NPASS Compound

Natural Product: NPC471190

Natural Product ID	NPC471190
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Euoluchumine
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2386526
PubChem CID	73348900
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids 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 101106 0 0 0 0 0 0 0 0999 V2000 -4.1151 -5.0241 0.1280 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0432 -4.2089 -0.4941 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 -4.5144 -1.6768 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4269 -3.1525 0.1040 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3894 -2.3477 -0.4711 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8732 -0.9666 -0.8480 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2669 -0.9944 -0.7062 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0890 -0.7189 -1.7821 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6021 -0.4331 -2.9272 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5730 -0.7483 -1.6330 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2467 0.0714 0.0986 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1170 -0.0509 1.2951 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2438 -1.3082 1.9090 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0056 -1.5652 3.0109 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6548 -0.6431 3.5445 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0672 -2.9361 3.5800 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3649 1.5087 -0.3253 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6923 1.9744 -0.3763 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2600 2.4809 -1.5202 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5057 2.4987 -2.5233 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6022 2.9697 -1.6359 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0626 3.4493 -2.8380 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3708 3.9278 -2.9580 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2345 3.9342 -1.8838 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7730 3.4544 -0.6829 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4659 2.9762 -0.5627 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4799 2.3972 0.5150 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5035 2.2966 1.8492 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9319 2.1955 0.0535 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1901 0.6868 -0.1589 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1752 -0.3180 0.0559 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3144 -1.3511 1.1139 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1413 -2.5495 0.2702 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9973 -2.2803 -0.8274 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6796 -3.2266 -1.9868 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2881 -2.6472 -0.3235 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4198 -2.0254 -0.0494 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4858 -1.4238 -0.5442 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6001 -1.3690 -1.7801 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6365 -0.7725 0.1205 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6684 -1.7165 0.3301 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8380 -1.3783 0.9285 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0227 -0.0782 1.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0196 0.7747 1.1183 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8461 0.4858 0.5305 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9399 1.6695 0.3676 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2947 2.1525 1.6189 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0357 2.9866 1.3226 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9197 4.1829 1.6956 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9929 2.5751 0.6865 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2572 3.1888 2.2361 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7451 2.8151 -0.2909 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4725 -1.1132 -1.1612 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5815 -1.5124 1.6259 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7840 0.6972 -1.5502 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1919 0.3398 0.7634 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6708 -5.5850 -0.6692 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8775 -4.4094 0.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6927 -5.8167 0.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2668 -2.8403 -1.4873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6199 -0.6598 -1.8630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9272 0.2728 -1.4929 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0068 -1.2282 -2.5483 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7983 -1.3972 -0.7689 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0670 0.7662 2.0385 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2006 0.0595 0.9137 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4019 -3.6218 3.0353 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7804 -2.8486 4.6689 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1196 -3.3344 3.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9633 1.5978 -1.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4727 3.4876 -3.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7412 4.3061 -3.8959 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2472 4.2929 -1.9343 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4447 3.4543 0.1714 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1818 2.6174 0.4149 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8101 3.4505 0.2543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0974 2.9423 2.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8968 2.7176 -0.9796 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3075 -1.3228 1.9810 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0071 -3.5034 0.7190 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2021 -2.7300 -2.8434 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 -3.5744 -2.4440 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2268 -4.1734 -1.6585 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0908 -3.3756 0.5588 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6759 -3.5202 -1.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4194 -2.7045 -0.0594 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6109 -2.1406 1.0721 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9509 0.1841 1.8155 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2209 1.3938 -0.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0575 1.4068 2.3647 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7933 3.4741 3.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2600 4.1098 1.6390 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2319 2.7580 2.4578 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0647 3.6614 -0.4865 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1857 2.4727 -1.2275 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5480 3.1657 0.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5498 -2.0256 2.4475 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4284 1.5810 -1.7519 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9723 0.8218 -2.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2844 -0.2175 -1.8463 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8751 0.7203 1.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 6 11 1 0 11 12 1 1 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 11 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 17 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 47 51 1 0 46 52 1 0 34 53 1 0 32 54 1 0 30 55 1 0 30 56 1 0 33 5 1 0 45 40 1 0 31 11 1 0 26 21 1 0 50 29 1 0 31 53 1 6 1 57 1 0 1 58 1 0 1 59 1 0 5 60 1 6 6 61 1 6 10 62 1 0 10 63 1 0 10 64 1 0 12 65 1 0 12 66 1 0 16 67 1 0 16 68 1 0 16 69 1 0 17 70 1 6 22 71 1 0 23 72 1 0 24 73 1 0 25 74 1 0 26 75 1 0 27 76 1 1 28 77 1 0 29 78 1 6 32 79 1 1 33 80 1 1 35 81 1 0 35 82 1 0 35 83 1 0 36 84 1 0 36 85 1 0 41 86 1 0 42 87 1 0 43 88 1 0 46 89 1 6 47 90 1 1 51 91 1 0 51 92 1 0 51 93 1 0 52 94 1 0 52 95 1 0 52 96 1 0 54 97 1 0 55 98 1 0 55 99 1 0 55100 1 0 56101 1 0 M END

Standard InCHIKey	VXQHTUMJTUETTQ-OWKYXKTCSA-N
Standard InCHI	InChI=1S/C39H45NO16/c1-18-19(2)33(46)54-30-27(44)31(55-34(47)23-12-9-8-10-13-23)38(17-50-20(3)41)32(53-22(5)43)28(52-21(4)42)25-29(45)39(38,37(30,7)49)56-36(25,6)16-51-35(48)24-14-11-15-40-26(18)24/h8-15,18-19,25,27-32,44-45,49H,16-17H2,1-7H3/t18-,19-,25-,27+,28-,29-,30-,31+,32-,36?,37?,38+,39+/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H](OC(=O)C)[C@]2(COC(=O)C)[C@@H](OC(=O)c3ccccc3)[C@@H](O)[C@@H]3C([C@]42[C@@H]([C@@H]1C(C)(COC(=O)c1cccnc1[C@@H]([C@H](C(=O)O3)C)C)O4)O)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	783.27	Volume:	751.764 ? Van der Waals volume.
Dense:	1.042	LogP:	0.972 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.332 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.895 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	41.0
TPSA:	240.61 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.275	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.474	Fsp³:	0.564
MCE-18:	214.033 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.677	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.139 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.009	Promiscuous compounds:	0.061

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.787	MDCK Permeability:	-5.183
Pgp-inhibitor:	0.023	Pgp-substrate:	0.434
PAMPA:	0.997 ? 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%):	0.0	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.495

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021	MRP1:	1.0
Plasma Protein Binding (PPB):	58.723%	Volume Distribution (VD):	-0.311
Fu:	41.708% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.638	BCRP inhibitor:	0.0
BSEP inhibitor:	0.556

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.339	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.778 ? 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):

0.57

Half-life (T1/2):

2.233

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.089
Human Hepatotoxicity (H-HT):	0.267	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.995	Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.749	Skin Sensitization:	1.0
Carcinogencity:	0.711	Eye Corrosion:	0.0
Eye Irritation:	0.161	Respiratory Toxicity:	0.195
Drug-induced Neurotoxicity:	0.801	Ototoxicity:	0.811
Hematotoxicity:	0.963	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.787
A549 Cytotoxicity:	0.897	Hek293 Cytotoxicity:	0.5
BCF:	0.533 ? 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:	3.237 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.553 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.058 ? 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
NPO32493	euonymus lutchuensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23755851]
NPO32493	euonymus lutchuensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	3

Activity Type	# Activity
Cell line	3

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
NPT393	Cell line	HCT-116	Homo sapiens	IC50	<	5.0	ug.mL-1	DOI[10.6019/CHEMBL1201861]
NPT116	Cell line	HL-60	Homo sapiens	IC50	<	5.0	ug.mL-1	PubChem BioAssay data set
NPT168	Cell line	P388	Mus musculus	IC50	<	5.0	ug.mL-1	PMID[17438050]

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 NPC471190 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	21104
0.1-0.2	27382
0.2-0.3	1128
0.3-0.4	169
0.4-0.5	27
0.5-0.6	27
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8265	Intermediate Similarity	NPC471977
0.8081	Intermediate Similarity	NPC470486
0.7921	Intermediate Similarity	NPC30456
0.7921	Intermediate Similarity	NPC475644
0.7921	Intermediate Similarity	NPC488904
0.7629	Intermediate Similarity	NPC475137
0.6887	Remote Similarity	NPC475631
0.6822	Remote Similarity	NPC475596
0.6822	Remote Similarity	NPC476110
0.6796	Remote Similarity	NPC475498
0.6729	Remote Similarity	NPC87152
0.6729	Remote Similarity	NPC475600
0.6636	Remote Similarity	NPC475303
0.6316	Remote Similarity	NPC327769
0.6195	Remote Similarity	NPC237702
0.6132	Remote Similarity	NPC76565
0.6132	Remote Similarity	NPC601313
0.6038	Remote Similarity	NPC473850
0.5909	Remote Similarity	NPC473506
0.5902	Remote Similarity	NPC482915
0.5893	Remote Similarity	NPC475301
0.5854	Remote Similarity	NPC483855
0.582	Remote Similarity	NPC483854
0.5804	Remote Similarity	NPC326930
0.5741	Remote Similarity	NPC35208
0.5478	Remote Similarity	NPC328186
0.5462	Remote Similarity	NPC477787
0.5431	Remote Similarity	NPC316841
0.5417	Remote Similarity	NPC328928
0.5372	Remote Similarity	NPC483853
0.5372	Remote Similarity	NPC608314
0.5345	Remote Similarity	NPC122968
0.5345	Remote Similarity	NPC228377
0.5333	Remote Similarity	NPC319880
0.5333	Remote Similarity	NPC320324
0.5315	Remote Similarity	NPC475408
0.5289	Remote Similarity	NPC327904
0.5169	Remote Similarity	NPC477788
0.5164	Remote Similarity	NPC38959
0.513	Remote Similarity	NPC473833
0.5078	Remote Similarity	NPC483856
0.5043	Remote Similarity	NPC475362
0.5041	Remote Similarity	NPC473689
0.5041	Remote Similarity	NPC292416
0.504	Remote Similarity	NPC475426

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4201
0.1-0.2	4906
0.2-0.3	41
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data