	0.957
Pgp-substrate:	26.363727569580078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.984
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.139
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	7.847
Half-life (T1/2):	0.838

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.865
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.675
Carcinogencity:	0.176
Eye Corrosion:	0.004
Eye Irritation:	0.062
Respiratory Toxicity:	0.626

Download Data

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

Natural Product: NPC476013

Natural Product ID:	NPC476013
*Common Name:**	Agelasine A
IUPAC Name:	7-[(E)-5-[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl]-9-methylpurin-9-ium-6-amine;chloride
Synonyms:
Standard InCHIKey:	XICLOSWTCINPKX-IFENWKNUSA-M
Standard InCHI:	InChI=1S/C26H40N5.ClH/c1-18(12-15-31-17-30(6)24-22(31)23(27)28-16-29-24)10-13-25(4)20(3)11-14-26(5)19(2)8-7-9-21(25)26;/h8,12,16-17,20-21H,7,9-11,13-15H2,1-6H3,(H2,27,28,29);1H/q+1;/p-1/b18-12+;/t20-,21-,25+,26-;/m0./s1
SMILES:	C/C(=CCn1c[n+](c2c1c(N)ncn2)C)/CC[C@]1(C)[C@@H](C)CC[C@@]2([C@H]1CCC=C2C)C.[Cl-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521614
PubChem CID:	10072839
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia	1997-AUG	PMID[10514317]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14677933]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332839]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562840]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19209898]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[26083682]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584409]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	papua new guinean	n.a.	PMID[9784179]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	3
Others	2

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	24000.0	nM	PMID[461061]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IZ	=	14.0	mm	PMID[461061]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IZ	=	12.0	mm	PMID[461061]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[461061]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	42000.0	nM	PMID[461061]

☑ 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 NPC476013 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	892
0.1-0.2	17769
0.2-0.3	18390
0.3-0.4	3566
0.4-0.5	1722
0.5-0.6	300
0.6-0.7	33
0.7-0.8	5
0.8-0.85	4
0.85-0.9	5
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474986
1.0	High Similarity	NPC476522
0.9924	High Similarity	NPC476521
0.9848	High Similarity	NPC476520
0.9773	High Similarity	NPC476528
0.9773	High Similarity	NPC476433
0.9771	High Similarity	NPC470266
0.9695	High Similarity	NPC296437
0.9485	High Similarity	NPC476408
0.9034	High Similarity	NPC472832
0.9034	High Similarity	NPC18308
0.9	High Similarity	NPC244700
0.8889	High Similarity	NPC472834
0.8828	High Similarity	NPC472833
0.8451	Intermediate Similarity	NPC217656
0.8187	Intermediate Similarity	NPC473585
0.8138	Intermediate Similarity	NPC89139
0.7988	Intermediate Similarity	NPC265111
0.7099	Intermediate Similarity	NPC87981
0.7099	Intermediate Similarity	NPC174114
0.6928	Remote Similarity	NPC167285
0.6882	Remote Similarity	NPC317054
0.6818	Remote Similarity	NPC226184
0.6818	Remote Similarity	NPC76544
0.68	Remote Similarity	NPC57279
0.6744	Remote Similarity	NPC164845
0.6569	Remote Similarity	NPC18335
0.6569	Remote Similarity	NPC476564
0.6447	Remote Similarity	NPC104011
0.6414	Remote Similarity	NPC68938
0.6369	Remote Similarity	NPC33996
0.6338	Remote Similarity	NPC312187
0.6338	Remote Similarity	NPC4837
0.6329	Remote Similarity	NPC129756
0.631	Remote Similarity	NPC239737
0.6236	Remote Similarity	NPC477119
0.6188	Remote Similarity	NPC317821
0.6145	Remote Similarity	NPC150853
0.6141	Remote Similarity	NPC313514
0.6129	Remote Similarity	NPC246193
0.6124	Remote Similarity	NPC313897
0.6118	Remote Similarity	NPC476219
0.6118	Remote Similarity	NPC93365
0.6087	Remote Similarity	NPC209525
0.6087	Remote Similarity	NPC161659
0.6081	Remote Similarity	NPC189314
0.6033	Remote Similarity	NPC477118
0.6023	Remote Similarity	NPC476297
0.6012	Remote Similarity	NPC300238
0.6012	Remote Similarity	NPC229974
0.6012	Remote Similarity	NPC314152
0.601	Remote Similarity	NPC469308
0.6	Remote Similarity	NPC477120
0.6	Remote Similarity	NPC469975
0.6	Remote Similarity	NPC189068
0.5964	Remote Similarity	NPC219313
0.5964	Remote Similarity	NPC309832
0.5943	Remote Similarity	NPC470203
0.5939	Remote Similarity	NPC21448
0.5939	Remote Similarity	NPC107374
0.5939	Remote Similarity	NPC156461
0.5909	Remote Similarity	NPC248007
0.5904	Remote Similarity	NPC164665
0.5893	Remote Similarity	NPC136349
0.5886	Remote Similarity	NPC470204
0.5868	Remote Similarity	NPC269827
0.5838	Remote Similarity	NPC120070
0.5833	Remote Similarity	NPC121222
0.5824	Remote Similarity	NPC114209
0.5824	Remote Similarity	NPC189261
0.5824	Remote Similarity	NPC161224
0.5805	Remote Similarity	NPC195140
0.5794	Remote Similarity	NPC158055
0.5789	Remote Similarity	NPC328479
0.5764	Remote Similarity	NPC476099
0.5756	Remote Similarity	NPC302778
0.5756	Remote Similarity	NPC212551
0.5731	Remote Similarity	NPC211025
0.5731	Remote Similarity	NPC185991
0.5731	Remote Similarity	NPC85689
0.5723	Remote Similarity	NPC174802
0.5723	Remote Similarity	NPC8590
0.5714	Remote Similarity	NPC139776
0.5706	Remote Similarity	NPC122141
0.57	Remote Similarity	NPC250178
0.5698	Remote Similarity	NPC472816
0.5698	Remote Similarity	NPC321814
0.569	Remote Similarity	NPC224076
0.5685	Remote Similarity	NPC276373
0.5674	Remote Similarity	NPC225018
0.5665	Remote Similarity	NPC130586
0.5665	Remote Similarity	NPC164952
0.566	Remote Similarity	NPC14330
0.5657	Remote Similarity	NPC5802
0.5657	Remote Similarity	NPC226245
0.5638	Remote Similarity	NPC24589
0.5635	Remote Similarity	NPC290959
0.5628	Remote Similarity	NPC157821
0.5625	Remote Similarity	NPC476561
0.5625	Remote Similarity	NPC287876
0.5607	Remote Similarity	NPC115595
0.5607	Remote Similarity	NPC207633

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 NPC476013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	1112
0.2-0.3	3223
0.3-0.4	2205
0.4-0.5	1523
0.5-0.6	645
0.6-0.7	69
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
0.7329	Intermediate Similarity	NPD1058	Discontinued
0.703	Intermediate Similarity	NPD1313	Approved
0.6747	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1333	Phase 3
0.6667	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7158	Phase 1
0.6644	Remote Similarity	NPD870	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5962	Phase 2
0.6629	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1015	Phase 2
0.6607	Remote Similarity	NPD1016	Phase 2
0.6587	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8836	Approved
0.6529	Remote Similarity	NPD8120	Approved
0.6529	Remote Similarity	NPD8121	Phase 3
0.6522	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.651	Remote Similarity	NPD9408	Phase 3
0.6503	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1215	Discontinued
0.649	Remote Similarity	NPD9633	Phase 3
0.6489	Remote Similarity	NPD6129	Phase 2
0.6484	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4240	Approved
0.6471	Remote Similarity	NPD6816	Phase 3
0.6467	Remote Similarity	NPD2927	Phase 3
0.6453	Remote Similarity	NPD2333	Discontinued
0.6447	Remote Similarity	NPD248	Discontinued
0.6433	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2457	Phase 2
0.6425	Remote Similarity	NPD2456	Phase 2
0.6421	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7111	Discontinued
0.6407	Remote Similarity	NPD5969	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3799	Suspended
0.6384	Remote Similarity	NPD40	Phase 2
0.6384	Remote Similarity	NPD5730	Phase 2
0.6369	Remote Similarity	NPD799	Phase 1
0.6364	Remote Similarity	NPD5843	Discontinued
0.6359	Remote Similarity	NPD3430	Approved
0.6359	Remote Similarity	NPD6619	Phase 3
0.6359	Remote Similarity	NPD3431	Approved
0.6359	Remote Similarity	NPD4352	Phase 1
0.6341	Remote Similarity	NPD4568	Phase 2
0.6304	Remote Similarity	NPD6761	Discontinued
0.6302	Remote Similarity	NPD7323	Phase 2
0.6301	Remote Similarity	NPD2647	Phase 3
0.6301	Remote Similarity	NPD6794	Approved
0.6289	Remote Similarity	NPD3695	Approved
0.6289	Remote Similarity	NPD3696	Approved
0.6287	Remote Similarity	NPD2524	Discontinued
0.627	Remote Similarity	NPD7722	Suspended
0.6264	Remote Similarity	NPD2591	Phase 2
0.6264	Remote Similarity	NPD2793	Discontinued
0.6264	Remote Similarity	NPD4902	Discontinued
0.6257	Remote Similarity	NPD5508	Phase 1
0.625	Remote Similarity	NPD5324	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5463	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD3041	Approved
0.6235	Remote Similarity	NPD171	Discontinued
0.6223	Remote Similarity	NPD5462	Discontinued
0.6222	Remote Similarity	NPD2523	Phase 2
0.6222	Remote Similarity	NPD1637	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD2526	Phase 2
0.6215	Remote Similarity	NPD7006	Approved
0.6207	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD1892	Phase 2
0.6201	Remote Similarity	NPD3409	Phase 1
0.6201	Remote Similarity	NPD1893	Phase 2
0.6193	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD6828	Phase 2
0.619	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1257	Approved
0.619	Remote Similarity	NPD6469	Phase 3
0.6186	Remote Similarity	NPD2452	Phase 2
0.6186	Remote Similarity	NPD2450	Phase 2
0.6186	Remote Similarity	NPD2453	Phase 2
0.6186	Remote Similarity	NPD2451	Phase 2
0.6183	Remote Similarity	NPD4615	Phase 2
0.6183	Remote Similarity	NPD2839	Phase 2
0.618	Remote Similarity	NPD2406	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD4763	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5682	Phase 3
0.6175	Remote Similarity	NPD6721	Phase 1
0.6162	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4612	Discontinued
0.6141	Remote Similarity	NPD7138	Phase 2
0.614	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD2876	Phase 3
0.6133	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD3107	Discontinued
0.6127	Remote Similarity	NPD6850	Phase 2
0.6127	Remote Similarity	NPD6849	Phase 2
0.6124	Remote Similarity	NPD7297	Phase 2
0.6121	Remote Similarity	NPD4182	Phase 3
0.6121	Remote Similarity	NPD4183	Phase 3
0.6118	Remote Similarity	NPD2646	Discontinued
0.6118	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD7445	Phase 1
0.6096	Remote Similarity	NPD6577	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6151	Phase 2
0.6093	Remote Similarity	NPD306	Approved
0.6091	Remote Similarity	NPD6192	Phase 3
0.6087	Remote Similarity	NPD5642	Approved
0.6087	Remote Similarity	NPD193	Suspended
0.6085	Remote Similarity	NPD3362	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5012	Phase 2
0.6081	Remote Similarity	NPD8831	Approved
0.6081	Remote Similarity	NPD8833	Approved
0.6075	Remote Similarity	NPD2818	Discontinued
0.6074	Remote Similarity	NPD174	Discontinued
0.6071	Remote Similarity	NPD2824	Phase 2
0.6071	Remote Similarity	NPD6520	Phase 3
0.6071	Remote Similarity	NPD6521	Phase 3
0.6057	Remote Similarity	NPD3889	Approved
0.6057	Remote Similarity	NPD509	Phase 3
0.6054	Remote Similarity	NPD6418	Phase 1
0.6048	Remote Similarity	NPD3708	Phase 2
0.6041	Remote Similarity	NPD3860	Discontinued
0.604	Remote Similarity	NPD6470	Phase 3
0.6036	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD1030	Approved
0.6036	Remote Similarity	NPD1027	Approved
0.6031	Remote Similarity	NPD2364	Suspended
0.6022	Remote Similarity	NPD7504	Discontinued
0.6012	Remote Similarity	NPD185	Approved
0.6011	Remote Similarity	NPD4441	Phase 2
0.601	Remote Similarity	NPD4142	Discontinued
0.601	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2963	Phase 1
0.6	Remote Similarity	NPD3612	Phase 2
0.6	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.599	Remote Similarity	NPD6352	Phase 2
0.5989	Remote Similarity	NPD702	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD4716	Approved
0.5989	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD1690	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4863	Approved
0.5978	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD1288	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD2880	Discontinued
0.5969	Remote Similarity	NPD6271	Approved
0.5967	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD2731	Phase 2
0.5966	Remote Similarity	NPD7988	Suspended
0.5965	Remote Similarity	NPD1303	Phase 1
0.5962	Remote Similarity	NPD1807	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7709	Discontinued
0.5956	Remote Similarity	NPD1895	Discontinued
0.5956	Remote Similarity	NPD1674	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD1675	Phase 1
0.5951	Remote Similarity	NPD4854	Phase 3
0.595	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.595	Remote Similarity	NPD2902	Phase 2
0.5946	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD2868	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD249	Approved
0.5939	Remote Similarity	NPD166	Approved
0.5939	Remote Similarity	NPD3905	Phase 3
0.5939	Remote Similarity	NPD250	Approved
0.5938	Remote Similarity	NPD5885	Approved
0.5934	Remote Similarity	NPD3432	Approved
0.5932	Remote Similarity	NPD4213	Clinical (unspecified phase)
0.593	Remote Similarity	NPD3405	Phase 3
0.5928	Remote Similarity	NPD1988	Phase 1
0.5926	Remote Similarity	NPD7127	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD7103	Approved
0.5914	Remote Similarity	NPD5757	Discontinued
0.5909	Remote Similarity	NPD9084	Phase 2
0.5906	Remote Similarity	NPD2128	Phase 1
0.59	Remote Similarity	NPD3265	Phase 1
0.5897	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD2807	Discontinued
0.5897	Remote Similarity	NPD5486	Discontinued
0.5896	Remote Similarity	NPD2150	Discontinued
0.5893	Remote Similarity	NPD548	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD3830	Phase 1
0.5882	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD4155	Approved
0.5879	Remote Similarity	NPD3706	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD8004	Discontinued
0.5875	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD1658	Discontinued
0.5871	Remote Similarity	NPD7164	Discontinued
0.5868	Remote Similarity	NPD4864	Approved
0.5868	Remote Similarity	NPD195	Approved
0.5868	Remote Similarity	NPD186	Discovery
0.5868	Remote Similarity	NPD4047	Discontinued
0.5864	Remote Similarity	NPD4294	Phase 2
0.5864	Remote Similarity	NPD5464	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