NPASS Compound

Natural Product: NPC202116

Natural Product ID	NPC202116
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CDICDSOGTRCHMG-LKVLSFTLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10987510
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

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 27 27 0 0 0 0 0 0 0 0999 V2000 -1.3095 -3.4077 -0.7214 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9856 -2.1901 -0.4823 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3461 -0.9959 -0.2426 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0304 -0.9370 -0.2253 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7357 0.2166 0.0067 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1841 0.2846 0.0261 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9235 -0.7752 -0.1812 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3962 -0.6889 -0.1581 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9620 0.4147 0.0634 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0195 1.3836 0.2353 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3855 1.3180 0.2167 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0876 0.1312 -0.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4749 0.1721 -0.0194 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1188 2.4836 0.4451 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4741 3.6988 0.6890 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0415 -4.1657 -1.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4794 -3.3073 -1.4169 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9140 -3.7747 0.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5611 -1.8716 -0.4086 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6665 1.2327 0.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5018 -1.7508 -0.3766 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9464 -1.5942 -0.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5408 2.2895 0.4174 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9589 -0.2612 0.7772 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6908 3.5986 1.4911 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2092 4.4492 1.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9532 4.0471 -0.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 5 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 11 14 1 0 14 15 1 0 12 3 1 0 1 16 1 0 1 17 1 0 1 18 1 0 4 19 1 0 6 20 1 0 7 21 1 0 8 22 1 0 10 23 1 0 13 24 1 0 15 25 1 0 15 26 1 0 15 27 1 0 M ISO 1 8 13 M END

Standard InCHIKey	CDICDSOGTRCHMG-LKVLSFTLSA-N
Standard InCHI	InChI=1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+/i5+1
SMILES	COc1cc(/C=C/[13CH]=O)cc(c1O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	209.08	Volume:	212.234 ? Van der Waals volume.
Dense:	0.985	LogP:	1.641 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.612 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.622 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	8.0
TPSA:	55.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.465	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.264	Fsp³:	0.182
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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.392	Fluc inhibitor:	0.913 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.184 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.395 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.975	Promiscuous compounds:	0.434

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.161	MDCK Permeability:	-4.837
Pgp-inhibitor:	0.84	Pgp-substrate:	0.151
PAMPA:	0.024 ? 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):	0.05
20% Bioavailability (F20%):	0.239	30% Bioavailability (F30%):	0.212
50% Bioavailability (F50%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153	MRP1:	0.9
Plasma Protein Binding (PPB):	93.085%	Volume Distribution (VD):	-0.59
Fu:	5.527% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.981
OATP1B3 inhibitor:	0.984	BCRP inhibitor:	0.92
BSEP inhibitor:	0.956

ADMET: Metabolism

CYP1A2-inhibitor:	0.012	CYP1A2-substrate:	0.791
CYP2C19-inhibitor:	0.487	CYP2C19-substrate:	0.517
CYP2C9-inhibitor:	0.746	CYP2C9-substrate:	0.79
CYP2D6-inhibitor:	0.703	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.921
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.518 ? 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):

8.75

Half-life (T1/2):

1.428

ADMET: Toxicity

hERG Blockers:	0.117	hERG Blockers (10um):	0.458
Human Hepatotoxicity (H-HT):	0.452	Drug-induced Liver Injury (DILI):	0.438
AMES Toxicity:	0.669	Rat Oral Acute Toxicity:	0.471
Maximum Recommended Daily Dose:	0.398	Skin Sensitization:	0.644
Carcinogencity:	0.698	Eye Corrosion:	0.554
Eye Irritation:	0.974	Respiratory Toxicity:	0.679
Drug-induced Neurotoxicity:	0.668	Ototoxicity:	0.205
Hematotoxicity:	0.299	Drug-induced Nephrotoxicity:	0.401
Genotoxicity:	0.514	RPMI-8226 Immunitoxicity:	0.115
A549 Cytotoxicity:	0.117	Hek293 Cytotoxicity:	0.225
BCF:	1.023 ? 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:	3.581 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.853 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.417 ? 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
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1007/s11418-005-0009-z]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678654]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787451]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17055270]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	Roots	Anhui, China	n.a.	PMID[22694318]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24176362]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25466198]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32004936]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39053741]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO17973	Sinapis arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17973	Sinapis arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17973	Sinapis arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17973	Sinapis arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7539	Raphanus sativus	Species	Brassicaceae	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC202116 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	24425
0.1-0.2	19760
0.2-0.3	5129
0.3-0.4	455
0.4-0.5	71
0.5-0.6	14
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271985
0.6765	Remote Similarity	NPC229401
0.6757	Remote Similarity	NPC39793
0.6486	Remote Similarity	NPC58279
0.5854	Remote Similarity	NPC200014
0.5854	Remote Similarity	NPC109275
0.5641	Remote Similarity	NPC300326
0.549	Remote Similarity	NPC193722
0.5455	Remote Similarity	NPC48315
0.5429	Remote Similarity	NPC13755
0.5405	Remote Similarity	NPC179309
0.5294	Remote Similarity	NPC274613
0.5192	Remote Similarity	NPC83375
0.5152	Remote Similarity	NPC193067
0.5143	Remote Similarity	NPC208760
0.5116	Remote Similarity	NPC483674
0.5106	Remote Similarity	NPC111635
0.5094	Remote Similarity	NPC473408

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC202116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4146
0.1-0.2	4816
0.2-0.3	178
0.3-0.4	9
0.4-0.5	1
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