NPASS Compound

Structure

NPC88560 OpenBabel07101718292D 45 48 0 0 1 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 8 1 0 0 0 0 2 18 2 0 0 0 0 3 9 2 0 0 0 0 3 18 1 0 0 0 0 4 10 1 0 0 0 0 4 19 2 0 0 0 0 5 11 2 0 0 0 0 5 19 1 0 0 0 0 6 13 2 0 0 0 0 6 18 1 0 0 0 0 7 15 2 0 0 0 0 7 19 1 0 0 0 0 8 20 2 0 0 0 0 9 20 1 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 16 42 1 0 0 0 0 17 33 2 0 0 0 0 17 42 1 0 0 0 0 20 34 1 0 0 0 0 21 35 1 0 0 0 0 22 23 1 0 0 0 0 22 27 2 0 0 0 0 23 36 2 0 0 0 0 24 28 2 0 0 0 0 24 43 1 0 0 0 0 25 16 1 1 0 0 0 25 29 1 0 0 0 0 25 44 1 0 0 0 0 26 37 2 0 0 0 0 26 45 1 0 0 0 0 27 28 1 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 29 30 1 0 0 0 0 29 40 1 6 0 0 0 30 31 1 0 0 0 0 30 41 1 1 0 0 0 31 32 1 0 0 0 0 31 45 1 6 0 0 0 32 43 1 1 0 0 0 32 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	622.17
Volume:	605.165
LogP:	3.116
LogD:	2.113
LogS:	-3.521
# Rotatable Bonds:	12
TPSA:	209.51
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.083
Synthetic Accessibility Score:	4.22
Fsp3:	0.219
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.2
MDCK Permeability:	1.9838320440612733e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.538
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	101.61698150634766%
Volume Distribution (VD):	0.48
Pgp-substrate:	0.7412636876106262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.337
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.346
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.716
CYP2C9-substrate:	0.7
CYP2D6-inhibitor:	0.763
CYP2D6-substrate:	0.227
CYP3A4-inhibitor:	0.621
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	5.086
Half-life (T1/2):	0.952

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.779
AMES Toxicity:	0.754
Rat Oral Acute Toxicity:	0.302
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.961
Carcinogencity:	0.347
Eye Corrosion:	0.003
Eye Irritation:	0.532
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC88560

Natural Product ID:	NPC88560
*Common Name:**	4'-O-Beta-D-(2''-P-Coumaroyl-6''-Acetyl)Glucopyranosyl-4,2',3'-Trihydroxychalcone
IUPAC Name:	[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-2-[2,3-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy]-4,5-dihydroxyoxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	MNTAKHYEMJWPAC-SHVUDZGFSA-N
Standard InCHI:	InChI=1S/C32H30O13/c1-17(33)42-16-25-29(40)30(41)31(45-26(37)15-7-19-4-10-21(35)11-5-19)32(44-25)43-24-14-12-22(27(38)28(24)39)23(36)13-6-18-2-8-20(34)9-3-18/h2-15,25,29-32,34-35,38-41H,16H2,1H3/b13-6+,15-7+/t25-,29-,30+,31-,32-/m1/s1
SMILES:	CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2ccc(C(=O)/C=C/c3ccc(cc3)O)c(c2O)O)O1)OC(=O)/C=C/c1ccc(cc1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458446
PubChem CID:	10908299
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

*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
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087602]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.71	mM	PMID[552586]

☑ 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 NPC88560 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	380
0.1-0.2	1663
0.2-0.3	3929
0.3-0.4	8551
0.4-0.5	9291
0.5-0.6	4334
0.6-0.7	4942
0.7-0.8	5710
0.8-0.85	2335
0.85-0.9	1071
0.9-0.95	463
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC172033
1.0	High Similarity	NPC175230
0.9876	High Similarity	NPC204937
0.9876	High Similarity	NPC149011
0.9755	High Similarity	NPC472993
0.9752	High Similarity	NPC116745
0.9639	High Similarity	NPC471030
0.9636	High Similarity	NPC472991
0.9636	High Similarity	NPC472992
0.9583	High Similarity	NPC470416
0.9578	High Similarity	NPC476623
0.9578	High Similarity	NPC477895
0.9578	High Similarity	NPC476621
0.9578	High Similarity	NPC217520
0.9578	High Similarity	NPC476620
0.9578	High Similarity	NPC472387
0.9578	High Similarity	NPC139571
0.9578	High Similarity	NPC476618
0.9578	High Similarity	NPC35167
0.9578	High Similarity	NPC476619
0.9578	High Similarity	NPC476622
0.9573	High Similarity	NPC172807
0.9573	High Similarity	NPC211594
0.9573	High Similarity	NPC67134
0.9573	High Similarity	NPC47140
0.9573	High Similarity	NPC254540
0.9571	High Similarity	NPC229687
0.9565	High Similarity	NPC88043
0.9524	High Similarity	NPC199172
0.9524	High Similarity	NPC36138
0.9524	High Similarity	NPC35924
0.9518	High Similarity	NPC144097
0.9518	High Similarity	NPC61904
0.9515	High Similarity	NPC4390
0.9509	High Similarity	NPC229729
0.9509	High Similarity	NPC45400
0.9506	High Similarity	NPC22832
0.9506	High Similarity	NPC311830
0.9506	High Similarity	NPC165720
0.9503	High Similarity	NPC33298
0.9503	High Similarity	NPC285108
0.9467	High Similarity	NPC470717
0.9467	High Similarity	NPC25946
0.9467	High Similarity	NPC460984
0.9467	High Similarity	NPC470720
0.9467	High Similarity	NPC470713
0.9467	High Similarity	NPC21359
0.9461	High Similarity	NPC293626
0.9461	High Similarity	NPC253521
0.9461	High Similarity	NPC267680
0.9461	High Similarity	NPC267549
0.9461	High Similarity	NPC217387
0.9461	High Similarity	NPC37668
0.9461	High Similarity	NPC196127
0.9461	High Similarity	NPC113836
0.9461	High Similarity	NPC258044
0.9458	High Similarity	NPC223426
0.9458	High Similarity	NPC81042
0.9458	High Similarity	NPC214621
0.9458	High Similarity	NPC34267
0.9458	High Similarity	NPC477848
0.9455	High Similarity	NPC307518
0.9455	High Similarity	NPC190003
0.9455	High Similarity	NPC175107
0.9455	High Similarity	NPC153755
0.9455	High Similarity	NPC48773
0.9455	High Similarity	NPC472386
0.9455	High Similarity	NPC205076
0.9451	High Similarity	NPC186807
0.9451	High Similarity	NPC105025
0.9451	High Similarity	NPC45638
0.9451	High Similarity	NPC469931
0.9451	High Similarity	NPC93337
0.9451	High Similarity	NPC201292
0.9451	High Similarity	NPC226294
0.9451	High Similarity	NPC58053
0.9451	High Similarity	NPC475942
0.9448	High Similarity	NPC236934
0.9448	High Similarity	NPC5778
0.9444	High Similarity	NPC191306
0.9444	High Similarity	NPC270335
0.9444	High Similarity	NPC222936
0.9444	High Similarity	NPC309025
0.9444	High Similarity	NPC88023
0.9444	High Similarity	NPC243930
0.9444	High Similarity	NPC284960
0.9444	High Similarity	NPC168822
0.9444	High Similarity	NPC19709
0.9412	High Similarity	NPC104910
0.9412	High Similarity	NPC473554
0.9412	High Similarity	NPC474093
0.9412	High Similarity	NPC295625
0.9412	High Similarity	NPC470719
0.9408	High Similarity	NPC135831
0.9408	High Similarity	NPC241781
0.9408	High Similarity	NPC297503
0.9408	High Similarity	NPC162394
0.9408	High Similarity	NPC156785
0.9408	High Similarity	NPC97119
0.9408	High Similarity	NPC470718
0.9401	High Similarity	NPC79736
0.9401	High Similarity	NPC67629
0.9401	High Similarity	NPC472385
0.9401	High Similarity	NPC198324
0.9401	High Similarity	NPC154741
0.9401	High Similarity	NPC296018
0.9401	High Similarity	NPC233994
0.9401	High Similarity	NPC211532
0.9394	High Similarity	NPC231194
0.9394	High Similarity	NPC244776
0.9394	High Similarity	NPC34287
0.9394	High Similarity	NPC105511
0.9394	High Similarity	NPC224462
0.9394	High Similarity	NPC44558
0.9394	High Similarity	NPC155763
0.9394	High Similarity	NPC474434
0.9394	High Similarity	NPC471416
0.9394	High Similarity	NPC212748
0.9394	High Similarity	NPC22195
0.9394	High Similarity	NPC206123
0.9394	High Similarity	NPC20505
0.9394	High Similarity	NPC116864
0.9394	High Similarity	NPC51326
0.9394	High Similarity	NPC235260
0.9394	High Similarity	NPC183357
0.9394	High Similarity	NPC21190
0.939	High Similarity	NPC45618
0.939	High Similarity	NPC58716
0.939	High Similarity	NPC146792
0.9383	High Similarity	NPC473043
0.9383	High Similarity	NPC300537
0.9383	High Similarity	NPC77660
0.9383	High Similarity	NPC189142
0.9383	High Similarity	NPC127782
0.9379	High Similarity	NPC203020
0.9379	High Similarity	NPC239966
0.9379	High Similarity	NPC289346
0.9357	High Similarity	NPC475179
0.9353	High Similarity	NPC223860
0.9353	High Similarity	NPC275977
0.9353	High Similarity	NPC249560
0.9353	High Similarity	NPC231254
0.9349	High Similarity	NPC469371
0.9345	High Similarity	NPC120952
0.9345	High Similarity	NPC476773
0.9341	High Similarity	NPC237435
0.9341	High Similarity	NPC115760
0.9341	High Similarity	NPC101191
0.9341	High Similarity	NPC135277
0.9341	High Similarity	NPC210094
0.9341	High Similarity	NPC49344
0.9341	High Similarity	NPC264735
0.9341	High Similarity	NPC43211
0.9337	High Similarity	NPC117260
0.9337	High Similarity	NPC235575
0.9337	High Similarity	NPC476405
0.9333	High Similarity	NPC658
0.9333	High Similarity	NPC219904
0.9333	High Similarity	NPC138927
0.9333	High Similarity	NPC183036
0.9333	High Similarity	NPC472381
0.9333	High Similarity	NPC170675
0.9333	High Similarity	NPC209296
0.9333	High Similarity	NPC197708
0.9333	High Similarity	NPC472383
0.9333	High Similarity	NPC195257
0.9333	High Similarity	NPC120099
0.9333	High Similarity	NPC95855
0.9333	High Similarity	NPC225434
0.9333	High Similarity	NPC223747
0.9333	High Similarity	NPC210042
0.9333	High Similarity	NPC203050
0.9333	High Similarity	NPC112755
0.9333	High Similarity	NPC471457
0.9329	High Similarity	NPC115674
0.9329	High Similarity	NPC210073
0.9329	High Similarity	NPC21100
0.9329	High Similarity	NPC197285
0.9325	High Similarity	NPC29830
0.9321	High Similarity	NPC182045
0.9317	High Similarity	NPC160780
0.9317	High Similarity	NPC289811
0.9298	High Similarity	NPC33083
0.9286	High Similarity	NPC472384
0.9286	High Similarity	NPC472380
0.9286	High Similarity	NPC472382
0.9286	High Similarity	NPC268533
0.9281	High Similarity	NPC476374
0.9281	High Similarity	NPC21666
0.9281	High Similarity	NPC236191
0.9281	High Similarity	NPC169977
0.9281	High Similarity	NPC204693
0.9281	High Similarity	NPC45522
0.9281	High Similarity	NPC42773
0.9281	High Similarity	NPC51774
0.9281	High Similarity	NPC24043
0.9281	High Similarity	NPC101026
0.9281	High Similarity	NPC239549
0.9277	High Similarity	NPC72249
0.9277	High Similarity	NPC476365

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 NPC88560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	914
0.2-0.3	1922
0.3-0.4	2604
0.4-0.5	1850
0.5-0.6	944
0.6-0.7	375
0.7-0.8	144
0.8-0.85	34
0.85-0.9	14
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9341	High Similarity	NPD4338	Clinical (unspecified phase)
0.9333	High Similarity	NPD7054	Approved
0.9277	High Similarity	NPD7472	Approved
0.9277	High Similarity	NPD7074	Phase 3
0.9273	High Similarity	NPD3818	Discontinued
0.9112	High Similarity	NPD7808	Phase 3
0.9107	High Similarity	NPD6797	Phase 2
0.9074	High Similarity	NPD4868	Clinical (unspecified phase)
0.9053	High Similarity	NPD7251	Discontinued
0.9036	High Similarity	NPD6167	Clinical (unspecified phase)
0.9036	High Similarity	NPD6168	Clinical (unspecified phase)
0.9036	High Similarity	NPD6166	Phase 2
0.9018	High Similarity	NPD4381	Clinical (unspecified phase)
0.8889	High Similarity	NPD1934	Approved
0.8772	High Similarity	NPD7993	Clinical (unspecified phase)
0.872	High Similarity	NPD2801	Approved
0.872	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD3817	Phase 2
0.8655	High Similarity	NPD7804	Clinical (unspecified phase)
0.8614	High Similarity	NPD3882	Suspended
0.8613	High Similarity	NPD6559	Discontinued
0.8452	Intermediate Similarity	NPD7075	Discontinued
0.8439	Intermediate Similarity	NPD5844	Phase 1
0.8424	Intermediate Similarity	NPD4380	Phase 2
0.8395	Intermediate Similarity	NPD1511	Approved
0.8373	Intermediate Similarity	NPD7411	Suspended
0.8363	Intermediate Similarity	NPD6232	Discontinued
0.8354	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5402	Approved
0.8324	Intermediate Similarity	NPD7473	Discontinued
0.8305	Intermediate Similarity	NPD8313	Approved
0.8305	Intermediate Similarity	NPD8312	Approved
0.8303	Intermediate Similarity	NPD1653	Approved
0.8295	Intermediate Similarity	NPD7685	Pre-registration
0.8293	Intermediate Similarity	NPD1512	Approved
0.8287	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7819	Suspended
0.8274	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD1465	Phase 2
0.8246	Intermediate Similarity	NPD5494	Approved
0.8225	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6801	Discontinued
0.8198	Intermediate Similarity	NPD7199	Phase 2
0.8171	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD7228	Approved
0.8161	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5403	Approved
0.8111	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD1549	Phase 2
0.8081	Intermediate Similarity	NPD6234	Discontinued
0.8025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD8151	Discontinued
0.8012	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD37	Approved
0.7989	Intermediate Similarity	NPD6959	Discontinued
0.7966	Intermediate Similarity	NPD3751	Discontinued
0.7965	Intermediate Similarity	NPD4966	Approved
0.7965	Intermediate Similarity	NPD4967	Phase 2
0.7965	Intermediate Similarity	NPD7768	Phase 2
0.7965	Intermediate Similarity	NPD4965	Approved
0.7952	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3749	Approved
0.7914	Intermediate Similarity	NPD7266	Discontinued
0.7904	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6599	Discontinued
0.7879	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2796	Approved
0.7849	Intermediate Similarity	NPD8455	Phase 2
0.7841	Intermediate Similarity	NPD3787	Discontinued
0.7831	Intermediate Similarity	NPD6190	Approved
0.7826	Intermediate Similarity	NPD1933	Approved
0.7826	Intermediate Similarity	NPD230	Phase 1
0.7791	Intermediate Similarity	NPD1510	Phase 2
0.776	Intermediate Similarity	NPD7435	Discontinued
0.7755	Intermediate Similarity	NPD7783	Phase 2
0.7755	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD447	Suspended
0.7711	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3926	Phase 2
0.7696	Intermediate Similarity	NPD6779	Approved
0.7696	Intermediate Similarity	NPD6778	Approved
0.7696	Intermediate Similarity	NPD6776	Approved
0.7696	Intermediate Similarity	NPD6777	Approved
0.7696	Intermediate Similarity	NPD6780	Approved
0.7696	Intermediate Similarity	NPD6782	Approved
0.7696	Intermediate Similarity	NPD6781	Approved
0.7692	Intermediate Similarity	NPD7240	Approved
0.767	Intermediate Similarity	NPD919	Approved
0.7665	Intermediate Similarity	NPD3750	Approved
0.7665	Intermediate Similarity	NPD4628	Phase 3
0.7654	Intermediate Similarity	NPD1240	Approved
0.7654	Intermediate Similarity	NPD943	Approved
0.7654	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1613	Approved
0.7651	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1551	Phase 2
0.7632	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7871	Phase 2
0.7629	Intermediate Similarity	NPD7870	Phase 2
0.7614	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7874	Approved
0.7577	Intermediate Similarity	NPD7697	Approved
0.7577	Intermediate Similarity	NPD7698	Approved
0.7577	Intermediate Similarity	NPD7696	Phase 3
0.7561	Intermediate Similarity	NPD1607	Approved
0.7551	Intermediate Similarity	NPD7584	Approved
0.7531	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2935	Discontinued
0.7514	Intermediate Similarity	NPD3226	Approved
0.7513	Intermediate Similarity	NPD7701	Phase 2
0.7487	Intermediate Similarity	NPD7680	Approved
0.7487	Intermediate Similarity	NPD8150	Discontinued
0.7486	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7469	Intermediate Similarity	NPD3027	Phase 3
0.7449	Intermediate Similarity	NPD8320	Phase 1
0.7449	Intermediate Similarity	NPD8319	Approved
0.7446	Intermediate Similarity	NPD5953	Discontinued
0.7436	Intermediate Similarity	NPD6823	Phase 2
0.7435	Intermediate Similarity	NPD6534	Approved
0.7435	Intermediate Similarity	NPD6535	Approved
0.7414	Intermediate Similarity	NPD7458	Discontinued
0.7409	Intermediate Similarity	NPD7699	Phase 2
0.7409	Intermediate Similarity	NPD7700	Phase 2
0.7407	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7801	Approved
0.7399	Intermediate Similarity	NPD920	Approved
0.7394	Intermediate Similarity	NPD8434	Phase 2
0.7371	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3748	Approved
0.7346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7585	Approved
0.7337	Intermediate Similarity	NPD7286	Phase 2
0.7333	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5353	Approved
0.7301	Intermediate Similarity	NPD6832	Phase 2
0.7293	Intermediate Similarity	NPD8127	Discontinued
0.7286	Intermediate Similarity	NPD7583	Approved
0.7283	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2346	Discontinued
0.7262	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2799	Discontinued
0.7239	Intermediate Similarity	NPD9494	Approved
0.7222	Intermediate Similarity	NPD1203	Approved
0.7219	Intermediate Similarity	NPD7038	Approved
0.7219	Intermediate Similarity	NPD7039	Approved
0.7213	Intermediate Similarity	NPD5242	Approved
0.7212	Intermediate Similarity	NPD6798	Discontinued
0.7212	Intermediate Similarity	NPD2313	Discontinued
0.7202	Intermediate Similarity	NPD6212	Phase 3
0.7202	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6213	Phase 3
0.7195	Intermediate Similarity	NPD4908	Phase 1
0.7193	Intermediate Similarity	NPD1243	Approved
0.7193	Intermediate Similarity	NPD2800	Approved
0.7193	Intermediate Similarity	NPD6674	Discontinued
0.7186	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2344	Approved
0.7174	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6233	Phase 2
0.7168	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7033	Discontinued
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7126	Intermediate Similarity	NPD7390	Discontinued
0.7108	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6844	Discontinued
0.7095	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1652	Phase 2
0.709	Intermediate Similarity	NPD7549	Discontinued
0.7086	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD5005	Approved
0.7085	Intermediate Similarity	NPD5006	Approved
0.7081	Intermediate Similarity	NPD1091	Approved
0.7065	Intermediate Similarity	NPD5710	Approved
0.7065	Intermediate Similarity	NPD7229	Phase 3
0.7065	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4287	Approved
0.7039	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7930	Approved
0.7037	Intermediate Similarity	NPD9717	Approved
0.7018	Intermediate Similarity	NPD6099	Approved
0.7018	Intermediate Similarity	NPD6100	Approved
0.7011	Intermediate Similarity	NPD2309	Approved
0.7	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7097	Phase 1

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