NPASS Compound

Natural Product: NPC104724

Natural Product ID	NPC104724
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ULTBCADWJVQRCF-QWHCGFSZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10798255
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

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 39 40 0 0 0 0 0 0 0 0999 V2000 3.3771 -0.9158 1.0477 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0869 -0.9366 0.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2602 -0.6597 -1.1797 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0615 -0.0405 0.9401 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4747 1.3755 1.0387 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0070 2.2657 -0.0687 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4335 2.1076 -0.4236 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3429 2.9734 0.4020 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9197 0.7057 -0.3165 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2541 -0.2432 0.2886 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8429 -1.5748 0.3215 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0038 -1.9004 -0.2156 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5124 -3.3259 -0.1151 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7819 -0.8743 -0.9021 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2427 0.4857 -0.9669 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9159 -1.8867 1.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0812 -0.1565 0.6355 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1804 -0.7356 2.1332 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6804 -1.9816 0.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4561 -1.5671 -1.7866 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4261 -0.1106 -1.6407 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1771 -0.0126 -1.2998 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9694 -0.4373 1.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1550 1.8385 2.0132 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5938 1.4336 1.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6614 2.2123 -0.9648 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1265 3.3260 0.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5484 2.3996 -1.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7743 3.8620 0.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7490 2.4352 1.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1873 3.3920 -0.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2880 -2.3863 0.8315 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4395 -3.8325 -1.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5495 -3.3053 0.2949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8784 -3.8575 0.6101 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8162 -0.8803 -0.4394 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9814 -1.2384 -1.9552 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1596 0.8459 -2.0166 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9853 1.2008 -0.5012 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 12 14 1 0 14 15 1 0 10 4 1 0 15 9 1 0 1 16 1 0 1 17 1 0 1 18 1 0 2 19 1 0 3 20 1 0 3 21 1 0 3 22 1 0 4 23 1 1 5 24 1 0 5 25 1 0 6 26 1 0 6 27 1 0 7 28 1 6 8 29 1 0 8 30 1 0 8 31 1 0 11 32 1 0 13 33 1 0 13 34 1 0 13 35 1 0 14 36 1 0 14 37 1 0 15 38 1 0 15 39 1 0 M END

Standard InCHIKey	ULTBCADWJVQRCF-QWHCGFSZSA-N
Standard InCHI	InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,12-13H,5-8H2,1-4H3/t12-,13+/m0/s1
SMILES	CC(C)[C@H]1CC[C@H](C)C2=C1C=C(C)CC2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	204.19	Volume:	245.61 ? Van der Waals volume.
Dense:	0.831	LogP:	4.393 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.425 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.413 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	11.0
TPSA:	0.0 ? Topological Polar Surface Area.	H-Bond Acceptor:	0.0
H-Bond Donor:	0.0	Rings:	2.0
Heavy Atoms:	0.0

MedChem Properties

QED Drug-Likeness Score:	0.579	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.029	Fsp³:	0.733
MCE-18:	29.538 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.503	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.14 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.885	Promiscuous compounds:	0.254

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.672	MDCK Permeability:	-4.636
Pgp-inhibitor:	0.98	Pgp-substrate:	0.366
PAMPA:	0.121 ? 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):	0.001
20% Bioavailability (F20%):	0.527	30% Bioavailability (F30%):	0.336
50% Bioavailability (F50%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.868
Plasma Protein Binding (PPB):	97.933%	Volume Distribution (VD):	0.085
Fu:	2.473% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.942	BCRP inhibitor:	0.222
BSEP inhibitor:	0.939

ADMET: Metabolism

CYP1A2-inhibitor:	0.949	CYP1A2-substrate:	0.993
CYP2C19-inhibitor:	0.965	CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.074	CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.026	CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.426	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.692	CYP2C8-inhibitor:	0.91
HLM stability:	0.987 ? 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):

8.912

Half-life (T1/2):

0.259

ADMET: Toxicity

hERG Blockers:	0.081	hERG Blockers (10um):	0.314
Human Hepatotoxicity (H-HT):	0.46	Drug-induced Liver Injury (DILI):	0.596
AMES Toxicity:	0.632	Rat Oral Acute Toxicity:	0.277
Maximum Recommended Daily Dose:	0.404	Skin Sensitization:	0.795
Carcinogencity:	0.845	Eye Corrosion:	0.826
Eye Irritation:	0.984	Respiratory Toxicity:	0.847
Drug-induced Neurotoxicity:	0.538	Ototoxicity:	0.359
Hematotoxicity:	0.494	Drug-induced Nephrotoxicity:	0.449
Genotoxicity:	0.083	RPMI-8226 Immunitoxicity:	0.092
A549 Cytotoxicity:	0.295	Hek293 Cytotoxicity:	0.342
BCF:	3.095 ? 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:	4.414 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.965 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.203 ? 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
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/(SICI)1097-0010(199909)79:12<1620::AID-JSFA410>3.0.CO;2-G]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1007/s00217-002-0656-1]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1007/s00217-015-2561-4]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-015-0798-z]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	DOI[10.1016/0045-6535(91)90110-Y]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.abb.2017.09.009]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.fitote.2006.01.011]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.foodchem.2007.07.014]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.foodchem.2010.05.061]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.foodchem.2010.05.061]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.indcrop.2013.08.051]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003Ã¢â‚¬â€œ2005	DOI[10.1016/j.jfca.2006.05.007]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plaphy.2005.07.013]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.ssnmr.2006.05.001]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.yclnex.2017.01.002; 10.31989/ffhd.v6i3.245]DOI[10.1016/j.yclnex.2017.01.002; 10.31989/ffhd.v6i3.245]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0885-5765(05)80069-4]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1078/0176-1617-00195]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1080/09064710.2011.598543]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1111/j.1365-2621.1989.tb04709.x]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1111/j.1745-4530.2009.00507.x]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1155/2014/609649]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.15835/NBHA4017181]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.17221/540/2012-CJFS]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.2137/145960607781635822]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.2478/aoas-2014-0072]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.3136/NSKKK.48.606]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.3390/agriculture2030244]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757735]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12088434]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14735439]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[15563205]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	callus	n.a.	PMID[15715262]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220354]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[19555125]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21707257]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21800857]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[22677314]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[25026919]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[25977015]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[26351516]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[27556441]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28445039]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29726697]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30024167]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Aug	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Cracow, Poland	2008-Sep	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Sep	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Oct	PMID[31206724]
NPO56029	Vitex gardneriana	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31229603]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[31619015]
NPO26620	Pulicaria arabica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32372353]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32560389]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32872604]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	PMID[33151073]
NPO61560	Ocotea quixos	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34203565]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34332066]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34443694]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34684884]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34770961]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35631245]
NPO5220	Knema globularia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35876169]
NPO56320	Pinus ponderosa var. ponderosa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36080426]
NPO44083	Plectranthus neochilus	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36270431]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36336219]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36352904]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36364159]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36401242]
NPO45619	Myrcia sylvatica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36558108]
NPO43457	Thymus holosericeus	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36679061]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37020229]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37226152]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446712]
NPO9773	Sideritis raeseri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37509192]
NPO64248	Eucalyptus patellaris	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37894690]
NPO62335	Eugenia brasiliensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37917799]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37939623]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38217369]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38257205]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38370080]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38381096]
NPO50815	Pistacia khinjuk	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38412297]
NPO26551	Artemisia ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38543021]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38688144]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38695450]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38810900]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893452]
NPO45785	Peperomia leptostachya	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38930872]
NPO60918	Drimys granadensis	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38999646]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39407547]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39679248]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39680258]
NPO53844	Gynoxys pulchella	Genus	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39771242]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Flowers	n.a.		PMID[9301422]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[9301422]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26551	Artemisia ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5220	Knema globularia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO44083	Plectranthus neochilus	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9773	Sideritis raeseri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26620	Pulicaria arabica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26551	Artemisia ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5220	Knema globularia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5220	Knema globularia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26551	Artemisia ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26551	Artemisia ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5220	Knema globularia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26620	Pulicaria arabica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9773	Sideritis raeseri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26551	Artemisia ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3689	Cinnamomum verum	Species	Lauraceae	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
NPO19472	Thymus vulgaris	Oil	n.a.	0.01	n.a.	n.a.	%	PMID[37226152]
NPO19472	Thymus vulgaris	Oil	n.a.	0.02	n.a.	n.a.	%	PMID[37226152]
NPO23234	Ageratum conyzoides	Oil	n.a.	0.09	n.a.	n.a.	%	PMID[38810900]
NPO23234	Ageratum conyzoides	Oil	n.a.	0.11	n.a.	n.a.	%	PMID[38810900]
NPO23234	Ageratum conyzoides	Oil	n.a.	0.06	n.a.	n.a.	%	PMID[38810900]
NPO23234	Ageratum conyzoides	Oil	n.a.	0.08	n.a.	n.a.	%	PMID[38810900]
NPO23234	Ageratum conyzoides	Oil	n.a.	0.1	n.a.	n.a.	%	PMID[38810900]
NPO26551	Artemisia ludoviciana	Oil	Aerial parts	0.1	n.a.	n.a.	%	PMID[38543021]
NPO26620	Pulicaria arabica	Oil	n.a.	3.2Â±0.7	n.a.	n.a.	%	PMID[32372353]
NPO31458	Cinnamomum cassia	Oil	n.a.	0.11	n.a.	n.a.	%	PMID[34332066]
NPO3689	Cinnamomum verum	Oil	Leaves	0.05	n.a.	n.a.	%	PMID[36364159]
NPO3689	Cinnamomum verum	Oil	Leaves	0.02	n.a.	n.a.	%	PMID[36364159]
NPO43457	Thymus holosericeus	Oil	n.a.	0.1	n.a.	n.a.	%	PMID[36679061]
NPO44083	Plectranthus neochilus	Oil	n.a.	0.15	n.a.	n.a.	%	PMID[36270431]
NPO45619	Myrcia sylvatica	Oil	Leaves	0.2	n.a.	n.a.	%	PMID[36558108]
NPO45785	Peperomia leptostachya	Oil	Leaves	1.3	n.a.	n.a.	%	PMID[38930872]
NPO50815	Pistacia khinjuk	Oil	Leaves	2.82	n.a.	n.a.	%	PMID[38412297]
NPO5220	Knema globularia	Oil	Leaves	0.17Â±0.01	n.a.	n.a.	%	PMID[35876169]
NPO53844	Gynoxys pulchella	Oil	n.a.	0.1	n.a.	n.a.	%	PMID[39771242]
NPO56029	Vitex gardneriana	Oil	n.a.	0.7	n.a.	n.a.	%	PMID[31229603]
NPO56320	Pinus ponderosa var. ponderosa	Oil	n.a.	0.1	n.a.	n.a.	%	PMID[36080426]
NPO60918	Drimys granadensis	Oil	n.a.	0.83	n.a.	n.a.	%	PMID[38999646]
NPO61560	Ocotea quixos	Oil	Leaves	0.27	n.a.	n.a.	%	PMID[34203565]
NPO61560	Ocotea quixos	Oil	Leaves	0.95	n.a.	n.a.	%	PMID[34203565]
NPO61560	Ocotea quixos	Oil	Leaves	2.16	n.a.	n.a.	%	PMID[34203565]
NPO61560	Ocotea quixos	Oil	Leaves	0.63	n.a.	n.a.	%	PMID[34203565]
NPO61560	Ocotea quixos	Oil	Leaves	0.35	n.a.	n.a.	%	PMID[34203565]
NPO61560	Ocotea quixos	Oil	Leaves	0.44	n.a.	n.a.	%	PMID[34203565]
NPO61560	Ocotea quixos	Oil	Leaves	1.71	n.a.	n.a.	%	PMID[34203565]
NPO61560	Ocotea quixos	Oil	Leaves	0.57	n.a.	n.a.	%	PMID[34203565]
NPO61560	Ocotea quixos	Oil	Leaves	0.24	n.a.	n.a.	%	PMID[34203565]
NPO61560	Ocotea quixos	Oil	Leaves	0.61	n.a.	n.a.	%	PMID[34203565]
NPO62335	Eugenia brasiliensis	Oil	n.a.	1.21Â±0.87	n.a.	n.a.	%	PMID[37917799]
NPO64248	Eucalyptus patellaris	Oil	n.a.	0.2	n.a.	n.a.	%	PMID[37894690]
NPO7269	Aronia melanocarpa	Hydro distillation	Fruits	0.3	n.a.	n.a.	%	PMID[38893452]
NPO9773	Sideritis raeseri	Oil	n.a.	0.15	n.a.	n.a.	%	PMID[37509192]

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 NPC104724 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	37819
0.1-0.2	11874
0.2-0.3	157
0.3-0.4	8
0.4-0.5	1
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC104724 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8421
0.1-0.2	725
0.2-0.3	3
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