NPASS Compound

Natural Product: NPC17525

Natural Product ID	NPC17525
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4,4'-Dihydroxychalcone
IUPAC Name	(E)-1,3-bis(4-hydroxyphenyl)prop-2-en-1-one
Synonyms	4',4-Dihydroxychalcone; 4,4'-Dihydroxychalcone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL145927
PubChem CID	5467477
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003474] Retrochalcones

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 30 31 0 0 0 0 0 0 0 0999 V2000 6.3605 1.0673 -0.2499 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0770 0.5608 -0.1171 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8686 -0.7819 0.1045 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6095 -1.3178 0.2410 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4629 -0.5124 0.1600 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6732 0.8262 -0.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9614 1.3610 -0.1985 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1495 -1.1271 0.3112 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0107 -0.4614 0.2521 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2635 -1.1671 0.4161 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2591 -2.3970 0.6112 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -0.4598 0.3549 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6196 0.8974 0.1438 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8515 1.5505 0.0904 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0124 0.8490 0.2493 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9425 -0.4954 0.4599 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7280 -1.1365 0.5120 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2230 1.5126 0.1934 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1351 0.5268 0.1413 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7577 -1.4092 0.1678 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4809 -2.3881 0.4161 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8064 1.4840 -0.1300 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0731 2.4215 -0.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0919 -2.2194 0.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0470 0.5968 0.0826 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7583 1.5040 0.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8850 2.6211 -0.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8713 -1.0555 0.5868 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7220 -2.2049 0.6814 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9154 1.3545 -0.5242 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 5 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 15 18 1 0 7 2 1 0 17 12 1 0 1 19 1 0 3 20 1 0 4 21 1 0 6 22 1 0 7 23 1 0 8 24 1 0 9 25 1 0 13 26 1 0 14 27 1 0 16 28 1 0 17 29 1 0 18 30 1 0 M END

Standard InCHIKey	FZQLEXXZAVVCCA-XCVCLJGOSA-N
Standard InCHI	InChI=1S/C15H12O3/c16-13-6-1-11(2-7-13)3-10-15(18)12-4-8-14(17)9-5-12/h1-10,16-17H/b10-3+
SMILES	Oc1ccc(cc1)/C=C/C(=O)c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	240.08	Volume:	256.162 ? Van der Waals volume.
Dense:	0.937	LogP:	2.55 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.557 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.545 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	14.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.64	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.814	Fsp³:	0.0
MCE-18:	11.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.968	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.03 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.442 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.998	Promiscuous compounds:	0.344

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.826	MDCK Permeability:	-4.792
Pgp-inhibitor:	0.126	Pgp-substrate:	0.022
PAMPA:	0.314 ? 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):	0.001
20% Bioavailability (F20%):	0.58	30% Bioavailability (F30%):	0.753
50% Bioavailability (F50%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.076
Plasma Protein Binding (PPB):	93.817%	Volume Distribution (VD):	-0.007
Fu:	8.442% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.436
BSEP inhibitor:	0.945

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.966
CYP2C9-inhibitor:	0.199	CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.958	CYP2D6-substrate:	0.988
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.58 ? 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):

12.46

Half-life (T1/2):

1.142

ADMET: Toxicity

hERG Blockers:	0.271	hERG Blockers (10um):	0.524
Human Hepatotoxicity (H-HT):	0.522	Drug-induced Liver Injury (DILI):	0.308
AMES Toxicity:	0.264	Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.553	Skin Sensitization:	0.834
Carcinogencity:	0.226	Eye Corrosion:	0.258
Eye Irritation:	0.996	Respiratory Toxicity:	0.51
Drug-induced Neurotoxicity:	0.758	Ototoxicity:	0.134
Hematotoxicity:	0.062	Drug-induced Nephrotoxicity:	0.163
Genotoxicity:	0.589	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.145	Hek293 Cytotoxicity:	0.72
BCF:	1.259 ? 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:	3.973 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.527 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.31 ? 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
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26690274]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25653	Spatholobus suberectus	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	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	8
Ki	1
Inhibition	6
ED50	2
GI50	68

Activity Type	# Activity
Individual protein	4
Cell line	72
Organism	2
Others	6
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual protein	Xanthine dehydrogenase	Bos taurus	IC50	=	117000.0	nM	PMID[28655421]
NPT677	Individual protein	Coagulation factor III	Homo sapiens	IC50	=	0.96	nM	PMID[8229017]
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	IC50	=	4800.0	nM	PMID[18267360]
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Ki	=	2900.0	nM	PMID[18490501]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell line	HT-1080	Homo sapiens	ED50	>	100.0	uM	PMID[25010936]
NPT319	Cell line	B16	Mus musculus	IC50	=	48700.0	nM	DrugMatrix in vitro pharmacology data
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[17261619]
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	27352.69	nM	PMID[19364864]
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	25527.01	nM	PMID[22758660]
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	23933.16	nM	PMID[19719245]
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	31550.05	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	22029.26	nM	PMID[25136754]
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	17021.59	nM	PMID[18672864]
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	34197.94	nM	PMID[18922036]
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	21086.28	nM	PMID[22530813]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	21527.82	nM	DOI[10.1016/S0960-894X(97)00380-6]
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	27669.42	nM	PMID[15332869]
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	31045.6	nM	DOI[10.1007/s00044-006-0142-6]
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	27227.01	nM	DOI[10.1039/C0MD00267D]
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	22029.26	nM	PMID[25615796]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	19319.68	nM	PMID[10785428]
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	21627.19	nM	Open TG-GATES in vivo data: Biochemistry
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	21777.1	nM	DrugMatrix in vitro pharmacology data
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	17988.71	nM	Open TG-GATES in vivo data: Biochemistry
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	16672.47	nM	PMID[12932128]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	33342.64	nM	PMID[25226228]
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	16519.62	nM	PMID[22934671]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	43651.58	nM	PMID[20627559]
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	32658.78	nM	PMID[24900628]
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	46881.34	nM	PMID[22037378]
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	9705.1	nM	PMID[22194678]
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	26061.54	nM	PMID[19228038]
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	21727.01	nM	PMID[20590148]
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	11912.42	nM	PMID[11141110]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	3944.57	nM	PMID[25729554]
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	19275.25	nM	PMID[19115838]
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	18836.49	nM	PMID[16040241]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	30199.52	nM	PMID[16989518]
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	11168.63	nM	PMID[16643030]
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	69823.24	nM	PMID[22652254]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	11350.11	nM	PMID[14987066]
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	32583.67	nM	PMID[18500841]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	19633.6	nM	PMID[22413911]
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	20276.83	nM	Open TG-GATES in vivo data: Hematology
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	30549.21	nM	DrugMatrix in vitro pharmacology data
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	24043.63	nM	PMID[24437979]
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	20941.12	nM	DrugMatrix in vivo data: Pathology
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	20276.83	nM	PMID[26227773]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	16788.04	nM	PMID[19327990]
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	21428.91	nM	PMID[18061460]
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	42266.86	nM	PMID[19994846]
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	32885.16	nM	PMID[18070975]
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	28707.81	nM	DrugMatrix in vitro pharmacology data
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	42559.84	nM	PMID[19804979]
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	18879.91	nM	PMID[10869203]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	26791.68	nM	PMID[23543830]
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	44055.49	nM	PMID[21955940]
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	18071.74	nM	PMID[19327990]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	25468.3	nM	PMID[18077425]
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	40179.08	nM	PMID[26213786]
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	32136.61	nM	PMID[17938181]
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	31841.98	nM	PMID[16933872]
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	26977.39	nM	PMID[20017491]
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	23173.95	nM	PMID[21741732]
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	45185.59	nM	DrugMatrix in vivo data: Pathology
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	29512.09	nM	PMID[23398362]
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	18030.18	nM	DOI[10.1007/s00044-011-9628-y]
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	13645.83	nM	PMID[16134928]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	16788.04	nM	PMID[20553004]
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	19906.73	nM	The Pharmaceutical Basis of Therapeutics, Goodman and Gilman Ed. 12
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	28054.34	nM	PMID[26160020]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	22908.68	nM	PMID[18362191]
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	30408.85	nM	PMID[17485145]
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	35156.04	nM	DOI[10.1007/s00044-013-0779-x]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[22439644]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[22537363]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	83000.0	nM	PMID[20666364]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	100.0	uM	PMID[11277741]
NPT610	Others	Molecular identity unknown	n.a.	Inhibition	=	89.6	%	PMID[24275249]
NPT610	Others	Molecular identity unknown	n.a.	Inhibition	=	68.3	%	PMID[24275249]
NPT610	Others	Molecular identity unknown	n.a.	Inhibition	=	92.7	%	PMID[24275249]
NPT610	Others	Molecular identity unknown	n.a.	Inhibition	=	70.9	%	PMID[24275249]
NPT2	Others	Unspecified	n.a.	IC50	>	50000.0	nM	PMID[19425589]
NPT2	Others	Unspecified	n.a.	Inhibition	=	28.2	%	Open TG-GATES in vivo data: Biochemistry

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	5.42	%	PMID[22342628]

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

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 NPC17525 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	22473
0.1-0.2	22772
0.2-0.3	3947
0.3-0.4	464
0.4-0.5	151
0.5-0.6	34
0.6-0.7	10
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	Natural Product ID
0.6829	Remote Similarity	NPC66905
0.6757	Remote Similarity	NPC19174
0.6757	Remote Similarity	NPC73532
0.6757	Remote Similarity	NPC115159
0.6757	Remote Similarity	NPC158222
0.6667	Remote Similarity	NPC482707
0.641	Remote Similarity	NPC116842
0.641	Remote Similarity	NPC122793
0.625	Remote Similarity	NPC167205
0.6098	Remote Similarity	NPC192304
0.5952	Remote Similarity	NPC257756
0.5952	Remote Similarity	NPC247779
0.5952	Remote Similarity	NPC336114
0.5882	Remote Similarity	NPC71664
0.5882	Remote Similarity	NPC286006
0.5882	Remote Similarity	NPC608893
0.5814	Remote Similarity	NPC205468
0.5714	Remote Similarity	NPC181709
0.5682	Remote Similarity	NPC312318
0.5682	Remote Similarity	NPC110419
0.5682	Remote Similarity	NPC477243
0.5625	Remote Similarity	NPC248817
0.561	Remote Similarity	NPC297186
0.5556	Remote Similarity	NPC119660
0.5556	Remote Similarity	NPC263670
0.5556	Remote Similarity	NPC129132
0.5476	Remote Similarity	NPC26697
0.5435	Remote Similarity	NPC186838
0.5405	Remote Similarity	NPC68269
0.5319	Remote Similarity	NPC72158
0.5319	Remote Similarity	NPC30501
0.5312	Remote Similarity	NPC6984
0.5294	Remote Similarity	NPC24394
0.5294	Remote Similarity	NPC239808
0.5294	Remote Similarity	NPC600683
0.5263	Remote Similarity	NPC253746
0.525	Remote Similarity	NPC304638
0.525	Remote Similarity	NPC141523
0.5208	Remote Similarity	NPC98254
0.5143	Remote Similarity	NPC104216
0.5122	Remote Similarity	NPC45438
0.5111	Remote Similarity	NPC262359
0.5102	Remote Similarity	NPC44960
0.5098	Remote Similarity	NPC27643

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC17525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4448
0.1-0.2	4486
0.2-0.3	200
0.3-0.4	16
0.4-0.5	0
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