NPASS Compound

Natural Product: NPC494078

Natural Product ID	NPC494078
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Q23058972
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-3-[(2~{S},3~{S},4~{R},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-7-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

Standard InCHIKey	JYXSWDCPHRTYGU-KSAWAZCGSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(38-9)39-12-6-13(30)16-14(7-12)40-24(10-2-4-11(29)5-3-10)25(19(16)33)42-27-23(37)21(35)18(32)15(8-28)41-27/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20-,21+,22+,23-,26-,27-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@@H](O)[C@@H]4O)=C(C4=CC=C(O)C=C4)OC3=C2)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	0.799 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.169 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.716 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.154	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.653	Fsp³:	0.444
MCE-18:	119.436 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.622	Fluc inhibitor:	0.272 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.781 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.608 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.209	Promiscuous compounds:	0.528

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.543	MDCK Permeability:	-5.011
Pgp-inhibitor:	0.0	Pgp-substrate:	0.859
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):	0.752
20% Bioavailability (F20%):	0.335	30% Bioavailability (F30%):	0.99
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.096
Plasma Protein Binding (PPB):	81.265%	Volume Distribution (VD):	0.031
Fu:	17.691% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.434
BSEP inhibitor:	0.002

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:	0.177
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.955
HLM stability:	0.015 ? 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):

1.83

Half-life (T1/2):

5.79

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.078
Human Hepatotoxicity (H-HT):	0.629	Drug-induced Liver Injury (DILI):	0.966
AMES Toxicity:	0.933	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.034	Skin Sensitization:	0.997
Carcinogencity:	0.055	Eye Corrosion:	0.0
Eye Irritation:	0.043	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.981
Hematotoxicity:	0.096	Drug-induced Nephrotoxicity:	0.543
Genotoxicity:	0.656	RPMI-8226 Immunitoxicity:	0.172
A549 Cytotoxicity:	0.648	Hek293 Cytotoxicity:	0.598
BCF:	0.405 ? 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:	2.986 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.572 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.608 ? 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
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/P19890001079]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[16180811]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	branch	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014228]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO21684	Lathyrus sativus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24954190]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39355945]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13979	Tilia argentea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50342	Shepherdia argentea	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO48755	Marah oreganus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21684	Lathyrus sativus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50795	Hymenophyton leptopodum	Species	Hymenophytaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14714	Equisetum silvaticum	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3945	Delphinium formosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26133	Eupatorium hookerianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47091	Asplenium bulbiferum	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO56737	Vigna spp.	Genus	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO52021	Asplenium trichomanes-ramosum	Genus	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO49941	Equisetum telmateja	Genus	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10433	Centipeda orbicularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO52238	Coronilla emerus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13979	Tilia argentea	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21684	Lathyrus sativus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21684	Lathyrus sativus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21684	Lathyrus sativus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13979	Tilia argentea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14714	Equisetum silvaticum	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3945	Delphinium formosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10433	Centipeda orbicularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21684	Lathyrus sativus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26133	Eupatorium hookerianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22337	Garcinia dulcis	Species	Clusiaceae	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

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 NPC494078 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	22370
0.1-0.2	23681
0.2-0.3	2597
0.3-0.4	658
0.4-0.5	267
0.5-0.6	77
0.6-0.7	84
0.7-0.8	0
0.8-0.85	8
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC116458
1.0	High Similarity	NPC246943
0.9286	High Similarity	NPC297987
0.9143	High Similarity	NPC249281
0.8919	High Similarity	NPC605784
0.863	High Similarity	NPC46420
0.8312	Intermediate Similarity	NPC276377
0.8293	Intermediate Similarity	NPC35119
0.8243	Intermediate Similarity	NPC136042
0.8108	Intermediate Similarity	NPC289667
0.8101	Intermediate Similarity	NPC251417
0.8072	Intermediate Similarity	NPC32641
0.8072	Intermediate Similarity	NPC256188
0.8025	Intermediate Similarity	NPC150164
0.7831	Intermediate Similarity	NPC64425
0.7711	Intermediate Similarity	NPC186816
0.7662	Intermediate Similarity	NPC84362
0.7662	Intermediate Similarity	NPC271692
0.7473	Intermediate Similarity	NPC25523
0.7442	Intermediate Similarity	NPC72016
0.7403	Intermediate Similarity	NPC77672
0.7403	Intermediate Similarity	NPC133671
0.7403	Intermediate Similarity	NPC135391
0.7403	Intermediate Similarity	NPC78263
0.7403	Intermediate Similarity	NPC250069
0.7273	Intermediate Similarity	NPC111929
0.7273	Intermediate Similarity	NPC320283
0.7273	Intermediate Similarity	NPC41121
0.725	Intermediate Similarity	NPC611303
0.7215	Intermediate Similarity	NPC24043
0.7209	Intermediate Similarity	NPC240306
0.7179	Intermediate Similarity	NPC39360
0.7179	Intermediate Similarity	NPC29763
0.7179	Intermediate Similarity	NPC210003
0.7089	Intermediate Similarity	NPC158674
0.7089	Intermediate Similarity	NPC323593
0.7089	Intermediate Similarity	NPC203500
0.7051	Intermediate Similarity	NPC331652
0.7033	Intermediate Similarity	NPC14187
0.6962	Remote Similarity	NPC108831
0.6962	Remote Similarity	NPC182634
0.679	Remote Similarity	NPC488080
0.679	Remote Similarity	NPC169977
0.6744	Remote Similarity	NPC480466
0.6737	Remote Similarity	NPC480441
0.6737	Remote Similarity	NPC164704
0.6667	Remote Similarity	NPC145038
0.6667	Remote Similarity	NPC8573
0.6667	Remote Similarity	NPC56077
0.6667	Remote Similarity	NPC281131
0.6667	Remote Similarity	NPC64305
0.6667	Remote Similarity	NPC253662
0.6667	Remote Similarity	NPC179950
0.6667	Remote Similarity	NPC277205
0.6667	Remote Similarity	NPC37919
0.6667	Remote Similarity	NPC88789
0.6667	Remote Similarity	NPC189142
0.6667	Remote Similarity	NPC77660
0.6667	Remote Similarity	NPC491374
0.6582	Remote Similarity	NPC288084
0.6543	Remote Similarity	NPC127546
0.6543	Remote Similarity	NPC57625
0.6543	Remote Similarity	NPC19709
0.6543	Remote Similarity	NPC173637
0.6543	Remote Similarity	NPC317489
0.6543	Remote Similarity	NPC238376
0.6543	Remote Similarity	NPC223424
0.6543	Remote Similarity	NPC600591
0.6506	Remote Similarity	NPC472459
0.6436	Remote Similarity	NPC470720
0.6429	Remote Similarity	NPC470716
0.6429	Remote Similarity	NPC488071
0.6392	Remote Similarity	NPC470715
0.6386	Remote Similarity	NPC27640
0.6364	Remote Similarity	NPC139320
0.6341	Remote Similarity	NPC261866
0.6337	Remote Similarity	NPC470717
0.631	Remote Similarity	NPC599850
0.6304	Remote Similarity	NPC606657
0.625	Remote Similarity	NPC121703
0.625	Remote Similarity	NPC480463
0.6237	Remote Similarity	NPC142142
0.6235	Remote Similarity	NPC307938
0.6207	Remote Similarity	NPC203050
0.6207	Remote Similarity	NPC225434
0.6163	Remote Similarity	NPC601144
0.6162	Remote Similarity	NPC277532
0.6145	Remote Similarity	NPC19388
0.6145	Remote Similarity	NPC240431
0.6145	Remote Similarity	NPC55786
0.6118	Remote Similarity	NPC42773
0.6118	Remote Similarity	NPC59534
0.6118	Remote Similarity	NPC45522
0.6111	Remote Similarity	NPC173582
0.6111	Remote Similarity	NPC265885
0.6111	Remote Similarity	NPC181465
0.6111	Remote Similarity	NPC215710
0.6111	Remote Similarity	NPC163242
0.6111	Remote Similarity	NPC272068
0.6111	Remote Similarity	NPC473438
0.6111	Remote Similarity	NPC253788
0.6092	Remote Similarity	NPC223747
0.6092	Remote Similarity	NPC311830
0.6071	Remote Similarity	NPC197896
0.6071	Remote Similarity	NPC95090
0.6071	Remote Similarity	NPC313163
0.6071	Remote Similarity	NPC27408
0.6064	Remote Similarity	NPC5319
0.6047	Remote Similarity	NPC168584
0.6047	Remote Similarity	NPC60735
0.6047	Remote Similarity	NPC26230
0.6047	Remote Similarity	NPC285197
0.6044	Remote Similarity	NPC65003
0.6024	Remote Similarity	NPC473043
0.6024	Remote Similarity	NPC135599
0.6024	Remote Similarity	NPC73855
0.6024	Remote Similarity	NPC113968
0.6024	Remote Similarity	NPC328940
0.6024	Remote Similarity	NPC277174
0.6024	Remote Similarity	NPC606877
0.6023	Remote Similarity	NPC488072
0.6023	Remote Similarity	NPC66087
0.6	Remote Similarity	NPC305811
0.5977	Remote Similarity	NPC22832
0.5977	Remote Similarity	NPC120099
0.5952	Remote Similarity	NPC348541
0.5934	Remote Similarity	NPC44931
0.593	Remote Similarity	NPC325555
0.593	Remote Similarity	NPC226304
0.5918	Remote Similarity	NPC203145
0.5905	Remote Similarity	NPC138990
0.5904	Remote Similarity	NPC67037
0.5904	Remote Similarity	NPC255615
0.5882	Remote Similarity	NPC265530
0.5862	Remote Similarity	NPC219904
0.5859	Remote Similarity	NPC189564
0.5843	Remote Similarity	NPC170052
0.5843	Remote Similarity	NPC135846
0.5843	Remote Similarity	NPC601586
0.5825	Remote Similarity	NPC295625
0.5795	Remote Similarity	NPC101026
0.5795	Remote Similarity	NPC243930
0.5795	Remote Similarity	NPC488077
0.5795	Remote Similarity	NPC486578
0.5778	Remote Similarity	NPC265115
0.5761	Remote Similarity	NPC471748
0.5747	Remote Similarity	NPC27942
0.5714	Remote Similarity	NPC473682
0.5714	Remote Similarity	NPC602448
0.5701	Remote Similarity	NPC175429
0.5699	Remote Similarity	NPC65563
0.5699	Remote Similarity	NPC470949
0.5699	Remote Similarity	NPC156869
0.5699	Remote Similarity	NPC605592
0.5698	Remote Similarity	NPC93337
0.5698	Remote Similarity	NPC146792
0.5682	Remote Similarity	NPC80140
0.5679	Remote Similarity	NPC191154
0.5676	Remote Similarity	NPC146679
0.5667	Remote Similarity	NPC476215
0.5652	Remote Similarity	NPC29958
0.5638	Remote Similarity	NPC115674
0.5638	Remote Similarity	NPC470444
0.5638	Remote Similarity	NPC473571
0.5638	Remote Similarity	NPC110941
0.5632	Remote Similarity	NPC84265
0.5632	Remote Similarity	NPC105025
0.5632	Remote Similarity	NPC349108
0.5632	Remote Similarity	NPC610763
0.5618	Remote Similarity	NPC21666
0.5618	Remote Similarity	NPC609478
0.561	Remote Similarity	NPC134819
0.5607	Remote Similarity	NPC209550
0.5591	Remote Similarity	NPC470405
0.5591	Remote Similarity	NPC67105
0.5581	Remote Similarity	NPC476405
0.5581	Remote Similarity	NPC83283
0.5567	Remote Similarity	NPC486577
0.5566	Remote Similarity	NPC470719
0.5556	Remote Similarity	NPC206123
0.5556	Remote Similarity	NPC607707
0.5532	Remote Similarity	NPC203259
0.5532	Remote Similarity	NPC33054
0.5532	Remote Similarity	NPC210073
0.5532	Remote Similarity	NPC155877
0.5532	Remote Similarity	NPC176740
0.5532	Remote Similarity	NPC471725
0.5532	Remote Similarity	NPC134532
0.5532	Remote Similarity	NPC602582
0.5521	Remote Similarity	NPC483414
0.5521	Remote Similarity	NPC483415
0.5506	Remote Similarity	NPC159579
0.5484	Remote Similarity	NPC471079
0.5476	Remote Similarity	NPC54802
0.5476	Remote Similarity	NPC197304
0.5464	Remote Similarity	NPC483416
0.5455	Remote Similarity	NPC603655
0.5444	Remote Similarity	NPC148710
0.5444	Remote Similarity	NPC224530
0.5412	Remote Similarity	NPC34531

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC494078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5596
0.1-0.2	3481
0.2-0.3	62
0.3-0.4	5
0.4-0.5	0
0.5-0.6	2
0.6-0.7	2
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
0.6344	Remote Similarity	NPD7251	Phase 2
0.6064	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7808	Phase 3
0.5532	Remote Similarity	NPD6797	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