NPASS Compound

Natural Product: NPC165133

Natural Product ID	NPC165133
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dihydroguaiaretic Acid
IUPAC Name	4-[4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1976696
PubChem CID	161924
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

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 50 51 0 0 0 0 0 0 0 0999 V2000 -0.0921 0.4314 -0.1214 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1891 -1.0640 -0.1321 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4713 -1.4894 0.5089 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6983 -0.9878 -0.1435 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2022 -1.6103 -1.2708 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3523 -1.1501 -1.8341 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0150 -0.0733 -1.2917 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5441 0.5654 -0.1765 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3585 0.0815 0.3949 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2191 1.6450 0.3576 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7962 2.3410 1.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1968 0.3905 -1.8811 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9553 -1.7746 0.5552 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5860 -3.2793 0.4565 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2593 -1.6833 -0.1884 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8136 -0.3496 -0.4311 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5776 0.3000 -1.6204 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1092 1.5451 -1.8402 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8843 2.1814 -0.8987 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1311 1.5469 0.2967 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5993 0.3115 0.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9163 2.2237 1.2159 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2559 1.7037 2.4831 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3986 3.4542 -1.1846 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9790 0.8941 0.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7646 0.7377 0.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1316 0.9026 -1.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1351 -1.4381 -1.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5720 -2.5961 0.5852 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4579 -1.1042 1.5512 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6810 -2.4519 -1.6918 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7502 -1.6310 -2.7129 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0437 0.6204 1.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7091 2.5433 1.4444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0396 1.8317 2.4448 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2888 3.3471 1.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0354 -0.1796 -1.7240 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0431 -1.5168 1.6141 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1109 -3.4958 -0.4942 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0059 -3.6005 1.3422 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5446 -3.8236 0.5124 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1079 -2.2166 -1.1836 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0379 -2.3454 0.3030 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9567 -0.2030 -2.3815 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9003 2.0394 -2.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7978 -0.1826 1.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4872 1.9478 3.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1996 2.1960 2.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4766 0.6080 2.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0386 3.8572 -0.4883 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 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 7 12 1 0 2 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 19 24 1 0 9 4 1 0 21 16 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 5 31 1 0 6 32 1 0 9 33 1 0 11 34 1 0 11 35 1 0 11 36 1 0 12 37 1 0 13 38 1 0 14 39 1 0 14 40 1 0 14 41 1 0 15 42 1 0 15 43 1 0 17 44 1 0 18 45 1 0 21 46 1 0 23 47 1 0 23 48 1 0 23 49 1 0 24 50 1 0 M END

Standard InCHIKey	ADFOLUXMYYCTRR-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3
SMILES	CC(Cc1ccc(c(c1)OC)O)C(C)Cc1ccc(c(c1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	330.18	Volume:	356.705 ? Van der Waals volume.
Dense:	0.926	LogP:	4.418 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.468 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.866 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	12.0
TPSA:	58.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.8	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.864	Fsp³:	0.4
MCE-18:	28.0 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.656	Fluc inhibitor:	0.013 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.289 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.614	Promiscuous compounds:	0.694

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.097	MDCK Permeability:	-4.784
Pgp-inhibitor:	0.425	Pgp-substrate:	0.136
PAMPA:	0.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.337	30% Bioavailability (F30%):	0.735
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031	MRP1:	0.991
Plasma Protein Binding (PPB):	91.993%	Volume Distribution (VD):	-0.143
Fu:	8.447% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.878
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.892	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.843	CYP2D6-substrate:	0.994
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.012	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

7.69

Half-life (T1/2):

1.211

ADMET: Toxicity

hERG Blockers:	0.446	hERG Blockers (10um):	0.865
Human Hepatotoxicity (H-HT):	0.627	Drug-induced Liver Injury (DILI):	0.047
AMES Toxicity:	0.153	Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.285	Skin Sensitization:	0.579
Carcinogencity:	0.107	Eye Corrosion:	0.041
Eye Irritation:	0.799	Respiratory Toxicity:	0.369
Drug-induced Neurotoxicity:	0.31	Ototoxicity:	0.651
Hematotoxicity:	0.16	Drug-induced Nephrotoxicity:	0.208
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.171
A549 Cytotoxicity:	0.502	Hek293 Cytotoxicity:	0.669
BCF:	1.762 ? 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:	4.348 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.315 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.836 ? 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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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
Inhibition	1
EC50	1
GI50	60
IC50	1

Activity Type	# Activity
Cell line	60
Protein complex	1
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT77	Individual protein	Transthyretin	Homo sapiens	Inhibition	<	20.0	%	PMID[25314129]
NPT77	Individual protein	Transthyretin	Homo sapiens	EC50	=	6300.0	nM	PMID[25314129]

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.	15381.55	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	17258.38	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	16904.41	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	12676.52	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	13061.71	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	9397.23	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	11721.95	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	31768.74	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	22335.72	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	8550.67	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	13061.71	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	18450.15	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	14962.36	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	16032.45	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	9289.66	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	23933.16	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	14791.08	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	16180.8	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	15559.66	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	50003.45	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	21827.3	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	10139.11	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	9204.5	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	34040.82	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	18197.01	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	9862.79	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	14689.26	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	14060.48	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	21232.44	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	7925.01	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	20090.93	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	11481.54	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	15100.8	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	9682.78	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	14521.12	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	18535.32	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	14223.29	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	17378.01	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	20044.72	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	15667.51	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	17947.34	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	15488.17	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	10814.34	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	14487.72	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	16292.96	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	20941.12	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	16749.43	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	13001.7	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	16865.53	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	12705.74	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	17218.69	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	8147.04	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	19906.73	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	15812.48	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	13304.54	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	14157.94	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	22542.39	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	21037.78	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	50003.45	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	13061.71	nM	PubChem BioAssay data set
NPT22752	Protein complex	Transcription factor AP1	Homo sapiens	IC50	=	210.0	nM	PMID[24831826]

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
-	Caenorhabditis elegans	LD50	=	10.0	ug ml-1	PMID[12147760]

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 NPC165133 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	22005
0.1-0.2	20820
0.2-0.3	5979
0.3-0.4	698
0.4-0.5	212
0.5-0.6	89
0.6-0.7	22
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC242885
1.0	High Similarity	NPC95614
1.0	High Similarity	NPC232316
0.8378	Intermediate Similarity	NPC56214
0.8158	Intermediate Similarity	NPC227217
0.8158	Intermediate Similarity	NPC117780
0.7949	Intermediate Similarity	NPC127587
0.7895	Intermediate Similarity	NPC487676
0.7576	Intermediate Similarity	NPC156840
0.7297	Intermediate Similarity	NPC85488
0.7209	Intermediate Similarity	NPC274356
0.7209	Intermediate Similarity	NPC101748
0.6944	Remote Similarity	NPC8547
0.6818	Remote Similarity	NPC487680
0.675	Remote Similarity	NPC31344
0.675	Remote Similarity	NPC317769
0.6739	Remote Similarity	NPC284464
0.6667	Remote Similarity	NPC257124
0.6486	Remote Similarity	NPC221049
0.6486	Remote Similarity	NPC140359
0.6364	Remote Similarity	NPC603109
0.6316	Remote Similarity	NPC471693
0.6316	Remote Similarity	NPC193544
0.625	Remote Similarity	NPC299406
0.62	Remote Similarity	NPC291101
0.62	Remote Similarity	NPC266197
0.6154	Remote Similarity	NPC255675
0.6136	Remote Similarity	NPC5428
0.6136	Remote Similarity	NPC607444
0.6	Remote Similarity	NPC487677
0.6	Remote Similarity	NPC57490
0.6	Remote Similarity	NPC487675
0.6	Remote Similarity	NPC603326
0.6	Remote Similarity	NPC603989
0.5854	Remote Similarity	NPC197757
0.5854	Remote Similarity	NPC17943
0.5833	Remote Similarity	NPC275950
0.5769	Remote Similarity	NPC161249
0.5745	Remote Similarity	NPC68779
0.5745	Remote Similarity	NPC108598
0.5745	Remote Similarity	NPC173308
0.5745	Remote Similarity	NPC181079
0.5714	Remote Similarity	NPC7097
0.5676	Remote Similarity	NPC293619
0.5641	Remote Similarity	NPC160380
0.5641	Remote Similarity	NPC38996
0.5581	Remote Similarity	NPC194416
0.5581	Remote Similarity	NPC177291
0.5581	Remote Similarity	NPC203133
0.5581	Remote Similarity	NPC312675
0.5581	Remote Similarity	NPC262156
0.5581	Remote Similarity	NPC127937
0.5581	Remote Similarity	NPC184651
0.5581	Remote Similarity	NPC113865
0.5556	Remote Similarity	NPC487679
0.5556	Remote Similarity	NPC487678
0.5526	Remote Similarity	NPC32163
0.55	Remote Similarity	NPC76451
0.5455	Remote Similarity	NPC117214
0.5455	Remote Similarity	NPC66518
0.5455	Remote Similarity	NPC476968
0.5435	Remote Similarity	NPC232275
0.54	Remote Similarity	NPC253481
0.54	Remote Similarity	NPC253722
0.54	Remote Similarity	NPC475875
0.5385	Remote Similarity	NPC23646
0.5385	Remote Similarity	NPC46880
0.5385	Remote Similarity	NPC485397
0.5333	Remote Similarity	NPC51840
0.5333	Remote Similarity	NPC82679
0.5319	Remote Similarity	NPC114298
0.5294	Remote Similarity	NPC273657
0.5283	Remote Similarity	NPC487681
0.5283	Remote Similarity	NPC476345
0.5283	Remote Similarity	NPC606339
0.5263	Remote Similarity	NPC246358
0.5263	Remote Similarity	NPC165106
0.5263	Remote Similarity	NPC203719
0.525	Remote Similarity	NPC36108
0.525	Remote Similarity	NPC233731
0.525	Remote Similarity	NPC610203
0.5217	Remote Similarity	NPC78974
0.5208	Remote Similarity	NPC164386
0.5208	Remote Similarity	NPC4181
0.5208	Remote Similarity	NPC201777
0.5208	Remote Similarity	NPC604524
0.52	Remote Similarity	NPC313081
0.5192	Remote Similarity	NPC102908
0.5192	Remote Similarity	NPC187998
0.5192	Remote Similarity	NPC257582
0.5192	Remote Similarity	NPC241522
0.5185	Remote Similarity	NPC106739
0.5185	Remote Similarity	NPC67247
0.5185	Remote Similarity	NPC610284
0.5128	Remote Similarity	NPC309203
0.5128	Remote Similarity	NPC604189
0.5122	Remote Similarity	NPC16651
0.5122	Remote Similarity	NPC181969
0.5116	Remote Similarity	NPC282703
0.5116	Remote Similarity	NPC184733
0.5116	Remote Similarity	NPC128208
0.5116	Remote Similarity	NPC129570
0.5116	Remote Similarity	NPC63238
0.5116	Remote Similarity	NPC602603
0.5106	Remote Similarity	NPC473853
0.5106	Remote Similarity	NPC98631
0.5106	Remote Similarity	NPC5018
0.5106	Remote Similarity	NPC206615
0.5106	Remote Similarity	NPC74817
0.5106	Remote Similarity	NPC470212
0.5106	Remote Similarity	NPC481914
0.5102	Remote Similarity	NPC266705
0.5102	Remote Similarity	NPC29008
0.5094	Remote Similarity	NPC110699
0.5094	Remote Similarity	NPC106920
0.5094	Remote Similarity	NPC300776
0.5094	Remote Similarity	NPC15811
0.5094	Remote Similarity	NPC176814
0.5094	Remote Similarity	NPC4982
0.5094	Remote Similarity	NPC106055
0.5094	Remote Similarity	NPC606629
0.5094	Remote Similarity	NPC610652
0.5091	Remote Similarity	NPC471505

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC165133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3533
0.1-0.2	5156
0.2-0.3	435
0.3-0.4	20
0.4-0.5	3
0.5-0.6	2
0.6-0.7	1
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
0.6667	Remote Similarity	NPD228	Phase 0
0.5263	Remote Similarity	NPD5283	Phase 2
0.5238	Remote Similarity	NPD824	Phase 4

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