NPASS Compound

Structure

NPC470789 OpenBabel07101719512D 46 50 0 0 1 0 0 0 0 0999 V2000 2.6228 -7.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8907 -5.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2209 1.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4912 -3.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6551 0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6802 1.1781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9481 -3.8145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1934 -0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -7.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8937 -2.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3059 -1.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5660 -4.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5660 -5.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -2.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0271 -4.9701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -6.4010 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3548 1.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4644 -3.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6149 -4.1610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3059 -3.2100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3548 -1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6228 -1.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4888 -3.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4888 -0.4010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -5.9010 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6228 -4.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -2.9010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4888 -1.4010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7568 -1.4010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4888 1.5990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6869 -4.6545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4339 -0.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -6.4010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -4.4010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6149 -5.7791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 0.0990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 -2.9994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -4.4010 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 10 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 33 1 0 0 0 0 6 33 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 2 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 42 1 0 0 0 0 15 25 1 0 0 0 0 15 28 1 0 0 0 0 16 26 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 22 2 0 0 0 0 18 42 1 0 0 0 0 19 31 1 0 0 0 0 20 37 2 0 0 0 0 20 43 1 0 0 0 0 21 38 2 0 0 0 0 21 44 1 0 0 0 0 22 23 1 0 0 0 0 23 34 1 1 0 0 0 24 34 1 0 0 0 0 24 35 1 0 0 0 0 25 33 1 0 0 0 0 25 36 1 6 0 0 0 26 35 1 6 0 0 0 26 36 1 0 0 0 0 27 34 1 1 0 0 0 27 45 1 0 0 0 0 28 35 1 1 0 0 0 28 43 1 0 0 0 0 29 36 1 1 0 0 0 29 44 1 0 0 0 0 30 39 2 0 0 0 0 30 46 1 0 0 0 0 31 32 1 0 0 0 0 31 40 1 0 0 0 0 32 41 2 0 0 0 0 32 45 1 0 0 0 0 33 46 1 0 0 0 0 34 7 1 1 0 0 0 35 8 1 6 0 0 0 36 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	642.34
Volume:	657.877
LogP:	4.083
LogD:	1.809
LogS:	-3.751
# Rotatable Bonds:	10
TPSA:	138.57
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.164
Synthetic Accessibility Score:	5.722
Fsp3:	0.722
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.045
MDCK Permeability:	3.893076427630149e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.52

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197
Plasma Protein Binding (PPB):	94.05170440673828%
Volume Distribution (VD):	1.964
Pgp-substrate:	7.928841590881348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.192
CYP2C9-inhibitor:	0.526
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.671
CYP3A4-substrate:	0.554

ADMET: Excretion

Clearance (CL):	3.716
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.613
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.176
Carcinogencity:	0.05
Eye Corrosion:	0.013
Eye Irritation:	0.052
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC470789

Natural Product ID:	NPC470789
*Common Name:**	Munronoid K
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TYLAQGXMVZCGEG-DCJBVYISSA-N
Standard InCHI:	InChI=1S/C36H50O10/c1-10-19(2)31(40)32(41)45-27-16-26-35(8,24-12-11-23(34(24,27)7)22-13-14-42-18-22)28(43-20(3)37)15-25-33(5,6)46-30(39)17-29(36(25,26)9)44-21(4)38/h12-14,18-19,23,25-29,31,40H,10-11,15-17H2,1-9H3/t19?,23-,25-,26-,27-,28+,29-,31?,34-,35-,36-/m0/s1
SMILES:	CCC(C(C(=O)O[C@H]1C[C@@H]2[C@@]3(C)[C@@H](OC(=O)C)CC(=O)OC([C@@H]3C[C@H]([C@]2(C2=CC[C@H]([C@]12C)c1cocc1)C)OC(=O)C)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229165
PubChem CID:	76333215
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
NPO33254	munronia unifoliolata oliv	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22500574]

☑ 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	1
Others	8

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	IC50	=	28.3	ug.mL-1	PMID[529442]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	6.5	%	PMID[529442]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	18.7	%	PMID[529442]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	28.6	%	PMID[529442]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	38.7	%	PMID[529442]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	45.7	%	PMID[529442]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	51.9	%	PMID[529442]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	67.2	%	PMID[529442]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	55.6	%	PMID[529442]

☑ 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 NPC470789 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	338
0.1-0.2	1284
0.2-0.3	3066
0.3-0.4	5421
0.4-0.5	10318
0.5-0.6	10543
0.6-0.7	9759
0.7-0.8	1559
0.8-0.85	249
0.85-0.9	147
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.94	High Similarity	NPC470790
0.94	High Similarity	NPC470791
0.9272	High Similarity	NPC472654
0.9245	High Similarity	NPC472652
0.9226	High Similarity	NPC45101
0.9226	High Similarity	NPC475066
0.9211	High Similarity	NPC156189
0.9187	High Similarity	NPC472659
0.9182	High Similarity	NPC472651
0.9167	High Similarity	NPC472671
0.9167	High Similarity	NPC475226
0.9156	High Similarity	NPC302054
0.9156	High Similarity	NPC253201
0.9091	High Similarity	NPC472672
0.9068	High Similarity	NPC470995
0.9062	High Similarity	NPC472774
0.9062	High Similarity	NPC472775
0.9051	High Similarity	NPC470792
0.9051	High Similarity	NPC329938
0.9045	High Similarity	NPC472779
0.9045	High Similarity	NPC475967
0.902	High Similarity	NPC69647
0.902	High Similarity	NPC125182
0.9018	High Similarity	NPC471632
0.9012	High Similarity	NPC285227
0.9	High Similarity	NPC472670
0.9	High Similarity	NPC470875
0.9	High Similarity	NPC307781
0.8994	High Similarity	NPC477405
0.8994	High Similarity	NPC472773
0.8987	High Similarity	NPC472653
0.8981	High Similarity	NPC470119
0.8981	High Similarity	NPC214495
0.8974	High Similarity	NPC44675
0.8974	High Similarity	NPC214541
0.8968	High Similarity	NPC29695
0.8968	High Similarity	NPC182427
0.8944	High Similarity	NPC476853
0.8944	High Similarity	NPC472282
0.8938	High Similarity	NPC469849
0.8938	High Similarity	NPC276551
0.8931	High Similarity	NPC69028
0.8931	High Similarity	NPC472771
0.891	High Similarity	NPC34421
0.891	High Similarity	NPC237259
0.891	High Similarity	NPC98206
0.8889	High Similarity	NPC216755
0.8889	High Similarity	NPC472766
0.8889	High Similarity	NPC271235
0.8889	High Similarity	NPC471174
0.8889	High Similarity	NPC472673
0.8889	High Similarity	NPC472765
0.8889	High Similarity	NPC255414
0.8875	High Similarity	NPC39986
0.8875	High Similarity	NPC472669
0.8875	High Similarity	NPC663
0.8875	High Similarity	NPC134254
0.8875	High Similarity	NPC292389
0.8875	High Similarity	NPC469338
0.8875	High Similarity	NPC224394
0.8875	High Similarity	NPC302369
0.8868	High Similarity	NPC335761
0.8868	High Similarity	NPC477402
0.8861	High Similarity	NPC261597
0.8861	High Similarity	NPC36655
0.8861	High Similarity	NPC472772
0.8854	High Similarity	NPC141538
0.8854	High Similarity	NPC296807
0.8854	High Similarity	NPC92979
0.8854	High Similarity	NPC155939
0.8846	High Similarity	NPC33938
0.8839	High Similarity	NPC470997
0.8834	High Similarity	NPC82602
0.8827	High Similarity	NPC476850
0.8827	High Similarity	NPC476861
0.8827	High Similarity	NPC472764
0.882	High Similarity	NPC476858
0.882	High Similarity	NPC476857
0.882	High Similarity	NPC470940
0.882	High Similarity	NPC476856
0.882	High Similarity	NPC123088
0.8812	High Similarity	NPC200782
0.8812	High Similarity	NPC82851
0.8812	High Similarity	NPC5079
0.8812	High Similarity	NPC263432
0.8812	High Similarity	NPC472767
0.8808	High Similarity	NPC121158
0.8797	High Similarity	NPC126723
0.8788	High Similarity	NPC94763
0.8788	High Similarity	NPC471437
0.8782	High Similarity	NPC18135
0.8774	High Similarity	NPC234494
0.8774	High Similarity	NPC195325
0.8773	High Similarity	NPC471397
0.8773	High Similarity	NPC160651
0.8765	High Similarity	NPC472141
0.8765	High Similarity	NPC149945
0.8765	High Similarity	NPC23387
0.8758	High Similarity	NPC234660
0.8758	High Similarity	NPC5676
0.8758	High Similarity	NPC51568
0.875	High Similarity	NPC191828
0.875	High Similarity	NPC25255
0.8742	High Similarity	NPC173544
0.8742	High Similarity	NPC470118
0.8742	High Similarity	NPC299038
0.8742	High Similarity	NPC472778
0.8742	High Similarity	NPC472776
0.8742	High Similarity	NPC249021
0.8742	High Similarity	NPC167142
0.8742	High Similarity	NPC187149
0.8742	High Similarity	NPC197137
0.8742	High Similarity	NPC472777
0.8726	High Similarity	NPC308205
0.8726	High Similarity	NPC469503
0.8726	High Similarity	NPC246164
0.8726	High Similarity	NPC268905
0.8726	High Similarity	NPC322546
0.872	High Similarity	NPC118086
0.8712	High Similarity	NPC478179
0.8712	High Similarity	NPC173516
0.8712	High Similarity	NPC476224
0.871	High Similarity	NPC471007
0.8704	High Similarity	NPC476860
0.8704	High Similarity	NPC271657
0.8704	High Similarity	NPC261184
0.8704	High Similarity	NPC259943
0.8696	High Similarity	NPC471167
0.8696	High Similarity	NPC471166
0.8696	High Similarity	NPC117986
0.8696	High Similarity	NPC193798
0.8696	High Similarity	NPC472668
0.8693	High Similarity	NPC251865
0.869	High Similarity	NPC470938
0.8688	High Similarity	NPC307383
0.8688	High Similarity	NPC237155
0.8688	High Similarity	NPC477403
0.8679	High Similarity	NPC469485
0.8675	High Similarity	NPC67003
0.8675	High Similarity	NPC236004
0.8671	High Similarity	NPC282445
0.8667	High Similarity	NPC159232
0.8667	High Similarity	NPC169299
0.8667	High Similarity	NPC475237
0.8667	High Similarity	NPC475641
0.8667	High Similarity	NPC160818
0.8662	High Similarity	NPC272590
0.8654	High Similarity	NPC470998
0.865	High Similarity	NPC478178
0.865	High Similarity	NPC214600
0.8647	High Similarity	NPC105395
0.8647	High Similarity	NPC242068
0.8647	High Similarity	NPC247563
0.8645	High Similarity	NPC221809
0.8645	High Similarity	NPC470941
0.8642	High Similarity	NPC469846
0.8642	High Similarity	NPC472139
0.8627	High Similarity	NPC243577
0.8625	High Similarity	NPC472283
0.8625	High Similarity	NPC286722
0.8625	High Similarity	NPC88007
0.8625	High Similarity	NPC194499
0.8623	High Similarity	NPC469633
0.8616	High Similarity	NPC476262
0.8616	High Similarity	NPC469336
0.8616	High Similarity	NPC264943
0.8608	High Similarity	NPC75906
0.8608	High Similarity	NPC476201
0.8599	High Similarity	NPC196846
0.8598	High Similarity	NPC100333
0.8589	High Similarity	NPC470182
0.858	High Similarity	NPC149896
0.858	High Similarity	NPC188649
0.858	High Similarity	NPC290400
0.858	High Similarity	NPC18347
0.858	High Similarity	NPC207978
0.858	High Similarity	NPC211777
0.858	High Similarity	NPC96443
0.858	High Similarity	NPC6326
0.8571	High Similarity	NPC475295
0.8571	High Similarity	NPC473473
0.8571	High Similarity	NPC478177
0.8563	High Similarity	NPC469576
0.8562	High Similarity	NPC107646
0.8562	High Similarity	NPC209364
0.8562	High Similarity	NPC204663
0.8553	High Similarity	NPC90296
0.8553	High Similarity	NPC178932
0.8553	High Similarity	NPC57998
0.8545	High Similarity	NPC327922
0.8537	High Similarity	NPC97574
0.8537	High Similarity	NPC121995
0.8537	High Similarity	NPC475779
0.8537	High Similarity	NPC93172
0.8535	High Similarity	NPC471001
0.8528	High Similarity	NPC288602
0.8528	High Similarity	NPC88841
0.8528	High Similarity	NPC471168
0.8528	High Similarity	NPC198047
0.8528	High Similarity	NPC165218

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 NPC470789 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	978
0.2-0.3	2136
0.3-0.4	2663
0.4-0.5	1848
0.5-0.6	933
0.6-0.7	288
0.7-0.8	20
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
0.8616	High Similarity	NPD5761	Phase 2
0.8616	High Similarity	NPD5760	Phase 2
0.8372	Intermediate Similarity	NPD8434	Phase 2
0.7977	Intermediate Similarity	NPD6764	Approved
0.7977	Intermediate Similarity	NPD6765	Approved
0.7797	Intermediate Similarity	NPD6784	Approved
0.7797	Intermediate Similarity	NPD6785	Approved
0.7751	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6599	Discontinued
0.7412	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7075	Discontinued
0.7356	Intermediate Similarity	NPD8127	Discontinued
0.7345	Intermediate Similarity	NPD7799	Discontinued
0.731	Intermediate Similarity	NPD7819	Suspended
0.7278	Intermediate Similarity	NPD6559	Discontinued
0.7273	Intermediate Similarity	NPD8404	Phase 2
0.7251	Intermediate Similarity	NPD6801	Discontinued
0.7186	Intermediate Similarity	NPD6799	Approved
0.7134	Intermediate Similarity	NPD5762	Approved
0.7134	Intermediate Similarity	NPD5763	Approved
0.7126	Intermediate Similarity	NPD7236	Approved
0.7112	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6273	Approved
0.7069	Intermediate Similarity	NPD3817	Phase 2
0.7045	Intermediate Similarity	NPD919	Approved
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.703	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7239	Suspended
0.7017	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2799	Discontinued
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.6983	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5402	Approved
0.6966	Remote Similarity	NPD7199	Phase 2
0.6959	Remote Similarity	NPD920	Approved
0.6959	Remote Similarity	NPD5403	Approved
0.6941	Remote Similarity	NPD5401	Approved
0.6941	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4380	Phase 2
0.6932	Remote Similarity	NPD3882	Suspended
0.6928	Remote Similarity	NPD1471	Phase 3
0.6923	Remote Similarity	NPD5844	Phase 1
0.6902	Remote Similarity	NPD7685	Pre-registration
0.6898	Remote Similarity	NPD8150	Discontinued
0.6893	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8407	Phase 2
0.6879	Remote Similarity	NPD3226	Approved
0.6875	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD3818	Discontinued
0.6851	Remote Similarity	NPD6166	Phase 2
0.6851	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2532	Approved
0.6842	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2534	Approved
0.6842	Remote Similarity	NPD2533	Approved
0.6842	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6005	Phase 3
0.6826	Remote Similarity	NPD6004	Phase 3
0.6826	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6002	Phase 3
0.6826	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5494	Approved
0.6813	Remote Similarity	NPD7473	Discontinued
0.6811	Remote Similarity	NPD8368	Discontinued
0.6807	Remote Similarity	NPD7033	Discontinued
0.6805	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7411	Suspended
0.6798	Remote Similarity	NPD3749	Approved
0.6782	Remote Similarity	NPD7458	Discontinued
0.6778	Remote Similarity	NPD1247	Approved
0.6776	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7808	Phase 3
0.6768	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1551	Phase 2
0.6761	Remote Similarity	NPD1934	Approved
0.6751	Remote Similarity	NPD7497	Discontinued
0.6742	Remote Similarity	NPD4967	Phase 2
0.6742	Remote Similarity	NPD4965	Approved
0.6742	Remote Similarity	NPD7768	Phase 2
0.6742	Remote Similarity	NPD4966	Approved
0.674	Remote Similarity	NPD6232	Discontinued
0.6728	Remote Similarity	NPD6832	Phase 2
0.6726	Remote Similarity	NPD2346	Discontinued
0.6723	Remote Similarity	NPD8455	Phase 2
0.672	Remote Similarity	NPD7251	Discontinued
0.6703	Remote Similarity	NPD7074	Phase 3
0.6703	Remote Similarity	NPD3926	Phase 2
0.6687	Remote Similarity	NPD7095	Approved
0.6686	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD37	Approved
0.6649	Remote Similarity	NPD7054	Approved
0.6649	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7315	Approved
0.6648	Remote Similarity	NPD7057	Phase 3
0.6648	Remote Similarity	NPD7058	Phase 2
0.6647	Remote Similarity	NPD1243	Approved
0.6646	Remote Similarity	NPD6798	Discontinued
0.6646	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2344	Approved
0.6613	Remote Similarity	NPD7472	Approved
0.6608	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4110	Phase 3
0.6606	Remote Similarity	NPD6233	Phase 2
0.6606	Remote Similarity	NPD8032	Phase 2
0.6605	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3751	Discontinued
0.6595	Remote Similarity	NPD7228	Approved
0.6593	Remote Similarity	NPD6959	Discontinued
0.659	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1549	Phase 2
0.6587	Remote Similarity	NPD6653	Approved
0.6585	Remote Similarity	NPD7930	Approved
0.6576	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2354	Approved
0.657	Remote Similarity	NPD6190	Approved
0.657	Remote Similarity	NPD3887	Approved
0.6568	Remote Similarity	NPD6099	Approved
0.6568	Remote Similarity	NPD6100	Approved
0.6566	Remote Similarity	NPD4140	Approved
0.6566	Remote Similarity	NPD4060	Phase 1
0.6562	Remote Similarity	NPD8435	Approved
0.6562	Remote Similarity	NPD8360	Approved
0.6562	Remote Similarity	NPD8361	Approved
0.6559	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3787	Discontinued
0.6552	Remote Similarity	NPD7874	Approved
0.6552	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2800	Approved
0.6545	Remote Similarity	NPD2313	Discontinued
0.6545	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2801	Approved
0.6531	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5735	Approved
0.6517	Remote Similarity	NPD7999	Approved
0.6515	Remote Similarity	NPD6777	Approved
0.6515	Remote Similarity	NPD6778	Approved
0.6515	Remote Similarity	NPD6779	Approved
0.6515	Remote Similarity	NPD6781	Approved
0.6515	Remote Similarity	NPD6776	Approved
0.6515	Remote Similarity	NPD6780	Approved
0.6515	Remote Similarity	NPD6782	Approved
0.6514	Remote Similarity	NPD1512	Approved
0.6512	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3750	Approved
0.6512	Remote Similarity	NPD7003	Approved
0.6503	Remote Similarity	NPD5647	Approved
0.65	Remote Similarity	NPD7698	Approved
0.65	Remote Similarity	NPD7697	Approved
0.65	Remote Similarity	NPD7696	Phase 3
0.6493	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4534	Discontinued
0.6478	Remote Similarity	NPD17	Approved
0.6477	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7907	Approved
0.6474	Remote Similarity	NPD2309	Approved
0.6471	Remote Similarity	NPD2438	Suspended
0.6468	Remote Similarity	NPD7871	Phase 2
0.6468	Remote Similarity	NPD7870	Phase 2
0.6468	Remote Similarity	NPD8320	Phase 1
0.6468	Remote Similarity	NPD8319	Approved
0.6467	Remote Similarity	NPD7229	Phase 3
0.6461	Remote Similarity	NPD7028	Phase 2
0.6458	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7240	Approved
0.6453	Remote Similarity	NPD7701	Phase 2
0.645	Remote Similarity	NPD7097	Phase 1
0.645	Remote Similarity	NPD3057	Approved
0.6446	Remote Similarity	NPD3764	Approved
0.6444	Remote Similarity	NPD1465	Phase 2
0.6439	Remote Similarity	NPD7801	Approved
0.6439	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7783	Phase 2
0.6432	Remote Similarity	NPD4107	Approved
0.6429	Remote Similarity	NPD447	Suspended
0.6429	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5049	Phase 3
0.642	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD8166	Discontinued
0.6416	Remote Similarity	NPD1878	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