NPASS Compound

Natural Product: NPC190003

Natural Product ID	NPC190003
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Luteolin-7-O-Beta-D-Glucuronide Ethyl Ester
IUPAC Name	ethyl (2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1272141
PubChem CID	52944072
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003534] Flavonoid-7-O-glucuronides

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 57 60 0 0 0 0 0 0 0 0999 V2000 -6.2180 -2.5267 -4.6473 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4241 -3.7727 -4.2902 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7822 -3.6407 -3.0424 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8521 -2.6704 -2.7419 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5437 -1.8287 -3.6484 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2144 -2.5996 -1.3858 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3138 -1.5530 -1.3075 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0797 -1.2008 0.0206 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0326 -0.3099 0.1325 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1253 -0.3742 0.8323 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4739 -1.4440 1.6188 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6827 -1.4672 2.3253 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9953 -2.5701 3.1094 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5423 -0.3914 2.2287 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2097 0.6957 1.4417 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0061 0.6844 0.7572 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0457 1.6939 1.3742 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2034 1.7521 2.0066 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5584 0.6937 2.7906 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7222 -0.4073 2.9144 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0558 -1.3778 3.6380 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0790 2.9041 1.8773 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2869 3.0224 2.5061 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1014 4.1537 2.3529 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7089 5.1896 1.5589 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4969 5.0859 0.9197 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6926 3.9769 1.0665 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1015 6.1518 0.1075 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4837 6.3319 1.3769 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3148 -0.5019 0.6094 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5358 -1.0147 -0.0870 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3270 -2.4882 -0.3782 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0623 -3.2086 0.7830 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6711 -0.3773 -1.3250 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2966 -0.7331 1.9682 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6016 -2.0594 -3.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5709 -1.8306 -5.2184 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0756 -2.8166 -5.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7055 -4.0000 -5.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1406 -4.6215 -4.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6892 -3.5750 -1.2226 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8930 -2.0952 0.6222 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1916 -2.2715 1.6906 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5860 -3.2997 2.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7937 1.5691 0.1502 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4750 0.6535 3.3386 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6489 2.2207 3.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0458 4.1879 2.8765 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7471 3.9170 0.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7380 6.9758 0.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4842 6.2967 1.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2183 0.5899 0.3702 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4479 -0.8161 0.4965 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2755 -2.8645 -0.8134 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4273 -2.7386 1.5588 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6371 0.5942 -1.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5480 0.1058 2.4355 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 12 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 18 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 25 29 1 0 8 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 30 35 1 0 32 6 1 0 16 10 1 0 27 22 1 0 20 14 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 0 2 40 1 0 6 41 1 1 8 42 1 1 11 43 1 0 13 44 1 0 16 45 1 0 19 46 1 0 23 47 1 0 24 48 1 0 27 49 1 0 28 50 1 0 29 51 1 0 30 52 1 1 31 53 1 1 32 54 1 6 33 55 1 0 34 56 1 0 35 57 1 0 M END

Standard InCHIKey	BEPOTAUCBSWOPK-KHYDEXNFSA-N
Standard InCHI	InChI=1S/C23H22O12/c1-2-32-22(31)21-19(29)18(28)20(30)23(35-21)33-10-6-13(26)17-14(27)8-15(34-16(17)7-10)9-3-4-11(24)12(25)5-9/h3-8,18-21,23-26,28-30H,2H2,1H3/t18-,19-,20+,21-,23+/m0/s1
SMILES	CCOC(=O)[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	490.11	Volume:	453.893 ? Van der Waals volume.
Dense:	1.08	LogP:	1.024 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.404 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.463 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	25.0
TPSA:	196.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.212	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.036	Fsp³:	0.304
MCE-18:	90.0 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.696	Fluc inhibitor:	0.291 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.992 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.902 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.126	Promiscuous compounds:	0.456

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.437	MDCK Permeability:	-5.223
Pgp-inhibitor:	0.0	Pgp-substrate:	0.036
PAMPA:	0.974 ? 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):	0.155
20% Bioavailability (F20%):	0.872	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.828
Plasma Protein Binding (PPB):	84.018%	Volume Distribution (VD):	0.015
Fu:	15.131% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.975
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.263
BSEP inhibitor:	0.085

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.598
HLM stability:	0.091 ? 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):

2.831

Half-life (T1/2):

3.626

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.478
Human Hepatotoxicity (H-HT):	0.212	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.662	Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.346	Skin Sensitization:	0.981
Carcinogencity:	0.067	Eye Corrosion:	0.0
Eye Irritation:	0.922	Respiratory Toxicity:	0.077
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.329
Hematotoxicity:	0.021	Drug-induced Nephrotoxicity:	0.119
Genotoxicity:	0.877	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.483	Hek293 Cytotoxicity:	0.493
BCF:	0.804 ? 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:	3.536 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.756 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.23 ? 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
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19499937]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20932762]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20289	Dracocephalum tanguticum	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
EC50	4

Activity Type	# Activity
Cell line	1
Others	1
Non-molecular	2

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
NPT1635	Cell line	H9c2	Rattus norvegicus	EC50	=	6340.0	nM	DrugMatrix in vivo data: Biochemistry
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	3310000.0	nM	PMID[20932762]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	87840.0	nM	PMID[20932762]
NPT1	Others	Radical scavenging activity	n.a.	EC50	=	13150.0	nM	PMID[19035792]

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 NPC190003 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	16243
0.1-0.2	29899
0.2-0.3	2734
0.3-0.4	598
0.4-0.5	261
0.5-0.6	70
0.6-0.7	35
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC19709
0.7692	Intermediate Similarity	NPC27942
0.7662	Intermediate Similarity	NPC189142
0.7662	Intermediate Similarity	NPC77660
0.7342	Intermediate Similarity	NPC181712
0.7294	Intermediate Similarity	NPC210073
0.7159	Intermediate Similarity	NPC229409
0.6962	Remote Similarity	NPC473043
0.6962	Remote Similarity	NPC331652
0.6854	Remote Similarity	NPC65711
0.6667	Remote Similarity	NPC39360
0.6667	Remote Similarity	NPC29763
0.6667	Remote Similarity	NPC210003
0.6471	Remote Similarity	NPC22832
0.6404	Remote Similarity	NPC44931
0.6386	Remote Similarity	NPC95090
0.6386	Remote Similarity	NPC27408
0.6374	Remote Similarity	NPC64051
0.6364	Remote Similarity	NPC8856
0.6364	Remote Similarity	NPC254540
0.6353	Remote Similarity	NPC20505
0.6344	Remote Similarity	NPC270675
0.6344	Remote Similarity	NPC195685
0.6279	Remote Similarity	NPC243930
0.6279	Remote Similarity	NPC601144
0.6265	Remote Similarity	NPC261866
0.6265	Remote Similarity	NPC238376
0.6264	Remote Similarity	NPC115674
0.6237	Remote Similarity	NPC209296
0.6207	Remote Similarity	NPC311830
0.6154	Remote Similarity	NPC22062
0.6154	Remote Similarity	NPC473634
0.6154	Remote Similarity	NPC138811
0.6146	Remote Similarity	NPC484301
0.6146	Remote Similarity	NPC472994
0.6042	Remote Similarity	NPC101636
0.6042	Remote Similarity	NPC298171
0.6022	Remote Similarity	NPC46202
0.6	Remote Similarity	NPC168822
0.6	Remote Similarity	NPC277205
0.6	Remote Similarity	NPC37919
0.6	Remote Similarity	NPC136042
0.5946	Remote Similarity	NPC108406
0.593	Remote Similarity	NPC58716
0.593	Remote Similarity	NPC84362
0.593	Remote Similarity	NPC271692
0.593	Remote Similarity	NPC45638
0.59	Remote Similarity	NPC472993
0.5895	Remote Similarity	NPC473623
0.587	Remote Similarity	NPC67105
0.5862	Remote Similarity	NPC201292
0.5843	Remote Similarity	NPC605784
0.5843	Remote Similarity	NPC607707
0.5833	Remote Similarity	NPC488089
0.5824	Remote Similarity	NPC606546
0.5714	Remote Similarity	NPC4390
0.5698	Remote Similarity	NPC249281
0.5618	Remote Similarity	NPC282169
0.5604	Remote Similarity	NPC276377
0.5543	Remote Similarity	NPC172807
0.5517	Remote Similarity	NPC108831
0.5517	Remote Similarity	NPC182634
0.5506	Remote Similarity	NPC198324
0.55	Remote Similarity	NPC179862
0.55	Remote Similarity	NPC253685
0.5474	Remote Similarity	NPC65003
0.5455	Remote Similarity	NPC297987
0.5444	Remote Similarity	NPC175107
0.5408	Remote Similarity	NPC72016
0.5393	Remote Similarity	NPC46420
0.5385	Remote Similarity	NPC80188
0.5385	Remote Similarity	NPC608742
0.5376	Remote Similarity	NPC211594
0.5341	Remote Similarity	NPC289667
0.5326	Remote Similarity	NPC116458
0.5326	Remote Similarity	NPC246943
0.5326	Remote Similarity	NPC220169
0.5312	Remote Similarity	NPC150164
0.5312	Remote Similarity	NPC607513
0.53	Remote Similarity	NPC80068
0.53	Remote Similarity	NPC475382
0.5294	Remote Similarity	NPC14187
0.5281	Remote Similarity	NPC158674
0.5281	Remote Similarity	NPC323593
0.5281	Remote Similarity	NPC203500
0.5275	Remote Similarity	NPC611303
0.5258	Remote Similarity	NPC186816
0.5253	Remote Similarity	NPC150767
0.5243	Remote Similarity	NPC11468
0.5222	Remote Similarity	NPC472385
0.5208	Remote Similarity	NPC227508
0.5204	Remote Similarity	NPC64425
0.52	Remote Similarity	NPC486577
0.5169	Remote Similarity	NPC58053
0.5169	Remote Similarity	NPC143851
0.5149	Remote Similarity	NPC195257
0.5138	Remote Similarity	NPC298666
0.5111	Remote Similarity	NPC93337
0.5111	Remote Similarity	NPC146792
0.5109	Remote Similarity	NPC191306
0.5109	Remote Similarity	NPC285197
0.5102	Remote Similarity	NPC122809
0.51	Remote Similarity	NPC210961
0.5094	Remote Similarity	NPC480441
0.5055	Remote Similarity	NPC186807
0.5055	Remote Similarity	NPC105025
0.5055	Remote Similarity	NPC610763
0.5054	Remote Similarity	NPC605067
0.5053	Remote Similarity	NPC116864
0.5053	Remote Similarity	NPC244776
0.5052	Remote Similarity	NPC275454
0.505	Remote Similarity	NPC479766

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC190003 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4429
0.1-0.2	4636
0.2-0.3	72
0.3-0.4	6
0.4-0.5	5
0.5-0.6	1
0.6-0.7	1
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
0.6237	Remote Similarity	NPD7054	Phase 4
0.53	Remote Similarity	NPD7251	Phase 2

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