NPASS Compound

Natural Product: NPC37009

Natural Product ID	NPC37009
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Nordentatin
IUPAC Name	5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)pyrano[3,2-g]chromen-8-one
Synonyms	Nordentatin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL158309
PubChem CID	5495613
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003486] Linear pyranocoumarins

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 43 45 0 0 0 0 0 0 0 0999 V2000 -0.3735 -2.3398 -1.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6658 -2.5539 -0.4510 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2776 -1.5078 0.4164 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8880 -0.1554 0.0238 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4571 0.2286 0.0297 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3921 -0.6867 0.4147 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7772 -0.4339 0.4669 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5643 -1.4074 -0.3926 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1833 -0.5711 1.9386 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1431 0.9378 0.0601 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2596 1.8199 -0.3094 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8524 1.4708 -0.3325 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0491 2.4115 -0.7226 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3968 2.0752 -0.7443 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8008 0.7822 -0.3666 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0889 0.5850 -0.4281 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9767 1.4710 -0.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2106 1.2118 -0.8362 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6149 2.7561 -1.1792 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2676 3.0367 -1.1388 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3756 3.6855 -1.0922 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6722 -1.7226 1.8227 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7624 -1.6563 0.5231 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5711 -1.3670 -2.1995 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0732 -3.1575 -2.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4567 -3.5172 -0.0228 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9502 -2.2437 -0.7629 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4182 -1.8339 0.2035 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0364 -0.9036 -1.2599 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8416 -1.5790 2.2978 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6022 0.2096 2.4797 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2705 -0.4623 2.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1951 1.2120 0.0731 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5445 2.8209 -0.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3539 3.4937 -1.4887 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8963 4.0335 -1.4242 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4736 4.4411 -0.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -0.7498 2.3123 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3991 -2.3254 2.3770 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2898 -2.2588 1.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2978 -1.6493 -0.4457 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0055 -2.6719 0.9783 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2154 -0.9288 1.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 7 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 13 21 1 0 3 22 1 0 3 23 1 0 15 4 1 0 12 5 1 0 20 14 1 0 1 24 1 0 1 25 1 0 2 26 1 0 8 27 1 0 8 28 1 0 8 29 1 0 9 30 1 0 9 31 1 0 9 32 1 0 10 33 1 0 11 34 1 0 19 35 1 0 20 36 1 0 21 37 1 0 22 38 1 0 22 39 1 0 22 40 1 0 23 41 1 0 23 42 1 0 23 43 1 0 M END

Standard InCHIKey	WYMMNGQSPNWCIK-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C19H20O4/c1-6-18(2,3)14-16-11(7-8-13(20)22-16)15(21)12-9-10-19(4,5)23-17(12)14/h6-10,21H,1H2,2-5H3
SMILES	C=CC(c1c2OC(C)(C)C=Cc2c(c2c1oc(=O)cc2)O)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	312.14	Volume:	328.216 ? Van der Waals volume.
Dense:	0.951	LogP:	3.539 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.17 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.489 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	18.0
TPSA:	59.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.668	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.351	Fsp³:	0.316
MCE-18:	45.76 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.54	Fluc inhibitor:	0.023 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.781 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.491 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.423	Promiscuous compounds:	0.237

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056	MDCK Permeability:	-4.774
Pgp-inhibitor:	0.069	Pgp-substrate:	0.0
PAMPA:	0.739 ? 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):	0.004
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.996
Plasma Protein Binding (PPB):	96.397%	Volume Distribution (VD):	0.214
Fu:	3.291% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.063
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.094	CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.97	CYP2C19-substrate:	0.311
CYP2C9-inhibitor:	0.998	CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.583	CYP2D6-substrate:	0.98
CYP3A4-inhibitor:	0.293	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.959	CYP2C8-inhibitor:	0.999
HLM stability:	0.767 ? 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):

5.912

Half-life (T1/2):

0.869

ADMET: Toxicity

hERG Blockers:	0.062	hERG Blockers (10um):	0.44
Human Hepatotoxicity (H-HT):	0.373	Drug-induced Liver Injury (DILI):	0.472
AMES Toxicity:	0.349	Rat Oral Acute Toxicity:	0.673
Maximum Recommended Daily Dose:	0.797	Skin Sensitization:	0.66
Carcinogencity:	0.706	Eye Corrosion:	0.484
Eye Irritation:	0.981	Respiratory Toxicity:	0.943
Drug-induced Neurotoxicity:	0.304	Ototoxicity:	0.196
Hematotoxicity:	0.137	Drug-induced Nephrotoxicity:	0.118
Genotoxicity:	0.669	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.117	Hek293 Cytotoxicity:	0.401
BCF:	1.737 ? 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:	4.38 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.133 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.59 ? 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
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 3619437]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/btpr.97]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11738-010-0631-6]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plaphy.2018.10.015]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/17429145.2017.1293852]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1186/1750-2187-3-9]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000023]
NPO18265	Citrus tamurana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11999424]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12628396]
NPO2236	Pyrola rotundifolia	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16079548]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	Hairy roots	n.a.	n.a.	PMID[19271765]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO5489	Cinnamomum tenuifolium	Species	Lauraceae	Eukaryota	stems	n.a.	n.a.	PMID[19754130]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21302964]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21953622]
NPO9537	Bauhinia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22348826]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24024688]
NPO8528	Citrus junos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25522543]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26285573]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3236015]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[32520551]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38194794]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38195615]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38681233]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38731845]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39553766]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39723058]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619887]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631435]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264679]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264682]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320741]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798960]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4311	Asterolasia squamuligera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5489	Cinnamomum tenuifolium	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8528	Citrus junos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9919	Jaspis stellifera	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9765	Petriella guttulata	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7263	Phyllobates aurotaenia	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17324	Pluchea dioscoridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2236	Pyrola rotundifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11107	Stevia alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29494	Stoeba extensa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7003	Streptomyces violaceochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10402	Strophanthus eminii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18677	Anagallis arvensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19014	Palythoa tuberculosa	Species	Sphenopidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14773	Uncaria perrottetii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5904	Grindelia humilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11978	Tanacetum argyrophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730.1	Citrus medica var. etrog	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8528	Citrus junos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14773	Uncaria perrottetii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18265	Citrus tamurana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2236	Pyrola rotundifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9955	Citrus jambhiri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7444	Clausena dentata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18265	Citrus tamurana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8528	Citrus junos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9955	Citrus jambhiri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2236	Pyrola rotundifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7444	Clausena dentata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730.1	Citrus medica var. etrog	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18677	Anagallis arvensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14773	Uncaria perrottetii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9765	Petriella guttulata	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4311	Asterolasia squamuligera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11107	Stevia alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7263	Phyllobates aurotaenia	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5489	Cinnamomum tenuifolium	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29494	Stoeba extensa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14773	Uncaria perrottetii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7003	Streptomyces violaceochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8528	Citrus junos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19014	Palythoa tuberculosa	Species	Sphenopidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10402	Strophanthus eminii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9537	Bauhinia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9919	Jaspis stellifera	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2236	Pyrola rotundifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2962	Curvularia spicifera	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7444	Clausena dentata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17324	Pluchea dioscoridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18677	Anagallis arvensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5904	Grindelia humilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11978	Tanacetum argyrophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12094	Cyclamen balearicum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24877	Maianthemum stellatum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18265	Citrus tamurana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9955	Citrus jambhiri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21978	Clausena harmandiana	Species	Rutaceae	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
EC50	5
IC50	3
Inhibition	1

Activity Type	# Activity
Cell line	6
Organism	2
Non-molecular	1

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
NPT91	Cell line	KB	Homo sapiens	EC50	=	9.63	ug.mL-1	PMID[19635670]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	17.32	ug.mL-1	PMID[19635670]
NPT81	Cell line	A549	Homo sapiens	EC50	=	8.7	ug.mL-1	PMID[19635670]
NPT639	Cell line	NCI-H187	Homo sapiens	IC50	=	11810.0	nM	PMID[21302964]
NPT91	Cell line	KB	Homo sapiens	IC50	=	20620.0	nM	PMID[21302964]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	56350.0	nM	PMID[21302964]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	9.96	ug.mL-1	PMID[19635670]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	EC50	=	6380.0	nM	PMID[19635670]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	91.2	%	PMID[10636244]

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 NPC37009 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	24449
0.1-0.2	23291
0.2-0.3	1746
0.3-0.4	327
0.4-0.5	36
0.5-0.6	4
0.6-0.7	4
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
0.7377	Intermediate Similarity	NPC83535
0.6349	Remote Similarity	NPC289316
0.625	Remote Similarity	NPC66430
0.625	Remote Similarity	NPC163248
0.6061	Remote Similarity	NPC206212
0.5694	Remote Similarity	NPC188433
0.5541	Remote Similarity	NPC57715
0.5231	Remote Similarity	NPC236419
0.5077	Remote Similarity	NPC143725

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC37009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4106
0.1-0.2	4985
0.2-0.3	57
0.3-0.4	2
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