NPASS Compound

Structure

CID210094 OpenBabel06191716002D 33 36 0 0 1 0 0 0 0 0999 V2000 -5.1962 0.0000 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -0.8660 -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 -2.5000 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 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 -1.7321 -1.0000 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 0.8660 0.5000 0.0000 C 0 0 1 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 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 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 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 -1.7321 0.0000 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 1 3 1 0 0 0 0 1 7 2 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 24 2 0 0 0 0 11 17 2 0 0 0 0 11 25 1 0 0 0 0 12 31 1 0 0 0 0 13 18 2 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 1 0 0 0 15 19 1 0 0 0 0 15 27 1 6 0 0 0 16 21 1 0 0 0 0 16 28 1 6 0 0 0 17 18 1 0 0 0 0 17 32 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 1 0 0 0 19 33 1 0 0 0 0 20 29 2 0 0 0 0 20 30 1 0 0 0 0 21 32 1 1 0 0 0 21 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.08
Volume:	419.301
LogP:	0.946
LogD:	0.358
LogS:	-4.269
# Rotatable Bonds:	4
TPSA:	207.35
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.27
Synthetic Accessibility Score:	4.021
Fsp3:	0.238
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.417
MDCK Permeability:	1.378613251290517e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.188
Human Intestinal Absorption (HIA):	0.353
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	90.00846099853516%
Volume Distribution (VD):	0.655
Pgp-substrate:	10.470006942749023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.348
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	1.608
Half-life (T1/2):	0.923

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.452
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.214
Carcinogencity:	0.081
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC210094

Natural Product ID:	NPC210094
*Common Name:**	Isoscutellarein 8-O-Beta-D-Glucuronide
IUPAC Name:	(2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms:
Standard InCHIKey:	FBDUYUDFMFZSDJ-ZUGPOPFOSA-N
Standard InCHI:	InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)12-6-10(24)13-9(23)5-11(25)17(18(13)31-12)32-21-16(28)14(26)15(27)19(33-21)20(29)30/h1-6,14-16,19,21-23,25-28H,(H,29,30)/t14-,15-,16+,19-,21+/m0/s1
SMILES:	Oc1ccc(cc1)c1cc(=O)c2c(o1)c(O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O)c(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462705
PubChem CID:	14332450
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:0003541] Flavonoid-8-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
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19829679]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[21087019]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22314230]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23521110]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	PMID[25637363]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834167]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28990	Bidens sulphureus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29106	Tanacetum argenteum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20278	Scutellaria indica	Species	Lamiaceae	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	=	68100.0	nM	PMID[496056]

☑ 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 NPC210094 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	439
0.1-0.2	1925
0.2-0.3	4492
0.3-0.4	9788
0.4-0.5	8060
0.5-0.6	4343
0.6-0.7	5366
0.7-0.8	5115
0.8-0.85	1602
0.85-0.9	1030
0.9-0.95	362
0.95-1	175

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43211
1.0	High Similarity	NPC49344
1.0	High Similarity	NPC237435
1.0	High Similarity	NPC115760
1.0	High Similarity	NPC135277
1.0	High Similarity	NPC101191
0.9939	High Similarity	NPC198324
0.9939	High Similarity	NPC472385
0.9877	High Similarity	NPC477848
0.9877	High Similarity	NPC264735
0.9817	High Similarity	NPC211532
0.9817	High Similarity	NPC268533
0.9817	High Similarity	NPC233994
0.9816	High Similarity	NPC4390
0.9816	High Similarity	NPC101026
0.9816	High Similarity	NPC24043
0.9816	High Similarity	NPC21666
0.9816	High Similarity	NPC169977
0.9816	High Similarity	NPC42773
0.9816	High Similarity	NPC45522
0.9815	High Similarity	NPC20505
0.9815	High Similarity	NPC155763
0.9815	High Similarity	NPC282987
0.9815	High Similarity	NPC245014
0.9815	High Similarity	NPC235260
0.9815	High Similarity	NPC84265
0.9759	High Similarity	NPC222674
0.9755	High Similarity	NPC254540
0.9755	High Similarity	NPC211594
0.9755	High Similarity	NPC476405
0.9755	High Similarity	NPC117260
0.9755	High Similarity	NPC172807
0.9755	High Similarity	NPC175107
0.9755	High Similarity	NPC190003
0.9755	High Similarity	NPC153755
0.9753	High Similarity	NPC138927
0.9701	High Similarity	NPC36138
0.9701	High Similarity	NPC107987
0.9701	High Similarity	NPC470446
0.9701	High Similarity	NPC470445
0.9701	High Similarity	NPC470447
0.9701	High Similarity	NPC470449
0.9697	High Similarity	NPC472382
0.9697	High Similarity	NPC472380
0.9697	High Similarity	NPC8573
0.9697	High Similarity	NPC472384
0.9693	High Similarity	NPC244776
0.9693	High Similarity	NPC116864
0.9691	High Similarity	NPC58716
0.9691	High Similarity	NPC146792
0.9691	High Similarity	NPC45618
0.9643	High Similarity	NPC470451
0.9643	High Similarity	NPC470416
0.9643	High Similarity	NPC470455
0.9639	High Similarity	NPC168584
0.9636	High Similarity	NPC253685
0.9632	High Similarity	NPC475942
0.9632	High Similarity	NPC219904
0.9632	High Similarity	NPC93337
0.9632	High Similarity	NPC186807
0.9632	High Similarity	NPC225434
0.9632	High Similarity	NPC469931
0.9632	High Similarity	NPC45638
0.9632	High Similarity	NPC105025
0.9632	High Similarity	NPC223747
0.9632	High Similarity	NPC226294
0.9632	High Similarity	NPC201292
0.9632	High Similarity	NPC120099
0.9632	High Similarity	NPC203050
0.9632	High Similarity	NPC58053
0.963	High Similarity	NPC56077
0.963	High Similarity	NPC21100
0.963	High Similarity	NPC145038
0.963	High Similarity	NPC179950
0.963	High Similarity	NPC281131
0.963	High Similarity	NPC253662
0.963	High Similarity	NPC88789
0.963	High Similarity	NPC308404
0.963	High Similarity	NPC197285
0.963	High Similarity	NPC118284
0.963	High Similarity	NPC274618
0.963	High Similarity	NPC276222
0.9581	High Similarity	NPC241423
0.9581	High Similarity	NPC473682
0.9581	High Similarity	NPC473571
0.9581	High Similarity	NPC470443
0.9581	High Similarity	NPC126784
0.9581	High Similarity	NPC470444
0.9581	High Similarity	NPC110941
0.9578	High Similarity	NPC169733
0.9578	High Similarity	NPC472991
0.9578	High Similarity	NPC472992
0.9578	High Similarity	NPC65563
0.9578	High Similarity	NPC144097
0.9578	High Similarity	NPC61904
0.9578	High Similarity	NPC470949
0.9573	High Similarity	NPC206123
0.9571	High Similarity	NPC127546
0.9571	High Similarity	NPC265530
0.9571	High Similarity	NPC173637
0.9571	High Similarity	NPC317489
0.9571	High Similarity	NPC325555
0.9571	High Similarity	NPC223424
0.9571	High Similarity	NPC84362
0.9571	High Similarity	NPC52550
0.9571	High Similarity	NPC226304
0.9568	High Similarity	NPC240431
0.9568	High Similarity	NPC55786
0.9568	High Similarity	NPC277205
0.9568	High Similarity	NPC19388
0.9524	High Similarity	NPC473071
0.9524	High Similarity	NPC473073
0.9521	High Similarity	NPC113836
0.9521	High Similarity	NPC253521
0.9521	High Similarity	NPC173837
0.9521	High Similarity	NPC35167
0.9521	High Similarity	NPC217520
0.9521	High Similarity	NPC37668
0.9521	High Similarity	NPC139571
0.9518	High Similarity	NPC34267
0.9518	High Similarity	NPC223426
0.9518	High Similarity	NPC81042
0.9518	High Similarity	NPC214621
0.9515	High Similarity	NPC205076
0.9515	High Similarity	NPC48773
0.9515	High Similarity	NPC60735
0.9515	High Similarity	NPC3583
0.9515	High Similarity	NPC307518
0.9515	High Similarity	NPC26230
0.9515	High Similarity	NPC259152
0.9515	High Similarity	NPC472386
0.9512	High Similarity	NPC471457
0.9512	High Similarity	NPC112755
0.9512	High Similarity	NPC170675
0.9509	High Similarity	NPC135599
0.9509	High Similarity	NPC328940
0.9509	High Similarity	NPC113968
0.9509	High Similarity	NPC277174
0.9509	High Similarity	NPC73855
0.9506	High Similarity	NPC270335
0.9506	High Similarity	NPC191306
0.9467	High Similarity	NPC473072
0.9461	High Similarity	NPC89127
0.9461	High Similarity	NPC296018
0.9461	High Similarity	NPC471669
0.9461	High Similarity	NPC154741
0.9458	High Similarity	NPC204693
0.9455	High Similarity	NPC204937
0.9455	High Similarity	NPC149011
0.9455	High Similarity	NPC254855
0.9455	High Similarity	NPC224462
0.9455	High Similarity	NPC29958
0.9455	High Similarity	NPC72249
0.9455	High Similarity	NPC21190
0.9455	High Similarity	NPC22195
0.9455	High Similarity	NPC95866
0.9455	High Similarity	NPC259896
0.9455	High Similarity	NPC136042
0.9455	High Similarity	NPC34287
0.9455	High Similarity	NPC285197
0.9455	High Similarity	NPC183357
0.9455	High Similarity	NPC67326
0.9455	High Similarity	NPC105511
0.9455	High Similarity	NPC156869
0.9455	High Similarity	NPC471416
0.9455	High Similarity	NPC255157
0.9451	High Similarity	NPC92565
0.9451	High Similarity	NPC116745
0.9451	High Similarity	NPC160156
0.9448	High Similarity	NPC311830
0.9448	High Similarity	NPC22832
0.9444	High Similarity	NPC77660
0.9444	High Similarity	NPC189142
0.9412	High Similarity	NPC148710
0.9405	High Similarity	NPC476773
0.9405	High Similarity	NPC293626
0.9405	High Similarity	NPC196127
0.9405	High Similarity	NPC476619
0.9405	High Similarity	NPC476622
0.9405	High Similarity	NPC477895
0.9405	High Similarity	NPC217387
0.9405	High Similarity	NPC476621
0.9405	High Similarity	NPC476623
0.9405	High Similarity	NPC267680
0.9405	High Similarity	NPC476618
0.9405	High Similarity	NPC258044
0.9405	High Similarity	NPC476620
0.9401	High Similarity	NPC476472
0.9401	High Similarity	NPC16194
0.9401	High Similarity	NPC472607
0.9401	High Similarity	NPC19108
0.9401	High Similarity	NPC294815
0.9401	High Similarity	NPC473327
0.9401	High Similarity	NPC220173
0.9398	High Similarity	NPC176740
0.9398	High Similarity	NPC134532
0.9398	High Similarity	NPC33054
0.9398	High Similarity	NPC155877
0.9398	High Similarity	NPC203259
0.9398	High Similarity	NPC471725

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 NPC210094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	963
0.2-0.3	2082
0.3-0.4	2650
0.4-0.5	1744
0.5-0.6	873
0.6-0.7	273
0.7-0.8	120
0.8-0.85	16
0.85-0.9	15
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4338	Clinical (unspecified phase)
0.9398	High Similarity	NPD6797	Phase 2
0.9341	High Similarity	NPD7251	Discontinued
0.9286	High Similarity	NPD7808	Phase 3
0.9277	High Similarity	NPD7054	Approved
0.9222	High Similarity	NPD7472	Approved
0.9217	High Similarity	NPD3818	Discontinued
0.9107	High Similarity	NPD7074	Phase 3
0.8963	High Similarity	NPD4381	Clinical (unspecified phase)
0.8957	High Similarity	NPD3817	Phase 2
0.8896	High Similarity	NPD2801	Approved
0.8869	High Similarity	NPD6168	Clinical (unspecified phase)
0.8869	High Similarity	NPD6167	Clinical (unspecified phase)
0.8869	High Similarity	NPD6166	Phase 2
0.8841	High Similarity	NPD5402	Approved
0.8824	High Similarity	NPD7804	Clinical (unspecified phase)
0.872	High Similarity	NPD1934	Approved
0.8675	High Similarity	NPD3882	Suspended
0.8675	High Similarity	NPD4868	Clinical (unspecified phase)
0.858	High Similarity	NPD1512	Approved
0.8554	High Similarity	NPD2393	Clinical (unspecified phase)
0.8512	High Similarity	NPD7075	Discontinued
0.8506	High Similarity	NPD7993	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD1653	Approved
0.8457	Intermediate Similarity	NPD1511	Approved
0.8415	Intermediate Similarity	NPD5403	Approved
0.8383	Intermediate Similarity	NPD6801	Discontinued
0.8373	Intermediate Similarity	NPD4380	Phase 2
0.8343	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5401	Approved
0.8249	Intermediate Similarity	NPD6559	Discontinued
0.8232	Intermediate Similarity	NPD6799	Approved
0.8198	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8125	Intermediate Similarity	NPD3751	Discontinued
0.8118	Intermediate Similarity	NPD1465	Phase 2
0.8103	Intermediate Similarity	NPD3787	Discontinued
0.8072	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD7685	Pre-registration
0.8	Intermediate Similarity	NPD6190	Approved
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7975	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7473	Discontinued
0.7955	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1549	Phase 2
0.7921	Intermediate Similarity	NPD7228	Approved
0.7907	Intermediate Similarity	NPD7819	Suspended
0.7906	Intermediate Similarity	NPD7435	Discontinued
0.7895	Intermediate Similarity	NPD7411	Suspended
0.787	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD8312	Approved
0.7857	Intermediate Similarity	NPD8313	Approved
0.7841	Intermediate Similarity	NPD1247	Approved
0.7841	Intermediate Similarity	NPD7199	Phase 2
0.7829	Intermediate Similarity	NPD6234	Discontinued
0.7829	Intermediate Similarity	NPD919	Approved
0.7759	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD6780	Approved
0.7749	Intermediate Similarity	NPD6782	Approved
0.7749	Intermediate Similarity	NPD6778	Approved
0.7749	Intermediate Similarity	NPD6779	Approved
0.7749	Intermediate Similarity	NPD6781	Approved
0.7749	Intermediate Similarity	NPD6777	Approved
0.7749	Intermediate Similarity	NPD6776	Approved
0.7746	Intermediate Similarity	NPD37	Approved
0.7744	Intermediate Similarity	NPD1510	Phase 2
0.7725	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4966	Approved
0.7714	Intermediate Similarity	NPD4967	Phase 2
0.7714	Intermediate Similarity	NPD4965	Approved
0.7697	Intermediate Similarity	NPD2796	Approved
0.7665	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7874	Approved
0.7651	Intermediate Similarity	NPD7266	Discontinued
0.7647	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6959	Discontinued
0.7619	Intermediate Similarity	NPD3750	Approved
0.7611	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1613	Approved
0.7607	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3749	Approved
0.7561	Intermediate Similarity	NPD1933	Approved
0.7561	Intermediate Similarity	NPD230	Phase 1
0.7556	Intermediate Similarity	NPD3926	Phase 2
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
0.7525	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7487	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD6535	Approved
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7475	Intermediate Similarity	NPD7701	Phase 2
0.7459	Intermediate Similarity	NPD7240	Approved
0.7455	Intermediate Similarity	NPD447	Suspended
0.7424	Intermediate Similarity	NPD7584	Approved
0.7416	Intermediate Similarity	NPD7768	Phase 2
0.7412	Intermediate Similarity	NPD4628	Phase 3
0.7394	Intermediate Similarity	NPD1240	Approved
0.7378	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7700	Phase 2
0.7371	Intermediate Similarity	NPD7699	Phase 2
0.7363	Intermediate Similarity	NPD7801	Approved
0.7362	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD8150	Discontinued
0.7354	Intermediate Similarity	NPD8434	Phase 2
0.7341	Intermediate Similarity	NPD2534	Approved
0.7341	Intermediate Similarity	NPD2532	Approved
0.7341	Intermediate Similarity	NPD2533	Approved
0.7333	Intermediate Similarity	NPD6233	Phase 2
0.7323	Intermediate Similarity	NPD8320	Phase 1
0.7323	Intermediate Similarity	NPD8319	Approved
0.7321	Intermediate Similarity	NPD3748	Approved
0.7321	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3027	Phase 3
0.731	Intermediate Similarity	NPD6823	Phase 2
0.7305	Intermediate Similarity	NPD1607	Approved
0.7301	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD920	Approved
0.7251	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5953	Discontinued
0.7214	Intermediate Similarity	NPD7585	Approved
0.7175	Intermediate Similarity	NPD3226	Approved
0.7169	Intermediate Similarity	NPD2313	Discontinued
0.7169	Intermediate Similarity	NPD6798	Discontinued
0.7164	Intermediate Similarity	NPD7583	Approved
0.7157	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7033	Discontinued
0.7112	Intermediate Similarity	NPD7286	Phase 2
0.71	Intermediate Similarity	NPD7680	Approved
0.7079	Intermediate Similarity	NPD7458	Discontinued
0.7077	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6212	Phase 3
0.7077	Intermediate Similarity	NPD6213	Phase 3
0.7073	Intermediate Similarity	NPD1203	Approved
0.7072	Intermediate Similarity	NPD5353	Approved
0.7052	Intermediate Similarity	NPD1652	Phase 2
0.7052	Intermediate Similarity	NPD1243	Approved
0.7052	Intermediate Similarity	NPD2800	Approved
0.7048	Intermediate Similarity	NPD6832	Phase 2
0.7041	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD1091	Approved
0.7035	Intermediate Similarity	NPD2346	Discontinued
0.7018	Intermediate Similarity	NPD2799	Discontinued
0.6994	Remote Similarity	NPD9269	Phase 2
0.6989	Remote Similarity	NPD5242	Approved
0.6988	Remote Similarity	NPD9494	Approved
0.6983	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD5005	Approved
0.6965	Remote Similarity	NPD5006	Approved
0.6963	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7549	Discontinued
0.6954	Remote Similarity	NPD4360	Phase 2
0.6954	Remote Similarity	NPD6674	Discontinued
0.6954	Remote Similarity	NPD4363	Phase 3
0.6946	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5124	Phase 1
0.6941	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5711	Approved
0.6935	Remote Similarity	NPD5710	Approved
0.6914	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3225	Approved
0.6906	Remote Similarity	NPD6385	Approved
0.6906	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6386	Approved
0.6891	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4060	Phase 1
0.6882	Remote Similarity	NPD8127	Discontinued
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6864	Remote Similarity	NPD3268	Approved
0.685	Remote Similarity	NPD4420	Approved
0.6848	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4908	Phase 1
0.6842	Remote Similarity	NPD4340	Discontinued
0.6842	Remote Similarity	NPD7930	Approved
0.6839	Remote Similarity	NPD2344	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