NPASS Compound

Natural Product: NPC105727

Natural Product ID	NPC105727
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4-[2-(3,5-Dihydroxyphenyl)Ethenyl]Benzene-1,2-Diol
IUPAC Name	4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1972346
PubChem CID	4813
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

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 5.0175 -1.2555 -1.9199 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1799 -0.7560 -0.9127 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8194 -0.7779 -1.1347 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9422 -0.2904 -0.1590 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4961 -0.3287 -0.4285 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4176 0.0958 0.4019 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8262 0.0446 0.1084 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3723 -0.4441 -1.0509 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7270 -0.4827 -1.3094 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5856 -0.0039 -0.3512 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1005 0.5016 0.8377 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7427 0.5210 1.0540 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9561 0.9918 1.8219 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9696 -0.0397 -0.6073 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4960 0.1941 0.9920 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8792 0.2121 1.2081 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7375 -0.2672 0.2485 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3584 0.7214 2.4051 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6368 -0.6643 -2.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3955 -1.1687 -2.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1531 -0.7426 -1.3951 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1010 0.5026 1.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7345 -0.8353 -1.8420 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1059 -0.8866 -2.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3325 0.9089 1.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8075 1.9323 2.1823 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3473 0.2994 -1.4702 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8243 0.5775 1.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8134 -0.2754 0.3671 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3770 1.7159 2.6116 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 1 0 5 6 2 3 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 10 14 1 0 4 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 17 2 1 0 12 7 1 0 1 19 1 0 3 20 1 0 5 21 1 0 6 22 1 0 8 23 1 0 9 24 1 0 12 25 1 0 13 26 1 0 14 27 1 0 15 28 1 0 17 29 1 0 18 30 1 0 M END

Standard InCHIKey	CDRPUGZCRXZLFL-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H
SMILES	Oc1cc(C=Cc2ccc(c(c2)O)O)cc(c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	244.07	Volume:	250.293 ? Van der Waals volume.
Dense:	0.975	LogP:	2.256 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.285 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.248 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	13.0
TPSA:	80.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.483	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.291	Fsp³:	0.0
MCE-18:	12.0 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.736	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.059 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.081 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.952	Promiscuous compounds:	0.846

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.183	MDCK Permeability:	-4.815
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
PAMPA:	0.39 ? 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%):	0.732	30% Bioavailability (F30%):	0.835
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059	MRP1:	0.559
Plasma Protein Binding (PPB):	83.462%	Volume Distribution (VD):	-0.196
Fu:	20.148% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.522
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.014	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.175	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.992	CYP2D6-substrate:	0.991
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.11
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.81 ? 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):

13.76

Half-life (T1/2):

1.897

ADMET: Toxicity

hERG Blockers:	0.391	hERG Blockers (10um):	0.762
Human Hepatotoxicity (H-HT):	0.814	Drug-induced Liver Injury (DILI):	0.024
AMES Toxicity:	0.841	Rat Oral Acute Toxicity:	0.334
Maximum Recommended Daily Dose:	0.786	Skin Sensitization:	1.0
Carcinogencity:	0.219	Eye Corrosion:	0.053
Eye Irritation:	0.996	Respiratory Toxicity:	0.204
Drug-induced Neurotoxicity:	0.552	Ototoxicity:	0.73
Hematotoxicity:	0.013	Drug-induced Nephrotoxicity:	0.198
Genotoxicity:	0.358	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.929	Hek293 Cytotoxicity:	0.718
BCF:	0.778 ? 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:	3.272 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.428 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.068 ? 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
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO9722	Strongylodesma aliwaliensis	n.a.	n.a.	n.a.	n.a.	South African	n.a.	PMID[15844938]
NPO2183	Eucalyptus sideroxylon	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840164]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO5544	Endiandra xanthocarpa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2183	Eucalyptus sideroxylon	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9722	Strongylodesma aliwaliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9	Camarops microspora	Species	Boliniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22771	Aleurodiscus mirabilis	Species	Stereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO921	Helichrysum subulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4620	Marasmius prasiosmus	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6497	Patiria miniata	Species	Asterinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2762	Senna lindheimeriana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23859	Primula elatior	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4884	Caulerpa bikinensis	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23859	Primula elatior	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23859	Primula elatior	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5544	Endiandra xanthocarpa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9	Camarops microspora	Species	Boliniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO921	Helichrysum subulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2762	Senna lindheimeriana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9722	Strongylodesma aliwaliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4620	Marasmius prasiosmus	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23859	Primula elatior	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4081	Aspilia floribunda	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6497	Patiria miniata	Species	Asterinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4884	Caulerpa bikinensis	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2183	Eucalyptus sideroxylon	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23295	Bulbophyllum rigidum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22771	Aleurodiscus mirabilis	Species	Stereaceae	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
Ki	51
AC50	3

Activity Type	# Activity
Individual protein	54

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3275	Individual protein	Inhibitor of nuclear factor kappa B kinase epsilon subunit	Homo sapiens	Ki	=	398.11	nM	PubChem BioAssay data set
NPT1682	Individual protein	Dual specificity protein kinase CLK2	Homo sapiens	Ki	=	501.19	nM	PubChem BioAssay data set
NPT3207	Individual protein	c-Jun N-terminal kinase 3	Homo sapiens	Ki	=	50.12	nM	PubChem BioAssay data set
NPT3327	Individual protein	Mitogen-activated protein kinase kinase kinase 10	Homo sapiens	Ki	=	100.0	nM	PubChem BioAssay data set
NPT1674	Individual protein	CaM kinase II alpha	Homo sapiens	Ki	=	794.33	nM	PubChem BioAssay data set
NPT3417	Individual protein	Serine/threonine-protein kinase TBK1	Homo sapiens	Ki	=	630.96	nM	PubChem BioAssay data set
NPT1661	Individual protein	ALK tyrosine kinase receptor	Homo sapiens	Ki	=	251.19	nM	PubChem BioAssay data set
NPT3318	Individual protein	MAP/microtubule affinity-regulating kinase 4	Homo sapiens	Ki	=	50.12	nM	PubChem BioAssay data set
NPT3267	Individual protein	Macrophage colony stimulating factor receptor	Homo sapiens	Ki	>	2511.89	nM	PubChem BioAssay data set
NPT3246	Individual protein	Tyrosine-protein kinase JAK2	Homo sapiens	Ki	=	794.33	nM	PubChem BioAssay data set
NPT3309	Individual protein	Leukocyte tyrosine kinase receptor	Homo sapiens	Ki	=	316.23	nM	PubChem BioAssay data set
NPT3370	Individual protein	Tyrosine-protein kinase receptor RET	Homo sapiens	Ki	=	398.11	nM	PubChem BioAssay data set
NPT1705	Individual protein	Ribosomal protein S6 kinase alpha 3	Homo sapiens	Ki	=	1584.89	nM	PubChem BioAssay data set
NPT3316	Individual protein	Mitogen-activated protein kinase kinase kinase kinase 4	Homo sapiens	Ki	=	501.19	nM	PubChem BioAssay data set
NPT3114	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	Ki	=	31.62	nM	PubChem BioAssay data set
NPT3331	Individual protein	Serine/threonine-protein kinase MST2	Homo sapiens	Ki	=	630.96	nM	PubChem BioAssay data set
NPT3205	Individual protein	Tyrosine-protein kinase HCK	Homo sapiens	Ki	=	398.11	nM	PubChem BioAssay data set
NPT1678	Individual protein	CaM-kinase kinase beta	Homo sapiens	Ki	=	63.1	nM	PubChem BioAssay data set
NPT3274	Individual protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Homo sapiens	Ki	=	100.0	nM	PubChem BioAssay data set
NPT3448	Individual protein	Leucine-rich repeat serine/threonine-protein kinase 2	Homo sapiens	Ki	=	501.19	nM	PubChem BioAssay data set
NPT3107	Individual protein	Rho-associated protein kinase 2	Homo sapiens	Ki	=	125.89	nM	PubChem BioAssay data set
NPT3456	Individual protein	Serine/threonine-protein kinase Sgk2	Homo sapiens	Ki	=	316.23	nM	PubChem BioAssay data set
NPT3280	Individual protein	Serine/threonine-protein kinase c-TAK1	Homo sapiens	Ki	=	251.19	nM	PubChem BioAssay data set
NPT1478	Individual protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Ki	>	2511.89	nM	PubChem BioAssay data set
NPT3245	Individual protein	Tyrosine kinase non-receptor protein 2	Homo sapiens	Ki	=	630.96	nM	PubChem BioAssay data set
NPT3262	Individual protein	Serine/threonine-protein kinase PRKX	Homo sapiens	Ki	=	630.96	nM	PubChem BioAssay data set
NPT3457	Individual protein	G protein-coupled receptor kinase 5	Homo sapiens	Ki	=	501.19	nM	PubChem BioAssay data set
NPT13	Individual protein	Tyrosine-protein kinase LCK	Homo sapiens	Ki	>	5011.87	nM	PubChem BioAssay data set
NPT3431	Individual protein	Serine/threonine-protein kinase TAO1	Homo sapiens	Ki	=	1000.0	nM	PubChem BioAssay data set
NPT1480	Individual protein	Fibroblast growth factor receptor 1	Homo sapiens	Ki	=	630.96	nM	PubChem BioAssay data set
NPT3373	Individual protein	Proto-oncogene tyrosine-protein kinase ROS	Homo sapiens	Ki	=	794.33	nM	PubChem BioAssay data set
NPT3290	Individual protein	Serine/threonine-protein kinase SIK2	Homo sapiens	Ki	=	100.0	nM	PubChem BioAssay data set
NPT1436	Individual protein	Focal adhesion kinase 1	Homo sapiens	Ki	=	794.33	nM	PubChem BioAssay data set
NPT1650	Individual protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	Ki	>	1995.26	nM	PubChem BioAssay data set
NPT3277	Individual protein	Tyrosine-protein kinase receptor TYRO3	Homo sapiens	Ki	=	79.43	nM	PubChem BioAssay data set
NPT3168	Individual protein	Casein kinase I alpha	Homo sapiens	Ki	=	316.23	nM	PubChem BioAssay data set
NPT3287	Individual protein	Activin receptor type-1	Homo sapiens	Ki	=	501.19	nM	PubChem BioAssay data set
NPT3282	Individual protein	Maternal embryonic leucine zipper kinase	Homo sapiens	Ki	=	79.43	nM	PubChem BioAssay data set
NPT1440	Individual protein	Tyrosine-protein kinase JAK3	Homo sapiens	Ki	=	1000.0	nM	PubChem BioAssay data set
NPT3020	Individual protein	Platelet-derived growth factor receptor alpha	Homo sapiens	Ki	=	1000.0	nM	PubChem BioAssay data set
NPT1265	Individual protein	Serine/threonine-protein kinase PIM1	Homo sapiens	Ki	=	2511.89	nM	PubChem BioAssay data set
NPT3324	Individual protein	Cell division protein kinase 8	Homo sapiens	Ki	=	251.19	nM	PubChem BioAssay data set
NPT1703	Individual protein	cAMP-dependent protein kinase alpha-catalytic subunit	Homo sapiens	Ki	=	1584.89	nM	PubChem BioAssay data set
NPT301	Individual protein	Vascular endothelial growth factor receptor 1	Homo sapiens	Ki	=	501.19	nM	PubChem BioAssay data set
NPT1672	Individual protein	CaM kinase I delta	Homo sapiens	Ki	=	501.19	nM	PubChem BioAssay data set
NPT1226	Individual protein	Caspase-7	Homo sapiens	AC50	>	70000.0	nM	PubChem BioAssay data set
NPT592	Individual protein	Rho-associated protein kinase 1	Homo sapiens	Ki	=	2511.89	nM	PubChem BioAssay data set
NPT491	Individual protein	Dual specificity mitogen-activated protein kinase kinase 1	Homo sapiens	Ki	>	3162.28	nM	PubChem BioAssay data set
NPT676	Individual protein	Glycogen synthase kinase-3 alpha	Homo sapiens	Ki	=	3162.28	nM	PubChem BioAssay data set
NPT591	Individual protein	Glycogen synthase kinase-3 beta	Homo sapiens	Ki	=	1000.0	nM	PubChem BioAssay data set
NPT4211	Individual protein	Caspase-8	Homo sapiens	AC50	>	70000.0	nM	PubChem BioAssay data set
NPT887	Individual protein	Protein kinase C theta	Homo sapiens	Ki	=	794.33	nM	PubChem BioAssay data set
NPT833	Individual protein	Tyrosine-protein kinase BTK	Homo sapiens	Ki	=	630.96	nM	PubChem BioAssay data set
NPT867	Individual protein	Caspase-6	Homo sapiens	AC50	=	1200.0	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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
-	Mus musculus	LD50	=	3.051367726	mg/kg	TOXRIC

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 NPC105727 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	33169
0.1-0.2	14372
0.2-0.3	1950
0.3-0.4	304
0.4-0.5	43
0.5-0.6	9
0.6-0.7	2
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC34864
1.0	High Similarity	NPC58427
0.7692	Intermediate Similarity	NPC223393
0.7241	Intermediate Similarity	NPC248573
0.7241	Intermediate Similarity	NPC161571
0.7241	Intermediate Similarity	NPC275053
0.6897	Remote Similarity	NPC114392
0.6129	Remote Similarity	NPC291789
0.5882	Remote Similarity	NPC292452
0.5641	Remote Similarity	NPC226629
0.5385	Remote Similarity	NPC10932
0.5366	Remote Similarity	NPC165770
0.5263	Remote Similarity	NPC232084
0.5263	Remote Similarity	NPC247364
0.5135	Remote Similarity	NPC296920
0.5135	Remote Similarity	NPC478886
0.5135	Remote Similarity	NPC90520

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC105727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7308
0.1-0.2	1708
0.2-0.3	116
0.3-0.4	17
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7241	Intermediate Similarity	NPD1242	Phase 3

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