NPASS Compound

Natural Product: NPC127857

Natural Product ID	NPC127857
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Secoorthosiphol B
IUPAC Name	2-[(1S,2R,4R,4aR,6R,8R,8aS)-4-acetyloxy-8-benzoyloxy-6-ethenyl-4a-hydroxy-2-(1-methoxy-2-methyl-1-oxopropan-2-yl)-1,6-dimethyl-5-oxo-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]acetic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL510190
PubChem CID	15548728
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

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 78 80 0 0 0 0 0 0 0 0999 V2000 -4.8053 2.3027 -2.5308 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8618 2.1938 -1.4784 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1420 1.5381 -0.2872 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2765 1.0339 -0.1647 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0765 1.4605 0.8024 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9525 0.7548 0.1889 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4505 -0.6066 -0.2249 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8019 -1.7557 0.4517 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2626 -2.9238 -0.2617 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8810 -3.9880 0.3374 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0518 -3.9320 1.5837 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3398 -5.1713 -0.4348 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3438 -1.6814 0.2207 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1802 -0.2547 -0.0272 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5778 0.7800 0.7619 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5280 0.4554 2.2608 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1199 2.0945 0.6408 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3850 2.6779 -0.6325 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1183 2.1500 -1.7155 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9788 3.9169 -0.7242 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6135 -0.3801 0.0718 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4629 0.7132 -0.0676 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5476 0.8840 0.7887 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7347 0.0305 1.6860 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4628 2.0118 0.6758 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3239 2.9791 -0.2947 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2149 4.0280 -0.3569 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2630 4.1484 0.5348 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4060 3.1763 1.5131 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5078 2.1343 1.5627 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0776 -1.1982 -1.1648 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5324 -2.5775 -1.1776 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0693 -2.4814 -0.9688 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6699 -3.0263 -1.7311 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1955 -3.4819 -0.1608 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7715 -3.1453 -2.5327 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0672 -4.3976 -2.7601 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3365 -2.2621 1.3068 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7951 0.7652 1.9367 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9550 2.8879 1.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6069 3.0293 -2.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2309 1.2841 -2.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2272 2.5757 -3.4447 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7833 1.2783 -0.8117 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5636 -0.7268 -0.0687 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3407 -0.8080 -1.3339 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0665 -1.9581 1.4883 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4974 -5.8233 -0.7452 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0203 -5.7523 0.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9148 -4.8659 -1.3459 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0997 -0.0831 -1.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4319 0.0130 2.6535 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3323 1.3675 2.8842 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3781 -0.1863 2.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0175 2.0314 1.3364 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4265 2.9049 1.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5523 4.2161 -1.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9025 -1.0370 0.9428 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4978 2.8832 -0.9999 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1079 4.7757 -1.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9588 4.9812 0.4742 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2316 3.2669 2.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6411 1.3854 2.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7013 -0.6468 -2.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1720 -1.2308 -1.2243 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5656 -4.3684 0.0549 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1359 -3.8638 -0.6353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4896 -2.9799 0.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6872 -2.4449 -3.3812 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1497 -5.0848 -1.9335 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2325 -4.7674 -3.7556 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2134 -2.9459 1.7189 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4921 1.1759 2.9453 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7054 -0.3012 1.9841 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9033 0.9834 1.9222 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5636 3.0397 2.2322 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0280 3.2552 1.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5711 3.5745 0.4389 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 3 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 2 0 10 12 1 0 8 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 14 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 21 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 32 35 1 1 32 36 1 0 36 37 2 0 13 38 1 1 5 39 1 0 5 40 1 0 15 6 1 0 30 25 1 0 33 13 1 0 1 41 1 0 1 42 1 0 1 43 1 0 6 44 1 6 7 45 1 0 7 46 1 0 8 47 1 1 12 48 1 0 12 49 1 0 12 50 1 0 14 51 1 6 16 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 20 57 1 0 21 58 1 1 26 59 1 0 27 60 1 0 28 61 1 0 29 62 1 0 30 63 1 0 31 64 1 0 31 65 1 0 35 66 1 0 35 67 1 0 35 68 1 0 36 69 1 0 37 70 1 0 37 71 1 0 38 72 1 0 39 73 1 0 39 74 1 0 39 75 1 0 40 76 1 0 40 77 1 0 40 78 1 0 M END

Standard InCHIKey	ZNOSNEAHXFOXRY-KKKLMDDUSA-N
Standard InCHI	InChI=1S/C30H38O10/c1-8-28(5)15-19(40-24(34)18-12-10-9-11-13-18)23-29(6,16-22(32)33)20(27(3,4)26(36)38-7)14-21(39-17(2)31)30(23,37)25(28)35/h8-13,19-21,23,37H,1,14-16H2,2-7H3,(H,32,33)/t19-,20+,21-,23-,28+,29+,30+/m1/s1
SMILES	COC(=O)C([C@@H]1C[C@@H](OC(=O)C)[C@@]2([C@@H]([C@@]1(C)CC(=O)O)[C@H](OC(=O)c1ccccc1)C[C@](C2=O)(C)C=C)O)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	558.25	Volume:	565.941 ? Van der Waals volume.
Dense:	0.986	LogP:	2.844 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.379 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.681 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	153.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.276	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.909	Fsp³:	0.567
MCE-18:	104.872 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.112	Fluc inhibitor:	0.021 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.026 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.194	Promiscuous compounds:	0.308

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.553	MDCK Permeability:	-5.042
Pgp-inhibitor:	0.002	Pgp-substrate:	0.821
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.933	30% Bioavailability (F30%):	0.59
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056	MRP1:	1.0
Plasma Protein Binding (PPB):	86.376%	Volume Distribution (VD):	-0.098
Fu:	11.695% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.968	BCRP inhibitor:	0.019
BSEP inhibitor:	0.968

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.023
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.849	CYP3A4-substrate:	0.071
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.372 ? 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):

1.014

Half-life (T1/2):

1.274

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.05
Human Hepatotoxicity (H-HT):	0.157	Drug-induced Liver Injury (DILI):	0.594
AMES Toxicity:	0.13	Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.145	Skin Sensitization:	0.869
Carcinogencity:	0.762	Eye Corrosion:	0.102
Eye Irritation:	0.796	Respiratory Toxicity:	0.483
Drug-induced Neurotoxicity:	0.07	Ototoxicity:	0.347
Hematotoxicity:	0.271	Drug-induced Nephrotoxicity:	0.952
Genotoxicity:	0.928	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.011	Hek293 Cytotoxicity:	0.069
BCF:	0.376 ? 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:	3.06 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.54 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.661 ? 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
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11356-018-3422-z]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654417]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374950]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[12467611]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	aerial parts	Bangdung, Indonesia	2000-Aug	PMID[12608860]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15104497]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18076141]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19691312]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22165973]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26473275]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28898076]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31707845]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[31713425]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32933154]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33081385]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34847783]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36671383]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38202742]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[385653815]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14797	Orthosiphon aristatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5890	Astragalus inopinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2499	Celmisia petriei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO592	Chroogomphus rutilus	Species	Gomphidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1408	Cirsium helenioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14887	Handroanthus guayacan	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23062	Melibe leonina	Species	Dendronotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1638	Ulmus laciniata	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5890	Astragalus inopinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1408	Cirsium helenioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14887	Handroanthus guayacan	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1638	Ulmus laciniata	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2499	Celmisia petriei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14797	Orthosiphon aristatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO592	Chroogomphus rutilus	Species	Gomphidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23062	Melibe leonina	Species	Dendronotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	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	1

Activity Type	# Activity
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20763	Cell line	J774.1	Mus musculus	IC50	=	127000.0	nM	PMID[12608860]

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 NPC127857 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	4601
0.1-0.2	39989
0.2-0.3	4962
0.3-0.4	278
0.4-0.5	18
0.5-0.6	1
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6154	Remote Similarity	NPC48568
0.6125	Remote Similarity	NPC306799
0.6076	Remote Similarity	NPC478503
0.6076	Remote Similarity	NPC237549
0.6	Remote Similarity	NPC257213
0.6	Remote Similarity	NPC478502
0.6	Remote Similarity	NPC249471
0.6	Remote Similarity	NPC472030
0.5854	Remote Similarity	NPC473414

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC127857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	1545
0.1-0.2	7096
0.2-0.3	505
0.3-0.4	4
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