NPASS Compound

Structure

NPC472139 OpenBabel07101718292D 48 53 0 0 1 0 0 0 0 0999 V2000 0.5127 4.5050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4766 1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5126 0.0482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9736 3.1668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9241 -1.7842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1777 -0.8169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3223 -2.5647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0325 -4.0650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7206 3.5269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5197 -1.3035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4978 -1.5115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1407 -2.5560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3287 0.0977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5939 0.4431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0225 2.8577 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7359 -1.6416 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5513 -3.3638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7925 -0.1550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1854 1.8796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0724 -0.3582 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3498 0.2323 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2132 -1.0809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4196 -0.0177 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9561 -4.2782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9098 -1.1481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1364 1.5706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3612 0.9806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4495 -1.3165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4430 -3.2572 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9978 -0.6454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8738 0.2399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5578 1.2105 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 18 1 0 0 0 0 3 18 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 8 33 1 0 0 0 0 9 43 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 32 1 0 0 0 0 14 44 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 16 25 1 0 0 0 0 17 20 2 0 0 0 0 17 44 1 0 0 0 0 18 27 1 0 0 0 0 19 4 1 1 0 0 0 19 28 1 0 0 0 0 20 26 1 0 0 0 0 21 33 1 1 0 0 0 21 34 1 0 0 0 0 22 31 1 0 0 0 0 22 33 1 6 0 0 0 23 32 1 1 0 0 0 23 34 1 0 0 0 0 24 37 2 0 0 0 0 24 43 1 0 0 0 0 25 38 2 0 0 0 0 25 45 1 0 0 0 0 26 32 1 6 0 0 0 26 45 1 0 0 0 0 27 39 2 0 0 0 0 27 46 1 0 0 0 0 28 40 2 0 0 0 0 28 47 1 0 0 0 0 29 31 1 0 0 0 0 29 35 1 1 0 0 0 29 46 1 0 0 0 0 30 34 1 6 0 0 0 30 35 1 0 0 0 0 30 47 1 0 0 0 0 32 7 1 6 0 0 0 33 36 1 6 0 0 0 34 48 1 6 0 0 0 35 36 1 6 0 0 0 35 41 1 0 0 0 0 36 42 1 6 0 0 0 36 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	674.33
Volume:	669.537
LogP:	5.121
LogD:	3.204
LogS:	-5.199
# Rotatable Bonds:	11
TPSA:	168.03
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	6.918
Fsp3:	0.778
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:	-5.365
MDCK Permeability:	6.913110701134428e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.184
Human Intestinal Absorption (HIA):	0.079
20% Bioavailability (F20%):	0.12
30% Bioavailability (F30%):	0.639

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.316
Plasma Protein Binding (PPB):	82.2262954711914%
Volume Distribution (VD):	1.448
Pgp-substrate:	7.223328113555908%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.422
CYP2C19-inhibitor:	0.264
CYP2C19-substrate:	0.328
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.758
CYP3A4-substrate:	0.714

ADMET: Excretion

Clearance (CL):	3.679
Half-life (T1/2):	0.307

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.77
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.785
Skin Sensitization:	0.111
Carcinogencity:	0.136
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC472139

Natural Product ID:	NPC472139
*Common Name:**	FGBXJGAAKNHCKE-GOIXFIAASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FGBXJGAAKNHCKE-GOIXFIAASA-N
Standard InCHI:	InChI=1S/C36H50O12/c1-10-19(4)28(40)47-30-34-21(11-13-32(7)23(34)16-25(38)45-26(32)20-12-14-44-17-20)33(8)22(15-24(37)43-9)31(5,6)29(46-27(39)18(2)3)35(30,41)36(33,42)48-34/h12,14,17-19,21-23,26,29-30,41-42H,10-11,13,15-16H2,1-9H3/t19-,21+,22-,23+,26-,29-,30-,32+,33+,34+,35-,36+/m0/s1
SMILES:	CCC(C)C(=O)OC1C23C(CCC4(C2CC(=O)OC4C5=COC=C5)C)C6(C(C(C(C1(C6(O3)O)O)OC(=O)C(C)C)(C)C)CC(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3341798
PubChem CID:	n.a.
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
NPO25789	Xylocarpus rumphii	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25140384]
NPO25789	Xylocarpus rumphii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28121439]
NPO25789	Xylocarpus rumphii	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	=	24500.0	nM	PMID[509838]

☑ 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 NPC472139 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	366
0.1-0.2	1419
0.2-0.3	3233
0.3-0.4	5558
0.4-0.5	10210
0.5-0.6	10308
0.6-0.7	9563
0.7-0.8	1578
0.8-0.85	294
0.85-0.9	155
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC472141
0.9231	High Similarity	NPC299038
0.9182	High Similarity	NPC470182
0.9177	High Similarity	NPC200782
0.9172	High Similarity	NPC475967
0.9125	High Similarity	NPC93172
0.9125	High Similarity	NPC97574
0.9103	High Similarity	NPC476262
0.9074	High Similarity	NPC82602
0.9051	High Similarity	NPC475226
0.9036	High Similarity	NPC470938
0.9012	High Similarity	NPC472652
0.9012	High Similarity	NPC271235
0.9	High Similarity	NPC472773
0.9	High Similarity	NPC419
0.8994	High Similarity	NPC472653
0.8987	High Similarity	NPC472776
0.8987	High Similarity	NPC261597
0.8987	High Similarity	NPC472777
0.8987	High Similarity	NPC472778
0.8987	High Similarity	NPC36655
0.8981	High Similarity	NPC214541
0.8981	High Similarity	NPC44675
0.8974	High Similarity	NPC268905
0.8974	High Similarity	NPC476201
0.8951	High Similarity	NPC472651
0.8951	High Similarity	NPC472774
0.8951	High Similarity	NPC100333
0.8951	High Similarity	NPC472775
0.8944	High Similarity	NPC469849
0.8938	High Similarity	NPC472771
0.8938	High Similarity	NPC82851
0.8938	High Similarity	NPC470792
0.8917	High Similarity	NPC282445
0.891	High Similarity	NPC18135
0.8909	High Similarity	NPC477824
0.8903	High Similarity	NPC69647
0.8903	High Similarity	NPC125182
0.8902	High Similarity	NPC160818
0.8902	High Similarity	NPC169299
0.8896	High Similarity	NPC160651
0.8896	High Similarity	NPC255414
0.8889	High Similarity	NPC470875
0.8882	High Similarity	NPC469338
0.8882	High Similarity	NPC292389
0.8882	High Similarity	NPC469846
0.8868	High Similarity	NPC187149
0.8868	High Similarity	NPC167142
0.8861	High Similarity	NPC264943
0.8854	High Similarity	NPC469503
0.8846	High Similarity	NPC476122
0.8834	High Similarity	NPC476861
0.8834	High Similarity	NPC173516
0.8834	High Similarity	NPC476850
0.8827	High Similarity	NPC470940
0.8827	High Similarity	NPC276551
0.8827	High Similarity	NPC271657
0.882	High Similarity	NPC211777
0.882	High Similarity	NPC96443
0.882	High Similarity	NPC117986
0.882	High Similarity	NPC149896
0.882	High Similarity	NPC188649
0.882	High Similarity	NPC18347
0.882	High Similarity	NPC329938
0.882	High Similarity	NPC207978
0.882	High Similarity	NPC290400
0.8812	High Similarity	NPC472671
0.8812	High Similarity	NPC307383
0.8802	High Similarity	NPC470181
0.8797	High Similarity	NPC57998
0.8795	High Similarity	NPC94763
0.8788	High Similarity	NPC294512
0.8782	High Similarity	NPC195325
0.878	High Similarity	NPC471397
0.8773	High Similarity	NPC472670
0.8773	High Similarity	NPC307781
0.8765	High Similarity	NPC134254
0.8765	High Similarity	NPC477405
0.8765	High Similarity	NPC105395
0.8765	High Similarity	NPC88841
0.8765	High Similarity	NPC198047
0.8765	High Similarity	NPC247563
0.8765	High Similarity	NPC242068
0.8765	High Similarity	NPC39986
0.8765	High Similarity	NPC288602
0.8765	High Similarity	NPC302369
0.875	High Similarity	NPC214495
0.875	High Similarity	NPC45101
0.875	High Similarity	NPC472772
0.875	High Similarity	NPC475066
0.875	High Similarity	NPC249021
0.875	High Similarity	NPC470119
0.872	High Similarity	NPC472282
0.8712	High Similarity	NPC123088
0.8712	High Similarity	NPC476858
0.8712	High Similarity	NPC476857
0.8712	High Similarity	NPC476856
0.8704	High Similarity	NPC69028
0.8701	High Similarity	NPC251865
0.8683	High Similarity	NPC236004
0.8679	High Similarity	NPC253201
0.8679	High Similarity	NPC34421
0.8679	High Similarity	NPC237259
0.8679	High Similarity	NPC98206
0.8679	High Similarity	NPC302054
0.8679	High Similarity	NPC30222
0.8675	High Similarity	NPC475237
0.8675	High Similarity	NPC475641
0.8675	High Similarity	NPC159232
0.8667	High Similarity	NPC472673
0.8654	High Similarity	NPC221809
0.865	High Similarity	NPC285567
0.865	High Similarity	NPC476197
0.865	High Similarity	NPC234660
0.865	High Similarity	NPC165218
0.865	High Similarity	NPC51568
0.8645	High Similarity	NPC5676
0.8642	High Similarity	NPC191828
0.8642	High Similarity	NPC470789
0.8642	High Similarity	NPC335761
0.8642	High Similarity	NPC477402
0.8642	High Similarity	NPC25255
0.8634	High Similarity	NPC88007
0.8634	High Similarity	NPC195954
0.8634	High Similarity	NPC470118
0.8631	High Similarity	NPC56953
0.8631	High Similarity	NPC176413
0.8631	High Similarity	NPC262386
0.8625	High Similarity	NPC141538
0.8625	High Similarity	NPC35000
0.8625	High Similarity	NPC469336
0.8625	High Similarity	NPC155939
0.8625	High Similarity	NPC296807
0.8616	High Similarity	NPC472672
0.8616	High Similarity	NPC322546
0.8616	High Similarity	NPC308205
0.8616	High Similarity	NPC182427
0.8616	High Similarity	NPC29695
0.8616	High Similarity	NPC476940
0.8616	High Similarity	NPC476939
0.8606	High Similarity	NPC476853
0.8598	High Similarity	NPC476860
0.859	High Similarity	NPC346
0.8589	High Similarity	NPC193798
0.8589	High Similarity	NPC68848
0.8589	High Similarity	NPC5079
0.8589	High Similarity	NPC263432
0.858	High Similarity	NPC475295
0.858	High Similarity	NPC262872
0.858	High Similarity	NPC478177
0.858	High Similarity	NPC473473
0.858	High Similarity	NPC477403
0.8571	High Similarity	NPC121158
0.8571	High Similarity	NPC126723
0.8562	High Similarity	NPC178932
0.8554	High Similarity	NPC472765
0.8554	High Similarity	NPC327922
0.8554	High Similarity	NPC472766
0.8554	High Similarity	NPC296558
0.8545	High Similarity	NPC121995
0.8545	High Similarity	NPC214600
0.8545	High Similarity	NPC23387
0.8545	High Similarity	NPC478178
0.8545	High Similarity	NPC86800
0.8544	High Similarity	NPC472654
0.8537	High Similarity	NPC471168
0.8537	High Similarity	NPC472669
0.8537	High Similarity	NPC283209
0.8535	High Similarity	NPC250228
0.8535	High Similarity	NPC470941
0.8521	High Similarity	NPC469633
0.8519	High Similarity	NPC194499
0.8519	High Similarity	NPC286722
0.8519	High Similarity	NPC469847
0.8519	High Similarity	NPC472283
0.8519	High Similarity	NPC197137
0.8519	High Similarity	NPC173544
0.8516	High Similarity	NPC223415
0.8509	High Similarity	NPC469850
0.8503	High Similarity	NPC470995
0.85	High Similarity	NPC75906
0.8494	Intermediate Similarity	NPC472764
0.8494	Intermediate Similarity	NPC270312
0.8491	Intermediate Similarity	NPC477404
0.8491	Intermediate Similarity	NPC159927
0.8491	Intermediate Similarity	NPC469335
0.8491	Intermediate Similarity	NPC196864
0.8485	Intermediate Similarity	NPC276735
0.8485	Intermediate Similarity	NPC259943
0.8476	Intermediate Similarity	NPC472668
0.8476	Intermediate Similarity	NPC5741
0.8476	Intermediate Similarity	NPC471166
0.8476	Intermediate Similarity	NPC18986
0.8476	Intermediate Similarity	NPC470939
0.8476	Intermediate Similarity	NPC471167
0.8471	Intermediate Similarity	NPC472665
0.8462	Intermediate Similarity	NPC471437
0.8462	Intermediate Similarity	NPC476944
0.8462	Intermediate Similarity	NPC469576
0.8457	Intermediate Similarity	NPC107646

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 NPC472139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	971
0.2-0.3	2261
0.3-0.4	2695
0.4-0.5	1875
0.5-0.6	770
0.6-0.7	246
0.7-0.8	19
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
0.8282	Intermediate Similarity	NPD5761	Phase 2
0.8282	Intermediate Similarity	NPD5760	Phase 2
0.8276	Intermediate Similarity	NPD8434	Phase 2
0.7611	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7819	Suspended
0.7486	Intermediate Similarity	NPD6559	Discontinued
0.7427	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7075	Discontinued
0.7374	Intermediate Similarity	NPD8404	Phase 2
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7314	Intermediate Similarity	NPD5494	Approved
0.7293	Intermediate Similarity	NPD6764	Approved
0.7293	Intermediate Similarity	NPD6765	Approved
0.7263	Intermediate Similarity	NPD3818	Discontinued
0.7257	Intermediate Similarity	NPD6234	Discontinued
0.7251	Intermediate Similarity	NPD6599	Discontinued
0.7241	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4967	Phase 2
0.7241	Intermediate Similarity	NPD4966	Approved
0.7241	Intermediate Similarity	NPD4965	Approved
0.7222	Intermediate Similarity	NPD5844	Phase 1
0.7213	Intermediate Similarity	NPD8312	Approved
0.7213	Intermediate Similarity	NPD8313	Approved
0.72	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD6785	Approved
0.7135	Intermediate Similarity	NPD6784	Approved
0.7127	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7473	Discontinued
0.7088	Intermediate Similarity	NPD7074	Phase 3
0.7086	Intermediate Similarity	NPD3817	Phase 2
0.7086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8407	Phase 2
0.7079	Intermediate Similarity	NPD8127	Discontinued
0.7079	Intermediate Similarity	NPD7199	Phase 2
0.7069	Intermediate Similarity	NPD37	Approved
0.7069	Intermediate Similarity	NPD1934	Approved
0.7069	Intermediate Similarity	NPD6801	Discontinued
0.7065	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4380	Phase 2
0.7039	Intermediate Similarity	NPD6232	Discontinued
0.7033	Intermediate Similarity	NPD7054	Approved
0.7024	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7411	Suspended
0.7011	Intermediate Similarity	NPD8368	Discontinued
0.7011	Intermediate Similarity	NPD7685	Pre-registration
0.7011	Intermediate Similarity	NPD7240	Approved
0.7006	Intermediate Similarity	NPD3749	Approved
0.7005	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6799	Approved
0.6995	Remote Similarity	NPD7472	Approved
0.6989	Remote Similarity	NPD5402	Approved
0.6978	Remote Similarity	NPD7799	Discontinued
0.6978	Remote Similarity	NPD3751	Discontinued
0.6977	Remote Similarity	NPD920	Approved
0.6973	Remote Similarity	NPD7808	Phase 3
0.6959	Remote Similarity	NPD2533	Approved
0.6959	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2532	Approved
0.6959	Remote Similarity	NPD2534	Approved
0.6949	Remote Similarity	NPD3882	Suspended
0.6944	Remote Similarity	NPD3787	Discontinued
0.6939	Remote Similarity	NPD7435	Discontinued
0.6932	Remote Similarity	NPD2801	Approved
0.6919	Remote Similarity	NPD7251	Discontinued
0.6901	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3226	Approved
0.6897	Remote Similarity	NPD7458	Discontinued
0.6879	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD919	Approved
0.6868	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6166	Phase 2
0.6868	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6797	Phase 2
0.686	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7768	Phase 2
0.6853	Remote Similarity	NPD7497	Discontinued
0.6845	Remote Similarity	NPD2346	Discontinued
0.6845	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD1465	Phase 2
0.6836	Remote Similarity	NPD8455	Phase 2
0.6821	Remote Similarity	NPD6273	Approved
0.6816	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7874	Approved
0.6812	Remote Similarity	NPD7907	Approved
0.6805	Remote Similarity	NPD1549	Phase 2
0.6796	Remote Similarity	NPD6959	Discontinued
0.6796	Remote Similarity	NPD1247	Approved
0.6786	Remote Similarity	NPD1551	Phase 2
0.6786	Remote Similarity	NPD6780	Approved
0.6786	Remote Similarity	NPD6778	Approved
0.6786	Remote Similarity	NPD6777	Approved
0.6786	Remote Similarity	NPD6781	Approved
0.6786	Remote Similarity	NPD6099	Approved
0.6786	Remote Similarity	NPD6782	Approved
0.6786	Remote Similarity	NPD2796	Approved
0.6786	Remote Similarity	NPD6776	Approved
0.6786	Remote Similarity	NPD6779	Approved
0.6786	Remote Similarity	NPD6100	Approved
0.6782	Remote Similarity	NPD5403	Approved
0.6782	Remote Similarity	NPD7783	Phase 2
0.6782	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7698	Approved
0.6768	Remote Similarity	NPD7696	Phase 3
0.6768	Remote Similarity	NPD7697	Approved
0.6766	Remote Similarity	NPD7097	Phase 1
0.6765	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5401	Approved
0.6763	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD8361	Approved
0.6754	Remote Similarity	NPD8435	Approved
0.6754	Remote Similarity	NPD8360	Approved
0.6746	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7871	Phase 2
0.6734	Remote Similarity	NPD7870	Phase 2
0.6726	Remote Similarity	NPD2799	Discontinued
0.6716	Remote Similarity	NPD7701	Phase 2
0.6706	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7801	Approved
0.6687	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2935	Discontinued
0.6683	Remote Similarity	NPD8151	Discontinued
0.6667	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2800	Approved
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8319	Approved
0.665	Remote Similarity	NPD8320	Phase 1
0.6647	Remote Similarity	NPD6355	Discontinued
0.6647	Remote Similarity	NPD1933	Approved
0.6646	Remote Similarity	NPD6832	Phase 2
0.6635	Remote Similarity	NPD4665	Approved
0.6635	Remote Similarity	NPD4111	Phase 1
0.6633	Remote Similarity	NPD6823	Phase 2
0.663	Remote Similarity	NPD3926	Phase 2
0.6628	Remote Similarity	NPD3750	Approved
0.6627	Remote Similarity	NPD7033	Discontinued
0.6613	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1511	Approved
0.6602	Remote Similarity	NPD7930	Approved
0.66	Remote Similarity	NPD7680	Approved
0.6599	Remote Similarity	NPD7700	Phase 2
0.6599	Remote Similarity	NPD7699	Phase 2
0.659	Remote Similarity	NPD6190	Approved
0.6576	Remote Similarity	NPD5711	Approved
0.6576	Remote Similarity	NPD5710	Approved
0.657	Remote Similarity	NPD1243	Approved
0.6566	Remote Similarity	NPD2313	Discontinued
0.6564	Remote Similarity	NPD7319	Approved
0.6552	Remote Similarity	NPD7236	Approved
0.655	Remote Similarity	NPD1471	Phase 3
0.6548	Remote Similarity	NPD447	Suspended
0.6535	Remote Similarity	NPD7999	Approved
0.6534	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1512	Approved
0.6532	Remote Similarity	NPD4110	Phase 3
0.6532	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6535	Approved
0.6531	Remote Similarity	NPD6534	Approved
0.6529	Remote Similarity	NPD1510	Phase 2
0.6529	Remote Similarity	NPD3748	Approved
0.6506	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD8285	Discontinued
0.6482	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD1608	Approved
0.648	Remote Similarity	NPD7028	Phase 2
0.6477	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3764	Approved
0.6467	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD1653	Approved
0.6461	Remote Similarity	NPD7239	Suspended
0.6458	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5762	Approved
0.6453	Remote Similarity	NPD2344	Approved
0.6453	Remote Similarity	NPD6004	Phase 3
0.6453	Remote Similarity	NPD6005	Phase 3
0.6453	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5763	Approved
0.6453	Remote Similarity	NPD6002	Phase 3
0.645	Remote Similarity	NPD4107	Approved
0.645	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.645	Remote Similarity	NPD230	Phase 1
0.6444	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7003	Approved
0.6437	Remote Similarity	NPD8166	Discontinued

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