NPASS Compound

Structure

NPC81042 OpenBabel07101719252D 45 49 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 2.5981 5.5000 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 -0.8660 4.5000 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 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 -1.7321 3.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -2.5981 1.5000 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 1 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 12 1 0 0 0 0 2 6 2 0 0 0 0 2 12 1 0 0 0 0 3 5 2 0 0 0 0 3 13 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 22 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 20 2 0 0 0 0 11 42 1 0 0 0 0 13 28 1 0 0 0 0 14 31 1 0 0 0 0 15 17 2 0 0 0 0 15 32 1 0 0 0 0 16 18 2 0 0 0 0 16 33 1 0 0 0 0 17 34 1 0 0 0 0 18 35 1 0 0 0 0 19 23 2 0 0 0 0 19 36 1 0 0 0 0 20 23 1 0 0 0 0 20 43 1 0 0 0 0 21 11 1 6 0 0 0 21 24 1 0 0 0 0 21 44 1 0 0 0 0 22 37 2 0 0 0 0 22 42 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 24 38 1 1 0 0 0 25 29 1 0 0 0 0 25 39 2 0 0 0 0 26 27 1 0 0 0 0 26 40 1 6 0 0 0 27 30 1 0 0 0 0 27 41 1 1 0 0 0 28 29 2 0 0 0 0 28 43 1 0 0 0 0 29 45 1 0 0 0 0 30 44 1 0 0 0 0 30 45 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	626.13
Volume:	582.233
LogP:	2.188
LogD:	1.179
LogS:	-4.536
# Rotatable Bonds:	8
TPSA:	257.04
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.079
Synthetic Accessibility Score:	4.345
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.437
MDCK Permeability:	9.929758562066127e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.47
Human Intestinal Absorption (HIA):	0.452
20% Bioavailability (F20%):	0.43
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	95.7411880493164%
Volume Distribution (VD):	0.522
Pgp-substrate:	8.0316801071167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.61
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.617
CYP2C9-substrate:	0.391
CYP2D6-inhibitor:	0.165
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	6.302
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.815
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.96
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.903
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC81042

Natural Product ID:	NPC81042
*Common Name:**	Quercetin 3-O-(6''-O-E-Caffeoyl)-Beta-D-Glucopyranoside
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	IHBVMUCQCZEAPW-PFNFWJRHSA-N
Standard InCHI:	InChI=1S/C30H26O15/c31-14-9-19(36)23-20(10-14)43-28(13-3-5-16(33)18(35)8-13)29(25(23)39)45-30-27(41)26(40)24(38)21(44-30)11-42-22(37)6-2-12-1-4-15(32)17(34)7-12/h1-10,21,24,26-27,30-36,38,40-41H,11H2/b6-2+/t21-,24-,26+,27-,30+/m1/s1
SMILES:	O=C(OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451072
PubChem CID:	10031891
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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
NPO6363	Conyza filaginoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374974]
NPO6363	Conyza filaginoides	Species	Asteraceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	14.0	ug.mL-1	PMID[568490]
NPT2645	Organism	Giardia intestinalis	Giardia intestinalis	IC50	=	104.9	ug.mL-1	PMID[568490]

☑ 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 NPC81042 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	446
0.1-0.2	1836
0.2-0.3	4325
0.3-0.4	9460
0.4-0.5	8451
0.5-0.6	4464
0.6-0.7	5404
0.7-0.8	5257
0.8-0.85	1698
0.85-0.9	732
0.9-0.95	451
0.95-1	173

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC214621
1.0	High Similarity	NPC223426
1.0	High Similarity	NPC34267
0.9939	High Similarity	NPC61904
0.9939	High Similarity	NPC144097
0.9878	High Similarity	NPC217520
0.9878	High Similarity	NPC113836
0.9878	High Similarity	NPC35167
0.9878	High Similarity	NPC37668
0.9878	High Similarity	NPC139571
0.9878	High Similarity	NPC253521
0.9758	High Similarity	NPC258044
0.9758	High Similarity	NPC267680
0.9758	High Similarity	NPC293626
0.9758	High Similarity	NPC196127
0.9758	High Similarity	NPC477895
0.9758	High Similarity	NPC217387
0.9701	High Similarity	NPC162394
0.9701	High Similarity	NPC36138
0.9701	High Similarity	NPC297503
0.9701	High Similarity	NPC241781
0.9701	High Similarity	NPC470718
0.9701	High Similarity	NPC97119
0.9701	High Similarity	NPC156785
0.9701	High Similarity	NPC135831
0.9697	High Similarity	NPC296018
0.9697	High Similarity	NPC154741
0.9695	High Similarity	NPC472993
0.9693	High Similarity	NPC20505
0.9693	High Similarity	NPC244776
0.9693	High Similarity	NPC116864
0.9693	High Similarity	NPC235260
0.9693	High Similarity	NPC155763
0.9643	High Similarity	NPC21359
0.9643	High Similarity	NPC275977
0.9643	High Similarity	NPC460984
0.9643	High Similarity	NPC249560
0.9643	High Similarity	NPC25946
0.9643	High Similarity	NPC470720
0.9643	High Similarity	NPC470717
0.9643	High Similarity	NPC470713
0.9643	High Similarity	NPC470416
0.9643	High Similarity	NPC223860
0.9639	High Similarity	NPC476773
0.9636	High Similarity	NPC253685
0.9634	High Similarity	NPC47140
0.9634	High Similarity	NPC67134
0.9634	High Similarity	NPC175107
0.9634	High Similarity	NPC153755
0.9634	High Similarity	NPC190003
0.9632	High Similarity	NPC138927
0.963	High Similarity	NPC179950
0.963	High Similarity	NPC253662
0.963	High Similarity	NPC281131
0.963	High Similarity	NPC88789
0.963	High Similarity	NPC308404
0.963	High Similarity	NPC118284
0.963	High Similarity	NPC274618
0.963	High Similarity	NPC145038
0.963	High Similarity	NPC276222
0.963	High Similarity	NPC56077
0.9586	High Similarity	NPC33083
0.9586	High Similarity	NPC474093
0.9586	High Similarity	NPC104910
0.9586	High Similarity	NPC295625
0.9586	High Similarity	NPC470719
0.9586	High Similarity	NPC473554
0.9578	High Similarity	NPC472991
0.9578	High Similarity	NPC472992
0.9578	High Similarity	NPC89127
0.9578	High Similarity	NPC471669
0.9576	High Similarity	NPC4390
0.9573	High Similarity	NPC29958
0.9573	High Similarity	NPC259896
0.9573	High Similarity	NPC206123
0.9573	High Similarity	NPC136042
0.9573	High Similarity	NPC95866
0.9573	High Similarity	NPC149011
0.9573	High Similarity	NPC255157
0.9573	High Similarity	NPC156869
0.9573	High Similarity	NPC204937
0.9573	High Similarity	NPC67326
0.9573	High Similarity	NPC254855
0.9571	High Similarity	NPC127546
0.9571	High Similarity	NPC173637
0.9571	High Similarity	NPC317489
0.9571	High Similarity	NPC223424
0.9571	High Similarity	NPC84362
0.9571	High Similarity	NPC52550
0.9568	High Similarity	NPC240431
0.9568	High Similarity	NPC55786
0.9568	High Similarity	NPC19388
0.9568	High Similarity	NPC205824
0.9568	High Similarity	NPC277205
0.9568	High Similarity	NPC129264
0.9568	High Similarity	NPC19240
0.9568	High Similarity	NPC85751
0.9529	High Similarity	NPC72554
0.9529	High Similarity	NPC30011
0.9529	High Similarity	NPC475179
0.9529	High Similarity	NPC97817
0.9521	High Similarity	NPC173837
0.9518	High Similarity	NPC101191
0.9518	High Similarity	NPC115760
0.9518	High Similarity	NPC237435
0.9518	High Similarity	NPC43211
0.9518	High Similarity	NPC49344
0.9518	High Similarity	NPC210094
0.9518	High Similarity	NPC135277
0.9515	High Similarity	NPC33054
0.9515	High Similarity	NPC155877
0.9515	High Similarity	NPC471725
0.9515	High Similarity	NPC471748
0.9515	High Similarity	NPC60735
0.9515	High Similarity	NPC134532
0.9515	High Similarity	NPC203259
0.9515	High Similarity	NPC176740
0.9515	High Similarity	NPC26230
0.9512	High Similarity	NPC120099
0.9512	High Similarity	NPC219904
0.9512	High Similarity	NPC225434
0.9512	High Similarity	NPC203050
0.9512	High Similarity	NPC223747
0.9509	High Similarity	NPC197285
0.9509	High Similarity	NPC135599
0.9509	High Similarity	NPC21100
0.9509	High Similarity	NPC328940
0.9509	High Similarity	NPC73855
0.9509	High Similarity	NPC113968
0.9509	High Similarity	NPC277174
0.9506	High Similarity	NPC168822
0.9506	High Similarity	NPC80068
0.9464	High Similarity	NPC471030
0.9461	High Similarity	NPC472385
0.9461	High Similarity	NPC198324
0.9461	High Similarity	NPC473862
0.9458	High Similarity	NPC172033
0.9458	High Similarity	NPC88560
0.9458	High Similarity	NPC175230
0.9455	High Similarity	NPC285197
0.9455	High Similarity	NPC67105
0.9451	High Similarity	NPC92565
0.9451	High Similarity	NPC275454
0.9451	High Similarity	NPC149244
0.9451	High Similarity	NPC325555
0.9451	High Similarity	NPC48640
0.9451	High Similarity	NPC160156
0.9451	High Similarity	NPC265530
0.9451	High Similarity	NPC226304
0.9448	High Similarity	NPC139060
0.9444	High Similarity	NPC77660
0.9444	High Similarity	NPC189142
0.9405	High Similarity	NPC476622
0.9405	High Similarity	NPC476621
0.9405	High Similarity	NPC476623
0.9405	High Similarity	NPC476618
0.9405	High Similarity	NPC476619
0.9405	High Similarity	NPC476620
0.9401	High Similarity	NPC16194
0.9401	High Similarity	NPC476472
0.9401	High Similarity	NPC477848
0.9401	High Similarity	NPC294629
0.9401	High Similarity	NPC294815
0.9401	High Similarity	NPC473327
0.9401	High Similarity	NPC264735
0.9401	High Similarity	NPC19108
0.9401	High Similarity	NPC220173
0.9398	High Similarity	NPC245452
0.9394	High Similarity	NPC227508
0.9394	High Similarity	NPC52382
0.9394	High Similarity	NPC270578
0.939	High Similarity	NPC115674
0.939	High Similarity	NPC67037
0.939	High Similarity	NPC255615
0.939	High Similarity	NPC210073
0.939	High Similarity	NPC8856
0.9387	High Similarity	NPC270335
0.9387	High Similarity	NPC191306
0.9387	High Similarity	NPC19709
0.9383	High Similarity	NPC472994
0.9383	High Similarity	NPC210961
0.9383	High Similarity	NPC477629
0.9383	High Similarity	NPC195685
0.9383	High Similarity	NPC270675
0.9383	High Similarity	NPC470125
0.9383	High Similarity	NPC477628
0.9353	High Similarity	NPC470445
0.9353	High Similarity	NPC470447
0.9353	High Similarity	NPC470446
0.9353	High Similarity	NPC35924
0.9353	High Similarity	NPC470449
0.9353	High Similarity	NPC199172
0.9345	High Similarity	NPC211532
0.9345	High Similarity	NPC233994
0.9345	High Similarity	NPC219043
0.9345	High Similarity	NPC14187
0.9345	High Similarity	NPC268533
0.9345	High Similarity	NPC202908
0.9345	High Similarity	NPC8573
0.9345	High Similarity	NPC122467

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 NPC81042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	958
0.2-0.3	2053
0.3-0.4	2637
0.4-0.5	1791
0.5-0.6	879
0.6-0.7	279
0.7-0.8	115
0.8-0.85	22
0.85-0.9	12
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9518	High Similarity	NPD4338	Clinical (unspecified phase)
0.9515	High Similarity	NPD6797	Phase 2
0.9458	High Similarity	NPD7251	Discontinued
0.9286	High Similarity	NPD7808	Phase 3
0.9277	High Similarity	NPD7054	Approved
0.9222	High Similarity	NPD7472	Approved
0.9107	High Similarity	NPD7074	Phase 3
0.9102	High Similarity	NPD3818	Discontinued
0.9096	High Similarity	NPD6167	Clinical (unspecified phase)
0.9096	High Similarity	NPD6166	Phase 2
0.9096	High Similarity	NPD6168	Clinical (unspecified phase)
0.908	High Similarity	NPD4381	Clinical (unspecified phase)
0.8935	High Similarity	NPD7804	Clinical (unspecified phase)
0.8902	High Similarity	NPD4868	Clinical (unspecified phase)
0.8841	High Similarity	NPD3817	Phase 2
0.883	High Similarity	NPD7993	Clinical (unspecified phase)
0.8623	High Similarity	NPD7075	Discontinued
0.8614	High Similarity	NPD5402	Approved
0.8606	High Similarity	NPD1934	Approved
0.858	High Similarity	NPD1512	Approved
0.8563	High Similarity	NPD3882	Suspended
0.8554	High Similarity	NPD2393	Clinical (unspecified phase)
0.8528	High Similarity	NPD5403	Approved
0.8494	Intermediate Similarity	NPD6801	Discontinued
0.8485	Intermediate Similarity	NPD4380	Phase 2
0.8457	Intermediate Similarity	NPD1511	Approved
0.8457	Intermediate Similarity	NPD6559	Discontinued
0.8443	Intermediate Similarity	NPD2801	Approved
0.8443	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD5401	Approved
0.8344	Intermediate Similarity	NPD6799	Approved
0.8343	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD1653	Approved
0.8229	Intermediate Similarity	NPD3751	Discontinued
0.8214	Intermediate Similarity	NPD7411	Suspended
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8156	Intermediate Similarity	NPD8313	Approved
0.8156	Intermediate Similarity	NPD8312	Approved
0.8103	Intermediate Similarity	NPD3787	Discontinued
0.8084	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6599	Discontinued
0.8037	Intermediate Similarity	NPD1549	Phase 2
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8012	Intermediate Similarity	NPD7819	Suspended
0.8011	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD6190	Approved
0.7975	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7473	Discontinued
0.7965	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7685	Pre-registration
0.7943	Intermediate Similarity	NPD6959	Discontinued
0.7943	Intermediate Similarity	NPD7199	Phase 2
0.7935	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD7228	Approved
0.7906	Intermediate Similarity	NPD7435	Discontinued
0.7886	Intermediate Similarity	NPD5494	Approved
0.7869	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1510	Phase 2
0.7829	Intermediate Similarity	NPD919	Approved
0.7805	Intermediate Similarity	NPD2796	Approved
0.7803	Intermediate Similarity	NPD8455	Phase 2
0.7795	Intermediate Similarity	NPD8151	Discontinued
0.7778	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3749	Approved
0.7758	Intermediate Similarity	NPD7266	Discontinued
0.7749	Intermediate Similarity	NPD6779	Approved
0.7749	Intermediate Similarity	NPD6780	Approved
0.7749	Intermediate Similarity	NPD6782	Approved
0.7749	Intermediate Similarity	NPD6778	Approved
0.7749	Intermediate Similarity	NPD6781	Approved
0.7749	Intermediate Similarity	NPD6777	Approved
0.7749	Intermediate Similarity	NPD6776	Approved
0.7727	Intermediate Similarity	NPD6234	Discontinued
0.7725	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3750	Approved
0.7714	Intermediate Similarity	NPD7768	Phase 2
0.7692	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7874	Approved
0.7644	Intermediate Similarity	NPD37	Approved
0.7614	Intermediate Similarity	NPD4966	Approved
0.7614	Intermediate Similarity	NPD4967	Phase 2
0.7614	Intermediate Similarity	NPD4965	Approved
0.7607	Intermediate Similarity	NPD1613	Approved
0.7607	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7870	Phase 2
0.759	Intermediate Similarity	NPD1551	Phase 2
0.759	Intermediate Similarity	NPD7871	Phase 2
0.7561	Intermediate Similarity	NPD1933	Approved
0.7561	Intermediate Similarity	NPD230	Phase 1
0.756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3926	Phase 2
0.7542	Intermediate Similarity	NPD1247	Approved
0.7538	Intermediate Similarity	NPD7696	Phase 3
0.7538	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7698	Approved
0.7538	Intermediate Similarity	NPD7697	Approved
0.7538	Intermediate Similarity	NPD7783	Phase 2
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7513	Intermediate Similarity	NPD7584	Approved
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD8319	Approved
0.75	Intermediate Similarity	NPD8320	Phase 1
0.7487	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD6535	Approved
0.7475	Intermediate Similarity	NPD7701	Phase 2
0.7459	Intermediate Similarity	NPD7240	Approved
0.7447	Intermediate Similarity	NPD8150	Discontinued
0.7442	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3748	Approved
0.741	Intermediate Similarity	NPD1607	Approved
0.7381	Intermediate Similarity	NPD2935	Discontinued
0.7379	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6798	Discontinued
0.7378	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7700	Phase 2
0.7371	Intermediate Similarity	NPD7699	Phase 2
0.7371	Intermediate Similarity	NPD7458	Discontinued
0.7363	Intermediate Similarity	NPD7801	Approved
0.7362	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD6233	Phase 2
0.7322	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6823	Phase 2
0.7301	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7585	Approved
0.7273	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7257	Intermediate Similarity	NPD920	Approved
0.725	Intermediate Similarity	NPD7583	Approved
0.7241	Intermediate Similarity	NPD2532	Approved
0.7241	Intermediate Similarity	NPD2533	Approved
0.7241	Intermediate Similarity	NPD2534	Approved
0.7241	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5953	Discontinued
0.7212	Intermediate Similarity	NPD3027	Phase 3
0.7186	Intermediate Similarity	NPD7680	Approved
0.7178	Intermediate Similarity	NPD1203	Approved
0.7169	Intermediate Similarity	NPD2313	Discontinued
0.7157	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7151	Intermediate Similarity	NPD1243	Approved
0.7143	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7033	Discontinued
0.7112	Intermediate Similarity	NPD7286	Phase 2
0.7086	Intermediate Similarity	NPD7390	Discontinued
0.7077	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6212	Phase 3
0.7077	Intermediate Similarity	NPD6213	Phase 3
0.7053	Intermediate Similarity	NPD7549	Discontinued
0.7052	Intermediate Similarity	NPD1652	Phase 2
0.7048	Intermediate Similarity	NPD4908	Phase 1
0.7041	Intermediate Similarity	NPD6355	Discontinued
0.7041	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1091	Approved
0.7035	Intermediate Similarity	NPD2346	Discontinued
0.7035	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2799	Discontinued
0.7011	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7039	Approved
0.7	Intermediate Similarity	NPD7038	Approved
0.6994	Remote Similarity	NPD9269	Phase 2
0.6978	Remote Similarity	NPD5353	Approved
0.6973	Remote Similarity	NPD8127	Discontinued
0.6964	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6844	Discontinued
0.6954	Remote Similarity	NPD6674	Discontinued
0.6954	Remote Similarity	NPD4363	Phase 3
0.6954	Remote Similarity	NPD2800	Approved
0.6954	Remote Similarity	NPD4360	Phase 2
0.6946	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5124	Phase 1
0.6941	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2344	Approved
0.6933	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2798	Approved
0.6923	Remote Similarity	NPD4287	Approved
0.6909	Remote Similarity	NPD3225	Approved
0.6898	Remote Similarity	NPD5242	Approved
0.689	Remote Similarity	NPD9717	Approved
0.6886	Remote Similarity	NPD9494	Approved
0.6885	Remote Similarity	NPD4288	Approved
0.6882	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD5406	Approved
0.6879	Remote Similarity	NPD5404	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6879	Remote Similarity	NPD5405	Approved
0.6879	Remote Similarity	NPD5408	Approved

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