NPASS Compound

Natural Product: NPC51695

Natural Product ID	NPC51695
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4-[(2R)-2-[(1R,3R,5S)-3,5-Dimethyl-2-Oxocyclohexyl]-2-Hydroxyethyl]Piperidine-2,6-Dione
IUPAC Name	4-[(2R)-2-[(1R,3R,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1358722
PubChem CID	6604199
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000195] Piperidines [CHEMONTID:0001581] Piperidinones [CHEMONTID:0001582] Piperidinediones

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 43 44 0 0 0 0 0 0 0 0999 V2000 -2.9950 2.4844 -1.7031 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5869 1.5639 -0.5969 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4786 0.3481 -0.4791 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2012 -0.2659 0.8799 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3810 -1.7543 0.8769 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8489 0.0808 1.3827 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 -0.0048 2.5863 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7271 0.5154 0.5415 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1693 1.0118 -0.8017 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3035 -0.6065 0.4337 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4204 -0.1094 -0.4320 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4766 -1.1487 -0.6246 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1381 -1.6212 0.6366 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8911 -0.5320 1.2987 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2964 0.4926 0.6592 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0560 0.6575 -0.7146 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2663 1.7779 -1.2716 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5531 -0.4855 -1.5198 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1596 -0.6393 2.6608 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7253 -0.7861 1.7747 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5795 3.3480 -1.2733 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1205 2.9762 -2.2101 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6424 2.0172 -2.4594 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6295 2.0854 0.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1078 -0.4070 -1.2327 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5401 0.5627 -0.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9460 0.1701 1.5771 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7897 -2.0613 1.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3847 -2.2714 0.7963 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0898 -2.1018 0.0972 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2115 1.3555 1.0606 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2384 0.1467 -1.5222 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5252 1.7998 -1.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1362 -1.5538 0.1145 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8470 0.8343 0.0278 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0544 0.2082 -1.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0603 -1.9833 -1.1957 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8817 -2.4136 0.3490 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4664 -2.1026 1.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0340 -0.1441 -2.4268 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3097 -1.2610 -1.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0204 -0.2588 3.0519 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0345 0.0760 2.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 4 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 14 19 1 0 10 20 1 0 9 2 1 0 18 12 1 0 1 21 1 0 1 22 1 0 1 23 1 0 2 24 1 1 3 25 1 0 3 26 1 0 4 27 1 1 5 28 1 0 5 29 1 0 5 30 1 0 8 31 1 1 9 32 1 0 9 33 1 0 10 34 1 6 11 35 1 0 11 36 1 0 12 37 1 0 13 38 1 0 13 39 1 0 18 40 1 0 18 41 1 0 19 42 1 0 20 43 1 0 M END

Standard InCHIKey	YPHMISFOHDHNIV-LUTQBAROSA-N
Standard InCHI	InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9+,11+,12+/m0/s1
SMILES	C[C@H]1C[C@@H](C)C(=O)[C@H](C1)[C@@H](CC1CC(=NC(=O)C1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	281.16	Volume:	289.132 ? Van der Waals volume.
Dense:	0.972	LogP:	0.989 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.207 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.263 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	14.0
TPSA:	86.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.827	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.713	Fsp³:	0.8
MCE-18:	36.296 ? 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:	0.265	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.023 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.179	Promiscuous compounds:	0.421

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.781	MDCK Permeability:	-4.62
Pgp-inhibitor:	0.073	Pgp-substrate:	0.056
PAMPA:	0.914 ? 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):	0.0
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054	MRP1:	0.962
Plasma Protein Binding (PPB):	43.551%	Volume Distribution (VD):	0.169
Fu:	53.055% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.967
OATP1B3 inhibitor:	0.944	BCRP inhibitor:	0.003
BSEP inhibitor:	0.979

ADMET: Metabolism

CYP1A2-inhibitor:	0.295	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.06	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.54	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.124	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.021
HLM stability:	0.341 ? 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):

5.978

Half-life (T1/2):

1.266

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.028
Human Hepatotoxicity (H-HT):	0.995	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.554	Rat Oral Acute Toxicity:	0.659
Maximum Recommended Daily Dose:	0.887	Skin Sensitization:	0.997
Carcinogencity:	0.925	Eye Corrosion:	0.0
Eye Irritation:	0.02	Respiratory Toxicity:	0.822
Drug-induced Neurotoxicity:	0.521	Ototoxicity:	0.92
Hematotoxicity:	0.874	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.992	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.008	Hek293 Cytotoxicity:	0.136
BCF:	0.189 ? 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:	2.834 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.077 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.302 ? 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
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880174]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800631]
NPO10867	Graphis elongata	Species	Aclididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7883	Albugo candida	Species	Albuginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1937	Andropogon nardus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7365	Clibadium pentaneuron	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12481	Croton californicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18350	Culcitium canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5219	Dendrobium rotundatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2805	Distolasterias nipon	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9020	Eriostemon fitzgeraldii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO729	Espeletia marcana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11355	Homarus americanus	Species	Nephropidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12309	Malva crispa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6787	Neoalsomitra integrifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3202	Nolina erumpens	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8547	Petasites niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3900	Phellinus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9937	Piptolepis leptospermoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24849	Rhinella paracnemis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12535	Solanum toxicarium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9320	Weddellina squamulosa	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9227	Xylaria berteri	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10867	Graphis elongata	Species	Aclididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8547	Petasites niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6787	Neoalsomitra integrifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5219	Dendrobium rotundatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO729	Espeletia marcana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2805	Distolasterias nipon	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24849	Rhinella paracnemis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7883	Albugo candida	Species	Albuginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3900	Phellinus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7365	Clibadium pentaneuron	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11355	Homarus americanus	Species	Nephropidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9020	Eriostemon fitzgeraldii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12481	Croton californicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12309	Malva crispa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12535	Solanum toxicarium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3202	Nolina erumpens	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9227	Xylaria berteri	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1937	Andropogon nardus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9320	Weddellina squamulosa	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18350	Culcitium canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9937	Piptolepis leptospermoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1526	Ratibida latipalearis	Species	Asteraceae	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
Potency	55
EC50	9
IC50	9
AC50	7
CC50	1

Activity Type	# Activity
Individual protein	37
Cell line	7
Organism	4
Nucleic acid	2
Others	31

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1197	Individual protein	Huntingtin	Homo sapiens	Potency	=	354.8	nM	PubChem BioAssay data set
NPT211	Individual protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	Potency	=	63.1	nM	PubChem BioAssay data set
NPT1415	Individual protein	Heat shock factor protein 1	Mus musculus	EC50	=	660.0	nM	PubChem BioAssay data set
NPT150	Individual protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	158.5	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	410.9	nM	PubChem BioAssay data set
NPT2892	Individual protein	X-box-binding protein 1	Homo sapiens	IC50	<	210.0	nM	PubChem BioAssay data set
NPT1415	Individual protein	Heat shock factor protein 1	Mus musculus	AC50	=	336.0	nM	PubChem BioAssay data set
NPT3132	Individual protein	60S ribosomal protein L19-A	Saccharomyces cerevisiae S288c	EC50	=	570.0	nM	PubChem BioAssay data set
NPT2893	Individual protein	DNA damage-inducible transcript 3 protein	Mus musculus	IC50	>	160.0	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	707.9	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	4610.9	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	20596.2	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	1000.0	nM	PubChem BioAssay data set
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	891.3	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	326.4	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	1032.3	nM	PubChem BioAssay data set
NPT1797	Individual protein	Alpha trans-inducing protein (VP16)	Herpes simplex virus (type 1 / strain 17)	IC50	>	85413.0	nM	PubChem BioAssay data set
NPT3133	Individual protein	COUP transcription factor 2	Homo sapiens	IC50	=	1032.0	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	12995.3	nM	PubChem BioAssay data set
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	1000.0	nM	PubChem BioAssay data set
NPT537	Individual protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	316.2	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	2818.4	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	251.2	nM	PubChem BioAssay data set
NPT919	Individual protein	HSP90	Plasmodium falciparum 3D7	AC50	<	195.0	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	4466.8	nM	PubChem BioAssay data set
NPT54	Individual protein	Nonstructural protein 1	Influenza A virus	Potency	=	316.2	nM	PubChem BioAssay data set
NPT538	Individual protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	316.2	nM	PubChem BioAssay data set
NPT93	Individual protein	Survival motor neuron protein	Homo sapiens	Potency	=	891.3	nM	PubChem BioAssay data set
NPT63	Individual protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	1000.0	nM	PubChem BioAssay data set
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	AC50	<	195.0	nM	PubChem BioAssay data set
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	1778.3	nM	PubChem BioAssay data set
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	891.3	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	651.3	nM	PubChem BioAssay data set
NPT920	Individual protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	3548.1	nM	PubChem BioAssay data set
NPT536	Nucleic acid	microRNA 21	Homo sapiens	Potency	=	232.8	nM	PubChem BioAssay data set
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	517.1	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	430.0	nM	PubChem BioAssay data set
NPT1160	Cell line	BJ	Homo sapiens	EC50	=	973.0	nM	PubChem BioAssay data set
NPT1160	Cell line	BJ	Homo sapiens	EC50	=	728.0	nM	PubChem BioAssay data set
NPT1160	Cell line	BJ	Homo sapiens	EC50	=	708.0	nM	PubChem BioAssay data set
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	6810.0	nM	PubChem BioAssay data set
NPT65	Cell line	HepG2	Homo sapiens	Potency	n.a.	398.1	nM	PubChem BioAssay data set
NPT189	Cell line	Vero	Chlorocebus aethiops	CC50	=	960.0	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	73.8	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	32.9	nM	PubChem BioAssay data set
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT586	Organism	Giardia	Giardia	Potency	n.a.	72.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	100.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	1032.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	EC50	<	4.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	EC50	<	100.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	1778.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	5623.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	EC50	=	637.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	231.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	251.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1258.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	309.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	>	80000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	450.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	891.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	79.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	31.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	>	70000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	=	307.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	=	2180.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	707.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	316.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1299.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1158.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3548.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1122.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	=	4920.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	794.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	EC50	=	1.0	nM	PubChem BioAssay data set

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

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 NPC51695 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	18066
0.1-0.2	31463
0.2-0.3	306
0.3-0.4	12
0.4-0.5	5
0.5-0.6	0
0.6-0.7	3
0.7-0.8	0
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	NPC200085
1.0	High Similarity	NPC253703
0.6957	Remote Similarity	NPC198855
0.6809	Remote Similarity	NPC279122
0.6667	Remote Similarity	NPC487836

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC51695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5185
0.1-0.2	3918
0.2-0.3	45
0.3-0.4	2
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