NPASS Compound

Natural Product: NPC293344

Natural Product ID	NPC293344
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OEAQELZCLQUGBM-BPBQHLHPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101259865
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 82 87 0 0 0 0 0 0 0 0999 V2000 -4.2481 -2.3250 2.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9590 -2.8367 1.0926 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6639 -3.9419 0.6735 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6220 -4.5229 1.4696 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8906 -3.9921 2.7211 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2056 -2.8936 3.1649 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4988 -2.3868 4.4235 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8506 -4.5915 3.4929 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3235 -5.6316 1.0393 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9407 -2.2102 0.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7186 -2.7097 -0.8699 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2227 -1.0975 0.6707 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2574 -0.5303 -0.1615 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1620 -0.7119 0.4474 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0714 -0.2227 -0.6020 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7414 1.2745 -0.8961 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7818 1.7665 -1.8689 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0748 1.4535 -1.2734 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3954 2.0706 -0.1022 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6079 2.9510 0.3180 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5814 1.7051 0.6484 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6977 2.4533 1.8404 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6065 2.1480 2.8164 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4251 1.0885 2.6359 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3166 0.3709 1.4905 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4027 0.6356 0.4326 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5760 -0.2079 -0.7311 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6733 -1.0002 -1.3950 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1561 -1.8459 -2.4055 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4790 -1.9173 -2.7729 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3813 -1.1338 -2.1363 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9269 -0.3066 -1.1469 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8219 0.5416 -0.4655 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7443 -1.1506 -2.4616 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8531 -2.7929 -3.7890 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2349 -0.9035 -1.3412 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5598 -1.3975 -2.3119 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4376 -0.3119 -0.3770 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1404 -0.7325 1.2981 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3531 0.7441 3.5992 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6863 2.9137 3.9726 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5163 1.3428 -1.4108 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4635 0.8994 -0.4699 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7403 1.1921 -1.0026 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5897 2.1324 -0.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1440 2.7078 0.5926 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9075 2.4392 -0.9760 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6546 3.3953 -0.3199 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9145 3.7681 -0.7401 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4096 3.1428 -1.8559 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6755 2.1854 -2.5229 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4198 1.8278 -2.0867 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1977 1.5806 -3.6323 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6816 3.5145 -2.2859 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6590 4.7383 -0.0648 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4055 -2.0480 0.6964 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6905 -1.4622 2.6660 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4658 -4.3694 -0.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4890 -2.3971 4.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9066 -5.5988 3.5915 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9848 -6.3213 0.4066 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1772 -1.0847 -1.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2074 -0.1001 1.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7432 -0.7104 -1.5779 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7556 1.7539 0.0921 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6744 2.8384 -2.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 1.1866 -2.7984 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0478 3.3262 2.0123 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4208 -2.4980 -2.9251 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3876 1.1943 -1.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4305 -1.6058 -1.8402 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1465 -3.7385 -3.6248 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6713 -1.1248 2.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1106 1.3532 3.9062 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4983 3.9133 3.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3086 1.5451 0.4451 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2798 3.9080 0.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8130 1.0819 -2.5819 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0202 0.9840 -3.4984 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0309 4.4544 -2.0919 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2363 5.3395 0.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.4983 1.1851 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 5 8 1 0 4 9 1 0 2 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 31 34 1 0 30 35 1 0 28 36 1 0 36 37 2 0 36 38 1 0 25 39 1 0 24 40 1 0 23 41 1 0 16 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 51 53 1 0 50 54 1 0 49 55 1 0 14 56 1 0 6 1 1 0 43 13 1 0 52 47 1 0 38 15 1 0 26 21 1 0 32 27 1 0 1 57 1 0 3 58 1 0 7 59 1 0 8 60 1 0 9 61 1 0 13 62 1 6 14 63 1 1 15 64 1 6 16 65 1 1 17 66 1 0 17 67 1 0 22 68 1 0 29 69 1 0 33 70 1 0 34 71 1 0 35 72 1 0 39 73 1 0 40 74 1 0 41 75 1 0 43 76 1 1 48 77 1 0 52 78 1 0 53 79 1 0 54 80 1 0 55 81 1 0 56 82 1 0 M END

Standard InCHIKey	OEAQELZCLQUGBM-BPBQHLHPSA-N
Standard InCHI	InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(48)55-29-27(47)28-18(53-34(29)56-31(49)9-3-14(37)22(42)15(38)4-9)7-52-32(50)10-5-16(39)23(43)25(45)19(10)20-11(33(51)54-28)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-47H,7H2/t18-,27+,28-,29-,34+/m1/s1
SMILES	c1c(cc(c(c1O)O)O)C(=O)O[C@@H]1[C@H]([C@H]2[C@@H](COC(=O)c3cc(c(c(c3-c3c(cc(c(c3O)O)O)C(=O)O2)O)O)O)O[C@H]1OC(=O)c1cc(c(c(c1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	786.09	Volume:	696.483 ? Van der Waals volume.
Dense:	1.129	LogP:	-0.406 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.578 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.05 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	42.0
TPSA:	377.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.077	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.405	Fsp³:	0.176
MCE-18:	148.5 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.987	Fluc inhibitor:	0.095 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.449 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.659 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.524	Promiscuous compounds:	0.982

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.559	MDCK Permeability:	-4.687
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	1.0 ? 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):	0.0
20% Bioavailability (F20%):	0.978	30% Bioavailability (F30%):	0.978
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	69.897%	Volume Distribution (VD):	-0.143
Fu:	20.434% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.771
OATP1B3 inhibitor:	0.625	BCRP inhibitor:	0.182
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.002 ? 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):

3.728

Half-life (T1/2):

4.707

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.965
Human Hepatotoxicity (H-HT):	0.268	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.995	Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.733	Skin Sensitization:	1.0
Carcinogencity:	0.293	Eye Corrosion:	0.0
Eye Irritation:	0.962	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.023
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.297
BCF:	0.097 ? 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:	3.138 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.015 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.065 ? 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
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785416]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11223086]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520228]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14559084]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36431782]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	Bay of Naples, Italy	n.a.	PMID[7714539]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8773	Sonchus ortunoi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7625	Scopolia hladnikiana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8909	Pteris radiata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2174	Polysiphonia elongata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5301	Haplophyllum ferganicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2723	Artemisia carvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO550	Callicarpa maingayi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3119	Cephalaria uralensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15448	Chrysothamnus parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5541	Crotalaria aegyptiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7013	Dicoma capensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO762	Digitalis isabelliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8437	Encyothalia cliftonii	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4073	Geranium sylvaticum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26170	Haliclona mucosa	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7625	Scopolia hladnikiana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7013	Dicoma capensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5301	Haplophyllum ferganicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4073	Geranium sylvaticum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26170	Haliclona mucosa	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8909	Pteris radiata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3119	Cephalaria uralensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO762	Digitalis isabelliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8437	Encyothalia cliftonii	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2174	Polysiphonia elongata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO550	Callicarpa maingayi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15448	Chrysothamnus parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5541	Crotalaria aegyptiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2723	Artemisia carvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8773	Sonchus ortunoi	Species	Asteraceae	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 NPC293344 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	19360
0.1-0.2	29523
0.2-0.3	792
0.3-0.4	71
0.4-0.5	66
0.5-0.6	31
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.697	Remote Similarity	NPC311389
0.6923	Remote Similarity	NPC291957
0.6769	Remote Similarity	NPC43918
0.6769	Remote Similarity	NPC261411
0.6769	Remote Similarity	NPC190204
0.6716	Remote Similarity	NPC302170
0.6667	Remote Similarity	NPC469651
0.6615	Remote Similarity	NPC47521
0.6269	Remote Similarity	NPC488888
0.6029	Remote Similarity	NPC14030
0.5789	Remote Similarity	NPC470271
0.5652	Remote Similarity	NPC175793
0.5652	Remote Similarity	NPC159913
0.5625	Remote Similarity	NPC44260
0.561	Remote Similarity	NPC470272
0.56	Remote Similarity	NPC470898
0.5556	Remote Similarity	NPC198125
0.5455	Remote Similarity	NPC205037
0.5455	Remote Similarity	NPC3746
0.5373	Remote Similarity	NPC172419
0.5366	Remote Similarity	NPC112211
0.5366	Remote Similarity	NPC254925
0.5238	Remote Similarity	NPC223534
0.5238	Remote Similarity	NPC483712
0.5238	Remote Similarity	NPC158214
0.5238	Remote Similarity	NPC97924
0.5238	Remote Similarity	NPC214202
0.5231	Remote Similarity	NPC142528
0.5176	Remote Similarity	NPC290289
0.5152	Remote Similarity	NPC114791
0.5152	Remote Similarity	NPC104222
0.5152	Remote Similarity	NPC210501
0.5152	Remote Similarity	NPC318826
0.5152	Remote Similarity	NPC141331
0.5147	Remote Similarity	NPC238419
0.5128	Remote Similarity	NPC8940
0.5122	Remote Similarity	NPC80956
0.5104	Remote Similarity	NPC93065
0.5104	Remote Similarity	NPC220876
0.5065	Remote Similarity	NPC217781
0.5059	Remote Similarity	NPC486113

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC293344 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5825
0.1-0.2	3309
0.2-0.3	15
0.3-0.4	1
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