NPASS Compound

Natural Product: NPC207633

Natural Product ID	NPC207633
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Nebularine
IUPAC Name	(2R,3S,4R,5R)-2-(hydroxymethyl)-5-purin-9-yloxolane-3,4-diol
Synonyms	Nebularine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1399702
PubChem CID	68368
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0000479] Purine nucleosides

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 32 0 0 0 0 0 0 0 0999 V2000 -4.2285 1.4623 -0.1800 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8893 1.2859 -0.3596 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2442 0.2336 0.2251 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9036 -0.6410 0.9807 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2311 -0.4416 1.1417 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8916 0.5841 0.5789 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9503 0.3382 -0.1392 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7926 1.4207 -0.9259 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9960 2.0039 -1.0592 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1482 -0.5545 0.2325 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8358 -0.9955 -1.0430 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2600 -1.1590 -0.5926 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3335 -0.3800 0.6752 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2852 0.8040 0.5154 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8102 1.5778 -0.5379 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0871 0.1417 0.9471 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5871 -2.5018 -0.4165 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3214 -2.2288 -1.3972 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7449 2.2896 -0.6375 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8218 -1.1251 1.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1180 1.7785 -1.3795 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2129 -1.4115 0.8101 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7027 -0.2276 -1.8156 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9108 -0.7538 -1.3905 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7183 -0.9809 1.5316 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3338 1.3730 1.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2750 0.4202 0.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4322 2.4231 -0.1364 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4147 -2.6058 0.0841 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6673 -2.1300 -1.4230 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 3 7 1 0 7 8 1 0 8 9 2 0 7 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 12 17 1 0 11 18 1 0 6 1 1 0 16 10 1 0 9 2 1 0 1 19 1 0 5 20 1 0 8 21 1 0 10 22 1 1 11 23 1 6 12 24 1 6 13 25 1 1 14 26 1 0 14 27 1 0 15 28 1 0 17 29 1 0 18 30 1 0 M END

Standard InCHIKey	MRWXACSTFXYYMV-FDDDBJFASA-N
Standard InCHI	InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2/t6-,7-,8-,10-/m1/s1
SMILES	c1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@@H]([C@@H](CO)O1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	252.09	Volume:	224.449 ? Van der Waals volume.
Dense:	1.123	LogP:	-0.937 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.64 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.964 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	15.0
TPSA:	113.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.592	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.646	Fsp³:	0.5
MCE-18:	56.533 ? 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:	0.142	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.023 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.033 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.036	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.933	MDCK Permeability:	-5.108
Pgp-inhibitor:	0.0	Pgp-substrate:	0.179
PAMPA:	0.996 ? 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):	0.792
20% Bioavailability (F20%):	0.711	30% Bioavailability (F30%):	0.92
50% Bioavailability (F50%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091	MRP1:	0.373
Plasma Protein Binding (PPB):	21.269%	Volume Distribution (VD):	0.063
Fu:	79.392% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.905
OATP1B3 inhibitor:	0.931	BCRP inhibitor:	0.127
BSEP inhibitor:	0.007

ADMET: Metabolism

CYP1A2-inhibitor:	0.017	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.283	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.98
HLM stability:	0.192 ? 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):

6.782

Half-life (T1/2):

1.939

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.139
Human Hepatotoxicity (H-HT):	0.754	Drug-induced Liver Injury (DILI):	0.968
AMES Toxicity:	0.891	Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.048	Skin Sensitization:	0.977
Carcinogencity:	0.59	Eye Corrosion:	0.0
Eye Irritation:	0.648	Respiratory Toxicity:	0.4
Drug-induced Neurotoxicity:	0.675	Ototoxicity:	0.795
Hematotoxicity:	0.719	Drug-induced Nephrotoxicity:	0.731
Genotoxicity:	0.969	RPMI-8226 Immunitoxicity:	0.189
A549 Cytotoxicity:	0.31	Hek293 Cytotoxicity:	0.207
BCF:	0.045 ? 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:	1.828 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.274 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.472 ? 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
NPO3862	Solanum habrochaites	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19155349]
NPO13620	Jatropha variegata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3862	Solanum habrochaites	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO3862	Solanum habrochaites	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16077	Rabdosia umbrosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15406	Allium magicum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13620	Jatropha variegata	Species	Euphorbiaceae	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
MPR	1
Ki	5
Potency	26
IC50	3
GI50	58
Weight change difference	4
ILS	4

Activity Type	# Activity
Individual protein	20
Cell line	61
Organism	11
Others	9

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	MPR	=	0.023	n.a.	PMID[2999397]
NPT1754	Individual protein	Adenosine deaminase	Bos taurus	Ki	=	15000.0	nM	PMID[6699873]
NPT2930	Individual protein	Hemoglobin beta chain	Homo sapiens	Potency	=	1258.9	nM	PubChem BioAssay data set
NPT1754	Individual protein	Adenosine deaminase	Bos taurus	Ki	=	7000.0	nM	PMID[21138280]
NPT1754	Individual protein	Adenosine deaminase	Bos taurus	Ki	=	9300.0	nM	DOI[10.1039/C1MD00134E]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	7079.5	nM	PubChem BioAssay data set
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	3548.1	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	3162.3	nM	PubChem BioAssay data set
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT58	Individual protein	Bloom syndrome protein	Homo sapiens	Potency	=	1.1	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	7079.5	nM	PubChem BioAssay data set
NPT3559	Individual protein	Cytidine deaminase	Mus musculus	Ki	=	10000.0	nM	PMID[3735306]
NPT93	Individual protein	Survival motor neuron protein	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT3838	Individual protein	Adenosine deaminase	Homo sapiens	Ki	=	7000.0	nM	PMID[21138280]
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	22.4	nM	PubChem BioAssay data set
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29081.0	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	12589.3	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	=	0.6	nM	PMID[10464017]
NPT71	Cell line	HEK293	Homo sapiens	Potency	n.a.	4609.0	nM	PubChem BioAssay data set
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	1402.81	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	1749.85	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	1276.44	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	656.15	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	325.84	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	1428.89	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	1667.25	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	2027.68	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	679.2	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	1520.55	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	1651.96	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	1264.74	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	2449.06	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	690.24	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	1633.05	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	1402.81	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	1174.9	nM	PubChem BioAssay data set
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	590.2	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	1445.44	nM	PubChem BioAssay data set
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	3265.88	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	462.38	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	2098.94	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	1009.25	nM	PubChem BioAssay data set
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	1686.55	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	714.5	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	1122.02	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	977.24	nM	PubChem BioAssay data set
NPT168	Cell line	P388	Mus musculus	GI50	n.a.	321.37	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	1674.94	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	903.65	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	1037.53	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	628.06	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	988.55	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	691.83	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	320.63	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	1091.44	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	306.9	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	605.34	nM	PubChem BioAssay data set
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	1205.04	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	952.8	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	592.93	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	1164.13	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	422.67	nM	PubChem BioAssay data set
NPT552	Cell line	P388/ADR	Mus musculus	GI50	n.a.	304.79	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	1995.26	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	639.73	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	4017.91	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	1610.65	nM	PubChem BioAssay data set
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	535.8	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	1315.22	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	1339.68	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	376.7	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	1393.16	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	1312.2	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	416.87	nM	PubChem BioAssay data set
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	2624.22	nM	PubChem BioAssay data set
NPT738	Cell line	SN12K1	Homo sapiens	GI50	n.a.	1482.52	nM	PubChem BioAssay data set
NPT1460	Cell line	L929	Mus musculus	IC50	=	2370.0	nM	PMID[24283924]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3294.4	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8275.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	3162.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	7079.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	12990.0	nM	PubChem BioAssay data set
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	1150.0	nM	PMID[24283924]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	7943.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3162.3	nM	PubChem BioAssay data set

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Weight change difference	=	-1.0	g	PMID[1956046]
NPT32	Organism	Mus musculus	Mus musculus	ILS	=	40.0	%	PMID[1956046]
NPT32	Organism	Mus musculus	Mus musculus	Weight change difference	=	0.0	g	PMID[1956046]
NPT32	Organism	Mus musculus	Mus musculus	ILS	=	60.0	%	PMID[1956046]
NPT32	Organism	Mus musculus	Mus musculus	Weight change difference	=	1.0	g	PMID[1956046]
NPT32	Organism	Mus musculus	Mus musculus	ILS	=	34.0	%	PMID[1956046]
NPT32	Organism	Mus musculus	Mus musculus	ILS	=	52.0	%	PMID[1956046]

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 NPC207633 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	36968
0.1-0.2	12664
0.2-0.3	137
0.3-0.4	47
0.4-0.5	25
0.5-0.6	8
0.6-0.7	6
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
0.6481	Remote Similarity	NPC485738
0.6182	Remote Similarity	NPC54320
0.6071	Remote Similarity	NPC156461
0.6071	Remote Similarity	NPC107374
0.6071	Remote Similarity	NPC600382
0.6071	Remote Similarity	NPC612067
0.5965	Remote Similarity	NPC608634
0.5714	Remote Similarity	NPC320818
0.5254	Remote Similarity	NPC311197
0.5167	Remote Similarity	NPC609036
0.5152	Remote Similarity	NPC239737
0.5082	Remote Similarity	NPC321052
0.5082	Remote Similarity	NPC483314
0.5082	Remote Similarity	NPC164665

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC207633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7295
0.1-0.2	1669
0.2-0.3	124
0.3-0.4	40
0.4-0.5	13
0.5-0.6	1
0.6-0.7	4
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
0.6182	Remote Similarity	NPD219	Phase 4
0.6182	Remote Similarity	NPD220	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD249	Phase 4
0.6071	Remote Similarity	NPD250	Phase 4
0.5397	Remote Similarity	NPD216	Approved

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