NPASS Compound

Structure

CID144097 OpenBabel06191715502D 42 46 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 -4.3301 1.5000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 3.4641 3.0000 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 -1.7321 5.0000 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 -5.1962 2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 1 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 1 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 0.0000 2.0000 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 -3.4641 0.0000 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 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 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 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 -6.9282 2.0000 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 -3.4641 -1.0000 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 3.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 9 1 0 0 0 0 2 12 1 0 0 0 0 3 9 2 0 0 0 0 3 13 1 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 10 1 0 0 0 0 5 16 2 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 18 2 0 0 0 0 8 17 1 0 0 0 0 8 39 1 0 0 0 0 9 23 1 0 0 0 0 10 26 1 0 0 0 0 11 28 1 0 0 0 0 12 13 2 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 19 2 0 0 0 0 14 31 1 0 0 0 0 15 20 2 0 0 0 0 15 32 1 0 0 0 0 16 20 1 0 0 0 0 16 33 1 0 0 0 0 17 21 1 0 0 0 0 17 34 1 6 0 0 0 18 19 1 0 0 0 0 18 40 1 0 0 0 0 19 22 1 0 0 0 0 20 35 1 0 0 0 0 21 25 1 0 0 0 0 21 36 1 6 0 0 0 22 24 1 0 0 0 0 22 37 2 0 0 0 0 23 24 2 0 0 0 0 23 40 1 0 0 0 0 24 42 1 0 0 0 0 25 27 1 0 0 0 0 25 41 1 1 0 0 0 26 38 2 0 0 0 0 26 41 1 0 0 0 0 27 39 1 0 0 0 0 27 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.1
Volume:	532.982
LogP:	1.7
LogD:	0.716
LogS:	-4.829
# Rotatable Bonds:	6
TPSA:	257.04
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.117
Synthetic Accessibility Score:	4.269
Fsp3:	0.185
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:	-6.355
MDCK Permeability:	8.525584235030692e-06
Pgp-inhibitor:	0.05
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.7
20% Bioavailability (F20%):	0.241
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	88.48787689208984%
Volume Distribution (VD):	0.646
Pgp-substrate:	17.01404571533203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.587
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.03
CYP2C9-inhibitor:	0.492
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	8.163
Half-life (T1/2):	0.956

ADMET: Toxicity

hERG Blockers:	0.165
Human Hepatotoxicity (H-HT):	0.161
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.526
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.946
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.915
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC144097

Natural Product ID:	NPC144097
*Common Name:**	Quercetin -3-O-(2''-Galloyl)-Alpha-L-Arabinopyranoside
IUPAC Name:	[(2S,3R,4S,5S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxyoxan-3-yl] 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	XLHGECRFSYAHQI-LEYCRWIUSA-N
Standard InCHI:	InChI=1S/C27H22O15/c28-11-6-14(31)19-18(7-11)40-23(9-1-2-12(29)13(30)3-9)24(22(19)37)42-27-25(21(36)17(34)8-39-27)41-26(38)10-4-15(32)20(35)16(33)5-10/h1-7,17,21,25,27-36H,8H2/t17-,21-,25+,27-/m0/s1
SMILES:	Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1OC[C@@H]([C@@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)O)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501837
PubChem CID:	9985767
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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
NPO12148.2	Acer pictum subsp. okamotoanum	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461665]
NPO19095	Strophanthus preussii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19095	Strophanthus preussii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17247	Actinoplanes friuliensis	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19521	Inella verrucosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18680	Larix decidua	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19095	Strophanthus preussii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2359	Cynoglossum germanicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12148.2	Acer pictum subsp. okamotoanum	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13823	Hypericum mysorense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18537	Leontopodium nanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18775	Cratena peregrina	Species	Facelinidae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	18.1	ug.mL-1	PMID[512689]

☑ 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 NPC144097 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	447
0.1-0.2	1939
0.2-0.3	4513
0.3-0.4	9714
0.4-0.5	8099
0.5-0.6	4405
0.6-0.7	5466
0.7-0.8	5151
0.8-0.85	1605
0.85-0.9	784
0.9-0.95	420
0.95-1	154

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC61904
0.9939	High Similarity	NPC34267
0.9939	High Similarity	NPC253521
0.9939	High Similarity	NPC35167
0.9939	High Similarity	NPC37668
0.9939	High Similarity	NPC223426
0.9939	High Similarity	NPC81042
0.9939	High Similarity	NPC113836
0.9939	High Similarity	NPC214621
0.9818	High Similarity	NPC196127
0.9818	High Similarity	NPC217387
0.9818	High Similarity	NPC267680
0.9818	High Similarity	NPC293626
0.9818	High Similarity	NPC258044
0.9818	High Similarity	NPC217520
0.9818	High Similarity	NPC139571
0.976	High Similarity	NPC135831
0.976	High Similarity	NPC297503
0.976	High Similarity	NPC36138
0.976	High Similarity	NPC97119
0.9758	High Similarity	NPC154741
0.9758	High Similarity	NPC296018
0.9755	High Similarity	NPC235260
0.9755	High Similarity	NPC20505
0.9755	High Similarity	NPC155763
0.9702	High Similarity	NPC470416
0.9699	High Similarity	NPC476773
0.9699	High Similarity	NPC477895
0.9697	High Similarity	NPC253685
0.9695	High Similarity	NPC175107
0.9695	High Similarity	NPC190003
0.9693	High Similarity	NPC138927
0.9643	High Similarity	NPC162394
0.9643	High Similarity	NPC241781
0.9643	High Similarity	NPC470718
0.9643	High Similarity	NPC156785
0.9639	High Similarity	NPC472991
0.9639	High Similarity	NPC472992
0.9636	High Similarity	NPC4390
0.9636	High Similarity	NPC472993
0.9634	High Similarity	NPC204937
0.9634	High Similarity	NPC244776
0.9634	High Similarity	NPC116864
0.9634	High Similarity	NPC149011
0.9586	High Similarity	NPC223860
0.9586	High Similarity	NPC470717
0.9586	High Similarity	NPC460984
0.9586	High Similarity	NPC249560
0.9586	High Similarity	NPC470713
0.9586	High Similarity	NPC25946
0.9586	High Similarity	NPC470720
0.9586	High Similarity	NPC275977
0.9586	High Similarity	NPC21359
0.9578	High Similarity	NPC115760
0.9578	High Similarity	NPC237435
0.9578	High Similarity	NPC43211
0.9578	High Similarity	NPC49344
0.9578	High Similarity	NPC135277
0.9578	High Similarity	NPC210094
0.9578	High Similarity	NPC101191
0.9576	High Similarity	NPC67134
0.9576	High Similarity	NPC47140
0.9576	High Similarity	NPC153755
0.9571	High Similarity	NPC308404
0.9571	High Similarity	NPC179950
0.9571	High Similarity	NPC274618
0.9571	High Similarity	NPC145038
0.9571	High Similarity	NPC118284
0.9571	High Similarity	NPC281131
0.9571	High Similarity	NPC56077
0.9571	High Similarity	NPC276222
0.9571	High Similarity	NPC88789
0.9571	High Similarity	NPC253662
0.9529	High Similarity	NPC33083
0.9529	High Similarity	NPC474093
0.9529	High Similarity	NPC473554
0.9529	High Similarity	NPC470719
0.9529	High Similarity	NPC295625
0.9529	High Similarity	NPC104910
0.9521	High Similarity	NPC472385
0.9521	High Similarity	NPC471669
0.9521	High Similarity	NPC89127
0.9521	High Similarity	NPC198324
0.9518	High Similarity	NPC172033
0.9518	High Similarity	NPC175230
0.9518	High Similarity	NPC88560
0.9515	High Similarity	NPC29958
0.9515	High Similarity	NPC259896
0.9515	High Similarity	NPC156869
0.9515	High Similarity	NPC136042
0.9515	High Similarity	NPC255157
0.9515	High Similarity	NPC95866
0.9515	High Similarity	NPC206123
0.9515	High Similarity	NPC67326
0.9515	High Similarity	NPC254855
0.9512	High Similarity	NPC127546
0.9512	High Similarity	NPC84362
0.9512	High Similarity	NPC223424
0.9512	High Similarity	NPC52550
0.9512	High Similarity	NPC173637
0.9512	High Similarity	NPC317489
0.9509	High Similarity	NPC277205
0.9509	High Similarity	NPC55786
0.9509	High Similarity	NPC19388
0.9509	High Similarity	NPC205824
0.9509	High Similarity	NPC85751
0.9509	High Similarity	NPC19240
0.9509	High Similarity	NPC129264
0.9509	High Similarity	NPC240431
0.9474	High Similarity	NPC30011
0.9474	High Similarity	NPC97817
0.9474	High Similarity	NPC475179
0.9474	High Similarity	NPC72554
0.9464	High Similarity	NPC476622
0.9464	High Similarity	NPC476619
0.9464	High Similarity	NPC476621
0.9464	High Similarity	NPC476623
0.9464	High Similarity	NPC476618
0.9464	High Similarity	NPC173837
0.9464	High Similarity	NPC476620
0.9461	High Similarity	NPC264735
0.9461	High Similarity	NPC477848
0.9458	High Similarity	NPC471725
0.9458	High Similarity	NPC26230
0.9458	High Similarity	NPC155877
0.9458	High Similarity	NPC134532
0.9458	High Similarity	NPC60735
0.9458	High Similarity	NPC203259
0.9458	High Similarity	NPC33054
0.9458	High Similarity	NPC471748
0.9458	High Similarity	NPC176740
0.9455	High Similarity	NPC223747
0.9455	High Similarity	NPC120099
0.9455	High Similarity	NPC225434
0.9455	High Similarity	NPC203050
0.9455	High Similarity	NPC219904
0.9451	High Similarity	NPC197285
0.9451	High Similarity	NPC113968
0.9451	High Similarity	NPC277174
0.9451	High Similarity	NPC328940
0.9451	High Similarity	NPC73855
0.9451	High Similarity	NPC135599
0.9451	High Similarity	NPC21100
0.9448	High Similarity	NPC80068
0.9448	High Similarity	NPC168822
0.9412	High Similarity	NPC470446
0.9412	High Similarity	NPC470445
0.9412	High Similarity	NPC470449
0.9412	High Similarity	NPC470447
0.9408	High Similarity	NPC471030
0.9405	High Similarity	NPC65563
0.9405	High Similarity	NPC470949
0.9405	High Similarity	NPC8573
0.9405	High Similarity	NPC473862
0.9405	High Similarity	NPC268533
0.9405	High Similarity	NPC233994
0.9405	High Similarity	NPC211532
0.9401	High Similarity	NPC21666
0.9401	High Similarity	NPC169977
0.9401	High Similarity	NPC101026
0.9401	High Similarity	NPC42773
0.9401	High Similarity	NPC45522
0.9401	High Similarity	NPC24043
0.9398	High Similarity	NPC285197
0.9398	High Similarity	NPC245014
0.9398	High Similarity	NPC72249
0.9398	High Similarity	NPC67105
0.9398	High Similarity	NPC84265
0.9398	High Similarity	NPC282987
0.9394	High Similarity	NPC48640
0.9394	High Similarity	NPC265530
0.9394	High Similarity	NPC92565
0.9394	High Similarity	NPC226304
0.9394	High Similarity	NPC275454
0.9394	High Similarity	NPC149244
0.9394	High Similarity	NPC160156
0.9394	High Similarity	NPC116745
0.9394	High Similarity	NPC325555
0.939	High Similarity	NPC139060
0.9387	High Similarity	NPC77660
0.9387	High Similarity	NPC189142
0.9357	High Similarity	NPC470451
0.9357	High Similarity	NPC470455
0.9353	High Similarity	NPC222674
0.9349	High Similarity	NPC472387
0.9345	High Similarity	NPC294815
0.9345	High Similarity	NPC473327
0.9345	High Similarity	NPC16194
0.9345	High Similarity	NPC220173
0.9345	High Similarity	NPC476472
0.9345	High Similarity	NPC19108
0.9345	High Similarity	NPC294629
0.9341	High Similarity	NPC211594
0.9341	High Similarity	NPC476405
0.9341	High Similarity	NPC117260
0.9341	High Similarity	NPC172807
0.9341	High Similarity	NPC245452
0.9341	High Similarity	NPC254540
0.9337	High Similarity	NPC227508
0.9337	High Similarity	NPC52382

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 NPC144097 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	961
0.2-0.3	2086
0.3-0.4	2652
0.4-0.5	1770
0.5-0.6	852
0.6-0.7	263
0.7-0.8	115
0.8-0.85	20
0.85-0.9	13
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9578	High Similarity	NPD4338	Clinical (unspecified phase)
0.9458	High Similarity	NPD6797	Phase 2
0.9401	High Similarity	NPD7251	Discontinued
0.9231	High Similarity	NPD7808	Phase 3
0.9222	High Similarity	NPD7054	Approved
0.9167	High Similarity	NPD7472	Approved
0.9162	High Similarity	NPD3818	Discontinued
0.9053	High Similarity	NPD7074	Phase 3
0.9042	High Similarity	NPD6168	Clinical (unspecified phase)
0.9042	High Similarity	NPD6167	Clinical (unspecified phase)
0.9042	High Similarity	NPD6166	Phase 2
0.9024	High Similarity	NPD4381	Clinical (unspecified phase)
0.8963	High Similarity	NPD4868	Clinical (unspecified phase)
0.8889	High Similarity	NPD7993	Clinical (unspecified phase)
0.8882	High Similarity	NPD7804	Clinical (unspecified phase)
0.8788	High Similarity	NPD3817	Phase 2
0.8675	High Similarity	NPD5402	Approved
0.8623	High Similarity	NPD3882	Suspended
0.8571	High Similarity	NPD7075	Discontinued
0.8554	High Similarity	NPD1934	Approved
0.8528	High Similarity	NPD1512	Approved
0.8503	High Similarity	NPD2393	Clinical (unspecified phase)
0.8503	High Similarity	NPD2801	Approved
0.8476	Intermediate Similarity	NPD5403	Approved
0.8443	Intermediate Similarity	NPD6801	Discontinued
0.8434	Intermediate Similarity	NPD4380	Phase 2
0.8409	Intermediate Similarity	NPD6559	Discontinued
0.8405	Intermediate Similarity	NPD1511	Approved
0.8398	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD5401	Approved
0.8293	Intermediate Similarity	NPD6799	Approved
0.8286	Intermediate Similarity	NPD3751	Discontinued
0.8212	Intermediate Similarity	NPD8313	Approved
0.8212	Intermediate Similarity	NPD8312	Approved
0.8204	Intermediate Similarity	NPD1653	Approved
0.8166	Intermediate Similarity	NPD7411	Suspended
0.8161	Intermediate Similarity	NPD3787	Discontinued
0.8136	Intermediate Similarity	NPD5844	Phase 1
0.807	Intermediate Similarity	NPD1465	Phase 2
0.8061	Intermediate Similarity	NPD6190	Approved
0.8057	Intermediate Similarity	NPD6232	Discontinued
0.8036	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8011	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD7685	Pre-registration
0.7989	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1549	Phase 2
0.7978	Intermediate Similarity	NPD7228	Approved
0.7966	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7819	Suspended
0.7958	Intermediate Similarity	NPD7435	Discontinued
0.7943	Intermediate Similarity	NPD5494	Approved
0.7927	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7898	Intermediate Similarity	NPD7199	Phase 2
0.7846	Intermediate Similarity	NPD8151	Discontinued
0.7829	Intermediate Similarity	NPD3749	Approved
0.7805	Intermediate Similarity	NPD1510	Phase 2
0.7801	Intermediate Similarity	NPD6781	Approved
0.7801	Intermediate Similarity	NPD6777	Approved
0.7801	Intermediate Similarity	NPD6782	Approved
0.7801	Intermediate Similarity	NPD6778	Approved
0.7801	Intermediate Similarity	NPD6780	Approved
0.7801	Intermediate Similarity	NPD6779	Approved
0.7801	Intermediate Similarity	NPD6776	Approved
0.7784	Intermediate Similarity	NPD6234	Discontinued
0.7784	Intermediate Similarity	NPD919	Approved
0.7784	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD8455	Phase 2
0.7758	Intermediate Similarity	NPD2796	Approved
0.7737	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7874	Approved
0.7711	Intermediate Similarity	NPD7266	Discontinued
0.7701	Intermediate Similarity	NPD37	Approved
0.7679	Intermediate Similarity	NPD3750	Approved
0.767	Intermediate Similarity	NPD7768	Phase 2
0.767	Intermediate Similarity	NPD4967	Phase 2
0.767	Intermediate Similarity	NPD4965	Approved
0.767	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD7870	Phase 2
0.7641	Intermediate Similarity	NPD7871	Phase 2
0.7622	Intermediate Similarity	NPD230	Phase 1
0.7611	Intermediate Similarity	NPD3926	Phase 2
0.7598	Intermediate Similarity	NPD1247	Approved
0.759	Intermediate Similarity	NPD7697	Approved
0.759	Intermediate Similarity	NPD7698	Approved
0.759	Intermediate Similarity	NPD7696	Phase 3
0.7588	Intermediate Similarity	NPD7783	Phase 2
0.7588	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD943	Approved
0.7561	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1613	Approved
0.756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD8319	Approved
0.7551	Intermediate Similarity	NPD8320	Phase 1
0.7545	Intermediate Similarity	NPD1551	Phase 2
0.7539	Intermediate Similarity	NPD6534	Approved
0.7539	Intermediate Similarity	NPD6535	Approved
0.7525	Intermediate Similarity	NPD7701	Phase 2
0.7515	Intermediate Similarity	NPD1933	Approved
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7475	Intermediate Similarity	NPD7584	Approved
0.7471	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD1240	Approved
0.7427	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7699	Phase 2
0.7423	Intermediate Similarity	NPD7700	Phase 2
0.7413	Intermediate Similarity	NPD7801	Approved
0.741	Intermediate Similarity	NPD447	Suspended
0.7399	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3748	Approved
0.7365	Intermediate Similarity	NPD1607	Approved
0.736	Intermediate Similarity	NPD6823	Phase 2
0.7337	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6798	Discontinued
0.733	Intermediate Similarity	NPD7458	Discontinued
0.733	Intermediate Similarity	NPD3226	Approved
0.7317	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD8434	Phase 2
0.7314	Intermediate Similarity	NPD920	Approved
0.7299	Intermediate Similarity	NPD2534	Approved
0.7299	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2533	Approved
0.7299	Intermediate Similarity	NPD2532	Approved
0.7289	Intermediate Similarity	NPD6233	Phase 2
0.7283	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5953	Discontinued
0.7264	Intermediate Similarity	NPD7585	Approved
0.7256	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7680	Approved
0.7232	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2313	Discontinued
0.7214	Intermediate Similarity	NPD7583	Approved
0.7208	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD3027	Phase 3
0.7166	Intermediate Similarity	NPD7286	Phase 2
0.7134	Intermediate Similarity	NPD1203	Approved
0.7128	Intermediate Similarity	NPD6213	Phase 3
0.7128	Intermediate Similarity	NPD6212	Phase 3
0.7128	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1243	Approved
0.7108	Intermediate Similarity	NPD6832	Phase 2
0.7093	Intermediate Similarity	NPD2346	Discontinued
0.7085	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2799	Discontinued
0.7076	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD9269	Phase 2
0.7045	Intermediate Similarity	NPD7390	Discontinued
0.7033	Intermediate Similarity	NPD5353	Approved
0.7017	Intermediate Similarity	NPD6844	Discontinued
0.7016	Intermediate Similarity	NPD7549	Discontinued
0.7011	Intermediate Similarity	NPD2800	Approved
0.7011	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2344	Approved
0.6994	Remote Similarity	NPD1091	Approved
0.6974	Remote Similarity	NPD4287	Approved
0.6971	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7038	Approved
0.6963	Remote Similarity	NPD7039	Approved
0.6952	Remote Similarity	NPD5242	Approved
0.6946	Remote Similarity	NPD9494	Approved
0.6935	Remote Similarity	NPD8127	Discontinued
0.6927	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4360	Phase 2
0.6919	Remote Similarity	NPD4363	Phase 3
0.6919	Remote Similarity	NPD7097	Phase 1
0.6914	Remote Similarity	NPD6674	Discontinued
0.691	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5124	Phase 1
0.6898	Remote Similarity	NPD5711	Approved
0.6898	Remote Similarity	NPD5710	Approved
0.6898	Remote Similarity	NPD7229	Phase 3
0.689	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2798	Approved
0.6879	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6386	Approved
0.6868	Remote Similarity	NPD6385	Approved
0.6867	Remote Similarity	NPD3225	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