NPASS Compound

Natural Product: NPC14121

Natural Product ID	NPC14121
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ACYXDIZTQDLTCB-YRZZOSFISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101249839
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 50 0 0 0 0 0 0 0 0999 V2000 6.0188 -0.4016 -0.5492 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1276 0.3166 -0.9508 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0493 1.6797 -1.0327 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8461 2.2910 -0.7053 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7424 1.5525 -0.3037 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8239 0.2009 -0.2238 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6913 -0.6075 0.1926 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5148 -0.1309 0.5214 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4329 -1.0586 0.9314 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6330 -2.2988 0.9668 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1930 -0.5946 1.2808 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8778 -1.4617 1.6825 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3148 -1.1739 3.0391 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7530 -0.1739 3.6221 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2486 -1.8226 3.7983 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9171 -1.3304 0.5958 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3856 0.0684 0.4839 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3920 0.3525 -0.5385 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0154 0.6588 -1.8464 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0145 0.9237 -2.7435 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3480 0.8980 -2.4040 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7343 0.5984 -1.1208 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7245 0.3257 -0.1933 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0807 0.5683 -0.7615 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3381 1.1745 -3.3503 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0221 -2.2607 0.8546 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1844 -3.2687 0.1109 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8923 -2.0590 1.8942 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2153 -1.7372 -0.5852 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7491 3.6526 -0.7811 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1351 2.4496 -1.4311 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0704 -1.4851 -0.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0674 -0.1810 -1.2050 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8505 2.1067 -0.0689 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7817 -1.7102 0.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3426 0.9310 0.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4709 -2.4907 1.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2794 -1.8145 4.8171 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4833 0.6990 0.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7986 0.3841 1.4736 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9660 0.6643 -2.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7325 1.1625 -3.7609 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0932 0.1011 0.8132 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5559 -0.2830 -0.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5347 2.1609 -3.5117 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6984 -2.6573 2.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6307 -0.9960 -0.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5942 4.0758 -1.6896 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0380 2.0016 -1.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 12 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 21 25 1 0 16 26 1 0 26 27 2 0 26 28 1 0 16 29 1 6 4 30 1 0 3 31 1 0 6 1 1 0 23 18 1 0 1 32 1 0 2 33 1 0 5 34 1 0 7 35 1 0 8 36 1 0 12 37 1 1 15 38 1 0 17 39 1 0 17 40 1 0 19 41 1 0 20 42 1 0 23 43 1 0 24 44 1 0 25 45 1 0 28 46 1 0 29 47 1 0 30 48 1 0 31 49 1 0 M END

Standard InCHIKey	ACYXDIZTQDLTCB-YRZZOSFISA-N
Standard InCHI	InChI=1S/C20H18O11/c21-12-4-1-10(7-14(12)23)3-6-16(25)31-17(18(26)27)20(30,19(28)29)9-11-2-5-13(22)15(24)8-11/h1-8,17,21-24,30H,9H2,(H,26,27)(H,28,29)/b6-3+/t17-,20+/m0/s1
SMILES	c1cc(c(cc1/C=C/C(=O)O[C@@H](C(=O)O)[C@](Cc1ccc(c(c1)O)O)(C(=O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	434.08	Volume:	407.691 ? Van der Waals volume.
Dense:	1.065	LogP:	1.214 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.479 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.647 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	16.0
TPSA:	202.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	2.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.174	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.613	Fsp³:	0.15
MCE-18:	38.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.616	Fluc inhibitor:	0.615 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.503 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.59	Promiscuous compounds:	0.201

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.776	MDCK Permeability:	-5.004
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	0.997 ? 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):	0.142
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.471
Plasma Protein Binding (PPB):	71.347%	Volume Distribution (VD):	-0.327
Fu:	15.84% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.017	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.789
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.978
HLM stability:	0.027 ? 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):

5.169

Half-life (T1/2):

2.71

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.061
Human Hepatotoxicity (H-HT):	0.678	Drug-induced Liver Injury (DILI):	0.881
AMES Toxicity:	0.406	Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.401	Skin Sensitization:	1.0
Carcinogencity:	0.075	Eye Corrosion:	0.055
Eye Irritation:	0.949	Respiratory Toxicity:	0.181
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.952
Hematotoxicity:	0.032	Drug-induced Nephrotoxicity:	0.293
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.004
A549 Cytotoxicity:	0.6	Hek293 Cytotoxicity:	0.035
BCF:	0.595 ? 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:	3.472 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.63 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.351 ? 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
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662092]
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15679308]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[1686898]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226514]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[26281591]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3404159]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37988956]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1049	Tethya amamensis	Species	Tethyidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7793	Matricaria matricarioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO117	Acacia armata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO643	Astragalus ernestii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1706	Eragrostis curvula	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8950	Stilpnopappus pickelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1203	Solanum pseudoquina	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4836	Sideritis arborescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2323	Plantago lundborgii	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19991	Mantella aurantiaca	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13682	Lonchocarpus laxiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5339	Isophysis tasmanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8132	Fritillaria meleagris	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2008	Streptomyces ehimensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17179	Elizabethkingia meningoseptica	Species	Flavobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3445	Dumoria heckeli	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1541	Clusia ellipticifolia	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21493	Bunodosoma caissarum	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8433	Bongardia chrysogonum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2323	Plantago lundborgii	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19991	Mantella aurantiaca	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7793	Matricaria matricarioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1049	Tethya amamensis	Species	Tethyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21493	Bunodosoma caissarum	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8950	Stilpnopappus pickelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1706	Eragrostis curvula	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13682	Lonchocarpus laxiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1541	Clusia ellipticifolia	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17179	Elizabethkingia meningoseptica	Species	Flavobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5339	Isophysis tasmanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1203	Solanum pseudoquina	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8433	Bongardia chrysogonum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO117	Acacia armata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8132	Fritillaria meleagris	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2008	Streptomyces ehimensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4836	Sideritis arborescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO643	Astragalus ernestii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3445	Dumoria heckeli	n.a.	n.a.	n.a.	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 NPC14121 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	12755
0.1-0.2	33598
0.2-0.3	3061
0.3-0.4	313
0.4-0.5	80
0.5-0.6	20
0.6-0.7	10
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC179505
0.8909	High Similarity	NPC156709
0.8909	High Similarity	NPC279676
0.8571	High Similarity	NPC67349
0.8167	Intermediate Similarity	NPC221383
0.7903	Intermediate Similarity	NPC283081
0.7857	Intermediate Similarity	NPC108553
0.7742	Intermediate Similarity	NPC143892
0.7742	Intermediate Similarity	NPC299090
0.7742	Intermediate Similarity	NPC246566
0.7031	Intermediate Similarity	NPC258671
0.7018	Intermediate Similarity	NPC18074
0.7018	Intermediate Similarity	NPC5419
0.7018	Intermediate Similarity	NPC25581
0.7018	Intermediate Similarity	NPC61
0.6792	Remote Similarity	NPC217052
0.6792	Remote Similarity	NPC329344
0.6792	Remote Similarity	NPC237506
0.6792	Remote Similarity	NPC32626
0.6667	Remote Similarity	NPC251407
0.6667	Remote Similarity	NPC168653
0.6515	Remote Similarity	NPC95498
0.6515	Remote Similarity	NPC304956
0.623	Remote Similarity	NPC198388
0.6207	Remote Similarity	NPC132921
0.5968	Remote Similarity	NPC229264
0.5909	Remote Similarity	NPC289690
0.5854	Remote Similarity	NPC44507
0.5571	Remote Similarity	NPC53884
0.5507	Remote Similarity	NPC38473
0.5385	Remote Similarity	NPC13818
0.5385	Remote Similarity	NPC219428
0.5342	Remote Similarity	NPC160378
0.5294	Remote Similarity	NPC477333
0.5254	Remote Similarity	NPC147654
0.5231	Remote Similarity	NPC475695
0.5079	Remote Similarity	NPC470849
0.5079	Remote Similarity	NPC488563
0.5072	Remote Similarity	NPC471027
0.5072	Remote Similarity	NPC37250
0.5072	Remote Similarity	NPC142703
0.5072	Remote Similarity	NPC152942
0.5072	Remote Similarity	NPC9991
0.5072	Remote Similarity	NPC302857
0.5072	Remote Similarity	NPC600892

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC14121 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2684
0.1-0.2	6182
0.2-0.3	264
0.3-0.4	15
0.4-0.5	5
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