NPASS Compound

Natural Product: NPC291724

Natural Product ID	NPC291724
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1R,2S,5R)-2-Isopropyl-5-Methylcyclohexyl Acetate
IUPAC Name	[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2236867
PubChem CID	220674
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001401] Menthane monoterpenoids

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 36 36 0 0 0 0 0 0 0 0999 V2000 2.2489 -1.7719 0.0309 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2721 -0.2708 -0.0848 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8773 0.3919 1.1220 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8897 0.2463 -0.4081 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9484 1.7676 -0.5182 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4322 2.2264 -0.9390 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3751 1.9523 0.1859 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7254 1.5066 -0.3315 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8100 0.9895 1.1948 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1555 -0.2124 0.5612 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0827 -1.0318 -0.1228 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3178 -2.3577 0.1891 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6483 -2.8292 1.1446 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3100 -3.1997 -0.5581 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0099 -2.1235 1.0510 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4517 -2.1328 -0.6650 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2553 -2.1420 -0.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9168 -0.0099 -0.9542 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1831 0.5469 1.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3142 1.3736 0.8578 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7115 -0.2628 1.4682 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6718 -0.1024 -1.4567 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6269 1.9834 -1.3904 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3071 2.2487 0.3880 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3561 3.3019 -1.1938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7221 1.6018 -1.8249 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5450 2.9198 0.7228 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3016 0.9729 0.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3216 2.4115 -0.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6444 0.8688 -1.2248 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5946 0.7244 1.9022 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0192 1.5255 1.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3592 -0.7637 1.3777 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8069 -3.9011 -1.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0834 -2.6028 -1.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7921 -3.8452 0.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 10 4 1 0 1 15 1 0 1 16 1 0 1 17 1 0 2 18 1 0 3 19 1 0 3 20 1 0 3 21 1 0 4 22 1 6 5 23 1 0 5 24 1 0 6 25 1 0 6 26 1 0 7 27 1 1 8 28 1 0 8 29 1 0 8 30 1 0 9 31 1 0 9 32 1 0 10 33 1 1 14 34 1 0 14 35 1 0 14 36 1 0 M END

Standard InCHIKey	XHXUANMFYXWVNG-ADEWGFFLSA-N
Standard InCHI	InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11+,12-/m1/s1
SMILES	CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	198.16	Volume:	222.496 ? Van der Waals volume.
Dense:	0.891	LogP:	3.134 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.874 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.628 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	7.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.637	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.141	Fsp³:	0.917
MCE-18:	20.174 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.311	Fluc inhibitor:	0.011 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.924	Promiscuous compounds:	0.498

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.041	MDCK Permeability:	-4.668
Pgp-inhibitor:	0.861	Pgp-substrate:	0.133
PAMPA:	0.029 ? 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):	0.002
20% Bioavailability (F20%):	0.1	30% Bioavailability (F30%):	0.278
50% Bioavailability (F50%):	0.825

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.434	MRP1:	0.921
Plasma Protein Binding (PPB):	63.119%	Volume Distribution (VD):	-0.05
Fu:	34.075% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.935	BCRP inhibitor:	0.345
BSEP inhibitor:	0.677

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.266	CYP2C19-substrate:	0.147
CYP2C9-inhibitor:	0.307	CYP2C9-substrate:	0.54
CYP2D6-inhibitor:	0.008	CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.566
CYP2B6-substrate:	0.013	CYP2C8-inhibitor:	0.909
HLM stability:	0.984 ? 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):

8.045

Half-life (T1/2):

0.898

ADMET: Toxicity

hERG Blockers:	0.118	hERG Blockers (10um):	0.466
Human Hepatotoxicity (H-HT):	0.623	Drug-induced Liver Injury (DILI):	0.234
AMES Toxicity:	0.273	Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.199	Skin Sensitization:	0.959
Carcinogencity:	0.583	Eye Corrosion:	0.985
Eye Irritation:	0.985	Respiratory Toxicity:	0.518
Drug-induced Neurotoxicity:	0.326	Ototoxicity:	0.421
Hematotoxicity:	0.442	Drug-induced Nephrotoxicity:	0.388
Genotoxicity:	0.01	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.237	Hek293 Cytotoxicity:	0.111
BCF:	1.486 ? 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:	3.409 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.581 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.195 ? 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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-011-0014-8]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2008.08.002]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(00)97029-8]
NPO6473.1	Perilla frutescens var. acuta	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757731]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	Leaves and branches	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	leaves	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18603435]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[20469887]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20584613]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	leaf	n.a.	PMID[21793559]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	twig	n.a.	PMID[21793559]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36365393]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37656744]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37959863]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38370080]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39141828]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39401641]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39633960]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6473.1	Perilla frutescens var. acuta	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31384	Thuja orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31056	Mentha haplocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13434	Acremonium furcatum	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20157	Boykinia tellimoides	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19830	Chamonixia caespitosa	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22349	Cucumaria frondosa	Species	Cucumariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23197	Juniperus oxycedrus	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21769	Pterocarpus dalbergioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23029	Tetradenia riparia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21902	Thalictrum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11329	Echinops grijsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30242	Sterculia lychnophora	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6473.1	Perilla frutescens var. acuta	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23197	Juniperus oxycedrus	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11329	Echinops grijsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31384	Thuja orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30242	Sterculia lychnophora	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31056	Mentha haplocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO15277	Pericarpium trichosanthis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO19054	Semen trichosanthis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11329	Echinops grijsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15277	Pericarpium trichosanthis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO6473.1	Perilla frutescens var. acuta	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26346	Semen sterculiae lychnophorae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO19054	Semen trichosanthis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23197	Juniperus oxycedrus	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31384	Thuja orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11329	Echinops grijsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30242	Sterculia lychnophora	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31056	Mentha haplocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11329	Echinops grijsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19830	Chamonixia caespitosa	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21902	Thalictrum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22349	Cucumaria frondosa	Species	Cucumariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20157	Boykinia tellimoides	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23197	Juniperus oxycedrus	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13434	Acremonium furcatum	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21769	Pterocarpus dalbergioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11329	Echinops grijsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23029	Tetradenia riparia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18951	Ligusticum sinense	Species	Apiaceae	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
-logMIC	5
Activity	1

Activity Type	# Activity
Organism	6

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
NPT21	Organism	Aspergillus niger	Aspergillus niger	-logMIC	=	1.98	n.a.	DOI[10.1007/s00044-011-9550-3]
NPT20	Organism	Candida albicans	Candida albicans	-logMIC	=	1.8	n.a.	DOI[10.1007/s00044-011-9550-3]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	-logMIC	=	1.8	n.a.	DOI[10.1007/s00044-011-9550-3]
NPT19	Organism	Escherichia coli	Escherichia coli	-logMIC	=	1.5	n.a.	DOI[10.1007/s00044-011-9550-3]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	-logMIC	=	1.5	n.a.	DOI[10.1007/s00044-011-9550-3]
NPT4976	Organism	Monographella nivalis var. nivalis	Monographella nivalis var. nivalis	Activity	=	51.2	%	PMID[12643645]

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
-	Rattus norvegicus	LD50	>	5000.0	mg/kg	ToxVal
-	Oryctolagus cuniculus	LD50	>	5000.0	mg/kg	ToxVal
-	Homo sapiens	DNEL systemic	=	33.6	mg/m3	ToxVal

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 NPC291724 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	24921
0.1-0.2	22434
0.2-0.3	2462
0.3-0.4	35
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC274261

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC291724 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6568
0.1-0.2	2502
0.2-0.3	76
0.3-0.4	2
0.4-0.5	0
0.5-0.6	2
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
0.5366	Remote Similarity	NPD8144	Pre-clinical
0.5238	Remote Similarity	NPD8143	Approved

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