NPASS Compound

Structure

NPC293626 OpenBabel07101718282D 45 49 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 1.7321 3.0000 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 -4.3301 2.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 4.3301 -1.5000 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 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 -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 2 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 -6.0622 2.5000 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 -0.8660 1.5000 0.0000 C 0 0 1 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 1 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 -3.4641 1.0000 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 1.7321 -2.0000 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 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 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 2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 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 0.0000 -0.0000 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 -2.5981 1.5000 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 2 41 1 0 0 0 0 3 10 2 0 0 0 0 3 14 1 0 0 0 0 4 10 1 0 0 0 0 4 15 2 0 0 0 0 5 11 2 0 0 0 0 5 16 1 0 0 0 0 6 11 1 0 0 0 0 6 17 2 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 18 2 0 0 0 0 9 1 1 6 0 0 0 9 20 1 0 0 0 0 9 42 1 0 0 0 0 10 25 1 0 0 0 0 11 28 1 0 0 0 0 12 41 1 0 0 0 0 13 19 2 0 0 0 0 13 30 1 0 0 0 0 14 21 2 0 0 0 0 14 31 1 0 0 0 0 15 21 1 0 0 0 0 15 32 1 0 0 0 0 16 22 2 0 0 0 0 16 33 1 0 0 0 0 17 22 1 0 0 0 0 17 34 1 0 0 0 0 18 19 1 0 0 0 0 18 43 1 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 20 35 1 1 0 0 0 21 36 1 0 0 0 0 22 37 1 0 0 0 0 23 27 1 0 0 0 0 23 38 2 0 0 0 0 24 26 1 0 0 0 0 24 29 1 0 0 0 0 24 39 1 6 0 0 0 25 27 2 0 0 0 0 25 43 1 0 0 0 0 26 44 1 6 0 0 0 27 45 1 0 0 0 0 28 40 2 0 0 0 0 28 44 1 0 0 0 0 29 42 1 0 0 0 0 29 45 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	630.12
Volume:	576.364
LogP:	2.603
LogD:	0.751
LogS:	-4.291
# Rotatable Bonds:	7
TPSA:	266.27
# H-Bond Aceptor:	16
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.108
Synthetic Accessibility Score:	4.457
Fsp3:	0.241
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:	-6.564
MDCK Permeability:	9.727576980367303e-06
Pgp-inhibitor:	0.704
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.833
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	87.66244506835938%
Volume Distribution (VD):	0.626
Pgp-substrate:	22.833982467651367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.593
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	6.544
Half-life (T1/2):	0.95

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.47
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.929
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.902
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC293626

Natural Product ID:	NPC293626
*Common Name:**	Myricetin 3-O-(3''-Galloyl)-Alpha-Rhamnopyranoside 7-Methyl Ether
IUPAC Name:	[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-[5-hydroxy-7-methoxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-6-methyloxan-4-yl] 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	PSLHITKXAIEMKE-JETVMTPSSA-N
Standard InCHI:	InChI=1S/C29H26O16/c1-9-20(35)26(44-28(40)11-5-16(33)22(37)17(34)6-11)24(39)29(42-9)45-27-23(38)19-13(30)7-12(41-2)8-18(19)43-25(27)10-3-14(31)21(36)15(32)4-10/h3-9,20,24,26,29-37,39H,1-2H3/t9-,20-,24+,26+,29-/m1/s1
SMILES:	COc1cc(O)c2c(c1)oc(c(c2=O)O[C@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)OC(=O)c1cc(O)c(c(c1)O)O)O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456032
PubChem CID:	10604042
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
NPO996	Acacia confusa	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[10843598]
NPO996	Acacia confusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20047272]
NPO996	Acacia confusa	Species	Fabaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	IC50	=	50.0	ug.mL-1	PMID[554463]

☑ 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 NPC293626 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	423
0.1-0.2	1794
0.2-0.3	4203
0.3-0.4	9156
0.4-0.5	8850
0.5-0.6	4530
0.6-0.7	5349
0.7-0.8	5307
0.8-0.85	1742
0.85-0.9	732
0.9-0.95	452
0.95-1	159

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC196127
1.0	High Similarity	NPC217387
1.0	High Similarity	NPC258044
1.0	High Similarity	NPC267680
0.9879	High Similarity	NPC113836
0.9879	High Similarity	NPC35167
0.9879	High Similarity	NPC37668
0.9879	High Similarity	NPC253521
0.9818	High Similarity	NPC144097
0.9818	High Similarity	NPC61904
0.9759	High Similarity	NPC217520
0.9759	High Similarity	NPC139571
0.9758	High Similarity	NPC214621
0.9758	High Similarity	NPC34267
0.9758	High Similarity	NPC223426
0.9758	High Similarity	NPC81042
0.9702	High Similarity	NPC162394
0.9702	High Similarity	NPC36138
0.9702	High Similarity	NPC297503
0.9702	High Similarity	NPC241781
0.9702	High Similarity	NPC97119
0.9702	High Similarity	NPC156785
0.9702	High Similarity	NPC135831
0.9645	High Similarity	NPC21359
0.9645	High Similarity	NPC275977
0.9645	High Similarity	NPC460984
0.9645	High Similarity	NPC249560
0.9645	High Similarity	NPC470416
0.9645	High Similarity	NPC25946
0.9645	High Similarity	NPC470720
0.9645	High Similarity	NPC470717
0.9645	High Similarity	NPC470713
0.9645	High Similarity	NPC223860
0.9641	High Similarity	NPC477895
0.9639	High Similarity	NPC253685
0.9636	High Similarity	NPC175107
0.9636	High Similarity	NPC190003
0.9634	High Similarity	NPC138927
0.9588	High Similarity	NPC33083
0.9588	High Similarity	NPC474093
0.9588	High Similarity	NPC295625
0.9588	High Similarity	NPC470719
0.9588	High Similarity	NPC104910
0.9588	High Similarity	NPC473554
0.9586	High Similarity	NPC470718
0.9581	High Similarity	NPC89127
0.9581	High Similarity	NPC296018
0.9581	High Similarity	NPC471669
0.9581	High Similarity	NPC154741
0.9578	High Similarity	NPC4390
0.9578	High Similarity	NPC472993
0.9576	High Similarity	NPC20505
0.9576	High Similarity	NPC244776
0.9576	High Similarity	NPC116864
0.9576	High Similarity	NPC235260
0.9576	High Similarity	NPC155763
0.9532	High Similarity	NPC30011
0.9532	High Similarity	NPC72554
0.9532	High Similarity	NPC475179
0.9532	High Similarity	NPC97817
0.9524	High Similarity	NPC173837
0.9524	High Similarity	NPC476773
0.9518	High Similarity	NPC155877
0.9518	High Similarity	NPC471725
0.9518	High Similarity	NPC134532
0.9518	High Similarity	NPC33054
0.9518	High Similarity	NPC203259
0.9518	High Similarity	NPC471748
0.9518	High Similarity	NPC176740
0.9518	High Similarity	NPC153755
0.9515	High Similarity	NPC227508
0.9512	High Similarity	NPC113968
0.9512	High Similarity	NPC277174
0.9512	High Similarity	NPC328940
0.9512	High Similarity	NPC73855
0.9512	High Similarity	NPC135599
0.9471	High Similarity	NPC470445
0.9471	High Similarity	NPC470446
0.9471	High Similarity	NPC470447
0.9471	High Similarity	NPC470449
0.9464	High Similarity	NPC65563
0.9464	High Similarity	NPC473862
0.9464	High Similarity	NPC472385
0.9464	High Similarity	NPC198324
0.9464	High Similarity	NPC470949
0.9464	High Similarity	NPC472991
0.9464	High Similarity	NPC472992
0.9461	High Similarity	NPC88560
0.9461	High Similarity	NPC172033
0.9461	High Similarity	NPC175230
0.9458	High Similarity	NPC204937
0.9458	High Similarity	NPC29958
0.9458	High Similarity	NPC95866
0.9458	High Similarity	NPC259896
0.9458	High Similarity	NPC149011
0.9458	High Similarity	NPC136042
0.9458	High Similarity	NPC254855
0.9458	High Similarity	NPC206123
0.9458	High Similarity	NPC67326
0.9458	High Similarity	NPC255157
0.9458	High Similarity	NPC67105
0.9458	High Similarity	NPC156869
0.9455	High Similarity	NPC127546
0.9455	High Similarity	NPC275454
0.9455	High Similarity	NPC173637
0.9455	High Similarity	NPC84362
0.9455	High Similarity	NPC317489
0.9455	High Similarity	NPC325555
0.9455	High Similarity	NPC52550
0.9455	High Similarity	NPC223424
0.9455	High Similarity	NPC265530
0.9455	High Similarity	NPC226304
0.9451	High Similarity	NPC55786
0.9451	High Similarity	NPC240431
0.9451	High Similarity	NPC19388
0.9415	High Similarity	NPC470455
0.9415	High Similarity	NPC470451
0.9405	High Similarity	NPC476472
0.9405	High Similarity	NPC43211
0.9405	High Similarity	NPC210094
0.9405	High Similarity	NPC16194
0.9405	High Similarity	NPC477848
0.9405	High Similarity	NPC115760
0.9405	High Similarity	NPC237435
0.9405	High Similarity	NPC294815
0.9405	High Similarity	NPC473327
0.9405	High Similarity	NPC264735
0.9405	High Similarity	NPC19108
0.9405	High Similarity	NPC135277
0.9405	High Similarity	NPC49344
0.9405	High Similarity	NPC220173
0.9405	High Similarity	NPC101191
0.9401	High Similarity	NPC60735
0.9401	High Similarity	NPC67134
0.9401	High Similarity	NPC26230
0.9401	High Similarity	NPC47140
0.9398	High Similarity	NPC225434
0.9398	High Similarity	NPC120099
0.9398	High Similarity	NPC219904
0.9398	High Similarity	NPC203050
0.9398	High Similarity	NPC223747
0.9394	High Similarity	NPC281131
0.9394	High Similarity	NPC145038
0.9394	High Similarity	NPC179950
0.9394	High Similarity	NPC253662
0.9394	High Similarity	NPC276222
0.9394	High Similarity	NPC118284
0.9394	High Similarity	NPC274618
0.9394	High Similarity	NPC56077
0.9394	High Similarity	NPC308404
0.9394	High Similarity	NPC88789
0.9357	High Similarity	NPC199172
0.9357	High Similarity	NPC35924
0.9353	High Similarity	NPC241423
0.9353	High Similarity	NPC470444
0.9353	High Similarity	NPC110941
0.9353	High Similarity	NPC473571
0.9353	High Similarity	NPC126784
0.9353	High Similarity	NPC473682
0.9353	High Similarity	NPC470443
0.9353	High Similarity	NPC471030
0.9349	High Similarity	NPC202908
0.9349	High Similarity	NPC8573
0.9349	High Similarity	NPC122467
0.9349	High Similarity	NPC169733
0.9349	High Similarity	NPC233994
0.9349	High Similarity	NPC292019
0.9349	High Similarity	NPC14187
0.9349	High Similarity	NPC211532
0.9345	High Similarity	NPC21666
0.9345	High Similarity	NPC169977
0.9345	High Similarity	NPC42773
0.9345	High Similarity	NPC45522
0.9345	High Similarity	NPC24043
0.9345	High Similarity	NPC101026
0.9341	High Similarity	NPC285197
0.9337	High Similarity	NPC116745
0.9333	High Similarity	NPC19240
0.9333	High Similarity	NPC129264
0.9333	High Similarity	NPC277205
0.9333	High Similarity	NPC139060
0.9333	High Similarity	NPC205824
0.9333	High Similarity	NPC85751
0.9329	High Similarity	NPC473043
0.9298	High Similarity	NPC473073
0.9298	High Similarity	NPC473071
0.9294	High Similarity	NPC476622
0.9294	High Similarity	NPC472387
0.9294	High Similarity	NPC476621
0.9294	High Similarity	NPC476618
0.9294	High Similarity	NPC476623
0.9294	High Similarity	NPC476619
0.9294	High Similarity	NPC251417
0.9294	High Similarity	NPC89052
0.9294	High Similarity	NPC476620
0.929	High Similarity	NPC294629
0.9286	High Similarity	NPC254540
0.9286	High Similarity	NPC476405
0.9286	High Similarity	NPC245452
0.9286	High Similarity	NPC211594

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 NPC293626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	970
0.2-0.3	2082
0.3-0.4	2624
0.4-0.5	1800
0.5-0.6	871
0.6-0.7	271
0.7-0.8	114
0.8-0.85	25
0.85-0.9	10
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9518	High Similarity	NPD6797	Phase 2
0.9461	High Similarity	NPD7251	Discontinued
0.9405	High Similarity	NPD4338	Clinical (unspecified phase)
0.929	High Similarity	NPD7808	Phase 3
0.9226	High Similarity	NPD7472	Approved
0.9167	High Similarity	NPD7054	Approved
0.9	High Similarity	NPD7074	Phase 3
0.8994	High Similarity	NPD3818	Discontinued
0.8988	High Similarity	NPD6167	Clinical (unspecified phase)
0.8988	High Similarity	NPD6168	Clinical (unspecified phase)
0.8988	High Similarity	NPD6166	Phase 2
0.8947	High Similarity	NPD7993	Clinical (unspecified phase)
0.8909	High Similarity	NPD4868	Clinical (unspecified phase)
0.8855	High Similarity	NPD4381	Clinical (unspecified phase)
0.883	High Similarity	NPD7804	Clinical (unspecified phase)
0.8735	High Similarity	NPD3817	Phase 2
0.8571	High Similarity	NPD3882	Suspended
0.8521	High Similarity	NPD7075	Discontinued
0.8512	High Similarity	NPD5402	Approved
0.8503	High Similarity	NPD1934	Approved
0.8452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD2801	Approved
0.8393	Intermediate Similarity	NPD6801	Discontinued
0.8364	Intermediate Similarity	NPD1512	Approved
0.8362	Intermediate Similarity	NPD6559	Discontinued
0.8352	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5403	Approved
0.8274	Intermediate Similarity	NPD4380	Phase 2
0.8242	Intermediate Similarity	NPD6799	Approved
0.8242	Intermediate Similarity	NPD1511	Approved
0.8193	Intermediate Similarity	NPD5401	Approved
0.8167	Intermediate Similarity	NPD8312	Approved
0.8167	Intermediate Similarity	NPD8313	Approved
0.8136	Intermediate Similarity	NPD3751	Discontinued
0.8118	Intermediate Similarity	NPD7411	Suspended
0.809	Intermediate Similarity	NPD5844	Phase 1
0.8047	Intermediate Similarity	NPD1653	Approved
0.8034	Intermediate Similarity	NPD7228	Approved
0.8023	Intermediate Similarity	NPD1465	Phase 2
0.8011	Intermediate Similarity	NPD3787	Discontinued
0.8011	Intermediate Similarity	NPD6232	Discontinued
0.799	Intermediate Similarity	NPD8151	Discontinued
0.7988	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7473	Discontinued
0.7976	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7685	Pre-registration
0.7955	Intermediate Similarity	NPD6959	Discontinued
0.7953	Intermediate Similarity	NPD6599	Discontinued
0.7946	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7819	Suspended
0.7917	Intermediate Similarity	NPD7435	Discontinued
0.7904	Intermediate Similarity	NPD6190	Approved
0.7898	Intermediate Similarity	NPD5494	Approved
0.788	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7199	Phase 2
0.7841	Intermediate Similarity	NPD6234	Discontinued
0.7831	Intermediate Similarity	NPD1549	Phase 2
0.7771	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD6777	Approved
0.776	Intermediate Similarity	NPD6780	Approved
0.776	Intermediate Similarity	NPD6776	Approved
0.776	Intermediate Similarity	NPD6781	Approved
0.776	Intermediate Similarity	NPD6778	Approved
0.776	Intermediate Similarity	NPD6779	Approved
0.776	Intermediate Similarity	NPD6782	Approved
0.7759	Intermediate Similarity	NPD37	Approved
0.774	Intermediate Similarity	NPD919	Approved
0.7738	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4965	Approved
0.7727	Intermediate Similarity	NPD4966	Approved
0.7727	Intermediate Similarity	NPD4967	Phase 2
0.7714	Intermediate Similarity	NPD8455	Phase 2
0.7711	Intermediate Similarity	NPD2796	Approved
0.7696	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD3749	Approved
0.7683	Intermediate Similarity	NPD230	Phase 1
0.7677	Intermediate Similarity	NPD7874	Approved
0.7677	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7266	Discontinued
0.7663	Intermediate Similarity	NPD7240	Approved
0.7651	Intermediate Similarity	NPD1510	Phase 2
0.7627	Intermediate Similarity	NPD7768	Phase 2
0.7619	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7870	Phase 2
0.7602	Intermediate Similarity	NPD7871	Phase 2
0.7569	Intermediate Similarity	NPD3926	Phase 2
0.7556	Intermediate Similarity	NPD1247	Approved
0.7551	Intermediate Similarity	NPD7697	Approved
0.7551	Intermediate Similarity	NPD7698	Approved
0.7551	Intermediate Similarity	NPD7696	Phase 3
0.755	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7783	Phase 2
0.7529	Intermediate Similarity	NPD3750	Approved
0.7513	Intermediate Similarity	NPD8320	Phase 1
0.7513	Intermediate Similarity	NPD8319	Approved
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7471	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1933	Approved
0.746	Intermediate Similarity	NPD8150	Discontinued
0.7437	Intermediate Similarity	NPD7584	Approved
0.7427	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD943	Approved
0.741	Intermediate Similarity	NPD1240	Approved
0.741	Intermediate Similarity	NPD1613	Approved
0.741	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1551	Phase 2
0.7391	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7699	Phase 2
0.7385	Intermediate Similarity	NPD7700	Phase 2
0.7376	Intermediate Similarity	NPD7801	Approved
0.7368	Intermediate Similarity	NPD8434	Phase 2
0.7365	Intermediate Similarity	NPD447	Suspended
0.7356	Intermediate Similarity	NPD2533	Approved
0.7356	Intermediate Similarity	NPD2534	Approved
0.7356	Intermediate Similarity	NPD2532	Approved
0.7323	Intermediate Similarity	NPD6823	Phase 2
0.7321	Intermediate Similarity	NPD1607	Approved
0.7294	Intermediate Similarity	NPD2935	Discontinued
0.7289	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6798	Discontinued
0.7288	Intermediate Similarity	NPD3226	Approved
0.7288	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD920	Approved
0.7259	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6233	Phase 2
0.7243	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3748	Approved
0.7234	Intermediate Similarity	NPD5953	Discontinued
0.7228	Intermediate Similarity	NPD7585	Approved
0.7212	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7680	Approved
0.7178	Intermediate Similarity	NPD7583	Approved
0.7169	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1243	Approved
0.7159	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7286	Phase 2
0.7126	Intermediate Similarity	NPD3027	Phase 3
0.7102	Intermediate Similarity	NPD7390	Discontinued
0.7095	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6212	Phase 3
0.7092	Intermediate Similarity	NPD6213	Phase 3
0.7092	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5353	Approved
0.7083	Intermediate Similarity	NPD2313	Discontinued
0.7069	Intermediate Similarity	NPD2800	Approved
0.7066	Intermediate Similarity	NPD6832	Phase 2
0.7052	Intermediate Similarity	NPD2346	Discontinued
0.705	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2799	Discontinued
0.7035	Intermediate Similarity	NPD7033	Discontinued
0.7029	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD9269	Phase 2
0.6988	Remote Similarity	NPD1203	Approved
0.6979	Remote Similarity	NPD7549	Discontinued
0.6978	Remote Similarity	NPD6844	Discontinued
0.6971	Remote Similarity	NPD6674	Discontinued
0.6971	Remote Similarity	NPD1652	Phase 2
0.6966	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4908	Phase 1
0.6961	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2344	Approved
0.6952	Remote Similarity	NPD5711	Approved
0.6952	Remote Similarity	NPD5710	Approved
0.6936	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7039	Approved
0.6927	Remote Similarity	NPD7038	Approved
0.6915	Remote Similarity	NPD5242	Approved
0.6907	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD9494	Approved
0.6898	Remote Similarity	NPD8127	Discontinued
0.6897	Remote Similarity	NPD6099	Approved
0.6897	Remote Similarity	NPD6100	Approved
0.6891	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4360	Phase 2
0.6884	Remote Similarity	NPD4363	Phase 3
0.6882	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7097	Phase 1
0.6862	Remote Similarity	NPD7229	Phase 3
0.686	Remote Similarity	NPD5124	Phase 1
0.686	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4287	Approved
0.6848	Remote Similarity	NPD1091	Approved
0.6845	Remote Similarity	NPD2798	Approved
0.6831	Remote Similarity	NPD6385	Approved
0.6831	Remote Similarity	NPD7615	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