NPASS Compound

Structure

NPC470792 OpenBabel07101718242D 43 48 0 0 1 0 0 0 0 0999 V2000 -2.2370 -4.8904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5941 -2.9226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0442 -0.7016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0627 -1.7019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9962 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2386 -1.8054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2744 -2.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4742 -4.2438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7340 1.0053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6000 0.5053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8733 1.2019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 -1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7557 -2.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3975 -0.5774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9517 -0.2198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6528 -3.2599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2227 -1.6855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9908 0.3362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6819 1.2869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7042 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.8131 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5185 -1.9948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4084 -0.8131 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8143 -2.3040 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0127 0.5441 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4285 0.3260 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3986 -0.6735 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6357 0.5070 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8899 -2.6133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3399 -1.0108 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4084 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6357 -1.3201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1641 -2.0228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1819 2.1529 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4132 1.4819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0685 -1.6294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2744 -1.3131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3921 -0.4728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3884 0.6065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4599 -2.3321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0515 -2.9506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 8 39 1 0 0 0 0 9 17 2 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 40 1 0 0 0 0 12 20 1 0 0 0 0 12 21 2 0 0 0 0 13 22 1 0 0 0 0 13 24 1 0 0 0 0 14 23 1 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 15 40 1 0 0 0 0 16 31 1 0 0 0 0 16 41 1 0 0 0 0 17 30 1 0 0 0 0 18 35 2 0 0 0 0 18 42 1 0 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 20 36 1 6 0 0 0 21 32 1 0 0 0 0 21 33 1 0 0 0 0 22 32 1 1 0 0 0 22 34 1 0 0 0 0 23 31 1 6 0 0 0 23 42 1 0 0 0 0 24 33 1 6 0 0 0 24 39 1 0 0 0 0 25 34 1 6 0 0 0 25 43 1 0 0 0 0 26 33 1 6 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 41 1 6 0 0 0 28 31 1 1 0 0 0 28 34 1 0 0 0 0 29 32 1 6 0 0 0 29 37 1 0 0 0 0 30 38 2 0 0 0 0 30 43 1 0 0 0 0 31 4 1 1 0 0 0 32 5 1 1 0 0 0 33 6 1 6 0 0 0 34 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	598.31
Volume:	608.574
LogP:	2.731
LogD:	2.456
LogS:	-4.624
# Rotatable Bonds:	7
TPSA:	124.66
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	5.892
Fsp3:	0.706
Lipinski Rule-of-5:	Accepted
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:	-5.069
MDCK Permeability:	3.756400474230759e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.069
30% Bioavailability (F30%):	0.813

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	82.29100799560547%
Volume Distribution (VD):	2.382
Pgp-substrate:	13.81673526763916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.267
CYP2C9-inhibitor:	0.332
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.795
CYP3A4-substrate:	0.535

ADMET: Excretion

Clearance (CL):	4.103
Half-life (T1/2):	0.627

ADMET: Toxicity

hERG Blockers:	0.55
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.104
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.866
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.09
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC470792

Natural Product ID:	NPC470792
*Common Name:**	Munronoid N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ARVSMUSRXNCDPF-WIARBTHKSA-N
Standard InCHI:	InChI=1S/C34H46O9/c1-9-17(2)30(38)43-25-14-23(42-18(3)35)31(4)16-41-27-28(31)34(25,7)22-13-24(39-8)33(6)21(32(22,5)29(27)37)12-20(36)26(33)19-10-11-40-15-19/h9-12,15,20,22-29,36-37H,13-14,16H2,1-8H3/b17-9+/t20-,22+,23-,24+,25+,26-,27-,28+,29-,31-,32+,33+,34+/m1/s1
SMILES:	C/C=C(/C(=O)O[C@H]1C[C@@H](OC(=O)C)[C@@]2([C@H]3[C@@]1(C)[C@H]1C[C@H](OC)[C@@]4(C(=C[C@H]([C@H]4c4ccoc4)O)[C@]1(C)[C@@H]([C@@H]3OC2)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229168
PubChem CID:	76325973
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	=	27.9	ug.mL-1	PMID[556308]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	8.3	%	PMID[556308]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	16.5	%	PMID[556308]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	26.4	%	PMID[556308]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	37.9	%	PMID[556308]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	44.6	%	PMID[556308]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	52.0	%	PMID[556308]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.2	%	PMID[556308]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	24.5	%	PMID[556308]

☑ 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 NPC470792 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	339
0.1-0.2	1227
0.2-0.3	2982
0.3-0.4	5020
0.4-0.5	9446
0.5-0.6	10842
0.6-0.7	10275
0.7-0.8	2049
0.8-0.85	303
0.85-0.9	170
0.9-0.95	40
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC302054
0.9603	High Similarity	NPC34421
0.9603	High Similarity	NPC253201
0.9603	High Similarity	NPC98206
0.9603	High Similarity	NPC237259
0.9536	High Similarity	NPC472672
0.9481	High Similarity	NPC472671
0.9481	High Similarity	NPC475226
0.9416	High Similarity	NPC475066
0.9416	High Similarity	NPC214495
0.9416	High Similarity	NPC470119
0.9412	High Similarity	NPC155939
0.9412	High Similarity	NPC141538
0.9412	High Similarity	NPC296807
0.929	High Similarity	NPC469847
0.9281	High Similarity	NPC33938
0.9272	High Similarity	NPC471007
0.9193	High Similarity	NPC475237
0.9193	High Similarity	NPC475641
0.9182	High Similarity	NPC307781
0.9182	High Similarity	NPC472670
0.9167	High Similarity	NPC197137
0.9167	High Similarity	NPC470118
0.9161	High Similarity	NPC92979
0.9156	High Similarity	NPC322546
0.9156	High Similarity	NPC29695
0.9156	High Similarity	NPC182427
0.9156	High Similarity	NPC308205
0.915	High Similarity	NPC470997
0.915	High Similarity	NPC196846
0.913	High Similarity	NPC118086
0.9125	High Similarity	NPC310572
0.9085	High Similarity	NPC472654
0.9085	High Similarity	NPC471001
0.9085	High Similarity	NPC125182
0.9085	High Similarity	NPC234494
0.9085	High Similarity	NPC69647
0.9079	High Similarity	NPC216755
0.9068	High Similarity	NPC472673
0.9062	High Similarity	NPC472141
0.9051	High Similarity	NPC470789
0.9045	High Similarity	NPC472778
0.9045	High Similarity	NPC472777
0.9045	High Similarity	NPC472776
0.9032	High Similarity	NPC268905
0.9012	High Similarity	NPC470995
0.8994	High Similarity	NPC200782
0.8987	High Similarity	NPC475967
0.8961	High Similarity	NPC470998
0.8954	High Similarity	NPC471174
0.8954	High Similarity	NPC255414
0.8951	High Similarity	NPC271235
0.8938	High Similarity	NPC283209
0.8938	High Similarity	NPC285567
0.8938	High Similarity	NPC472139
0.8924	High Similarity	NPC194499
0.8924	High Similarity	NPC88007
0.8924	High Similarity	NPC299038
0.8916	High Similarity	NPC11062
0.891	High Similarity	NPC470996
0.8889	High Similarity	NPC470999
0.8882	High Similarity	NPC27541
0.8882	High Similarity	NPC126984
0.8882	High Similarity	NPC62692
0.8882	High Similarity	NPC61967
0.8875	High Similarity	NPC68848
0.8846	High Similarity	NPC116717
0.8841	High Similarity	NPC285227
0.8839	High Similarity	NPC195325
0.8834	High Similarity	NPC472652
0.8824	High Similarity	NPC5676
0.882	High Similarity	NPC472773
0.882	High Similarity	NPC288602
0.882	High Similarity	NPC88841
0.8817	High Similarity	NPC105395
0.8805	High Similarity	NPC36655
0.8805	High Similarity	NPC261597
0.8805	High Similarity	NPC195954
0.879	High Similarity	NPC121615
0.879	High Similarity	NPC469503
0.879	High Similarity	NPC471002
0.879	High Similarity	NPC294511
0.8773	High Similarity	NPC472651
0.8765	High Similarity	NPC470182
0.8758	High Similarity	NPC329938
0.8758	High Similarity	NPC472771
0.8758	High Similarity	NPC188649
0.8758	High Similarity	NPC82851
0.8758	High Similarity	NPC471003
0.8758	High Similarity	NPC251865
0.875	High Similarity	NPC470938
0.875	High Similarity	NPC84349
0.8735	High Similarity	NPC471437
0.8735	High Similarity	NPC94763
0.8734	High Similarity	NPC282445
0.8726	High Similarity	NPC471000
0.8726	High Similarity	NPC18135
0.872	High Similarity	NPC160651
0.8718	High Similarity	NPC470790
0.8718	High Similarity	NPC470791
0.8712	High Similarity	NPC93172
0.8712	High Similarity	NPC97574
0.8712	High Similarity	NPC121995
0.8712	High Similarity	NPC470875
0.871	High Similarity	NPC302987
0.8706	High Similarity	NPC247563
0.8706	High Similarity	NPC242068
0.8704	High Similarity	NPC302369
0.8704	High Similarity	NPC134254
0.8704	High Similarity	NPC469846
0.8704	High Similarity	NPC39986
0.8696	High Similarity	NPC472653
0.8688	High Similarity	NPC304692
0.8679	High Similarity	NPC44675
0.8679	High Similarity	NPC476262
0.8679	High Similarity	NPC214541
0.8675	High Similarity	NPC469848
0.8671	High Similarity	NPC476201
0.8671	High Similarity	NPC246164
0.8667	High Similarity	NPC82602
0.8662	High Similarity	NPC156189
0.8659	High Similarity	NPC472282
0.8659	High Similarity	NPC472774
0.8659	High Similarity	NPC472775
0.8659	High Similarity	NPC100333
0.865	High Similarity	NPC276551
0.865	High Similarity	NPC469849
0.865	High Similarity	NPC470940
0.8642	High Similarity	NPC18986
0.8642	High Similarity	NPC79571
0.8642	High Similarity	NPC69028
0.8634	High Similarity	NPC307383
0.8631	High Similarity	NPC478177
0.8627	High Similarity	NPC121158
0.8625	High Similarity	NPC41880
0.8625	High Similarity	NPC104736
0.8623	High Similarity	NPC236004
0.8623	High Similarity	NPC471632
0.8614	High Similarity	NPC294512
0.8608	High Similarity	NPC272590
0.8608	High Similarity	NPC291150
0.8606	High Similarity	NPC296558
0.8606	High Similarity	NPC472765
0.8606	High Similarity	NPC472766
0.8606	High Similarity	NPC471397
0.859	High Similarity	NPC250228
0.8589	High Similarity	NPC469338
0.8589	High Similarity	NPC477405
0.8589	High Similarity	NPC224394
0.8589	High Similarity	NPC292389
0.8589	High Similarity	NPC198047
0.8589	High Similarity	NPC471168
0.8589	High Similarity	NPC472669
0.8589	High Similarity	NPC165218
0.8589	High Similarity	NPC663
0.858	High Similarity	NPC477402
0.858	High Similarity	NPC335761
0.858	High Similarity	NPC8389
0.8571	High Similarity	NPC249021
0.8571	High Similarity	NPC187149
0.8571	High Similarity	NPC45101
0.8571	High Similarity	NPC167142
0.8571	High Similarity	NPC469633
0.8571	High Similarity	NPC472772
0.8562	High Similarity	NPC35000
0.8562	High Similarity	NPC469336
0.8562	High Similarity	NPC264943
0.8554	High Similarity	NPC472659
0.8553	High Similarity	NPC90953
0.8545	High Similarity	NPC173516
0.8545	High Similarity	NPC476861
0.8545	High Similarity	NPC472764
0.8545	High Similarity	NPC476850
0.8544	High Similarity	NPC228842
0.8544	High Similarity	NPC5180
0.8544	High Similarity	NPC212257
0.8537	High Similarity	NPC259943
0.8537	High Similarity	NPC123088
0.8537	High Similarity	NPC271657
0.8528	High Similarity	NPC263432
0.8528	High Similarity	NPC5741
0.8528	High Similarity	NPC471166
0.8528	High Similarity	NPC471167
0.8528	High Similarity	NPC211777
0.8528	High Similarity	NPC207978
0.8528	High Similarity	NPC472668
0.8526	High Similarity	NPC471292
0.8519	High Similarity	NPC474611
0.8516	High Similarity	NPC476944
0.8512	High Similarity	NPC469576
0.8503	High Similarity	NPC160818
0.8503	High Similarity	NPC169299
0.85	High Similarity	NPC57998
0.85	High Similarity	NPC178932
0.85	High Similarity	NPC30222
0.8497	Intermediate Similarity	NPC67003
0.8497	Intermediate Similarity	NPC56197
0.8494	Intermediate Similarity	NPC327922
0.8485	Intermediate Similarity	NPC277618
0.8476	Intermediate Similarity	NPC476197

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 NPC470792 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	880
0.2-0.3	2100
0.3-0.4	2630
0.4-0.5	1963
0.5-0.6	964
0.6-0.7	291
0.7-0.8	31
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8679	High Similarity	NPD5761	Phase 2
0.8679	High Similarity	NPD5760	Phase 2
0.8324	Intermediate Similarity	NPD8434	Phase 2
0.7727	Intermediate Similarity	NPD6765	Approved
0.7727	Intermediate Similarity	NPD6764	Approved
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7654	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD8127	Discontinued
0.7556	Intermediate Similarity	NPD6784	Approved
0.7556	Intermediate Similarity	NPD6785	Approved
0.75	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4966	Approved
0.7384	Intermediate Similarity	NPD4965	Approved
0.7384	Intermediate Similarity	NPD4967	Phase 2
0.736	Intermediate Similarity	NPD5844	Phase 1
0.7333	Intermediate Similarity	NPD6559	Discontinued
0.7314	Intermediate Similarity	NPD7199	Phase 2
0.7299	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD7819	Suspended
0.7262	Intermediate Similarity	NPD6273	Approved
0.7241	Intermediate Similarity	NPD7075	Discontinued
0.7236	Intermediate Similarity	NPD8404	Phase 2
0.7209	Intermediate Similarity	NPD37	Approved
0.7207	Intermediate Similarity	NPD7228	Approved
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8313	Approved
0.7158	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3818	Discontinued
0.711	Intermediate Similarity	NPD6801	Discontinued
0.7108	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6599	Discontinued
0.7091	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6232	Discontinued
0.7074	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3226	Approved
0.7035	Intermediate Similarity	NPD7458	Discontinued
0.7029	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7799	Discontinued
0.6994	Remote Similarity	NPD4380	Phase 2
0.6982	Remote Similarity	NPD7236	Approved
0.6974	Remote Similarity	NPD7497	Discontinued
0.6971	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5494	Approved
0.6964	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7240	Approved
0.6954	Remote Similarity	NPD7411	Suspended
0.6949	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3749	Approved
0.6941	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5402	Approved
0.6932	Remote Similarity	NPD3817	Phase 2
0.6919	Remote Similarity	NPD920	Approved
0.6914	Remote Similarity	NPD1934	Approved
0.6906	Remote Similarity	NPD6166	Phase 2
0.6906	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2532	Approved
0.6901	Remote Similarity	NPD2533	Approved
0.6901	Remote Similarity	NPD2534	Approved
0.6893	Remote Similarity	NPD3882	Suspended
0.6893	Remote Similarity	NPD7768	Phase 2
0.6886	Remote Similarity	NPD6005	Phase 3
0.6886	Remote Similarity	NPD6002	Phase 3
0.6886	Remote Similarity	NPD5762	Approved
0.6886	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6004	Phase 3
0.6886	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5763	Approved
0.6885	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7239	Suspended
0.6878	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1465	Phase 2
0.6875	Remote Similarity	NPD8455	Phase 2
0.6862	Remote Similarity	NPD8150	Discontinued
0.6848	Remote Similarity	NPD7074	Phase 3
0.6842	Remote Similarity	NPD6799	Approved
0.6824	Remote Similarity	NPD6190	Approved
0.6821	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5403	Approved
0.6816	Remote Similarity	NPD919	Approved
0.6813	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7229	Phase 3
0.6793	Remote Similarity	NPD7054	Approved
0.6788	Remote Similarity	NPD6355	Discontinued
0.678	Remote Similarity	NPD2801	Approved
0.6768	Remote Similarity	NPD8032	Phase 2
0.6765	Remote Similarity	NPD8166	Discontinued
0.6765	Remote Similarity	NPD3750	Approved
0.6765	Remote Similarity	NPD7003	Approved
0.6757	Remote Similarity	NPD7472	Approved
0.6755	Remote Similarity	NPD8407	Phase 2
0.674	Remote Similarity	NPD6959	Discontinued
0.6738	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7808	Phase 3
0.6727	Remote Similarity	NPD4140	Approved
0.6726	Remote Similarity	NPD1551	Phase 2
0.6726	Remote Similarity	NPD6099	Approved
0.6726	Remote Similarity	NPD6100	Approved
0.6717	Remote Similarity	NPD7680	Approved
0.6707	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3764	Approved
0.6705	Remote Similarity	NPD5401	Approved
0.6705	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5735	Approved
0.6686	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2346	Discontinued
0.6684	Remote Similarity	NPD7251	Discontinued
0.6684	Remote Similarity	NPD8368	Discontinued
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD2799	Discontinued
0.6649	Remote Similarity	NPD3751	Discontinued
0.6649	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1247	Approved
0.6647	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6653	Approved
0.6647	Remote Similarity	NPD1549	Phase 2
0.6646	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7435	Discontinued
0.6631	Remote Similarity	NPD6797	Phase 2
0.6627	Remote Similarity	NPD2796	Approved
0.6625	Remote Similarity	NPD1608	Approved
0.6615	Remote Similarity	NPD8360	Approved
0.6615	Remote Similarity	NPD8361	Approved
0.6609	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2800	Approved
0.6607	Remote Similarity	NPD7097	Phase 1
0.6606	Remote Similarity	NPD6798	Discontinued
0.6588	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1471	Phase 3
0.6588	Remote Similarity	NPD2344	Approved
0.6588	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD230	Phase 1
0.6576	Remote Similarity	NPD3926	Phase 2
0.6568	Remote Similarity	NPD3748	Approved
0.6566	Remote Similarity	NPD6233	Phase 2
0.6566	Remote Similarity	NPD6663	Approved
0.6559	Remote Similarity	NPD7177	Discontinued
0.6552	Remote Similarity	NPD1511	Approved
0.6552	Remote Similarity	NPD8151	Discontinued
0.6545	Remote Similarity	NPD7095	Approved
0.6529	Remote Similarity	NPD2935	Discontinued
0.6528	Remote Similarity	NPD8435	Approved
0.6524	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7047	Phase 3
0.6522	Remote Similarity	NPD3787	Discontinued
0.652	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7874	Approved
0.6519	Remote Similarity	NPD7058	Phase 2
0.6519	Remote Similarity	NPD7057	Phase 3
0.6517	Remote Similarity	NPD7028	Phase 2
0.6515	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1243	Approved
0.651	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3268	Approved
0.6506	Remote Similarity	NPD2313	Discontinued
0.6503	Remote Similarity	NPD2797	Approved
0.65	Remote Similarity	NPD3057	Approved
0.6497	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD447	Suspended
0.6488	Remote Similarity	NPD7783	Phase 2
0.6485	Remote Similarity	NPD6832	Phase 2
0.6485	Remote Similarity	NPD7999	Approved
0.6482	Remote Similarity	NPD6782	Approved
0.6482	Remote Similarity	NPD6777	Approved
0.6482	Remote Similarity	NPD6778	Approved
0.6482	Remote Similarity	NPD6779	Approved
0.6482	Remote Similarity	NPD6780	Approved
0.6482	Remote Similarity	NPD6781	Approved
0.6482	Remote Similarity	NPD6776	Approved
0.648	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD1512	Approved
0.6473	Remote Similarity	NPD7930	Approved
0.6471	Remote Similarity	NPD4308	Phase 3
0.6471	Remote Similarity	NPD1510	Phase 2
0.6468	Remote Similarity	NPD7697	Approved
0.6468	Remote Similarity	NPD7698	Approved
0.6468	Remote Similarity	NPD7696	Phase 3
0.6463	Remote Similarity	NPD5647	Approved
0.6462	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7907	Approved
0.6438	Remote Similarity	NPD17	Approved
0.6437	Remote Similarity	NPD2309	Approved
0.6436	Remote Similarity	NPD8319	Approved
0.6436	Remote Similarity	NPD7871	Phase 2
0.6436	Remote Similarity	NPD7870	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