NPASS Compound

Natural Product: NPC308311

Natural Product ID	NPC308311
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hinokiol
IUPAC Name	(2S,4aS,10aR)-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-2,6-diol
Synonyms	Hinokiol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1277661
PubChem CID	12310492
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 52 54 0 0 0 0 0 0 0 0999 V2000 5.4307 0.8440 -0.1903 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6493 -0.1855 0.6101 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2056 -0.1690 0.2668 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3398 0.6505 0.9615 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9937 0.7091 0.6894 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1730 1.6348 1.5130 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2128 1.8373 0.8855 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7043 0.4621 0.5008 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9549 -0.0924 -0.6907 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4862 -0.0773 -0.3127 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3360 -0.9029 -1.0182 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6979 -0.9613 -0.7419 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5217 -1.8053 -1.4744 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0935 0.7582 -1.9240 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3455 -1.5142 -0.9252 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8310 -1.7584 -0.9028 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5459 -1.0999 0.2261 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1807 0.3487 0.4044 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7591 0.7827 1.7480 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8263 1.1683 -0.6506 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9271 -1.1561 -0.0678 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2727 -1.5342 0.4967 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9215 1.8083 -0.2314 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4205 0.9519 0.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6345 0.4000 -1.1837 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7385 0.1486 1.6838 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7626 1.2692 1.7558 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0200 1.1473 2.4958 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6708 2.5901 1.7170 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2041 2.5596 0.0748 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8704 2.2192 1.6809 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3931 -0.2026 1.3647 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9954 -1.5423 -1.8153 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9839 -1.5279 -2.3293 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6469 0.1403 -2.6847 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0916 0.9426 -2.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5327 1.7391 -1.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0194 -1.7689 -1.9769 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8254 -2.2430 -0.2709 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3116 -1.5397 -1.8800 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9593 -2.8728 -0.7669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4110 -1.6055 1.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0495 0.5302 2.5675 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8828 1.8843 1.6976 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7728 0.3569 1.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5483 2.2483 -0.5656 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7291 0.7777 -1.6779 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9380 1.1591 -0.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1118 -1.8096 -0.7970 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0366 -1.7255 1.3046 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8605 -1.5964 -0.4635 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5677 -2.3779 0.5361 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 9 14 1 6 9 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 17 21 1 0 2 22 1 0 12 3 1 0 10 5 2 0 18 8 1 0 1 23 1 0 1 24 1 0 1 25 1 0 2 26 1 0 4 27 1 0 6 28 1 0 6 29 1 0 7 30 1 0 7 31 1 0 8 32 1 1 11 33 1 0 13 34 1 0 14 35 1 0 14 36 1 0 14 37 1 0 15 38 1 0 15 39 1 0 16 40 1 0 16 41 1 0 17 42 1 1 19 43 1 0 19 44 1 0 19 45 1 0 20 46 1 0 20 47 1 0 20 48 1 0 21 49 1 0 22 50 1 0 22 51 1 0 22 52 1 0 M END

Standard InCHIKey	ODFCWXVQZAQDSO-CMKODMSKSA-N
Standard InCHI	InChI=1S/C20H30O2/c1-12(2)14-10-13-6-7-17-19(3,4)18(22)8-9-20(17,5)15(13)11-16(14)21/h10-12,17-18,21-22H,6-9H2,1-5H3/t17-,18-,20+/m0/s1
SMILES	CC(c1cc2CC[C@@H]3[C@](c2cc1O)(C)CC[C@@H](C3(C)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	302.22	Volume:	338.478 ? Van der Waals volume.
Dense:	0.893	LogP:	3.626 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.352 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.202 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	16.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.801	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.583	Fsp³:	0.7
MCE-18:	76.353 ? 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:	0.285	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.119 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.454	Promiscuous compounds:	0.042

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.597	MDCK Permeability:	-4.678
Pgp-inhibitor:	0.64	Pgp-substrate:	0.395
PAMPA:	0.508 ? 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):	0.018
20% Bioavailability (F20%):	0.967	30% Bioavailability (F30%):	0.927
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16	MRP1:	0.983
Plasma Protein Binding (PPB):	95.702%	Volume Distribution (VD):	0.106
Fu:	5.568% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.98	BCRP inhibitor:	0.229
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.996	CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.57
CYP2C9-inhibitor:	0.599	CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.9	CYP3A4-substrate:	0.948
CYP2B6-substrate:	0.749	CYP2C8-inhibitor:	0.902
HLM stability:	0.364 ? 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):

9.61

Half-life (T1/2):

0.959

ADMET: Toxicity

hERG Blockers:	0.077	hERG Blockers (10um):	0.449
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.176
AMES Toxicity:	0.564	Rat Oral Acute Toxicity:	0.665
Maximum Recommended Daily Dose:	0.753	Skin Sensitization:	0.939
Carcinogencity:	0.746	Eye Corrosion:	0.009
Eye Irritation:	0.839	Respiratory Toxicity:	0.906
Drug-induced Neurotoxicity:	0.162	Ototoxicity:	0.711
Hematotoxicity:	0.43	Drug-induced Nephrotoxicity:	0.752
Genotoxicity:	0.418	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.653	Hek293 Cytotoxicity:	0.506
BCF:	1.875 ? 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:	4.22 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.38 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.961 ? 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
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 36006216]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[11473432]
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[12713411]
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]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124776]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17907781]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18804027]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[19646881]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20233596]
NPO1994	Panax stipuleanatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20951582]
NPO25054	Phaleria macrocarpa	Species	Thymelaeaceae	Eukaryota	nut shell	n.a.	n.a.	PMID[23044367]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24460410]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058711]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8557595]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[8991951]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644081]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28466	Torreya nucifera	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3721	Achyranthes obtusifolia	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28460	Achyrocline tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25389	Allium angulosum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18706	Anemone thalictroides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25492	Botryllus leachi	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24461	Clusia sandiensis	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25441	Desmodium pulchellu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24802	Diploprion bifasciatum	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24882	Erythrophleum chlorostachys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24607	Goniothalamus dolichocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24730	Lactarius deliciosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25466	Lecanora sulphurella	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24566	Marasmiellus ramealis	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20264	Moonia heterophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23994	Ormosia macrophylla	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14189	Osmundaria spiralis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25054	Phaleria macrocarpa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22618	Psolus eximius	Species	Psolidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23894	Pulicaria insignis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25277	Seiridium cupressi	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22152	Tecoma undulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15482	Vanderbylia fraxinea	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27390	Vernonia brevifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3881	Erucastrum gallicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20487	Isodon flavidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20487	Isodon flavidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	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]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28460	Achyrocline tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25389	Allium angulosum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25492	Botryllus leachi	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18706	Anemone thalictroides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23894	Pulicaria insignis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14189	Osmundaria spiralis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24730	Lactarius deliciosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25277	Seiridium cupressi	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20264	Moonia heterophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15482	Vanderbylia fraxinea	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9837	Athrotaxis cupressoides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24566	Marasmiellus ramealis	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23994	Ormosia macrophylla	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22618	Psolus eximius	Species	Psolidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24461	Clusia sandiensis	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24607	Goniothalamus dolichocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3721	Achyranthes obtusifolia	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24882	Erythrophleum chlorostachys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27390	Vernonia brevifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24802	Diploprion bifasciatum	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25441	Desmodium pulchellu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22152	Tecoma undulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25466	Lecanora sulphurella	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25054	Phaleria macrocarpa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3881	Erucastrum gallicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1994	Panax stipuleanatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17373	Cunninghamia lanceolata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20487	Isodon flavidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28466	Torreya nucifera	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6932	Libanotis montana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28256	Platycladus orientalis	Species	Cupressaceae	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
IC50	13
Activity	2

Activity Type	# Activity
Cell line	15

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
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[33978415]
NPT113	Cell line	RAW264.7	Mus musculus	Activity	n.a.	n.a.	n.a.	PMID[37146221]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[33978415]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[33978415]
NPT660	Cell line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[33978415]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[33978415]
NPT23095	Cell line	BEAS-2B	Homo sapiens	IC50	>	10000.0	nM	PMID[33978415]

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 NPC308311 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	17425
0.1-0.2	31175
0.2-0.3	1083
0.3-0.4	113
0.4-0.5	34
0.5-0.6	13
0.6-0.7	10
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC8776
0.7755	Intermediate Similarity	NPC477137
0.7692	Intermediate Similarity	NPC600507
0.7	Intermediate Similarity	NPC324602
0.6538	Remote Similarity	NPC260323
0.6481	Remote Similarity	NPC192948
0.6481	Remote Similarity	NPC147179
0.6481	Remote Similarity	NPC35797
0.6296	Remote Similarity	NPC150601
0.6296	Remote Similarity	NPC601694
0.625	Remote Similarity	NPC36765
0.6226	Remote Similarity	NPC27252
0.6226	Remote Similarity	NPC472979
0.6182	Remote Similarity	NPC11250
0.5893	Remote Similarity	NPC219112
0.5763	Remote Similarity	NPC58560
0.5614	Remote Similarity	NPC172219
0.5614	Remote Similarity	NPC304510
0.5593	Remote Similarity	NPC471187
0.5536	Remote Similarity	NPC604259
0.541	Remote Similarity	NPC481087
0.5357	Remote Similarity	NPC176279
0.5345	Remote Similarity	NPC606176
0.5345	Remote Similarity	NPC606869
0.5323	Remote Similarity	NPC481011
0.5254	Remote Similarity	NPC137750
0.5172	Remote Similarity	NPC38893

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC308311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5519
0.1-0.2	3585
0.2-0.3	43
0.3-0.4	3
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