NPASS Compound

Natural Product: NPC217854

Natural Product ID	NPC217854
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2,5-Di-O-Beta-D-Glucopyranosyloxy-1,3-Dimethoxybenzene
IUPAC Name	(2S,3R,4S,5S,6R)-2-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL227814
PubChem CID	16681194
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

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 64 66 0 0 0 0 0 0 0 0999 V2000 6.5602 2.6453 -1.6747 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8204 1.7256 -0.6643 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5942 1.7058 0.2365 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4840 1.3297 -0.4804 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8731 0.1817 0.0275 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9023 -0.2266 -0.8936 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5569 -0.3824 -0.6689 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9095 -0.1604 0.5234 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4622 -0.3442 0.6612 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0383 -0.0994 1.8950 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3180 0.3249 3.0186 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2337 -0.7611 -0.4064 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5751 -0.9797 -1.5930 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7750 -0.8011 -1.7370 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2779 -1.4006 -2.7159 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6528 -1.6382 -3.9568 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6017 -0.9543 -0.3030 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5580 0.0939 -0.5395 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1130 0.4382 0.6623 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4591 0.6816 0.5168 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0829 1.3263 1.7301 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4364 1.5253 1.4747 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0983 -0.6878 0.2445 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7606 -0.9418 -1.2315 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4599 -0.3470 -1.6191 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7082 0.7609 -2.4573 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8371 -2.3107 -1.4930 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4527 -0.6652 0.4422 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8828 -0.9477 0.1563 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7894 -0.5616 1.3131 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8423 0.9202 1.4806 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0053 1.3178 2.5161 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0439 -1.1168 1.0970 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2100 -2.1033 0.4959 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6845 2.1863 -2.5543 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9547 0.7119 -1.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7129 2.0602 -0.1033 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4377 2.7741 0.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4673 0.3887 1.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5157 0.1670 1.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3622 1.1650 2.7155 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3392 -0.4722 3.3940 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0183 0.6650 3.8123 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2523 -0.9854 -2.6929 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1787 -2.3649 -3.7409 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3030 -2.1306 -4.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2338 -0.6961 -4.3693 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9324 0.9802 -0.8598 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6047 1.3204 -0.3764 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6439 2.3343 1.8819 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9755 0.7232 2.6373 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0347 1.0107 2.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5633 -1.4567 0.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5849 -0.4744 -1.8060 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9647 -1.0917 -2.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0091 1.4467 -2.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8419 -2.4366 -2.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8355 -1.4903 0.0572 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4238 -1.1120 -0.7793 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3814 -1.0377 2.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8775 1.1756 1.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9870 2.3122 2.5870 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5097 -1.1084 1.9898 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3378 -2.1121 0.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 9 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 5 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 29 34 1 0 31 3 1 0 14 7 1 0 25 18 1 0 1 35 1 0 2 36 1 0 2 37 1 0 3 38 1 1 5 39 1 1 8 40 1 0 11 41 1 0 11 42 1 0 11 43 1 0 14 44 1 0 16 45 1 0 16 46 1 0 16 47 1 0 18 48 1 6 20 49 1 6 21 50 1 0 21 51 1 0 22 52 1 0 23 53 1 1 24 54 1 6 25 55 1 6 26 56 1 0 27 57 1 0 28 58 1 0 29 59 1 6 30 60 1 1 31 61 1 1 32 62 1 0 33 63 1 0 34 64 1 0 M END

Standard InCHIKey	LCLGWQMTPQRCAN-YXGWTYEDSA-N
Standard InCHI	InChI=1S/C20H30O14/c1-29-8-3-7(31-19-16(27)14(25)12(23)10(5-21)32-19)4-9(30-2)18(8)34-20-17(28)15(26)13(24)11(6-22)33-20/h3-4,10-17,19-28H,5-6H2,1-2H3/t10-,11-,12-,13-,14+,15+,16-,17-,19-,20+/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2cc(OC)c(c(c2)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	494.16	Volume:	443.961 ? Van der Waals volume.
Dense:	1.113	LogP:	-1.249 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.405 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.936 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	18.0
TPSA:	217.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	3.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.173	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.315	Fsp³:	0.7
MCE-18:	82.529 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.451	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.145 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.033 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.26	Promiscuous compounds:	0.038

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.007	MDCK Permeability:	-5.069
Pgp-inhibitor:	0.0	Pgp-substrate:	0.404
PAMPA:	0.992 ? 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):	0.986
20% Bioavailability (F20%):	0.031	30% Bioavailability (F30%):	0.975
50% Bioavailability (F50%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063	MRP1:	0.01
Plasma Protein Binding (PPB):	56.04%	Volume Distribution (VD):	-0.296
Fu:	40.75% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.052
BSEP inhibitor:	0.0

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.005
HLM stability:	0.001 ? 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):

1.063

Half-life (T1/2):

5.223

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.022
Human Hepatotoxicity (H-HT):	0.811	Drug-induced Liver Injury (DILI):	0.963
AMES Toxicity:	0.964	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.12	Eye Corrosion:	0.0
Eye Irritation:	0.006	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.995
Hematotoxicity:	0.544	Drug-induced Nephrotoxicity:	0.925
Genotoxicity:	0.268	RPMI-8226 Immunitoxicity:	0.148
A549 Cytotoxicity:	0.166	Hek293 Cytotoxicity:	0.098
BCF:	0.183 ? 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:	2.407 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.03 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.184 ? 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
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	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
Inhibition	1
IC50	4

Activity Type	# Activity
Cell line	3
Subcellular	1
Others	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
NPT179	Cell line	A2780	Homo sapiens	IC50	>	5000.0	nM	PMID[26428873]
NPT180	Cell line	HCT-8	Homo sapiens	IC50	>	5000.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	>	5000.0	nM	DrugMatrix in vivo data: Hematology
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	>	10000.0	nM	PMID[9822551]
NPT2	Others	Unspecified	n.a.	Inhibition	=	25.2	%	PMID[25007124]

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 NPC217854 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	23830
0.1-0.2	22644
0.2-0.3	2398
0.3-0.4	589
0.4-0.5	304
0.5-0.6	58
0.6-0.7	21
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC276195
0.75	Intermediate Similarity	NPC153149
0.7333	Intermediate Similarity	NPC25817
0.7333	Intermediate Similarity	NPC152722
0.7174	Intermediate Similarity	NPC299144
0.7111	Intermediate Similarity	NPC192810
0.6875	Remote Similarity	NPC69513
0.6875	Remote Similarity	NPC145900
0.6735	Remote Similarity	NPC48863
0.6735	Remote Similarity	NPC95292
0.6735	Remote Similarity	NPC251981
0.6735	Remote Similarity	NPC13745
0.66	Remote Similarity	NPC215833
0.6512	Remote Similarity	NPC228907
0.6471	Remote Similarity	NPC218685
0.6471	Remote Similarity	NPC49074
0.6346	Remote Similarity	NPC162093
0.6304	Remote Similarity	NPC142319
0.6226	Remote Similarity	NPC210478
0.62	Remote Similarity	NPC221090
0.6182	Remote Similarity	NPC232673
0.6038	Remote Similarity	NPC23084
0.6	Remote Similarity	NPC95392
0.6	Remote Similarity	NPC84013
0.6	Remote Similarity	NPC55715
0.6	Remote Similarity	NPC35877
0.6	Remote Similarity	NPC104167
0.5957	Remote Similarity	NPC212729
0.5957	Remote Similarity	NPC604498
0.5893	Remote Similarity	NPC247146
0.5862	Remote Similarity	NPC479030
0.5833	Remote Similarity	NPC269242
0.58	Remote Similarity	NPC609376
0.5789	Remote Similarity	NPC470236
0.5769	Remote Similarity	NPC166040
0.5741	Remote Similarity	NPC479028
0.5741	Remote Similarity	NPC479031
0.5714	Remote Similarity	NPC294470
0.5686	Remote Similarity	NPC226712
0.5686	Remote Similarity	NPC608788
0.5574	Remote Similarity	NPC99233
0.5536	Remote Similarity	NPC473044
0.5536	Remote Similarity	NPC479029
0.5536	Remote Similarity	NPC607702
0.551	Remote Similarity	NPC484157
0.55	Remote Similarity	NPC604892
0.549	Remote Similarity	NPC60589
0.549	Remote Similarity	NPC469708
0.549	Remote Similarity	NPC604439
0.5455	Remote Similarity	NPC472024
0.5455	Remote Similarity	NPC270849
0.5455	Remote Similarity	NPC606892
0.5439	Remote Similarity	NPC189589
0.5385	Remote Similarity	NPC200092
0.5385	Remote Similarity	NPC12308
0.537	Remote Similarity	NPC40377
0.537	Remote Similarity	NPC310661
0.5357	Remote Similarity	NPC26653
0.5357	Remote Similarity	NPC214910
0.5357	Remote Similarity	NPC80600
0.5357	Remote Similarity	NPC164599
0.5345	Remote Similarity	NPC473045
0.5345	Remote Similarity	NPC171533
0.5345	Remote Similarity	NPC208769
0.5323	Remote Similarity	NPC216129
0.5323	Remote Similarity	NPC130449
0.5323	Remote Similarity	NPC248132
0.5294	Remote Similarity	NPC9248
0.5283	Remote Similarity	NPC80098
0.5263	Remote Similarity	NPC248355
0.5238	Remote Similarity	NPC479447
0.5238	Remote Similarity	NPC606849
0.5185	Remote Similarity	NPC214454
0.5179	Remote Similarity	NPC604356
0.5172	Remote Similarity	NPC55040
0.5161	Remote Similarity	NPC210192
0.5152	Remote Similarity	NPC206378
0.5152	Remote Similarity	NPC106625
0.5091	Remote Similarity	NPC9912
0.5085	Remote Similarity	NPC302378
0.5085	Remote Similarity	NPC34456
0.5085	Remote Similarity	NPC604162
0.5082	Remote Similarity	NPC37468
0.5082	Remote Similarity	NPC486107
0.5077	Remote Similarity	NPC76128

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC217854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6179
0.1-0.2	2854
0.2-0.3	93
0.3-0.4	21
0.4-0.5	2
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5686	Remote Similarity	NPD1091	Pre-clinical

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