NPASS Compound

Natural Product: NPC121259

Natural Product ID	NPC121259
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-(2,6-Dihydroxyphenyl)Dodecan-1-One
IUPAC Name	1-(2,6-dihydroxyphenyl)dodecan-1-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1528835
PubChem CID	365016
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

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 49 49 0 0 0 0 0 0 0 0999 V2000 7.7889 0.2477 1.0561 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3133 -0.2038 0.9600 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0734 -0.5572 -0.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7968 -1.0831 -0.9141 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5277 -0.3645 -0.8715 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 0.0182 0.4664 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6772 0.7013 0.4309 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6043 -0.1512 -0.1554 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6863 0.6769 -0.0920 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8486 -0.0814 -0.6786 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0749 0.8124 -0.5410 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2915 0.2026 -1.0911 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3537 -0.2409 -2.2714 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4961 0.0841 -0.2666 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5885 -1.1009 0.4630 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6896 -1.2779 1.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6809 -0.3275 1.3478 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5634 0.8432 0.6096 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4692 1.0474 -0.1982 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3562 2.2129 -0.9318 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5918 -2.0692 0.3800 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9052 0.9679 1.8771 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0832 0.7236 0.1023 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4481 -0.6000 1.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2496 -1.0615 1.6672 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7566 0.6219 1.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8589 -1.3589 -0.7061 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4489 0.3029 -1.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -1.3934 -2.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6878 -2.1235 -0.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7112 -0.9997 -1.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6318 0.5583 -1.5385 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7066 0.8651 0.8452 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0041 -0.7636 1.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7185 1.6708 -0.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4325 0.9183 1.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7826 -0.4141 -1.2013 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3813 -1.0470 0.4903 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5164 1.5911 -0.7117 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9117 0.9747 0.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0715 -0.9990 -0.0688 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7298 -0.3181 -1.7510 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8308 1.7875 -1.0382 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2308 1.0730 0.5344 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7896 -2.1961 1.8438 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5460 -0.4979 1.9921 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3469 1.6024 0.6799 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7972 3.0869 -0.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1544 -2.3607 -0.4771 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 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 15 21 1 0 19 14 1 0 1 22 1 0 1 23 1 0 1 24 1 0 2 25 1 0 2 26 1 0 3 27 1 0 3 28 1 0 4 29 1 0 4 30 1 0 5 31 1 0 5 32 1 0 6 33 1 0 6 34 1 0 7 35 1 0 7 36 1 0 8 37 1 0 8 38 1 0 9 39 1 0 9 40 1 0 10 41 1 0 10 42 1 0 11 43 1 0 11 44 1 0 16 45 1 0 17 46 1 0 18 47 1 0 20 48 1 0 21 49 1 0 M END

Standard InCHIKey	WPFIJMIBEGNIHW-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H28O3/c1-2-3-4-5-6-7-8-9-10-12-15(19)18-16(20)13-11-14-17(18)21/h11,13-14,20-21H,2-10,12H2,1H3
SMILES	CCCCCCCCCCCC(=O)c1c(cccc1O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	292.2	Volume:	327.153 ? Van der Waals volume.
Dense:	0.893	LogP:	6.479 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.068 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.23 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	7.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.435	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.05	Fsp³:	0.611
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:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.449	Fluc inhibitor:	0.43 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.138 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.119 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.861	Promiscuous compounds:	0.189

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.035	MDCK Permeability:	-4.755
Pgp-inhibitor:	0.021	Pgp-substrate:	0.043
PAMPA:	0.016 ? 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):	0.076
20% Bioavailability (F20%):	0.172	30% Bioavailability (F30%):	0.685
50% Bioavailability (F50%):	0.846

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.285	MRP1:	0.934
Plasma Protein Binding (PPB):	98.218%	Volume Distribution (VD):	0.909
Fu:	1.768% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.797
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.503
BSEP inhibitor:	0.471

ADMET: Metabolism

CYP1A2-inhibitor:	0.738	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.999
CYP2C9-inhibitor:	0.959	CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.927	CYP2D6-substrate:	0.489
CYP3A4-inhibitor:	0.993	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.898 ? 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):

3.394

Half-life (T1/2):

0.962

ADMET: Toxicity

hERG Blockers:	0.139	hERG Blockers (10um):	0.776
Human Hepatotoxicity (H-HT):	0.346	Drug-induced Liver Injury (DILI):	0.062
AMES Toxicity:	0.163	Rat Oral Acute Toxicity:	0.284
Maximum Recommended Daily Dose:	0.306	Skin Sensitization:	0.934
Carcinogencity:	0.184	Eye Corrosion:	0.815
Eye Irritation:	0.997	Respiratory Toxicity:	0.978
Drug-induced Neurotoxicity:	0.067	Ototoxicity:	0.12
Hematotoxicity:	0.128	Drug-induced Nephrotoxicity:	0.21
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.078
A549 Cytotoxicity:	0.792	Hek293 Cytotoxicity:	0.358
BCF:	1.701 ? 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:	5.086 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.288 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.646 ? 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
NPO1768	Sansevieria ehrenbergii	Species	Asparagaceae	Eukaryota	n.a.	African	n.a.	PMID[15921418]
NPO8160	Diospyros montana	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17400463]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19102656]
NPO17154	Hymenaea oblongifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14332	Uvaria ferruginea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1768	Sansevieria ehrenbergii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9374	Veronica anagallis-aquatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8160	Diospyros montana	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17618	Flaveria bidentis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17618	Flaveria bidentis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14611	Teucrium fragile	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2535	Bunodactis xanthogrammica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14332	Uvaria ferruginea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22851	Kryptoperidinium foliaceum	Species	Peridiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9374	Veronica anagallis-aquatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17009	Ptelea crenulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17154	Hymenaea oblongifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO668	Cnidoscolus texanus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1768	Sansevieria ehrenbergii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12642	Podadenia thwaitesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16062	Trichilia dregeana	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8160	Diospyros montana	Species	Ebenaceae	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	23
EC50	5
GI50	59
IC50	2

Activity Type	# Activity
Individual protein	21
Cell line	59
Organism	4
Protein-protein interaction	1
Others	4

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	=	11220.2	nM	PubChem BioAssay data set
NPT1254	Individual protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	1581.0	nM	PubChem BioAssay data set
NPT1254	Individual protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	>	150000.0	nM	PubChem BioAssay data set
NPT1415	Individual protein	Heat shock factor protein 1	Mus musculus	EC50	=	60150.0	nM	PubChem BioAssay data set
NPT135	Individual protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	9200.0	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT11	Individual protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	2238.7	nM	PubChem BioAssay data set
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT803	Individual protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	70794.6	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	37650.5	nM	PubChem BioAssay data set
NPT524	Individual protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT484	Individual protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	16944.1	nM	PubChem BioAssay data set
NPT446	Individual protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	1000.0	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PubChem BioAssay data set
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	23778.1	nM	PubChem BioAssay data set
NPT920	Individual protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT535	Individual protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	100000.0	nM	PubChem BioAssay data set
NPT442	Individual protein	Ferritin light chain	Equus caballus	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	19010.78	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	19498.45	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	17619.76	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	18113.4	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	16481.62	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	19906.73	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	13645.83	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	17988.71	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	31915.38	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	14554.59	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	17458.22	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	20370.42	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	17579.24	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	17947.34	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	19319.68	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	16519.62	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	15170.5	nM	PubChem BioAssay data set
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	18879.91	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	32960.97	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	20989.4	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	18749.95	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	19054.61	nM	PubChem BioAssay data set
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	18836.49	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	15995.58	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	18620.87	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	19186.69	nM	PubChem BioAssay data set
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	18323.14	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	26668.59	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	20417.38	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	18836.49	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	15417.0	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	21677.04	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	19724.23	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	18030.18	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	16826.74	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	18578.04	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	18030.18	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	19054.61	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	16255.49	nM	PubChem BioAssay data set
NPT731	Cell line	LXFL 529	Homo sapiens	GI50	n.a.	18492.69	nM	PubChem BioAssay data set
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	19186.69	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	30831.88	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	21677.04	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	19633.6	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	23388.37	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	17218.69	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	18113.4	nM	PubChem BioAssay data set
NPT577	Cell line	RXF 631	Homo sapiens	GI50	n.a.	18706.82	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	18071.74	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	21827.3	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	16749.43	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	24490.63	nM	PubChem BioAssay data set
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	17782.79	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	22335.72	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	19319.68	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	17782.79	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	24378.11	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	15346.17	nM	PubChem BioAssay data set
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	16218.1	nM	PubChem BioAssay data set
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	7148.0	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4147.5	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	7.4	nM	PubChem BioAssay data set
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	1529.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	92.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	15848.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	15801.0	nM	PubChem BioAssay data set
NPT35	Others	n.a.	n.a.	IC50	>	9968.0	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 NPC121259 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	18826
0.1-0.2	27279
0.2-0.3	3518
0.3-0.4	205
0.4-0.5	18
0.5-0.6	5
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC600129
0.8	Intermediate Similarity	NPC276111
0.7059	Intermediate Similarity	NPC149246
0.6341	Remote Similarity	NPC188814
0.6341	Remote Similarity	NPC608141
0.619	Remote Similarity	NPC196976
0.6	Remote Similarity	NPC118288
0.5909	Remote Similarity	NPC244441
0.5854	Remote Similarity	NPC195262
0.5676	Remote Similarity	NPC95172
0.5263	Remote Similarity	NPC320819
0.5098	Remote Similarity	NPC88345

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC121259 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3531
0.1-0.2	5337
0.2-0.3	271
0.3-0.4	11
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