NPASS Compound

Structure

CID175107 OpenBabel06191715552D 35 38 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 -1.7321 -3.0000 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 -3.4641 -3.0000 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 -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 1.5000 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 -3.4641 -4.0000 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 -3.4641 0.0000 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 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -0.8660 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 2.5981 0.5000 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 0.0000 2.0000 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 -3.4641 -1.0000 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 1 32 1 0 0 0 0 2 3 2 0 0 0 0 2 7 1 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 18 1 0 0 0 0 8 23 1 0 0 0 0 9 10 2 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 13 2 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 12 33 1 0 0 0 0 13 14 1 0 0 0 0 14 19 1 0 0 0 0 14 27 2 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 6 0 0 0 16 20 1 0 0 0 0 16 29 1 1 0 0 0 17 22 1 0 0 0 0 17 30 1 1 0 0 0 18 19 2 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 20 21 1 6 0 0 0 20 35 1 0 0 0 0 21 31 2 0 0 0 0 21 32 1 0 0 0 0 22 34 1 6 0 0 0 22 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.09
Volume:	445.387
LogP:	0.737
LogD:	0.503
LogS:	-4.162
# Rotatable Bonds:	5
TPSA:	216.58
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.183
Synthetic Accessibility Score:	4.109
Fsp3:	0.273
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.231
MDCK Permeability:	1.3989648323331494e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.172
Human Intestinal Absorption (HIA):	0.209
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	86.11202239990234%
Volume Distribution (VD):	0.92
Pgp-substrate:	15.842731475830078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.186
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.131
CYP2C9-substrate:	0.412
CYP2D6-inhibitor:	0.211
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.146
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	6.065
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.115
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.782
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.299
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.32
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC175107

Natural Product ID:	NPC175107
*Common Name:**	Quercetin 3-O-Beta-D-Glucuronide 6''-Methyl Ester
IUPAC Name:	methyl (2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
Synonyms:
Standard InCHIKey:	DAKHAONGVOPWRO-NTKSAMNMSA-N
Standard InCHI:	InChI=1S/C22H20O13/c1-32-21(31)20-16(29)15(28)17(30)22(35-20)34-19-14(27)13-11(26)5-8(23)6-12(13)33-18(19)7-2-3-9(24)10(25)4-7/h2-6,15-17,20,22-26,28-30H,1H3/t15-,16-,17+,20-,22+/m0/s1
SMILES:	COC(=O)[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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468872
PubChem CID:	21722016
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003532] Flavonoid-3-O-glucuronides

*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
NPO15339	Artemisia afra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29106	Tanacetum argenteum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2373	Popillia japonica	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15339	Artemisia afra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29403	Ophiopogon chekiangensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29052	Papaver hybridum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28990	Bidens sulphureus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8843	Epipactis palustris	Species	Orchidaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	41600.0	nM	PMID[536081]

☑ 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 NPC175107 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	412
0.1-0.2	1806
0.2-0.3	4130
0.3-0.4	9292
0.4-0.5	8598
0.5-0.6	4442
0.6-0.7	5185
0.7-0.8	5347
0.8-0.85	1768
0.85-0.9	1092
0.9-0.95	429
0.95-1	196

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC190003
0.9938	High Similarity	NPC116864
0.9938	High Similarity	NPC4390
0.9938	High Similarity	NPC20505
0.9938	High Similarity	NPC155763
0.9938	High Similarity	NPC235260
0.9938	High Similarity	NPC244776
0.9876	High Similarity	NPC153755
0.9875	High Similarity	NPC138927
0.9816	High Similarity	NPC472385
0.9816	High Similarity	NPC198324
0.9812	High Similarity	NPC173637
0.9812	High Similarity	NPC127546
0.9812	High Similarity	NPC52550
0.9812	High Similarity	NPC223424
0.9812	High Similarity	NPC317489
0.9812	High Similarity	NPC84362
0.9756	High Similarity	NPC35167
0.9755	High Similarity	NPC264735
0.9755	High Similarity	NPC135277
0.9755	High Similarity	NPC477848
0.9755	High Similarity	NPC101191
0.9755	High Similarity	NPC210094
0.9755	High Similarity	NPC43211
0.9755	High Similarity	NPC49344
0.9755	High Similarity	NPC253685
0.9755	High Similarity	NPC237435
0.9755	High Similarity	NPC115760
0.9752	High Similarity	NPC223747
0.9752	High Similarity	NPC225434
0.9752	High Similarity	NPC203050
0.9752	High Similarity	NPC120099
0.9752	High Similarity	NPC219904
0.975	High Similarity	NPC274618
0.975	High Similarity	NPC276222
0.975	High Similarity	NPC253662
0.975	High Similarity	NPC118284
0.975	High Similarity	NPC145038
0.975	High Similarity	NPC73855
0.975	High Similarity	NPC179950
0.975	High Similarity	NPC281131
0.975	High Similarity	NPC277174
0.975	High Similarity	NPC113968
0.975	High Similarity	NPC88789
0.975	High Similarity	NPC308404
0.975	High Similarity	NPC135599
0.975	High Similarity	NPC56077
0.975	High Similarity	NPC328940
0.9695	High Similarity	NPC471669
0.9695	High Similarity	NPC144097
0.9695	High Similarity	NPC233994
0.9695	High Similarity	NPC89127
0.9695	High Similarity	NPC61904
0.9695	High Similarity	NPC211532
0.9693	High Similarity	NPC21666
0.9693	High Similarity	NPC101026
0.9693	High Similarity	NPC24043
0.9693	High Similarity	NPC45522
0.9693	High Similarity	NPC169977
0.9693	High Similarity	NPC42773
0.9691	High Similarity	NPC95866
0.9691	High Similarity	NPC206123
0.9689	High Similarity	NPC265530
0.9689	High Similarity	NPC226304
0.9689	High Similarity	NPC325555
0.9688	High Similarity	NPC240431
0.9688	High Similarity	NPC277205
0.9688	High Similarity	NPC55786
0.9688	High Similarity	NPC19388
0.9636	High Similarity	NPC217520
0.9636	High Similarity	NPC173837
0.9636	High Similarity	NPC217387
0.9636	High Similarity	NPC258044
0.9636	High Similarity	NPC253521
0.9636	High Similarity	NPC293626
0.9636	High Similarity	NPC113836
0.9636	High Similarity	NPC196127
0.9636	High Similarity	NPC37668
0.9636	High Similarity	NPC267680
0.9636	High Similarity	NPC139571
0.9634	High Similarity	NPC214621
0.9634	High Similarity	NPC34267
0.9634	High Similarity	NPC223426
0.9634	High Similarity	NPC81042
0.9632	High Similarity	NPC254540
0.9632	High Similarity	NPC176740
0.9632	High Similarity	NPC245452
0.9632	High Similarity	NPC476405
0.9632	High Similarity	NPC203259
0.9632	High Similarity	NPC33054
0.9632	High Similarity	NPC117260
0.9632	High Similarity	NPC471748
0.9632	High Similarity	NPC172807
0.9632	High Similarity	NPC211594
0.9632	High Similarity	NPC471725
0.9632	High Similarity	NPC134532
0.9632	High Similarity	NPC155877
0.963	High Similarity	NPC270578
0.963	High Similarity	NPC52382
0.9627	High Similarity	NPC197285
0.9627	High Similarity	NPC21100
0.9625	High Similarity	NPC19709
0.9581	High Similarity	NPC36138
0.9581	High Similarity	NPC470445
0.9581	High Similarity	NPC470447
0.9581	High Similarity	NPC470449
0.9581	High Similarity	NPC470446
0.9576	High Similarity	NPC473862
0.9576	High Similarity	NPC472382
0.9576	High Similarity	NPC268533
0.9576	High Similarity	NPC472384
0.9576	High Similarity	NPC65563
0.9576	High Similarity	NPC154741
0.9576	High Similarity	NPC472380
0.9576	High Similarity	NPC470949
0.9576	High Similarity	NPC296018
0.9571	High Similarity	NPC282987
0.9571	High Similarity	NPC29958
0.9571	High Similarity	NPC259896
0.9571	High Similarity	NPC136042
0.9571	High Similarity	NPC255157
0.9571	High Similarity	NPC67105
0.9571	High Similarity	NPC245014
0.9571	High Similarity	NPC67326
0.9571	High Similarity	NPC254855
0.9571	High Similarity	NPC156869
0.9571	High Similarity	NPC84265
0.9568	High Similarity	NPC160156
0.9568	High Similarity	NPC92565
0.9568	High Similarity	NPC116745
0.9565	High Similarity	NPC311830
0.9565	High Similarity	NPC22832
0.9563	High Similarity	NPC473043
0.9563	High Similarity	NPC189142
0.9563	High Similarity	NPC27942
0.9563	High Similarity	NPC77660
0.9524	High Similarity	NPC470451
0.9524	High Similarity	NPC470416
0.9524	High Similarity	NPC470455
0.9521	High Similarity	NPC222674
0.9518	High Similarity	NPC476773
0.9518	High Similarity	NPC168584
0.9518	High Similarity	NPC477895
0.9515	High Similarity	NPC19108
0.9515	High Similarity	NPC220173
0.9515	High Similarity	NPC294629
0.9515	High Similarity	NPC473327
0.9515	High Similarity	NPC16194
0.9515	High Similarity	NPC294815
0.9515	High Similarity	NPC476472
0.9512	High Similarity	NPC60735
0.9512	High Similarity	NPC26230
0.9509	High Similarity	NPC45638
0.9509	High Similarity	NPC201292
0.9509	High Similarity	NPC58053
0.9509	High Similarity	NPC105025
0.9509	High Similarity	NPC475942
0.9509	High Similarity	NPC476771
0.9509	High Similarity	NPC186807
0.9509	High Similarity	NPC93337
0.9509	High Similarity	NPC226294
0.9509	High Similarity	NPC227508
0.9509	High Similarity	NPC469931
0.9506	High Similarity	NPC255615
0.9506	High Similarity	NPC115674
0.9506	High Similarity	NPC67037
0.9506	High Similarity	NPC210073
0.9503	High Similarity	NPC88023
0.9503	High Similarity	NPC270335
0.9503	High Similarity	NPC243930
0.9503	High Similarity	NPC284960
0.9503	High Similarity	NPC168822
0.9503	High Similarity	NPC309025
0.9503	High Similarity	NPC222936
0.9503	High Similarity	NPC191306
0.95	High Similarity	NPC282169
0.95	High Similarity	NPC159579
0.95	High Similarity	NPC259957
0.95	High Similarity	NPC224530
0.95	High Similarity	NPC216496
0.95	High Similarity	NPC129217
0.95	High Similarity	NPC85707
0.95	High Similarity	NPC48093
0.9464	High Similarity	NPC241781
0.9464	High Similarity	NPC162394
0.9464	High Similarity	NPC297503
0.9464	High Similarity	NPC156785
0.9464	High Similarity	NPC107987
0.9464	High Similarity	NPC97119
0.9464	High Similarity	NPC135831
0.9461	High Similarity	NPC473682
0.9461	High Similarity	NPC126784
0.9461	High Similarity	NPC470443
0.9461	High Similarity	NPC470444
0.9461	High Similarity	NPC110941
0.9461	High Similarity	NPC241423
0.9461	High Similarity	NPC473571
0.9458	High Similarity	NPC122467
0.9458	High Similarity	NPC202908
0.9458	High Similarity	NPC8573

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 NPC175107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	959
0.2-0.3	1979
0.3-0.4	2611
0.4-0.5	1837
0.5-0.6	898
0.6-0.7	312
0.7-0.8	128
0.8-0.85	20
0.85-0.9	17
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9755	High Similarity	NPD4338	Clinical (unspecified phase)
0.9632	High Similarity	NPD6797	Phase 2
0.9573	High Similarity	NPD7251	Discontinued
0.9398	High Similarity	NPD7808	Phase 3
0.939	High Similarity	NPD7054	Approved
0.9333	High Similarity	NPD7472	Approved
0.9217	High Similarity	NPD7074	Phase 3
0.9212	High Similarity	NPD3818	Discontinued
0.9074	High Similarity	NPD4381	Clinical (unspecified phase)
0.9068	High Similarity	NPD3817	Phase 2
0.9042	High Similarity	NPD7804	Clinical (unspecified phase)
0.8976	High Similarity	NPD6167	Clinical (unspecified phase)
0.8976	High Similarity	NPD6168	Clinical (unspecified phase)
0.8976	High Similarity	NPD6166	Phase 2
0.8827	High Similarity	NPD1934	Approved
0.878	High Similarity	NPD4868	Clinical (unspecified phase)
0.878	High Similarity	NPD3882	Suspended
0.8773	High Similarity	NPD2801	Approved
0.8773	High Similarity	NPD2393	Clinical (unspecified phase)
0.8727	High Similarity	NPD7075	Discontinued
0.872	High Similarity	NPD5402	Approved
0.8688	High Similarity	NPD1512	Approved
0.8605	High Similarity	NPD7993	Clinical (unspecified phase)
0.8598	High Similarity	NPD6801	Discontinued
0.8562	High Similarity	NPD1511	Approved
0.8545	High Similarity	NPD7096	Clinical (unspecified phase)
0.8519	High Similarity	NPD5403	Approved
0.8476	Intermediate Similarity	NPD4380	Phase 2
0.8448	Intermediate Similarity	NPD6559	Discontinued
0.8447	Intermediate Similarity	NPD6799	Approved
0.8395	Intermediate Similarity	NPD5401	Approved
0.8333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD1653	Approved
0.8144	Intermediate Similarity	NPD6599	Discontinued
0.8136	Intermediate Similarity	NPD7685	Pre-registration
0.8114	Intermediate Similarity	NPD3751	Discontinued
0.8107	Intermediate Similarity	NPD1465	Phase 2
0.8107	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD7411	Suspended
0.8092	Intermediate Similarity	NPD3787	Discontinued
0.8092	Intermediate Similarity	NPD6232	Discontinued
0.8081	Intermediate Similarity	NPD5494	Approved
0.8075	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD5844	Phase 1
0.8057	Intermediate Similarity	NPD7473	Discontinued
0.8046	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1549	Phase 2
0.8011	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD6190	Approved
0.7964	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD8313	Approved
0.7944	Intermediate Similarity	NPD8312	Approved
0.7931	Intermediate Similarity	NPD7199	Phase 2
0.7927	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD919	Approved
0.7919	Intermediate Similarity	NPD6234	Discontinued
0.7901	Intermediate Similarity	NPD2796	Approved
0.7895	Intermediate Similarity	NPD7435	Discontinued
0.7853	Intermediate Similarity	NPD7266	Discontinued
0.7844	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1510	Phase 2
0.7836	Intermediate Similarity	NPD37	Approved
0.7829	Intermediate Similarity	NPD6959	Discontinued
0.7826	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4965	Approved
0.7803	Intermediate Similarity	NPD4966	Approved
0.7803	Intermediate Similarity	NPD4967	Phase 2
0.7797	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD230	Phase 1
0.7737	Intermediate Similarity	NPD6777	Approved
0.7737	Intermediate Similarity	NPD6781	Approved
0.7737	Intermediate Similarity	NPD6782	Approved
0.7737	Intermediate Similarity	NPD6778	Approved
0.7737	Intermediate Similarity	NPD6776	Approved
0.7737	Intermediate Similarity	NPD6779	Approved
0.7737	Intermediate Similarity	NPD6780	Approved
0.7727	Intermediate Similarity	NPD1247	Approved
0.7711	Intermediate Similarity	NPD3750	Approved
0.7702	Intermediate Similarity	NPD1613	Approved
0.7702	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8151	Discontinued
0.7679	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD3749	Approved
0.7654	Intermediate Similarity	NPD1933	Approved
0.7653	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD7874	Approved
0.764	Intermediate Similarity	NPD3926	Phase 2
0.7605	Intermediate Similarity	NPD4628	Phase 3
0.76	Intermediate Similarity	NPD7768	Phase 2
0.7593	Intermediate Similarity	NPD1240	Approved
0.7593	Intermediate Similarity	NPD943	Approved
0.759	Intermediate Similarity	NPD7584	Approved
0.7586	Intermediate Similarity	NPD8455	Phase 2
0.7578	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1551	Phase 2
0.7546	Intermediate Similarity	NPD447	Suspended
0.7541	Intermediate Similarity	NPD7240	Approved
0.7529	Intermediate Similarity	NPD2533	Approved
0.7529	Intermediate Similarity	NPD2534	Approved
0.7529	Intermediate Similarity	NPD2532	Approved
0.7526	Intermediate Similarity	NPD7696	Phase 3
0.7526	Intermediate Similarity	NPD7697	Approved
0.7526	Intermediate Similarity	NPD7698	Approved
0.7525	Intermediate Similarity	NPD7783	Phase 2
0.7525	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1607	Approved
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD8319	Approved
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7487	Intermediate Similarity	NPD8320	Phase 1
0.7474	Intermediate Similarity	NPD6535	Approved
0.7474	Intermediate Similarity	NPD6534	Approved
0.747	Intermediate Similarity	NPD2935	Discontinued
0.7462	Intermediate Similarity	NPD7701	Phase 2
0.7453	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD920	Approved
0.744	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD8150	Discontinued
0.7433	Intermediate Similarity	NPD8434	Phase 2
0.741	Intermediate Similarity	NPD3748	Approved
0.741	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7403	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7391	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7585	Approved
0.7362	Intermediate Similarity	NPD6798	Discontinued
0.7358	Intermediate Similarity	NPD7700	Phase 2
0.7358	Intermediate Similarity	NPD7699	Phase 2
0.7356	Intermediate Similarity	NPD3226	Approved
0.735	Intermediate Similarity	NPD7801	Approved
0.7326	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7583	Approved
0.7317	Intermediate Similarity	NPD6233	Phase 2
0.7305	Intermediate Similarity	NPD7033	Discontinued
0.7296	Intermediate Similarity	NPD6823	Phase 2
0.7283	Intermediate Similarity	NPD7286	Phase 2
0.7282	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7458	Discontinued
0.7256	Intermediate Similarity	NPD2313	Discontinued
0.7239	Intermediate Similarity	NPD6832	Phase 2
0.7235	Intermediate Similarity	NPD1243	Approved
0.7235	Intermediate Similarity	NPD2800	Approved
0.7235	Intermediate Similarity	NPD1652	Phase 2
0.7231	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD2346	Discontinued
0.7212	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2799	Discontinued
0.7194	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7680	Approved
0.716	Intermediate Similarity	NPD1203	Approved
0.7151	Intermediate Similarity	NPD5353	Approved
0.7135	Intermediate Similarity	NPD6844	Discontinued
0.7128	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5124	Phase 1
0.7125	Intermediate Similarity	NPD1091	Approved
0.7113	Intermediate Similarity	NPD4363	Phase 3
0.7113	Intermediate Similarity	NPD4360	Phase 2
0.7104	Intermediate Similarity	NPD5710	Approved
0.7104	Intermediate Similarity	NPD5711	Approved
0.7093	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD9269	Phase 2
0.7079	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD9494	Approved
0.7066	Intermediate Similarity	NPD4060	Phase 1
0.7065	Intermediate Similarity	NPD5242	Approved
0.7062	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6213	Phase 3
0.7062	Intermediate Similarity	NPD6212	Phase 3
0.7059	Intermediate Similarity	NPD6100	Approved
0.7059	Intermediate Similarity	NPD6099	Approved
0.7048	Intermediate Similarity	NPD3268	Approved
0.7035	Intermediate Similarity	NPD6674	Discontinued
0.7035	Intermediate Similarity	NPD5005	Approved
0.7035	Intermediate Similarity	NPD5006	Approved
0.703	Intermediate Similarity	NPD4908	Phase 1
0.7019	Intermediate Similarity	NPD422	Phase 1
0.7018	Intermediate Similarity	NPD2344	Approved
0.7012	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD4062	Phase 3
0.6994	Remote Similarity	NPD3225	Approved
0.699	Remote Similarity	NPD7930	Approved
0.6983	Remote Similarity	NPD6385	Approved
0.6983	Remote Similarity	NPD6386	Approved
0.6982	Remote Similarity	NPD6651	Approved
0.6975	Remote Similarity	NPD9717	Approved
0.6971	Remote Similarity	NPD7390	Discontinued
0.6963	Remote Similarity	NPD7090	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