NPASS Compound

Natural Product: NPC589115

Natural Product ID	NPC589115
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]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

RDKit 3D 85 89 0 0 0 0 0 0 0 0999 V2000 -6.4929 -5.5966 -0.1808 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3768 -4.1942 -0.1784 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2077 -3.5149 0.1307 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0631 -4.2064 0.4590 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9306 -3.5249 0.7571 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7535 -4.1130 1.0865 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5720 -5.4891 1.1800 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9351 -2.1154 0.7296 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8099 -1.4206 1.0300 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7474 -2.0010 1.3327 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8099 -0.0171 1.0092 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6246 0.6350 1.3216 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3626 0.9318 0.3636 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2372 -0.1850 0.2156 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3140 -0.1450 1.0661 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8970 -1.5116 1.2659 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4094 -2.0700 0.0955 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4732 -1.3741 -0.4173 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2834 -0.8743 -1.7105 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2499 0.1265 -1.8646 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1754 0.8681 -3.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6417 -0.3791 -1.6423 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5510 0.0929 -2.5847 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5739 -1.9120 -1.6450 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9114 -2.3689 -2.7783 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6899 -2.2731 -0.4446 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4270 -2.0325 0.7160 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9898 0.4672 2.3873 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0477 -0.1868 3.1385 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6989 1.9299 2.1353 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8836 2.4388 3.1083 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1405 2.1368 0.7447 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1826 2.4028 -0.1686 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9484 0.6062 0.6871 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1106 2.0536 0.6228 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2852 2.9757 1.1791 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4837 4.3492 1.0115 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5363 4.8180 0.2696 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7238 6.1655 0.1090 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8342 7.0714 0.7034 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4113 3.9063 -0.3194 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4454 4.4433 -1.0510 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4360 3.6979 -1.7299 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1775 2.5845 -0.1294 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0505 -0.1210 0.3911 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0730 -1.4170 0.4043 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2154 -2.1455 0.1026 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1343 -6.0367 -1.1294 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6001 -5.8129 -0.1321 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9899 -6.0696 0.6731 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1081 -5.2993 0.4656 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8300 -5.7328 1.9889 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1408 -5.8870 0.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5021 -6.0279 1.4285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1439 1.0716 -0.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1519 0.4813 0.6427 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0210 -2.1696 1.5459 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5901 -1.5970 2.1205 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7806 -0.4869 0.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0486 0.8829 -1.0593 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2074 1.3050 -3.3215 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4995 1.7491 -3.1020 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9845 0.2474 -4.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0417 -0.0822 -0.6430 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2158 0.7282 -2.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5780 -2.3671 -1.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1963 -1.9404 -3.6129 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3652 -3.3205 -0.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3142 -2.8440 1.2858 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9375 0.4475 3.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4319 -0.9485 3.5994 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6521 2.5084 2.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2119 1.7985 3.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5220 3.0409 0.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7670 2.3848 -1.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4742 2.6389 1.7984 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7903 5.0530 1.4787 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2192 8.0851 0.5434 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8449 6.9771 0.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6802 6.8581 1.7894 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9271 4.3909 -2.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0351 2.8003 -2.2330 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2082 3.4118 -1.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8544 1.8789 -0.5862 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1196 -1.6298 -0.1566 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 4 5 1 0 5 6 1 0 6 7 1 0 5 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 15 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 11 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 1 0 38 41 1 0 41 42 1 0 42 43 1 0 41 44 2 0 34 45 1 0 45 46 1 0 46 47 2 0 47 3 1 0 46 8 1 0 32 13 1 0 44 35 1 0 26 18 1 0 1 48 1 0 1 49 1 0 1 50 1 0 4 51 1 0 7 52 1 0 7 53 1 0 7 54 1 0 13 55 1 6 15 56 1 6 16 57 1 0 16 58 1 0 18 59 1 1 20 60 1 1 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 1 23 65 1 0 24 66 1 1 25 67 1 0 26 68 1 6 27 69 1 0 28 70 1 1 29 71 1 0 30 72 1 6 31 73 1 0 32 74 1 1 33 75 1 0 36 76 1 0 37 77 1 0 40 78 1 0 40 79 1 0 40 80 1 0 43 81 1 0 43 82 1 0 43 83 1 0 44 84 1 0 47 85 1 0 M END

Standard InCHIKey	MEJNXDYVXPUWEN-JJLQAKBHSA-N
Standard InCHI	InChI=1S/C31H38O16/c1-12-21(32)24(35)26(37)30(44-12)43-11-19-22(33)25(36)27(38)31(46-19)47-29-23(34)20-17(42-5)9-14(39-2)10-18(20)45-28(29)13-6-7-15(40-3)16(8-13)41-4/h6-10,12,19,21-22,24-27,30-33,35-38H,11H2,1-5H3/t12-,19-,21+,22+,24+,25+,26-,27-,30-,31+/m1/s1
SMILES	COC1=CC(OC)=C2C(=O)C(O[C@@H]3O[C@H](CO[C@@H]4O[C@H](C)[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H](O)[C@H]3O)=C(C3=CC=C(OC)C(OC)=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.22	Volume:	621.502 ? Van der Waals volume.
Dense:	1.072	LogP:	1.499 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.818 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.615 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	225.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.161	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.669	Fsp³:	0.516
MCE-18:	119.894 ? 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:	0.581	Fluc inhibitor:	0.226 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.7 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.433 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.028	Promiscuous compounds:	0.124

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.941	MDCK Permeability:	-5.285
Pgp-inhibitor:	0.056	Pgp-substrate:	0.759
PAMPA:	0.801 ? 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):	0.991
20% Bioavailability (F20%):	0.087	30% Bioavailability (F30%):	0.784
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.125
Plasma Protein Binding (PPB):	83.643%	Volume Distribution (VD):	-0.182
Fu:	16.771% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.969
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.812
BSEP inhibitor:	0.613

ADMET: Metabolism

CYP1A2-inhibitor:	0.064	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.011
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.091
HLM stability:	0.72 ? 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):

1.404

Half-life (T1/2):

2.963

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.137
Human Hepatotoxicity (H-HT):	0.649	Drug-induced Liver Injury (DILI):	0.962
AMES Toxicity:	0.972	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.05	Skin Sensitization:	0.999
Carcinogencity:	0.272	Eye Corrosion:	0.0
Eye Irritation:	0.214	Respiratory Toxicity:	0.084
Drug-induced Neurotoxicity:	0.168	Ototoxicity:	0.871
Hematotoxicity:	0.764	Drug-induced Nephrotoxicity:	0.78
Genotoxicity:	0.62	RPMI-8226 Immunitoxicity:	0.289
A549 Cytotoxicity:	0.907	Hek293 Cytotoxicity:	0.716
BCF:	0.338 ? 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:	3.234 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.675 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.904 ? 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
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	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 NPC589115 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	19323
0.1-0.2	26989
0.2-0.3	2746
0.3-0.4	476
0.4-0.5	249
0.5-0.6	58
0.6-0.7	12
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
0.7931	Intermediate Similarity	NPC475366
0.6774	Remote Similarity	NPC284277
0.6774	Remote Similarity	NPC475497
0.6186	Remote Similarity	NPC470443
0.6146	Remote Similarity	NPC186816
0.6122	Remote Similarity	NPC473327
0.6082	Remote Similarity	NPC126784
0.6082	Remote Similarity	NPC241423
0.6	Remote Similarity	NPC476472
0.6	Remote Similarity	NPC294815
0.6	Remote Similarity	NPC295613
0.6	Remote Similarity	NPC16194
0.6	Remote Similarity	NPC473657
0.598	Remote Similarity	NPC244875
0.5979	Remote Similarity	NPC473571
0.5979	Remote Similarity	NPC110941
0.5938	Remote Similarity	NPC15358
0.5876	Remote Similarity	NPC22062
0.5876	Remote Similarity	NPC203259
0.5876	Remote Similarity	NPC473634
0.5876	Remote Similarity	NPC33054
0.5876	Remote Similarity	NPC176740
0.5876	Remote Similarity	NPC471725
0.5876	Remote Similarity	NPC134532
0.5876	Remote Similarity	NPC138811
0.5876	Remote Similarity	NPC602582
0.5842	Remote Similarity	NPC473073
0.5816	Remote Similarity	NPC204693
0.5773	Remote Similarity	NPC173582
0.5773	Remote Similarity	NPC265885
0.5773	Remote Similarity	NPC181465
0.5773	Remote Similarity	NPC215710
0.5773	Remote Similarity	NPC39834
0.5773	Remote Similarity	NPC473438
0.5773	Remote Similarity	NPC253788
0.5714	Remote Similarity	NPC65563
0.5714	Remote Similarity	NPC470949
0.5644	Remote Similarity	NPC209296
0.5612	Remote Similarity	NPC67105
0.5591	Remote Similarity	NPC182045
0.557	Remote Similarity	NPC310259
0.5556	Remote Similarity	NPC473512
0.5556	Remote Similarity	NPC129827
0.5556	Remote Similarity	NPC475155
0.551	Remote Similarity	NPC187379
0.5455	Remote Similarity	NPC227508
0.5437	Remote Similarity	NPC142142
0.54	Remote Similarity	NPC210073
0.5361	Remote Similarity	NPC61791
0.5321	Remote Similarity	NPC480441
0.5319	Remote Similarity	NPC271692
0.53	Remote Similarity	NPC44931
0.5294	Remote Similarity	NPC488073
0.5258	Remote Similarity	NPC293004
0.5229	Remote Similarity	NPC477895
0.5213	Remote Similarity	NPC158674
0.5208	Remote Similarity	NPC611303
0.5189	Remote Similarity	NPC470445
0.5182	Remote Similarity	NPC25523
0.5176	Remote Similarity	NPC474388
0.5161	Remote Similarity	NPC114740
0.5158	Remote Similarity	NPC46420
0.5152	Remote Similarity	NPC52353
0.5146	Remote Similarity	NPC488074
0.514	Remote Similarity	NPC470446
0.5098	Remote Similarity	NPC102028
0.5098	Remote Similarity	NPC156869
0.5094	Remote Similarity	NPC470447
0.5091	Remote Similarity	NPC173837
0.5047	Remote Similarity	NPC470449
0.5046	Remote Similarity	NPC89052

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC589115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4852
0.1-0.2	4221
0.2-0.3	67
0.3-0.4	4
0.4-0.5	1
0.5-0.6	2
0.6-0.7	3
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
0.6907	Remote Similarity	NPD7808	Phase 3
0.6078	Remote Similarity	NPD7472	Pre-clinical
0.6	Remote Similarity	NPD7251	Phase 2
0.5876	Remote Similarity	NPD6797	Phase 2
0.5644	Remote Similarity	NPD7054	Phase 4

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