NPASS Compound

Structure

CID170204 OpenBabel06191715542D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 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 -5.1962 0.0000 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 1.7321 -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 -3.4641 0.0000 0.0000 C 0 0 2 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 -4.3301 -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 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 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 2.5981 -0.5000 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 -0.0000 -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 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 3 4 1 0 0 0 0 3 8 2 0 0 0 0 4 22 1 0 0 0 0 5 17 1 0 0 0 0 6 9 2 0 0 0 0 6 23 1 0 0 0 0 7 2 1 1 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 9 14 1 0 0 0 0 10 5 1 6 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 16 1 0 0 0 0 13 20 1 1 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 25 1 6 0 0 0 16 24 1 0 0 0 0 16 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.11
Volume:	328.189
LogP:	-0.315
LogD:	-0.293
LogS:	-1.311
# Rotatable Bonds:	4
TPSA:	134.91
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	4.811
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.652
MDCK Permeability:	3.975113213527948e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.952
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	39.78767395019531%
Volume Distribution (VD):	0.845
Pgp-substrate:	51.10758590698242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	1.388
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.148
AMES Toxicity:	0.369
Rat Oral Acute Toxicity:	0.284
Maximum Recommended Daily Dose:	0.224
Skin Sensitization:	0.223
Carcinogencity:	0.907
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC170204

Natural Product ID:	NPC170204
*Common Name:**	Gentiopicroside
IUPAC Name:	(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
Synonyms:	Gentiopicroside
Standard InCHIKey:	DUAGQYUORDTXOR-GPQRQXLASA-N
Standard InCHI:	InChI=1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
SMILES:	C=C[C@@H]1C2=CCOC(=O)C2=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508320
PubChem CID:	88708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10705751]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	seed	n.a.	PMID[12822897]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[16335823]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	roots	n.a.	n.a.	PMID[17375953]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17404979]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[18064621]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18064621]
NPO1905	Fagraea fragrans	Species	Gentianaceae	Eukaryota	bark and leaves	Koh Kong Province, Cambodia	2005-DEC	PMID[19053508]
NPO1215	Cephalaria kotschyi	Species	n.a.	n.a.	Roots	n.a.	n.a.	PMID[20055434]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20813533]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[22233034]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23599008]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[24257774]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[26129938]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562611]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[29140705]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33052051]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[9397205]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25975	Radix gentianae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1905	Fagraea fragrans	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20836	Gentiana manshurica	Species	Gentianaceae	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
Others	41
Potency	5

Activity Type	# Activity
Cell Line	3
Individual Protein	3
Organism	8
Others	32
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1161	Cell Line	CHO	Cricetulus griseus	Activity	=	95.0	%	PMID[514811]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[514812]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	891.3	nM	PMID[514812]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[514812]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	<=	64.0	%	PMID[514815]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	<=	72.0	%	PMID[514815]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	50.0	ug.mL-1	PMID[514810]
NPT27	Others	Unspecified		Activity	=	19.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	22.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	26.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	32.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	29.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	28.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	31.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	117.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	135.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	138.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	136.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	119.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	116.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	140.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	368.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	378.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	395.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	392.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	376.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	385.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	413.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	188.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	174.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	180.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	274.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	186.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	178.0	n.a.	PMID[514811]
NPT27	Others	Unspecified		Activity	=	173.0	n.a.	PMID[514811]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[514812]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[514812]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	0.6	%	PMID[514813]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	2.1	%	PMID[514813]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	4.88	%	PMID[514814]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	9.468	%	PMID[514816]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.02	%	PMID[514817]

☑ 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 NPC170204 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	228
0.1-0.2	1326
0.2-0.3	4762
0.3-0.4	9704
0.4-0.5	15742
0.5-0.6	8674
0.6-0.7	1965
0.7-0.8	243
0.8-0.85	25
0.85-0.9	26
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9121	High Similarity	NPC61201
0.8901	High Similarity	NPC6414
0.8901	High Similarity	NPC307699
0.8901	High Similarity	NPC303451
0.8804	High Similarity	NPC472124
0.8804	High Similarity	NPC472125
0.8804	High Similarity	NPC472126
0.8723	High Similarity	NPC469543
0.871	High Similarity	NPC320552
0.8696	High Similarity	NPC327253
0.8696	High Similarity	NPC117596
0.8571	High Similarity	NPC13171
0.8571	High Similarity	NPC195510
0.8571	High Similarity	NPC222062
0.8557	High Similarity	NPC255677
0.8557	High Similarity	NPC306344
0.8557	High Similarity	NPC22149
0.8526	High Similarity	NPC101051
0.8485	Intermediate Similarity	NPC284929
0.8485	Intermediate Similarity	NPC197541
0.8485	Intermediate Similarity	NPC118761
0.8485	Intermediate Similarity	NPC267869
0.8485	Intermediate Similarity	NPC234304
0.8469	Intermediate Similarity	NPC28304
0.8469	Intermediate Similarity	NPC298255
0.8438	Intermediate Similarity	NPC241911
0.8384	Intermediate Similarity	NPC261117
0.8384	Intermediate Similarity	NPC250545
0.8384	Intermediate Similarity	NPC310804
0.8298	Intermediate Similarity	NPC231710
0.8298	Intermediate Similarity	NPC270908
0.8298	Intermediate Similarity	NPC216826
0.8298	Intermediate Similarity	NPC65665
0.8298	Intermediate Similarity	NPC470573
0.8298	Intermediate Similarity	NPC120021
0.8229	Intermediate Similarity	NPC294293
0.8218	Intermediate Similarity	NPC86095
0.8152	Intermediate Similarity	NPC470124
0.8119	Intermediate Similarity	NPC197736
0.8058	Intermediate Similarity	NPC254538
0.8058	Intermediate Similarity	NPC474285
0.8043	Intermediate Similarity	NPC475035
0.8043	Intermediate Similarity	NPC266718
0.8022	Intermediate Similarity	NPC251026
0.8	Intermediate Similarity	NPC285588
0.7979	Intermediate Similarity	NPC118077
0.7979	Intermediate Similarity	NPC475186
0.7979	Intermediate Similarity	NPC475037
0.7935	Intermediate Similarity	NPC142111
0.7935	Intermediate Similarity	NPC473315
0.7917	Intermediate Similarity	NPC473311
0.7895	Intermediate Similarity	NPC470137
0.7879	Intermediate Similarity	NPC306041
0.7849	Intermediate Similarity	NPC473308
0.7843	Intermediate Similarity	NPC471599
0.7835	Intermediate Similarity	NPC110072
0.7835	Intermediate Similarity	NPC9447
0.7822	Intermediate Similarity	NPC244878
0.781	Intermediate Similarity	NPC473807
0.7766	Intermediate Similarity	NPC475034
0.7755	Intermediate Similarity	NPC472196
0.7755	Intermediate Similarity	NPC238090
0.7755	Intermediate Similarity	NPC472195
0.7745	Intermediate Similarity	NPC471637
0.7745	Intermediate Similarity	NPC154132
0.7745	Intermediate Similarity	NPC219038
0.7745	Intermediate Similarity	NPC475157
0.7745	Intermediate Similarity	NPC20673
0.7745	Intermediate Similarity	NPC475655
0.7745	Intermediate Similarity	NPC57586
0.7745	Intermediate Similarity	NPC2313
0.7723	Intermediate Similarity	NPC151093
0.7708	Intermediate Similarity	NPC137368
0.7684	Intermediate Similarity	NPC208473
0.7677	Intermediate Similarity	NPC159698
0.7677	Intermediate Similarity	NPC256368
0.767	Intermediate Similarity	NPC201191
0.7653	Intermediate Similarity	NPC477749
0.7624	Intermediate Similarity	NPC475332
0.7609	Intermediate Similarity	NPC163362
0.7609	Intermediate Similarity	NPC127295
0.7576	Intermediate Similarity	NPC280390
0.7573	Intermediate Similarity	NPC98859
0.7573	Intermediate Similarity	NPC4637
0.757	Intermediate Similarity	NPC133625
0.7549	Intermediate Similarity	NPC40182
0.7549	Intermediate Similarity	NPC198422
0.7527	Intermediate Similarity	NPC469469
0.7525	Intermediate Similarity	NPC173329
0.7525	Intermediate Similarity	NPC161293
0.7525	Intermediate Similarity	NPC288350
0.7524	Intermediate Similarity	NPC469869
0.75	Intermediate Similarity	NPC25701
0.75	Intermediate Similarity	NPC2003
0.7477	Intermediate Similarity	NPC193765
0.7477	Intermediate Similarity	NPC472507
0.7475	Intermediate Similarity	NPC472197
0.7475	Intermediate Similarity	NPC472199
0.7474	Intermediate Similarity	NPC220167
0.7474	Intermediate Similarity	NPC136699
0.7453	Intermediate Similarity	NPC315070
0.7453	Intermediate Similarity	NPC41681
0.7453	Intermediate Similarity	NPC82251
0.7451	Intermediate Similarity	NPC472290
0.7449	Intermediate Similarity	NPC477748
0.7429	Intermediate Similarity	NPC475928
0.74	Intermediate Similarity	NPC159092
0.74	Intermediate Similarity	NPC320089
0.7391	Intermediate Similarity	NPC133377
0.7379	Intermediate Similarity	NPC473307
0.7379	Intermediate Similarity	NPC203627
0.7374	Intermediate Similarity	NPC274075
0.7374	Intermediate Similarity	NPC202886
0.7374	Intermediate Similarity	NPC475995
0.7374	Intermediate Similarity	NPC177668
0.7374	Intermediate Similarity	NPC118078
0.7374	Intermediate Similarity	NPC474098
0.7363	Intermediate Similarity	NPC229655
0.7353	Intermediate Similarity	NPC54731
0.7353	Intermediate Similarity	NPC255410
0.7347	Intermediate Similarity	NPC473151
0.7347	Intermediate Similarity	NPC471756
0.7347	Intermediate Similarity	NPC471755
0.7339	Intermediate Similarity	NPC472508
0.7333	Intermediate Similarity	NPC106668
0.7333	Intermediate Similarity	NPC177013
0.7333	Intermediate Similarity	NPC474730
0.7333	Intermediate Similarity	NPC35185
0.7333	Intermediate Similarity	NPC4899
0.7327	Intermediate Similarity	NPC472198
0.7327	Intermediate Similarity	NPC71589
0.732	Intermediate Similarity	NPC47220
0.732	Intermediate Similarity	NPC186332
0.7315	Intermediate Similarity	NPC392
0.7315	Intermediate Similarity	NPC177524
0.7315	Intermediate Similarity	NPC219900
0.7312	Intermediate Similarity	NPC321728
0.73	Intermediate Similarity	NPC114172
0.73	Intermediate Similarity	NPC472010
0.73	Intermediate Similarity	NPC206679
0.73	Intermediate Similarity	NPC471324
0.729	Intermediate Similarity	NPC476738
0.729	Intermediate Similarity	NPC170432
0.729	Intermediate Similarity	NPC476740
0.7283	Intermediate Similarity	NPC110813
0.7282	Intermediate Similarity	NPC120299
0.7282	Intermediate Similarity	NPC153559
0.7273	Intermediate Similarity	NPC133450
0.7264	Intermediate Similarity	NPC27687
0.7264	Intermediate Similarity	NPC309398
0.7264	Intermediate Similarity	NPC37240
0.7255	Intermediate Similarity	NPC300710
0.7255	Intermediate Similarity	NPC241407
0.7255	Intermediate Similarity	NPC291709
0.7245	Intermediate Similarity	NPC313658
0.7245	Intermediate Similarity	NPC316138
0.7245	Intermediate Similarity	NPC45409
0.7245	Intermediate Similarity	NPC142583
0.7238	Intermediate Similarity	NPC198992
0.7228	Intermediate Similarity	NPC109406
0.7222	Intermediate Similarity	NPC80338
0.7222	Intermediate Similarity	NPC132938
0.7222	Intermediate Similarity	NPC197813
0.7222	Intermediate Similarity	NPC148270
0.7216	Intermediate Similarity	NPC477747
0.7216	Intermediate Similarity	NPC477746
0.7212	Intermediate Similarity	NPC307517
0.7212	Intermediate Similarity	NPC475653
0.7212	Intermediate Similarity	NPC81483
0.7212	Intermediate Similarity	NPC124181
0.7212	Intermediate Similarity	NPC472015
0.7212	Intermediate Similarity	NPC169468
0.7212	Intermediate Similarity	NPC61630
0.72	Intermediate Similarity	NPC3952
0.7193	Intermediate Similarity	NPC13710
0.7188	Intermediate Similarity	NPC44261
0.7184	Intermediate Similarity	NPC143446
0.7182	Intermediate Similarity	NPC83005
0.7174	Intermediate Similarity	NPC326661
0.717	Intermediate Similarity	NPC473596
0.7158	Intermediate Similarity	NPC280367
0.7157	Intermediate Similarity	NPC477345
0.7157	Intermediate Similarity	NPC477348
0.7157	Intermediate Similarity	NPC238264
0.7156	Intermediate Similarity	NPC327106
0.7155	Intermediate Similarity	NPC470829
0.7155	Intermediate Similarity	NPC170880
0.7155	Intermediate Similarity	NPC473228
0.7143	Intermediate Similarity	NPC472173
0.7143	Intermediate Similarity	NPC324667
0.7143	Intermediate Similarity	NPC475053
0.7143	Intermediate Similarity	NPC107654
0.713	Intermediate Similarity	NPC219656
0.7129	Intermediate Similarity	NPC470373
0.7129	Intermediate Similarity	NPC476075
0.7129	Intermediate Similarity	NPC470379
0.7129	Intermediate Similarity	NPC476084
0.7128	Intermediate Similarity	NPC179933
0.7128	Intermediate Similarity	NPC323472
0.7115	Intermediate Similarity	NPC474194

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 NPC170204 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1529
0.2-0.3	3919
0.3-0.4	2355
0.4-0.5	926
0.5-0.6	188
0.6-0.7	37
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7549	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6686	Approved
0.72	Intermediate Similarity	NPD7838	Discovery
0.72	Intermediate Similarity	NPD46	Approved
0.72	Intermediate Similarity	NPD6698	Approved
0.7155	Intermediate Similarity	NPD8513	Phase 3
0.7009	Intermediate Similarity	NPD8517	Approved
0.7009	Intermediate Similarity	NPD8515	Approved
0.7009	Intermediate Similarity	NPD8516	Approved
0.7009	Intermediate Similarity	NPD7503	Approved
0.6964	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7983	Approved
0.6891	Remote Similarity	NPD7829	Approved
0.6891	Remote Similarity	NPD7830	Approved
0.661	Remote Similarity	NPD7641	Discontinued
0.6583	Remote Similarity	NPD8444	Approved
0.6542	Remote Similarity	NPD7839	Suspended
0.6504	Remote Similarity	NPD8451	Approved
0.6452	Remote Similarity	NPD8074	Phase 3
0.6452	Remote Similarity	NPD8448	Approved
0.6429	Remote Similarity	NPD8392	Approved
0.6429	Remote Similarity	NPD8391	Approved
0.6429	Remote Similarity	NPD8390	Approved
0.6371	Remote Similarity	NPD7507	Approved
0.6341	Remote Similarity	NPD7642	Approved
0.6337	Remote Similarity	NPD6110	Phase 1
0.6325	Remote Similarity	NPD6053	Discontinued
0.6311	Remote Similarity	NPD4249	Approved
0.629	Remote Similarity	NPD8299	Approved
0.629	Remote Similarity	NPD8342	Approved
0.629	Remote Similarity	NPD8341	Approved
0.629	Remote Similarity	NPD8340	Approved
0.6275	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5778	Approved
0.6262	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD4250	Approved
0.622	Remote Similarity	NPD7319	Approved
0.6198	Remote Similarity	NPD7328	Approved
0.6198	Remote Similarity	NPD7327	Approved
0.6179	Remote Similarity	NPD8033	Approved
0.6174	Remote Similarity	NPD6412	Phase 2
0.6161	Remote Similarity	NPD5344	Discontinued
0.6148	Remote Similarity	NPD7516	Approved
0.6132	Remote Similarity	NPD6101	Approved
0.6132	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8294	Approved
0.6098	Remote Similarity	NPD8377	Approved
0.6071	Remote Similarity	NPD6648	Approved
0.6053	Remote Similarity	NPD1407	Approved
0.6048	Remote Similarity	NPD8378	Approved
0.6048	Remote Similarity	NPD8296	Approved
0.6048	Remote Similarity	NPD8380	Approved
0.6048	Remote Similarity	NPD8335	Approved
0.6048	Remote Similarity	NPD8379	Approved
0.6034	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7637	Suspended
0.6019	Remote Similarity	NPD6411	Approved
0.6019	Remote Similarity	NPD7154	Phase 3
0.6015	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8133	Approved
0.5984	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4225	Approved
0.5952	Remote Similarity	NPD8328	Phase 3
0.5932	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6371	Approved
0.5882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD7260	Phase 2
0.5873	Remote Similarity	NPD8080	Discontinued
0.5854	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7638	Approved
0.5794	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD897	Approved
0.5789	Remote Similarity	NPD7639	Approved
0.5789	Remote Similarity	NPD7640	Approved
0.5789	Remote Similarity	NPD898	Approved
0.5789	Remote Similarity	NPD896	Approved
0.5769	Remote Similarity	NPD5209	Approved
0.5755	Remote Similarity	NPD7266	Discontinued
0.5743	Remote Similarity	NPD4756	Discovery
0.5736	Remote Similarity	NPD8273	Phase 1
0.5726	Remote Similarity	NPD7115	Discovery
0.5726	Remote Similarity	NPD7500	Approved
0.5714	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4268	Approved
0.5686	Remote Similarity	NPD4271	Approved
0.5667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD969	Suspended
0.5652	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD7736	Approved
0.5636	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7329	Approved
0.5625	Remote Similarity	NPD6370	Approved
0.5625	Remote Similarity	NPD5282	Discontinued
0.562	Remote Similarity	NPD6421	Discontinued
0.56	Remote Similarity	NPD6009	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