NPASS Compound

Structure

NPC471166 OpenBabel07101719512D 44 48 0 0 1 0 0 0 0 0999 V2000 1.0833 -0.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0016 -3.9178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2078 -5.1931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8078 -1.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8589 -0.2064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8189 -0.2064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6328 -3.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5457 -2.3802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5075 1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9180 -2.8680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8661 -3.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9069 -0.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6761 -1.0378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1702 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6231 -1.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4044 -1.0536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1702 -4.3978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4563 -4.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5593 -2.8416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7678 -1.9198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0570 -1.0481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5075 -1.5178 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1702 -1.5178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3389 -2.9578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9587 0.0502 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6761 -0.0778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6529 -1.9809 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0259 -2.6597 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9532 -2.4112 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3389 -1.0378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5075 -2.4778 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2017 -1.4839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5229 -0.8051 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1702 -5.3578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3836 -4.0173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2381 -3.5204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0016 -1.0378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8447 0.4022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5075 0.4022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3020 -2.1628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3389 -3.9178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 -3.5870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6320 -3.0901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 8 32 1 0 0 0 0 9 39 1 0 0 0 0 10 11 2 0 0 0 0 10 20 1 0 0 0 0 11 40 1 0 0 0 0 12 21 1 0 0 0 0 12 25 1 0 0 0 0 13 22 1 0 0 0 0 13 26 1 0 0 0 0 14 23 1 0 0 0 0 14 24 1 0 0 0 0 15 20 2 0 0 0 0 15 40 1 0 0 0 0 17 34 2 0 0 0 0 17 41 1 0 0 0 0 18 35 2 0 0 0 0 18 42 1 0 0 0 0 19 36 2 0 0 0 0 19 43 1 0 0 0 0 20 21 1 0 0 0 0 21 32 1 6 0 0 0 22 30 1 0 0 0 0 22 31 1 1 0 0 0 23 30 1 0 0 0 0 23 37 2 0 0 0 0 24 31 1 1 0 0 0 24 41 1 0 0 0 0 25 33 1 6 0 0 0 25 44 1 0 0 0 0 26 38 2 0 0 0 0 26 39 1 0 0 0 0 27 16 1 1 0 0 0 27 28 1 0 0 0 0 27 31 1 0 0 0 0 28 29 1 0 0 0 0 28 42 1 1 0 0 0 29 32 1 6 0 0 0 29 43 1 0 0 0 0 31 7 1 1 0 0 0 32 33 1 6 0 0 0 33 16 1 6 0 0 0 33 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.27
Volume:	612.143
LogP:	2.892
LogD:	1.943
LogS:	-4.535
# Rotatable Bonds:	11
TPSA:	147.94
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	5.85
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.337
MDCK Permeability:	5.822602906846441e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.305
20% Bioavailability (F20%):	0.859
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	69.28531646728516%
Volume Distribution (VD):	1.83
Pgp-substrate:	21.22696876525879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.728
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.448
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.602

ADMET: Excretion

Clearance (CL):	5.124
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.945
Drug-inuced Liver Injury (DILI):	0.896
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.897
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.109
Carcinogencity:	0.049
Eye Corrosion:	0.006
Eye Irritation:	0.047
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC471166

Natural Product ID:	NPC471166
*Common Name:**	Turrapubin A
IUPAC Name:	methyl 2-[(1R,2S,3R)-2-[(1aR,3S,3aR,4R,5R,6R,7aS)-4,5-diacetyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-6-yl]-3-acetyloxy-2,6,6-trimethyl-5-oxocyclohexyl]acetate
Synonyms:
Standard InCHIKey:	VXKJLBGAQIDBPO-YILSLSMRSA-N
Standard InCHI:	InChI=1S/C33H42O11/c1-16-27(31(7)22(13-26(38)39-9)30(5,6)23(37)14-24(31)41-17(2)34)28(42-18(3)35)29(43-19(4)36)32(8)21(20-10-11-40-15-20)12-25-33(16,32)44-25/h10-11,15,21-22,24-25,27-29H,1,12-14H2,2-9H3/t21-,22-,24+,25+,27+,28+,29-,31+,32+,33+/m0/s1
SMILES:	COC(=O)C[C@@H]1[C@](C)([C@H](OC(=O)C)CC(=O)C1(C)C)[C@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@]2([C@]3(C1=C)O[C@@H]3C[C@H]2c1ccoc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386289
PubChem CID:	71725783
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO10033	Turraea pubescens	Species	Meliaceae	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	2
Others	3

Activity Type	# Activity
Cell Line	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[535821]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[535821]
NPT176	Organism	Artemia salina	Artemia salina	mortality	=	0.0	%	PMID[535821]
NPT176	Organism	Artemia salina	Artemia salina	mortality	=	0.8	%	PMID[535821]
NPT176	Organism	Artemia salina	Artemia salina	mortality	=	54.7	%	PMID[535821]

☑ 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 NPC471166 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	425
0.1-0.2	1554
0.2-0.3	3383
0.3-0.4	6273
0.4-0.5	11251
0.5-0.6	9809
0.6-0.7	8639
0.7-0.8	966
0.8-0.85	302
0.85-0.9	72
0.9-0.95	15
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471167
0.9804	High Similarity	NPC471168
0.9675	High Similarity	NPC472669
0.961	High Similarity	NPC472668
0.9477	High Similarity	NPC175964
0.9477	High Similarity	NPC471169
0.9412	High Similarity	NPC471175
0.9375	High Similarity	NPC469848
0.9231	High Similarity	NPC474932
0.9125	High Similarity	NPC476224
0.9114	High Similarity	NPC5741
0.9114	High Similarity	NPC197596
0.9103	High Similarity	NPC204663
0.9091	High Similarity	NPC18135
0.9057	High Similarity	NPC476197
0.9045	High Similarity	NPC195131
0.9045	High Similarity	NPC167142
0.9042	High Similarity	NPC105395
0.9042	High Similarity	NPC242068
0.9042	High Similarity	NPC247563
0.9032	High Similarity	NPC84063
0.9006	High Similarity	NPC472764
0.8963	High Similarity	NPC471632
0.8961	High Similarity	NPC470791
0.8961	High Similarity	NPC470790
0.8957	High Similarity	NPC285227
0.8951	High Similarity	NPC472765
0.8951	High Similarity	NPC472766
0.8924	High Similarity	NPC469847
0.8917	High Similarity	NPC476262
0.8917	High Similarity	NPC469850
0.891	High Similarity	NPC29695
0.891	High Similarity	NPC182427
0.891	High Similarity	NPC308205
0.891	High Similarity	NPC322546
0.8903	High Similarity	NPC156189
0.8875	High Similarity	NPC470939
0.8875	High Similarity	NPC6326
0.8875	High Similarity	NPC472767
0.8868	High Similarity	NPC475226
0.8846	High Similarity	NPC116717
0.8834	High Similarity	NPC327922
0.8834	High Similarity	NPC160651
0.8831	High Similarity	NPC221809
0.8831	High Similarity	NPC255414
0.882	High Similarity	NPC469846
0.8812	High Similarity	NPC191828
0.879	High Similarity	NPC268905
0.879	High Similarity	NPC476201
0.878	High Similarity	NPC472659
0.8773	High Similarity	NPC173516
0.8773	High Similarity	NPC476861
0.8773	High Similarity	NPC476850
0.8765	High Similarity	NPC476857
0.8765	High Similarity	NPC476856
0.8765	High Similarity	NPC476858
0.8758	High Similarity	NPC472771
0.875	High Similarity	NPC475295
0.875	High Similarity	NPC237155
0.875	High Similarity	NPC473473
0.8743	High Similarity	NPC478177
0.8735	High Similarity	NPC471437
0.8735	High Similarity	NPC94763
0.872	High Similarity	NPC471397
0.8718	High Similarity	NPC125182
0.8718	High Similarity	NPC69647
0.8712	High Similarity	NPC149945
0.8704	High Similarity	NPC472773
0.8704	High Similarity	NPC165218
0.8701	High Similarity	NPC34056
0.8696	High Similarity	NPC470789
0.8696	High Similarity	NPC25255
0.8696	High Similarity	NPC305016
0.8696	High Similarity	NPC472653
0.8688	High Similarity	NPC472283
0.8688	High Similarity	NPC214495
0.8688	High Similarity	NPC470119
0.8688	High Similarity	NPC286722
0.8688	High Similarity	NPC475066
0.8688	High Similarity	NPC299038
0.8683	High Similarity	NPC167340
0.8671	High Similarity	NPC75906
0.8671	High Similarity	NPC472672
0.8667	High Similarity	NPC470995
0.8662	High Similarity	NPC476122
0.8662	High Similarity	NPC469335
0.8662	High Similarity	NPC477404
0.8662	High Similarity	NPC196864
0.8662	High Similarity	NPC159927
0.8659	High Similarity	NPC476853
0.8659	High Similarity	NPC472282
0.8659	High Similarity	NPC472774
0.8659	High Similarity	NPC472775
0.865	High Similarity	NPC123088
0.865	High Similarity	NPC259943
0.865	High Similarity	NPC476860
0.865	High Similarity	NPC469849
0.8642	High Similarity	NPC193798
0.8642	High Similarity	NPC329938
0.8634	High Similarity	NPC472671
0.8625	High Similarity	NPC60973
0.8625	High Similarity	NPC263265
0.8625	High Similarity	NPC209364
0.8625	High Similarity	NPC107646
0.8625	High Similarity	NPC126723
0.8623	High Similarity	NPC236004
0.8623	High Similarity	NPC477824
0.8616	High Similarity	NPC302054
0.8616	High Similarity	NPC253201
0.8614	High Similarity	NPC159232
0.8608	High Similarity	NPC291150
0.8606	High Similarity	NPC472673
0.8599	High Similarity	NPC471001
0.8599	High Similarity	NPC472654
0.8598	High Similarity	NPC478178
0.8598	High Similarity	NPC472141
0.8598	High Similarity	NPC470875
0.8598	High Similarity	NPC23387
0.8589	High Similarity	NPC469338
0.8589	High Similarity	NPC224394
0.8589	High Similarity	NPC663
0.8589	High Similarity	NPC292389
0.858	High Similarity	NPC475381
0.8571	High Similarity	NPC195954
0.8571	High Similarity	NPC469633
0.8571	High Similarity	NPC470118
0.8571	High Similarity	NPC472772
0.8571	High Similarity	NPC197137
0.8562	High Similarity	NPC92979
0.8562	High Similarity	NPC264943
0.8545	High Similarity	NPC270312
0.8545	High Similarity	NPC473753
0.8545	High Similarity	NPC473766
0.8545	High Similarity	NPC478179
0.8544	High Similarity	NPC5180
0.8537	High Similarity	NPC276551
0.8537	High Similarity	NPC470940
0.8529	High Similarity	NPC470938
0.8528	High Similarity	NPC200782
0.8528	High Similarity	NPC82851
0.8528	High Similarity	NPC470792
0.8526	High Similarity	NPC471292
0.8521	High Similarity	NPC470181
0.8512	High Similarity	NPC469576
0.8506	High Similarity	NPC121158
0.8494	Intermediate Similarity	NPC271235
0.8494	Intermediate Similarity	NPC472652
0.8485	Intermediate Similarity	NPC121995
0.8481	Intermediate Similarity	NPC329180
0.8476	Intermediate Similarity	NPC134254
0.8476	Intermediate Similarity	NPC472139
0.8476	Intermediate Similarity	NPC51568
0.8476	Intermediate Similarity	NPC476035
0.8476	Intermediate Similarity	NPC302369
0.8476	Intermediate Similarity	NPC14499
0.8476	Intermediate Similarity	NPC477405
0.8476	Intermediate Similarity	NPC39986
0.8476	Intermediate Similarity	NPC475039
0.8476	Intermediate Similarity	NPC234660
0.8462	Intermediate Similarity	NPC5676
0.8457	Intermediate Similarity	NPC88007
0.8447	Intermediate Similarity	NPC469336
0.8443	Intermediate Similarity	NPC472650
0.8434	Intermediate Similarity	NPC472651
0.8424	Intermediate Similarity	NPC61967
0.8424	Intermediate Similarity	NPC56358
0.8424	Intermediate Similarity	NPC126984
0.8424	Intermediate Similarity	NPC27541
0.8424	Intermediate Similarity	NPC271657
0.8424	Intermediate Similarity	NPC62692
0.8418	Intermediate Similarity	NPC19747
0.8415	Intermediate Similarity	NPC69028
0.8415	Intermediate Similarity	NPC18986
0.8415	Intermediate Similarity	NPC18347
0.8415	Intermediate Similarity	NPC149896
0.8415	Intermediate Similarity	NPC68848
0.8415	Intermediate Similarity	NPC188649
0.8415	Intermediate Similarity	NPC5079
0.8408	Intermediate Similarity	NPC470999
0.8405	Intermediate Similarity	NPC477403
0.8405	Intermediate Similarity	NPC475967
0.8397	Intermediate Similarity	NPC238843
0.8397	Intermediate Similarity	NPC251865
0.8397	Intermediate Similarity	NPC199044
0.8393	Intermediate Similarity	NPC475237
0.8393	Intermediate Similarity	NPC475641
0.8385	Intermediate Similarity	NPC178932
0.8385	Intermediate Similarity	NPC282445
0.8385	Intermediate Similarity	NPC57998
0.8385	Intermediate Similarity	NPC237259
0.8385	Intermediate Similarity	NPC34421
0.8385	Intermediate Similarity	NPC98206
0.8377	Intermediate Similarity	NPC56197
0.8373	Intermediate Similarity	NPC214600
0.8373	Intermediate Similarity	NPC307781
0.8373	Intermediate Similarity	NPC472670
0.8364	Intermediate Similarity	NPC88841
0.8364	Intermediate Similarity	NPC288602
0.8364	Intermediate Similarity	NPC419
0.8364	Intermediate Similarity	NPC285567

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 NPC471166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	1025
0.2-0.3	2336
0.3-0.4	2731
0.4-0.5	1742
0.5-0.6	750
0.6-0.7	208
0.7-0.8	7
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8447	Intermediate Similarity	NPD5760	Phase 2
0.8447	Intermediate Similarity	NPD5761	Phase 2
0.8114	Intermediate Similarity	NPD8434	Phase 2
0.7917	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6765	Approved
0.7829	Intermediate Similarity	NPD6764	Approved
0.7654	Intermediate Similarity	NPD6784	Approved
0.7654	Intermediate Similarity	NPD6785	Approved
0.7174	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7819	Suspended
0.7159	Intermediate Similarity	NPD5494	Approved
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7119	Intermediate Similarity	NPD1247	Approved
0.7118	Intermediate Similarity	NPD920	Approved
0.7111	Intermediate Similarity	NPD7799	Discontinued
0.7102	Intermediate Similarity	NPD919	Approved
0.7093	Intermediate Similarity	NPD6599	Discontinued
0.7066	Intermediate Similarity	NPD4628	Phase 3
0.7017	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1471	Phase 3
0.6982	Remote Similarity	NPD643	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8404	Phase 2
0.6971	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD6559	Discontinued
0.6957	Remote Similarity	NPD7685	Pre-registration
0.6949	Remote Similarity	NPD7075	Discontinued
0.6932	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7497	Discontinued
0.6882	Remote Similarity	NPD7236	Approved
0.686	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7411	Suspended
0.6842	Remote Similarity	NPD6799	Approved
0.6839	Remote Similarity	NPD3226	Approved
0.6836	Remote Similarity	NPD3817	Phase 2
0.6826	Remote Similarity	NPD2796	Approved
0.6818	Remote Similarity	NPD6801	Discontinued
0.6805	Remote Similarity	NPD1243	Approved
0.6805	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5844	Phase 1
0.6786	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7239	Suspended
0.6776	Remote Similarity	NPD7473	Discontinued
0.6768	Remote Similarity	NPD8032	Phase 2
0.6758	Remote Similarity	NPD3926	Phase 2
0.674	Remote Similarity	NPD7199	Phase 2
0.6724	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6832	Phase 2
0.6686	Remote Similarity	NPD6002	Phase 3
0.6686	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5763	Approved
0.6686	Remote Similarity	NPD6005	Phase 3
0.6686	Remote Similarity	NPD6004	Phase 3
0.6686	Remote Similarity	NPD5762	Approved
0.6685	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8285	Discontinued
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3818	Discontinued
0.6648	Remote Similarity	NPD5402	Approved
0.6629	Remote Similarity	NPD1934	Approved
0.6614	Remote Similarity	NPD8312	Approved
0.6614	Remote Similarity	NPD8313	Approved
0.6612	Remote Similarity	NPD6232	Discontinued
0.6612	Remote Similarity	NPD6808	Phase 2
0.6611	Remote Similarity	NPD3882	Suspended
0.6611	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4380	Phase 2
0.661	Remote Similarity	NPD7028	Phase 2
0.6609	Remote Similarity	NPD2532	Approved
0.6609	Remote Similarity	NPD2533	Approved
0.6609	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2534	Approved
0.6579	Remote Similarity	NPD8407	Phase 2
0.6575	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD2799	Discontinued
0.6568	Remote Similarity	NPD3748	Approved
0.6554	Remote Similarity	NPD7458	Discontinued
0.6534	Remote Similarity	NPD5403	Approved
0.6529	Remote Similarity	NPD1551	Phase 2
0.6528	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4967	Phase 2
0.6519	Remote Similarity	NPD4966	Approved
0.6519	Remote Similarity	NPD7768	Phase 2
0.6519	Remote Similarity	NPD4965	Approved
0.6514	Remote Similarity	NPD5401	Approved
0.6514	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8150	Discontinued
0.6508	Remote Similarity	NPD8368	Discontinued
0.65	Remote Similarity	NPD2801	Approved
0.6491	Remote Similarity	NPD2346	Discontinued
0.6489	Remote Similarity	NPD7074	Phase 3
0.6488	Remote Similarity	NPD6355	Discontinued
0.6474	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4110	Phase 3
0.6471	Remote Similarity	NPD7033	Discontinued
0.6471	Remote Similarity	NPD3751	Discontinued
0.6467	Remote Similarity	NPD6959	Discontinued
0.6463	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD1549	Phase 2
0.6452	Remote Similarity	NPD2403	Approved
0.6452	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6166	Phase 2
0.6448	Remote Similarity	NPD6234	Discontinued
0.6444	Remote Similarity	NPD37	Approved
0.6442	Remote Similarity	NPD1876	Approved
0.6438	Remote Similarity	NPD17	Approved
0.6437	Remote Similarity	NPD3887	Approved
0.6436	Remote Similarity	NPD7054	Approved
0.6433	Remote Similarity	NPD2438	Suspended
0.6433	Remote Similarity	NPD6099	Approved
0.6433	Remote Similarity	NPD6100	Approved
0.6433	Remote Similarity	NPD2935	Discontinued
0.6432	Remote Similarity	NPD3787	Discontinued
0.6432	Remote Similarity	NPD7315	Approved
0.6429	Remote Similarity	NPD7058	Phase 2
0.6429	Remote Similarity	NPD7057	Phase 3
0.6429	Remote Similarity	NPD4140	Approved
0.642	Remote Similarity	NPD3972	Approved
0.642	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD2800	Approved
0.6407	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3266	Approved
0.6402	Remote Similarity	NPD3267	Approved
0.6402	Remote Similarity	NPD7472	Approved
0.64	Remote Similarity	NPD4107	Approved
0.6395	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2344	Approved
0.6391	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7808	Phase 3
0.638	Remote Similarity	NPD5327	Phase 3
0.6379	Remote Similarity	NPD3750	Approved
0.6368	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5647	Approved
0.6364	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6653	Approved
0.6335	Remote Similarity	NPD7251	Discontinued
0.6319	Remote Similarity	NPD1608	Approved
0.6316	Remote Similarity	NPD7930	Approved
0.631	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3268	Approved
0.631	Remote Similarity	NPD2313	Discontinued
0.6305	Remote Similarity	NPD7435	Discontinued
0.6298	Remote Similarity	NPD6385	Approved
0.6298	Remote Similarity	NPD6386	Approved
0.6296	Remote Similarity	NPD7228	Approved
0.6296	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1933	Approved
0.6294	Remote Similarity	NPD5735	Approved
0.6291	Remote Similarity	NPD7907	Approved
0.6287	Remote Similarity	NPD4482	Phase 3
0.6284	Remote Similarity	NPD5353	Approved
0.6284	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6797	Phase 2
0.6279	Remote Similarity	NPD1510	Phase 2
0.6278	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD8361	Approved
0.6276	Remote Similarity	NPD8360	Approved
0.6276	Remote Similarity	NPD8435	Approved
0.6273	Remote Similarity	NPD5585	Approved
0.6272	Remote Similarity	NPD6663	Approved
0.6271	Remote Similarity	NPD1511	Approved
0.6258	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1607	Approved
0.6257	Remote Similarity	NPD7229	Phase 3
0.6257	Remote Similarity	NPD6353	Approved
0.625	Remote Similarity	NPD2309	Approved
0.6244	Remote Similarity	NPD7999	Approved
0.6235	Remote Similarity	NPD1240	Approved
0.6235	Remote Similarity	NPD4307	Phase 2
0.6235	Remote Similarity	NPD2979	Phase 3
0.623	Remote Similarity	NPD1465	Phase 2
0.623	Remote Similarity	NPD8455	Phase 2
0.6225	Remote Similarity	NPD7698	Approved
0.6225	Remote Similarity	NPD7697	Approved
0.6225	Remote Similarity	NPD7696	Phase 3
0.6223	Remote Similarity	NPD5242	Approved
0.6207	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2353	Approved
0.6205	Remote Similarity	NPD7319	Approved
0.6205	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD7874	Approved
0.6201	Remote Similarity	NPD1512	Approved
0.6199	Remote Similarity	NPD447	Suspended
0.6198	Remote Similarity	NPD5953	Discontinued
0.6197	Remote Similarity	NPD4111	Phase 1
0.6195	Remote Similarity	NPD7870	Phase 2
0.6195	Remote Similarity	NPD7871	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data