NPASS Compound

Natural Product: NPC57601

Natural Product ID	NPC57601
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	7-Hydroxyflavone
IUPAC Name	7-hydroxy-2-phenylchromen-4-one
Synonyms	NSC-94258
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL276915
PubChem CID	5281894
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 28 30 0 0 0 0 0 0 0 0999 V2000 -4.5327 -0.7458 2.4225 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6970 -0.3643 1.3683 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2683 0.1311 0.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4840 0.5164 -0.8453 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1170 0.4022 -0.7371 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4966 -0.0834 0.3887 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3287 -0.4674 1.4485 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2024 -0.1922 0.4926 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6383 0.1545 -0.4759 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0626 0.6454 -1.6205 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3006 0.7799 -1.7794 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8505 1.2257 -2.8155 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0825 0.0004 -0.2787 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5526 -0.5085 0.9243 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9079 -0.6545 1.1128 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8349 -0.3154 0.1522 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3451 0.1873 -1.0328 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9909 0.3414 -1.2417 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4363 -1.1934 2.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3670 0.2033 0.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9192 0.9032 -1.7495 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8853 -0.8537 2.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7072 0.9452 -2.4474 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8666 -0.7857 1.7004 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3225 -1.0526 2.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9073 -0.4322 0.3045 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0095 0.4757 -1.8340 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6577 0.7374 -2.1818 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 9 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 7 2 1 0 18 13 1 0 11 5 1 0 1 19 1 0 3 20 1 0 4 21 1 0 7 22 1 0 10 23 1 0 14 24 1 0 15 25 1 0 16 26 1 0 17 27 1 0 18 28 1 0 M END

Standard InCHIKey	MQGPSCMMNJKMHQ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H
SMILES	Oc1ccc2c(c1)oc(cc2=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	238.06	Volume:	247.606 ? Van der Waals volume.
Dense:	0.961	LogP:	3.466 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.501 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.098 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	18.0
TPSA:	50.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.708	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.872	Fsp³:	0.0
MCE-18:	15.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.464	Fluc inhibitor:	0.995 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.956 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.583 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.87	Promiscuous compounds:	0.677

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862	MDCK Permeability:	-4.754
Pgp-inhibitor:	0.449	Pgp-substrate:	0.418
PAMPA:	0.298 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.213	30% Bioavailability (F30%):	0.81
50% Bioavailability (F50%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.245	MRP1:	0.869
Plasma Protein Binding (PPB):	98.046%	Volume Distribution (VD):	-0.25
Fu:	1.223% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.72
OATP1B3 inhibitor:	0.972	BCRP inhibitor:	0.907
BSEP inhibitor:	0.976

ADMET: Metabolism

CYP1A2-inhibitor:	0.966	CYP1A2-substrate:	0.707
CYP2C19-inhibitor:	0.387	CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.996	CYP2C9-substrate:	0.459
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.984
CYP3A4-inhibitor:	0.227	CYP3A4-substrate:	0.906
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.998
HLM stability:	0.548 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.371

Half-life (T1/2):

1.248

ADMET: Toxicity

hERG Blockers:	0.132	hERG Blockers (10um):	0.481
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.833
AMES Toxicity:	0.595	Rat Oral Acute Toxicity:	0.468
Maximum Recommended Daily Dose:	0.822	Skin Sensitization:	0.427
Carcinogencity:	0.821	Eye Corrosion:	0.396
Eye Irritation:	0.992	Respiratory Toxicity:	0.683
Drug-induced Neurotoxicity:	0.193	Ototoxicity:	0.063
Hematotoxicity:	0.134	Drug-induced Nephrotoxicity:	0.065
Genotoxicity:	0.987	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.158	Hek293 Cytotoxicity:	0.685
BCF:	1.216 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.217 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.92 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.639 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO19860	Jasminum sambac	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26555361]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31323754]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37513176]
NPO19470	Xanthorrhoea minor	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18385	Rabdosia parvifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19597	Populus sieboldi	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20782	Philodendron hederaceum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19860	Jasminum sambac	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20623	Dendrobium farmeri	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18625	Chlorocodon whitei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19860	Jasminum sambac	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19860	Jasminum sambac	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19860	Jasminum sambac	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20782	Philodendron hederaceum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19860	Jasminum sambac	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20623	Dendrobium farmeri	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19470	Xanthorrhoea minor	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19597	Populus sieboldi	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18385	Rabdosia parvifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18625	Chlorocodon whitei	n.a.	n.a.	n.a.	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	Organism Name	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	38
Inhibition	13
Ki	12
GABA ratio	1
pKi(uM)	2
Displacement	1
-Log IC50	1
Activity	31
EC150	2
Ratio IC50	3
Kd	2
Potency	5
T	3
Tm	4
Ratio	4
EC50	1
pID50	1
Emax	2
log10LT50	1
ED50	1
log(ratio)	1
ID50	2
Systolic blood pressure	1
Protection	1

Activity Type	# Activity
Individual protein	58
Cell line	8
Protein family	4
Lipid	7
Organism	22
Tissue	7
Others	20
Unchecked	1
Protein complex	2
Non-molecular	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1315	Individual protein	Adenosine A1 receptor	Rattus norvegicus	pKi(uM)	=	-0.48	n.a.	PMID[9438021]
NPT1316	Individual protein	Adenosine A2a receptor	Rattus norvegicus	pKi(uM)	=	-0.43	n.a.	PMID[9438021]
NPT1315	Individual protein	Adenosine A1 receptor	Rattus norvegicus	Ki	=	3030.0	nM	PMID[8576921]
NPT1316	Individual protein	Adenosine A2a receptor	Rattus norvegicus	Ki	=	2680.0	nM	PMID[8576921]
NPT218	Individual protein	Adenosine A3 receptor	Homo sapiens	Displacement	=	41.0	%	PMID[8576921]
NPT299	Individual protein	Androgen Receptor	Rattus norvegicus	IC50	>	42657.95	nM	PMID[16134935]
NPT1332	Individual protein	Fatty acid synthase	Plasmodium falciparum	IC50	=	20000.0	nM	PMID[16722653]
NPT1119	Individual protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	>	100000.0	nM	PMID[17869117]
NPT1139	Individual protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	IC50	>	100000.0	nM	PMID[17869117]
NPT1265	Individual protein	Serine/threonine-protein kinase PIM1	Homo sapiens	-Log IC50	=	-1.15	uM	PMID[17637507]
NPT13	Individual protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	=	80.0	ug.mL-1	PMID[1479375]
NPT1587	Individual protein	Estradiol 17-beta-dehydrogenase 1	Homo sapiens	Activity	=	16.0	%	PMID[18533708]
NPT1588	Individual protein	Estradiol 17-beta-dehydrogenase 2	Homo sapiens	Activity	=	23.1	%	PMID[18533708]
NPT1587	Individual protein	Estradiol 17-beta-dehydrogenase 1	Homo sapiens	IC50	=	5250.0	nM	PMID[18533708]
NPT1588	Individual protein	Estradiol 17-beta-dehydrogenase 2	Homo sapiens	IC50	>	20000.0	nM	PMID[18533708]
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	EC150	=	3.1	uM	PMID[19592245]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	EC150	=	3.1	uM	PMID[19592245]
NPT208	Individual protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	240.0	nM	PMID[20832301]
NPT1621	Individual protein	Calmodulin	Homo sapiens	IC50	=	37100.0	nM	PMID[21129983]
NPT1621	Individual protein	Calmodulin	Homo sapiens	Ratio IC50	=	0.54	n.a.	PMID[21129983]
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Ki	=	2240.0	nM	PMID[22487176]
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Ki	=	2320.0	nM	PMID[22487176]
NPT157	Individual protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT1270	Individual protein	Aldo-keto reductase family 1 member B10	Homo sapiens	Inhibition	=	19.0	%	PMID[26529431]
NPT1270	Individual protein	Aldo-keto reductase family 1 member B10	Homo sapiens	IC50	=	160000.0	nM	PMID[26529431]
NPT1270	Individual protein	Aldo-keto reductase family 1 member B10	Homo sapiens	IC50	=	8300.0	nM	PMID[26529431]
NPT1270	Individual protein	Aldo-keto reductase family 1 member B10	Homo sapiens	Ratio IC50	=	10.0	n.a.	PMID[26529431]
NPT1604	Individual protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	250.0	nM	PMID[28458135]
NPT2266	Individual protein	Fructose-1,6-bisphosphatase	Homo sapiens	Inhibition	<	20.0	%	PMID[32364726]
NPT3213	Individual protein	MAP kinase signal-integrating kinase 2	Homo sapiens	Inhibition	>	50.0	%	PMID[33026809]
NPT958	Individual protein	Estradiol 17-beta-dehydrogenase 3	Homo sapiens	IC50	=	66980.0	nM	PMID[16797984]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	246.04	nM	PMID[21236664]
NPT2731	Protein family	Monoamine oxidase	Homo sapiens	IC50	=	120.0	nM	PMID[11563931]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	-0.25	%	PMID[23062825]
NPT67	Individual protein	Cholinesterase	Equus caballus	IC50	>	100000.0	nM	PMID[24095756]
NPT41	Individual protein	Aldose reductase	Homo sapiens	IC50	=	12300.0	nM	PMID[26529431]
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	>	100000.0	nM	PMID[17869117]
NPT967	Individual protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	38000.0	nM	PMID[9461655]
NPT948	Individual protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	4920.0	nM	PMID[22487176]
NPT948	Individual protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	4850.0	nM	PMID[22487176]
NPT949	Individual protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	8400.0	nM	PMID[22487176]
NPT949	Individual protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	8510.0	nM	PMID[22487176]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	24.35	%	PMID[23062825]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	85000.0	nM	PMID[24095756]
NPT21750	Lipid	Lipid bilayer	n.a.	T	=	31.9	degrees C	PMID[24793879]
NPT21750	Lipid	Lipid bilayer	n.a.	T	=	31.8	degrees C	PMID[24793879]
NPT21750	Lipid	Lipid bilayer	n.a.	T	=	27.4	degrees C	PMID[24793879]
NPT21750	Lipid	Lipid bilayer	n.a.	Tm	=	40.7	degrees C	PMID[24793879]
NPT21750	Lipid	Lipid bilayer	n.a.	Tm	=	40.5	degrees C	PMID[24793879]
NPT21750	Lipid	Lipid bilayer	n.a.	Tm	=	40.4	degrees C	PMID[24793879]
NPT21750	Lipid	Lipid bilayer	n.a.	Tm	=	39.8	degrees C	PMID[24793879]
NPT711	Individual protein	Aldose reductase	Bos taurus	IC50	=	14650.0	nM	PMID[10354396]
NPT711	Individual protein	Aldose reductase	Bos taurus	IC50	=	45210.0	nM	PMID[10354396]
NPT581	Individual protein	Cyclooxygenase-2	Mus musculus	Inhibition	=	70.8	%	PMID[14980657]
NPT805	Protein complex	GABA-A receptor; anion channel	Rattus norvegicus	Ki	=	4200.0	nM	PMID[10543878]
NPT805	Protein complex	GABA-A receptor; anion channel	Rattus norvegicus	GABA ratio	=	1.14	n.a.	PMID[10543878]
NPT441	Individual protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	30.5	nM	PMID[20413308]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Kd	=	34673.69	nM	PMID[21723648]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Ki	=	3370.0	nM	PMID[22487176]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Ki	=	3430.0	nM	PMID[22487176]
NPT78	Individual protein	Beta amyloid A4 protein	Homo sapiens	Inhibition	=	27.2	%	PMID[24095756]
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	53.1	%	PMID[24368208]
NPT441	Individual protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	209.89	nM	PMID[28622580]
NPT441	Individual protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	1900.0	nM	PMID[35576701]
NPT52	Individual protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	IC50	=	2120.0	nM	PMID[34726055]
NPT52	Individual protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	Ki	=	3530.0	nM	PMID[34726055]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	17.1	%	PMID[21493073]
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	13.7	%	PMID[21493073]
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	12.2	%	PMID[21493073]
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	5.3	%	PMID[21493073]
NPT65	Cell line	HepG2	Homo sapiens	Activity	=	98.8	%	PMID[24793879]
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	26.6	%	PMID[24793879]
NPT111	Cell line	K562	Homo sapiens	Activity	=	22.3	%	PMID[24793879]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	65500.0	nM	PMID[16722653]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	pID50	=	5.456	n.a.	PMID[20696502]
NPT632	Tissue	Brain	Rattus norvegicus	Activity	=	0.42	nmol	PMID[22197671]
NPT632	Tissue	Brain	Rattus norvegicus	Activity	=	0.48	nmol	PMID[22197671]
NPT632	Tissue	Brain	Rattus norvegicus	Activity	=	0.91	nmol	PMID[22197671]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	DOI[10.6019/CHEMBL4651402]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	DOI[10.6019/CHEMBL4651402]
NPT28438	Unchecked	Unchecked	n.a.	log(ratio)	=	-0.41	n.a.	PMID[35576701]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[9461655]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	37800.0	nM	PMID[21129983]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	167040.0	nM	PMID[21129983]
NPT177	Tissue	Aorta	Rattus norvegicus	Emax	=	80.59	%	PMID[21129983]
NPT177	Tissue	Aorta	Rattus norvegicus	Emax	=	40.39	%	PMID[21129983]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Ratio	=	2.04	n.a.	PMID[22197671]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Ratio	=	2.52	n.a.	PMID[22197671]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Ratio	=	15.13	n.a.	PMID[22197671]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	log10LT50	=	2.029	n.a.	PMID[20415424]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	ED50	>	10.0	umol/cm2	PMID[12517100]
NPT29337	Protein family	Cytochrome P450	Homo sapiens	Inhibition	=	35.0	%	PMID[35576701]
NPT29337	Protein family	Cytochrome P450	Homo sapiens	Inhibition	<	15.0	%	PMID[35576701]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>=	100000.0	nM	PMID[17189684]
NPT1	Others	Radical scavenging activity	n.a.	Inhibition	=	2.8	%	DOI[10.1007/s00044-007-9060-5]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	24.2	ug.mL-1	PMID[24793879]
NPT2	Others	Unspecified	n.a.	Ratio	=	3.1	n.a.	PMID[10354396]
NPT2	Others	Unspecified	n.a.	IC50	=	146500.0	nM	PMID[17624791]
NPT2	Others	Unspecified	n.a.	IC50	=	80.0	ug.mL-1	PMID[1800636]
NPT2	Others	Unspecified	n.a.	Activity	=	54.2	%	PMID[2959755]
NPT2	Others	Unspecified	n.a.	Activity	=	91.3	%	PMID[2959755]
NPT2	Others	Unspecified	n.a.	Activity	=	95.1	%	PMID[2959755]
NPT2	Others	Unspecified	n.a.	IC50	=	1400.0	nM	PMID[2959755]
NPT35	Others	n.a.	n.a.	Activity	=	5.3	mg/L	PMID[19944611]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Inhibition	<	40.0	%	PMID[23871908]
NPT2	Others	Unspecified	n.a.	IC50	=	33000.0	nM	PMID[23871908]
NPT2	Others	Unspecified	n.a.	Ratio IC50	>	1.2	n.a.	PMID[24095756]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	5011.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	6309.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3162.3	nM	PubChem BioAssay data set
NPT22036	Cell line	HL	Homo sapiens	Activity	=	71.1	%	PMID[29043803]
NPT2	Others	Unspecified	n.a.	ID50	>	419.7	uM	PMID[1378087]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Systolic blood pressure	=	217.0	n.a.	PMID[2909730]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Protection	=	75.0	%	PMID[8523407]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	20.4	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	36.0	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	35.5	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	8.8	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-12.18	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-10.03	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-12.69	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-12.79	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-4.81	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	7.39	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-6.19	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	5.05	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	38.5	%	PMID[20346546]

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference
-	Spodoptera frugiperda	LT50	=	106.94	hr	PMID[20415424]

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC57601 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	35496
0.1-0.2	12107
0.2-0.3	1697
0.3-0.4	413
0.4-0.5	113
0.5-0.6	16
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8372	Intermediate Similarity	NPC172262
0.7609	Intermediate Similarity	NPC70136
0.7234	Intermediate Similarity	NPC603556
0.72	Intermediate Similarity	NPC266597
0.6667	Remote Similarity	NPC299379
0.6481	Remote Similarity	NPC115323
0.6481	Remote Similarity	NPC604422
0.6481	Remote Similarity	NPC607642
0.6458	Remote Similarity	NPC168803
0.6327	Remote Similarity	NPC22783
0.6327	Remote Similarity	NPC78540
0.6304	Remote Similarity	NPC32298
0.6	Remote Similarity	NPC12367
0.5932	Remote Similarity	NPC261227
0.58	Remote Similarity	NPC197425
0.5741	Remote Similarity	NPC194281
0.5686	Remote Similarity	NPC239312
0.5472	Remote Similarity	NPC284424
0.5385	Remote Similarity	NPC50898
0.5385	Remote Similarity	NPC51443
0.5385	Remote Similarity	NPC118726
0.537	Remote Similarity	NPC201395
0.5357	Remote Similarity	NPC250266
0.5283	Remote Similarity	NPC74881
0.5283	Remote Similarity	NPC193805
0.5273	Remote Similarity	NPC293183
0.5179	Remote Similarity	NPC482122
0.5179	Remote Similarity	NPC609062
0.5088	Remote Similarity	NPC602791

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC57601 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6267
0.1-0.2	2778
0.2-0.3	93
0.3-0.4	9
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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