NPASS Compound

Structure

NPC45224 OpenBabel07101718232D 43 45 0 0 1 0 0 0 0 0999 V2000 3.9234 -0.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -0.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2728 5.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3431 2.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0559 3.5737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6958 1.8795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0122 3.1579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7251 4.3168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7177 2.0874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6386 -1.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0574 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9234 0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 -0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 4.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3649 2.6226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7032 4.1089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0485 1.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 3.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3253 3.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4593 3.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4593 2.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4476 -2.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7894 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 -0.5865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 5.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3723 4.8521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3576 0.3932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0574 3.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5227 -0.5759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 4.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0574 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 3.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 1.5522 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 -0.4067 1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 7 1 0 0 0 0 4 16 2 0 0 0 0 5 8 2 0 0 0 0 5 16 1 0 0 0 0 6 9 2 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 28 1 0 0 0 0 11 37 1 0 0 0 0 12 38 1 0 0 0 0 13 29 2 0 0 0 0 13 37 1 0 0 0 0 14 30 2 0 0 0 0 14 38 1 0 0 0 0 15 31 2 0 0 0 0 15 39 1 0 0 0 0 17 32 1 0 0 0 0 18 10 1 6 0 0 0 18 22 1 0 0 0 0 18 42 1 0 0 0 0 19 11 1 1 0 0 0 19 21 1 0 0 0 0 19 40 1 0 0 0 0 20 33 2 0 0 0 0 20 41 1 0 0 0 0 21 23 1 0 0 0 0 21 34 1 6 0 0 0 22 25 1 0 0 0 0 22 35 1 1 0 0 0 23 24 1 0 0 0 0 23 36 1 1 0 0 0 24 26 1 0 0 0 0 24 39 1 6 0 0 0 25 27 1 6 0 0 0 25 41 1 0 0 0 0 26 40 1 0 0 0 0 26 43 1 6 0 0 0 27 12 1 1 0 0 0 27 42 1 0 0 0 0 27 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.18
Volume:	569.431
LogP:	0.421
LogD:	0.182
LogS:	-2.356
# Rotatable Bonds:	15
TPSA:	234.04
# H-Bond Aceptor:	16
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.106
Synthetic Accessibility Score:	4.782
Fsp3:	0.556
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:	-6.275
MDCK Permeability:	0.00010844830831047148
Pgp-inhibitor:	0.01
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.995
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	22.32915496826172%
Volume Distribution (VD):	0.409
Pgp-substrate:	50.25643539428711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	1.759
Half-life (T1/2):	0.947

ADMET: Toxicity

hERG Blockers:	0.401
Human Hepatotoxicity (H-HT):	0.161
Drug-inuced Liver Injury (DILI):	0.776
AMES Toxicity:	0.177
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.835
Carcinogencity:	0.127
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC45224

Natural Product ID:	NPC45224
*Common Name:**	3-P-O-Coumaroyl-1,2',6'-O-Triacetyl Sucrose
IUPAC Name:	[(2S,3S,4R,5R)-2-[(2R,3R,4S,5S,6R)-3-acetyloxy-6-(acetyloxymethyl)-4,5-dihydroxyoxan-2-yl]oxy-2-(acetyloxymethyl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	IUWNEFXWBDZQHK-PZHMIARSSA-N
Standard InCHI:	InChI=1S/C27H34O16/c1-13(29)37-11-19-21(34)23(36)24(39-15(3)31)26(40-19)43-27(12-38-14(2)30)25(22(35)18(10-28)42-27)41-20(33)9-6-16-4-7-17(32)8-5-16/h4-9,18-19,21-26,28,32,34-36H,10-12H2,1-3H3/b9-6+/t18-,19-,21-,22-,23+,24-,25+,26-,27+/m1/s1
SMILES:	CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@]1(COC(=O)C)[C@H]([C@@H]([C@@H](CO)O1)O)OC(=O)/C=C/c1ccc(cc1)O)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3262775
PubChem CID:	14841107
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[18449498]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24767839]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27241	Prunus tomentosa	Species	Rosaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3440.0	nM	PMID[455835]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3200.0	nM	PMID[455835]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2490.0	nM	PMID[455835]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	3960.0	nM	PMID[455835]

☑ 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 NPC45224 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	245
0.1-0.2	1036
0.2-0.3	2884
0.3-0.4	7522
0.4-0.5	10590
0.5-0.6	9530
0.6-0.7	9001
0.7-0.8	1589
0.8-0.85	178
0.85-0.9	99
0.9-0.95	15
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC35288
1.0	High Similarity	NPC173150
1.0	High Similarity	NPC471882
1.0	High Similarity	NPC156692
1.0	High Similarity	NPC471881
0.9752	High Similarity	NPC61181
0.9672	High Similarity	NPC103533
0.9593	High Similarity	NPC225307
0.9583	High Similarity	NPC52097
0.9512	High Similarity	NPC106677
0.95	High Similarity	NPC11724
0.9449	High Similarity	NPC471883
0.9431	High Similarity	NPC471157
0.9417	High Similarity	NPC476872
0.937	High Similarity	NPC28637
0.9365	High Similarity	NPC281798
0.9365	High Similarity	NPC478255
0.935	High Similarity	NPC83218
0.935	High Similarity	NPC126991
0.9274	High Similarity	NPC252114
0.9219	High Similarity	NPC254398
0.9213	High Similarity	NPC219677
0.9213	High Similarity	NPC138777
0.9213	High Similarity	NPC46137
0.9213	High Similarity	NPC235294
0.9213	High Similarity	NPC246869
0.9213	High Similarity	NPC225384
0.92	High Similarity	NPC288416
0.9141	High Similarity	NPC473924
0.9077	High Similarity	NPC263829
0.9062	High Similarity	NPC254819
0.9055	High Similarity	NPC253595
0.9055	High Similarity	NPC477294
0.9055	High Similarity	NPC477293
0.9055	High Similarity	NPC229784
0.9016	High Similarity	NPC282409
0.9016	High Similarity	NPC469702
0.8992	High Similarity	NPC473285
0.8976	High Similarity	NPC232880
0.8943	High Similarity	NPC469548
0.8943	High Similarity	NPC476445
0.8943	High Similarity	NPC476448
0.8939	High Similarity	NPC476376
0.8898	High Similarity	NPC476873
0.8872	High Similarity	NPC328273
0.8872	High Similarity	NPC171134
0.8872	High Similarity	NPC220942
0.8872	High Similarity	NPC226005
0.8872	High Similarity	NPC321184
0.8872	High Similarity	NPC321638
0.8864	High Similarity	NPC470572
0.8855	High Similarity	NPC169398
0.8833	High Similarity	NPC313193
0.8824	High Similarity	NPC196063
0.8824	High Similarity	NPC300894
0.8824	High Similarity	NPC296954
0.8824	High Similarity	NPC141455
0.8797	High Similarity	NPC469364
0.8797	High Similarity	NPC65262
0.8797	High Similarity	NPC101686
0.876	High Similarity	NPC295970
0.8759	High Similarity	NPC262182
0.8759	High Similarity	NPC287615
0.8759	High Similarity	NPC216819
0.8759	High Similarity	NPC83743
0.875	High Similarity	NPC293154
0.875	High Similarity	NPC105005
0.875	High Similarity	NPC40305
0.8741	High Similarity	NPC476385
0.8741	High Similarity	NPC134405
0.8741	High Similarity	NPC47471
0.8741	High Similarity	NPC476377
0.8731	High Similarity	NPC220936
0.8731	High Similarity	NPC197316
0.8731	High Similarity	NPC31745
0.8731	High Similarity	NPC64141
0.8731	High Similarity	NPC476383
0.8731	High Similarity	NPC472350
0.8731	High Similarity	NPC205195
0.8731	High Similarity	NPC68092
0.8731	High Similarity	NPC89105
0.8731	High Similarity	NPC81515
0.8731	High Similarity	NPC49597
0.8722	High Similarity	NPC157554
0.8712	High Similarity	NPC287597
0.8712	High Similarity	NPC886
0.8712	High Similarity	NPC34293
0.8696	High Similarity	NPC229505
0.8689	High Similarity	NPC148055
0.8689	High Similarity	NPC175771
0.8686	High Similarity	NPC297342
0.8686	High Similarity	NPC110063
0.8667	High Similarity	NPC475530
0.8667	High Similarity	NPC473799
0.8657	High Similarity	NPC260425
0.8651	High Similarity	NPC471067
0.8647	High Similarity	NPC476870
0.8636	High Similarity	NPC114116
0.8615	High Similarity	NPC469549
0.8613	High Similarity	NPC264632
0.8613	High Similarity	NPC476378
0.8613	High Similarity	NPC476375
0.8613	High Similarity	NPC476380
0.8613	High Similarity	NPC247032
0.8613	High Similarity	NPC112
0.8613	High Similarity	NPC298257
0.8613	High Similarity	NPC205864
0.8613	High Similarity	NPC476397
0.8613	High Similarity	NPC175214
0.8613	High Similarity	NPC478250
0.8613	High Similarity	NPC96795
0.8613	High Similarity	NPC76406
0.8613	High Similarity	NPC476384
0.8613	High Similarity	NPC476381
0.8613	High Similarity	NPC119537
0.8613	High Similarity	NPC269141
0.8593	High Similarity	NPC100389
0.8583	High Similarity	NPC232454
0.8583	High Similarity	NPC178449
0.8583	High Similarity	NPC470907
0.8582	High Similarity	NPC472132
0.8582	High Similarity	NPC166180
0.8582	High Similarity	NPC37468
0.8582	High Similarity	NPC471345
0.8571	High Similarity	NPC80732
0.8571	High Similarity	NPC199311
0.8571	High Similarity	NPC201148
0.8571	High Similarity	NPC215095
0.8571	High Similarity	NPC55608
0.8571	High Similarity	NPC192763
0.8571	High Similarity	NPC261122
0.8571	High Similarity	NPC28651
0.8571	High Similarity	NPC300262
0.8571	High Similarity	NPC3460
0.8571	High Similarity	NPC210611
0.8551	High Similarity	NPC64195
0.8551	High Similarity	NPC251062
0.8551	High Similarity	NPC296659
0.8551	High Similarity	NPC202391
0.8551	High Similarity	NPC63304
0.8551	High Similarity	NPC184464
0.854	High Similarity	NPC222433
0.854	High Similarity	NPC265648
0.8538	High Similarity	NPC146540
0.8525	High Similarity	NPC157338
0.8519	High Similarity	NPC78363
0.8511	High Similarity	NPC283839
0.8511	High Similarity	NPC90896
0.8507	High Similarity	NPC185778
0.8492	Intermediate Similarity	NPC201402
0.8492	Intermediate Similarity	NPC469703
0.8492	Intermediate Similarity	NPC160854
0.8492	Intermediate Similarity	NPC229600
0.8492	Intermediate Similarity	NPC469704
0.8478	Intermediate Similarity	NPC88754
0.8478	Intermediate Similarity	NPC152796
0.8478	Intermediate Similarity	NPC237872
0.8478	Intermediate Similarity	NPC475213
0.8478	Intermediate Similarity	NPC263397
0.8478	Intermediate Similarity	NPC204644
0.8478	Intermediate Similarity	NPC302286
0.8478	Intermediate Similarity	NPC186296
0.8478	Intermediate Similarity	NPC116104
0.8467	Intermediate Similarity	NPC137501
0.8467	Intermediate Similarity	NPC7518
0.8467	Intermediate Similarity	NPC159387
0.8467	Intermediate Similarity	NPC46644
0.8467	Intermediate Similarity	NPC154262
0.8462	Intermediate Similarity	NPC469687
0.8451	Intermediate Similarity	NPC188393
0.8451	Intermediate Similarity	NPC470934
0.8444	Intermediate Similarity	NPC186418
0.8429	Intermediate Similarity	NPC320734
0.8429	Intermediate Similarity	NPC37838
0.8429	Intermediate Similarity	NPC473147
0.8429	Intermediate Similarity	NPC476865
0.8425	Intermediate Similarity	NPC469686
0.8417	Intermediate Similarity	NPC194938
0.8417	Intermediate Similarity	NPC476867
0.8406	Intermediate Similarity	NPC296643
0.8406	Intermediate Similarity	NPC157816
0.8406	Intermediate Similarity	NPC140502
0.8394	Intermediate Similarity	NPC202700
0.8392	Intermediate Similarity	NPC85192
0.8392	Intermediate Similarity	NPC125823
0.8392	Intermediate Similarity	NPC7145
0.8392	Intermediate Similarity	NPC143480
0.8372	Intermediate Similarity	NPC287429
0.8357	Intermediate Similarity	NPC476382
0.8357	Intermediate Similarity	NPC34927
0.8357	Intermediate Similarity	NPC252292
0.8357	Intermediate Similarity	NPC100998
0.8357	Intermediate Similarity	NPC476864
0.8357	Intermediate Similarity	NPC476868
0.8357	Intermediate Similarity	NPC34587
0.8357	Intermediate Similarity	NPC476869
0.8357	Intermediate Similarity	NPC476866
0.8347	Intermediate Similarity	NPC43584
0.8345	Intermediate Similarity	NPC478239
0.8333	Intermediate Similarity	NPC289967

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 NPC45224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	665
0.2-0.3	1545
0.3-0.4	2980
0.4-0.5	2151
0.5-0.6	1270
0.6-0.7	327
0.7-0.8	12
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8731	High Similarity	NPD7266	Discontinued
0.7863	Intermediate Similarity	NPD1091	Approved
0.7755	Intermediate Similarity	NPD1653	Approved
0.7698	Intermediate Similarity	NPD969	Suspended
0.752	Intermediate Similarity	NPD1358	Approved
0.7466	Intermediate Similarity	NPD6190	Approved
0.7424	Intermediate Similarity	NPD9545	Approved
0.7302	Intermediate Similarity	NPD3134	Approved
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7244	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7685	Pre-registration
0.7239	Intermediate Similarity	NPD1357	Approved
0.7222	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1652	Phase 2
0.7185	Intermediate Similarity	NPD5125	Phase 3
0.7185	Intermediate Similarity	NPD5126	Approved
0.7162	Intermediate Similarity	NPD4628	Phase 3
0.7134	Intermediate Similarity	NPD6559	Discontinued
0.7133	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7097	Phase 1
0.7099	Intermediate Similarity	NPD7843	Approved
0.7099	Intermediate Similarity	NPD7228	Approved
0.7083	Intermediate Similarity	NPD230	Phase 1
0.708	Intermediate Similarity	NPD422	Phase 1
0.708	Intermediate Similarity	NPD3705	Approved
0.7067	Intermediate Similarity	NPD5058	Phase 3
0.7042	Intermediate Similarity	NPD3027	Phase 3
0.7012	Intermediate Similarity	NPD7472	Approved
0.6994	Remote Similarity	NPD3818	Discontinued
0.6993	Remote Similarity	NPD3764	Approved
0.6987	Remote Similarity	NPD37	Approved
0.6981	Remote Similarity	NPD6234	Discontinued
0.6978	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5124	Phase 1
0.6966	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4340	Discontinued
0.6962	Remote Similarity	NPD4965	Approved
0.6962	Remote Similarity	NPD4967	Phase 2
0.6962	Remote Similarity	NPD4966	Approved
0.6951	Remote Similarity	NPD7054	Approved
0.6951	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6233	Phase 2
0.694	Remote Similarity	NPD7157	Approved
0.6928	Remote Similarity	NPD7251	Discontinued
0.6923	Remote Similarity	NPD2684	Approved
0.6918	Remote Similarity	NPD7075	Discontinued
0.6918	Remote Similarity	NPD6653	Approved
0.6909	Remote Similarity	NPD7074	Phase 3
0.6889	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7808	Phase 3
0.6875	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6797	Phase 2
0.6864	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4380	Phase 2
0.6849	Remote Similarity	NPD6355	Discontinued
0.6846	Remote Similarity	NPD290	Approved
0.6845	Remote Similarity	NPD8313	Approved
0.6845	Remote Similarity	NPD8312	Approved
0.6826	Remote Similarity	NPD7240	Approved
0.6821	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2424	Discontinued
0.6786	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4060	Phase 1
0.6781	Remote Similarity	NPD1613	Approved
0.6777	Remote Similarity	NPD689	Discontinued
0.6774	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2933	Approved
0.6774	Remote Similarity	NPD2934	Approved
0.6765	Remote Similarity	NPD9493	Approved
0.6763	Remote Similarity	NPD3496	Discontinued
0.6759	Remote Similarity	NPD6798	Discontinued
0.6755	Remote Similarity	NPD6674	Discontinued
0.675	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5763	Approved
0.6733	Remote Similarity	NPD5762	Approved
0.673	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2859	Approved
0.672	Remote Similarity	NPD2860	Approved
0.6718	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5647	Approved
0.6712	Remote Similarity	NPD4062	Phase 3
0.6711	Remote Similarity	NPD8166	Discontinued
0.6711	Remote Similarity	NPD7033	Discontinued
0.6711	Remote Similarity	NPD5588	Approved
0.6688	Remote Similarity	NPD6799	Approved
0.6687	Remote Similarity	NPD7199	Phase 2
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD6647	Phase 2
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3536	Discontinued
0.6645	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4538	Approved
0.6644	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4536	Approved
0.6643	Remote Similarity	NPD6362	Approved
0.6643	Remote Similarity	NPD3094	Phase 2
0.6623	Remote Similarity	NPD6002	Phase 3
0.6623	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6005	Phase 3
0.6623	Remote Similarity	NPD6004	Phase 3
0.6621	Remote Similarity	NPD4908	Phase 1
0.6603	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD5536	Phase 2
0.6593	Remote Similarity	NPD5535	Approved
0.6589	Remote Similarity	NPD846	Approved
0.6589	Remote Similarity	NPD940	Approved
0.6583	Remote Similarity	NPD111	Approved
0.6582	Remote Similarity	NPD7458	Discontinued
0.6575	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7095	Approved
0.6573	Remote Similarity	NPD3225	Approved
0.6573	Remote Similarity	NPD8651	Approved
0.6571	Remote Similarity	NPD4626	Approved
0.6562	Remote Similarity	NPD3020	Approved
0.6556	Remote Similarity	NPD2935	Discontinued
0.6547	Remote Similarity	NPD1548	Phase 1
0.6538	Remote Similarity	NPD5401	Approved
0.6531	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD3847	Discontinued
0.6522	Remote Similarity	NPD2977	Approved
0.6522	Remote Similarity	NPD2978	Approved
0.6519	Remote Similarity	NPD228	Approved
0.6515	Remote Similarity	NPD968	Approved
0.6512	Remote Similarity	NPD1242	Phase 1
0.651	Remote Similarity	NPD1933	Approved
0.6507	Remote Similarity	NPD6832	Phase 2
0.6507	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3685	Discontinued
0.65	Remote Similarity	NPD7411	Suspended
0.65	Remote Similarity	NPD5691	Approved
0.6494	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3022	Approved
0.6493	Remote Similarity	NPD3021	Approved
0.6493	Remote Similarity	NPD2067	Discontinued
0.649	Remote Similarity	NPD5960	Phase 3
0.6486	Remote Similarity	NPD6663	Approved
0.6485	Remote Similarity	NPD8127	Discontinued
0.6481	Remote Similarity	NPD5402	Approved
0.6479	Remote Similarity	NPD1535	Discovery
0.6479	Remote Similarity	NPD1610	Phase 2
0.6479	Remote Similarity	NPD3092	Approved
0.6478	Remote Similarity	NPD3455	Phase 2
0.6475	Remote Similarity	NPD1282	Approved
0.6471	Remote Similarity	NPD1549	Phase 2
0.6471	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2492	Phase 1
0.6463	Remote Similarity	NPD3179	Approved
0.6463	Remote Similarity	NPD3180	Approved
0.646	Remote Similarity	NPD1934	Approved
0.6454	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD1778	Approved
0.6449	Remote Similarity	NPD4198	Discontinued
0.6449	Remote Similarity	NPD6671	Approved
0.6447	Remote Similarity	NPD1551	Phase 2
0.6443	Remote Similarity	NPD4140	Approved
0.6442	Remote Similarity	NPD3882	Suspended
0.6439	Remote Similarity	NPD5048	Discontinued
0.6439	Remote Similarity	NPD9697	Approved
0.6438	Remote Similarity	NPD6599	Discontinued
0.6438	Remote Similarity	NPD9494	Approved
0.6438	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD9717	Approved
0.6434	Remote Similarity	NPD9269	Phase 2
0.6434	Remote Similarity	NPD1481	Phase 2
0.6429	Remote Similarity	NPD1894	Discontinued
0.6429	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD1241	Discontinued
0.642	Remote Similarity	NPD7819	Suspended
0.642	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD1048	Approved
0.6415	Remote Similarity	NPD3686	Approved
0.6415	Remote Similarity	NPD3687	Approved
0.6414	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD1203	Approved
0.6414	Remote Similarity	NPD2797	Approved
0.6405	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7978	Discontinued
0.6405	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6841	Approved
0.64	Remote Similarity	NPD6843	Phase 3
0.64	Remote Similarity	NPD6842	Approved
0.6398	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2983	Phase 2
0.6389	Remote Similarity	NPD2982	Phase 2
0.6387	Remote Similarity	NPD3750	Approved
0.638	Remote Similarity	NPD3817	Phase 2
0.6378	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD2629	Approved
0.6377	Remote Similarity	NPD690	Clinical (unspecified phase)
0.637	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6168	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