NPASS Compound

Natural Product: NPC258824

Natural Product ID	NPC258824
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Myriocin
IUPAC Name	(E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Synonyms	Myriocin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL55076
PubChem CID	6438394
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

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 67 66 0 0 0 0 0 0 0 0999 V2000 9.4732 1.1335 -1.0152 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6645 0.0516 -0.2942 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5078 0.7552 0.3489 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6655 -0.2381 1.0957 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1415 -1.2890 0.1635 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2951 -0.7227 -0.9340 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0921 0.0113 -0.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7271 1.0381 -1.0343 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2819 -0.3926 0.7200 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9726 -1.0318 0.3863 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1434 -0.0344 -0.4165 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1710 -0.7818 -0.7080 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0441 0.1086 -1.5146 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4280 1.3449 -0.7907 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3064 1.0944 0.3605 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8020 -0.0828 0.6503 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6981 -0.2656 1.8621 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0246 -0.7766 1.3128 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5474 0.2546 0.3751 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7422 -0.1206 -0.4265 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0906 0.9939 -1.3781 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2147 0.7678 -2.5945 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2673 2.2629 -0.8756 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9268 -0.3030 0.5031 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0320 -0.5194 -0.3266 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6036 -1.3171 -1.1859 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7313 1.4283 1.1018 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8390 -1.0647 2.3875 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4058 1.3769 -0.4308 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7343 0.7365 -2.0046 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9233 2.0665 -1.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3054 -0.6990 -1.0192 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3482 -0.4115 0.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8665 1.5084 1.1048 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8760 1.2493 -0.4145 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8116 0.3215 1.5369 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2639 -0.6991 1.9306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5604 -2.0028 0.8090 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9277 -1.9281 -0.2885 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9739 -1.5353 -1.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9170 -0.0560 -1.5571 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8661 -1.0552 1.4176 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0375 0.5070 1.3597 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4727 -1.2849 1.3360 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 -1.9329 -0.2205 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9658 0.8724 0.1534 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5884 0.1981 -1.3943 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5177 -1.0859 0.2832 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1115 -1.7224 -1.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5927 0.3290 -2.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9502 -0.5119 -1.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5402 1.9310 -0.4330 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9217 2.0764 -1.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5667 1.9490 1.0240 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6336 -0.9351 0.0323 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8098 0.7123 2.3541 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1963 -1.0249 2.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7445 -1.7282 0.7687 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7125 0.4875 -0.3420 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2758 3.0967 -1.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0070 0.5985 1.1226 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7692 -1.2140 1.1381 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5342 0.3366 -0.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3250 -1.4784 -1.8910 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6312 -1.5182 -1.5004 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1489 2.1667 0.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6211 -2.0015 2.6942 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 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 20 24 1 0 24 25 1 0 20 26 1 6 19 27 1 0 18 28 1 0 1 29 1 0 1 30 1 0 1 31 1 0 2 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 9 42 1 0 9 43 1 0 10 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 13 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 6 19 59 1 6 23 60 1 0 24 61 1 0 24 62 1 0 25 63 1 0 26 64 1 0 26 65 1 0 27 66 1 0 28 67 1 0 M END

Standard InCHIKey	ZZIKIHCNFWXKDY-GNTQXERDSA-N
Standard InCHI	InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
SMILES	CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H]([C@](C(=O)O)(CO)N)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	401.28	Volume:	427.601 ? Van der Waals volume.
Dense:	0.938	LogP:	2.314 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.595 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.322 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	3.0
TPSA:	141.08 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	6.0	Rings:	0.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.175	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.878	Fsp³:	0.81
MCE-18:	7.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.077	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.297	Promiscuous compounds:	0.607

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212	MDCK Permeability:	-4.684
Pgp-inhibitor:	0.0	Pgp-substrate:	0.012
PAMPA:	0.655 ? 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):	0.002
20% Bioavailability (F20%):	0.058	30% Bioavailability (F30%):	0.079
50% Bioavailability (F50%):	0.503

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.464
Plasma Protein Binding (PPB):	94.853%	Volume Distribution (VD):	-0.548
Fu:	4.732% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.052
OATP1B3 inhibitor:	0.955	BCRP inhibitor:	0.003
BSEP inhibitor:	0.987

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.213
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.011
CYP2C9-inhibitor:	0.026	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.04	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.032
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.36 ? 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):

3.604

Half-life (T1/2):

1.079

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.149
Human Hepatotoxicity (H-HT):	0.721	Drug-induced Liver Injury (DILI):	0.092
AMES Toxicity:	0.02	Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.069	Skin Sensitization:	0.997
Carcinogencity:	0.075	Eye Corrosion:	0.051
Eye Irritation:	0.869	Respiratory Toxicity:	0.819
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.704
Hematotoxicity:	0.346	Drug-induced Nephrotoxicity:	0.54
Genotoxicity:	0.005	RPMI-8226 Immunitoxicity:	0.051
A549 Cytotoxicity:	0.093	Hek293 Cytotoxicity:	0.062
BCF:	0.994 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.129 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.46 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.593 ? 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
NPO33185	cordyceps heteropoda	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679316]
NPO1825	Isaria sinclairii	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21456524]
NPO29751	Myriococcum albomyces	Species	Atheliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21456524]
NPO1825	Isaria sinclairii	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8893839]
NPO27451	Ophiocordyceps sinensis	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27451	Ophiocordyceps sinensis	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27451	Ophiocordyceps sinensis	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27451	Ophiocordyceps sinensis	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1825	Isaria sinclairii	Species	Cordycipitaceae	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
Activity	19
Inhibition	6
Potency	13
IC50	5
EC50	1
IZ	4
AC50	1
IP	1
MST	5
TIME	1

Activity Type	# Activity
Individual protein	9
Single protein	2
Organism	13
Others	30
Non-molecular	1
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT55	Individual protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	15811.4	nM	PubChem BioAssay data set
NPT26858	Single protein	Serine palmitoyltransferase 1	Homo sapiens	EC50	=	49.5	nM	PMID[27213958]
NPT4221	Individual protein	Squalene synthetase	Homo sapiens	Activity	=	97.0	%	PMID[18641634]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	1.5	%	PMID[23062825]
NPT26856	Single protein	Serine palmitoyltransferase 2	Homo sapiens	IC50	=	0.13	nM	PMID[29669694]
NPT4901	Individual protein	RAC-alpha serine/threonine-protein kinase	Mus musculus	Inhibition	=	50.8	%	PMID[18641634]
NPT4901	Individual protein	RAC-alpha serine/threonine-protein kinase	Mus musculus	Inhibition	=	51.2	%	PMID[18641634]
NPT728	Individual protein	Serine/threonine-protein kinase AKT	Homo sapiens	Inhibition	=	46.1	%	PMID[18641634]
NPT728	Individual protein	Serine/threonine-protein kinase AKT	Homo sapiens	Inhibition	=	48.8	%	PMID[18641634]
NPT445	Individual protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	2.3	nM	PubChem BioAssay data set
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-8.15	%	PMID[23062825]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	IZ	=	28.0	mm	PMID[15679316]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3.0	nM	PMID[21456524]
NPT851	Organism	Colletotrichum fragariae	Colletotrichum fragariae	IZ	=	14.0	mm	PMID[15679316]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	IZ	=	17.0	mm	PMID[15679316]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	5353.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	8197.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	21.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	13.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	13333.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	3.0	nM	PMID[21456524]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	IZ	=	8.0	mm	PMID[15679316]
NPT2	Others	Unspecified	n.a.	Activity	=	10.5	ms	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	0.8	um2/s	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	0.9	ms	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	22.6	ms	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	12.3	ms	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	0.7	um2/s	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	19.3	ms	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	5.7	ms	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	1.0	um2/s	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	98.0	%	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	24.0	%	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	28.0	%	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	92.0	%	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Activity	=	30.0	%	PMID[18641634]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	316.2	nM	PubChem BioAssay data set
NPT26857	Cell line	HCC4006	Homo sapiens	IP	=	2.1	nM	PMID[29669694]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	3.0	nM	DOI[10.1016/0960-894X(95)00126-E]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	8.0	nM	DOI[10.1016/0960-894X(95)00304-C]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	MST	=	7.8	day	DOI[10.1016/0960-894X(95)00126-E]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	MST	=	9.2	day	DOI[10.1016/0960-894X(95)00126-E]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	MST	=	11.2	day	DOI[10.1016/0960-894X(95)00126-E]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1.0	mg kg-1	PMID[21456524]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	TIME	=	48.0	hr	PMID[21456524]

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	=	300.0	mg/kg	ToxVal

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 NPC258824 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	20074
0.1-0.2	27679
0.2-0.3	1893
0.3-0.4	191
0.4-0.5	20
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC258824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5010
0.1-0.2	3925
0.2-0.3	194
0.3-0.4	17
0.4-0.5	3
0.5-0.6	1
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
0.5957	Remote Similarity	NPD3732	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