NPASS Compound

Natural Product: NPC515326

Natural Product ID	NPC515326
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-methoxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-methoxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-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 79 83 0 0 0 0 0 0 0 0999 V2000 -8.7402 4.6334 -0.0250 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2051 3.3283 0.0042 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8445 3.1642 0.1420 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0422 4.2747 0.2479 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6778 4.1265 0.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8067 5.1921 0.4985 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1664 2.8545 0.4136 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7972 2.6525 0.5478 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0448 3.6424 0.6459 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2292 1.3824 0.5783 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8846 1.2910 0.7023 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0218 1.3700 -0.3929 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7527 0.2266 -0.5018 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8464 0.2775 -1.3416 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1899 -1.0265 -1.9663 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5265 -2.0593 -1.1309 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6658 -1.7880 -0.4328 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7129 -2.6753 -0.7918 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7021 -2.6754 0.1906 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0042 -3.0395 -0.5249 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8889 -1.2954 0.7970 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0034 -1.2711 1.6029 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6755 -0.9889 1.6304 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8657 -1.2357 2.9801 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5381 -1.8561 1.0709 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3275 -1.3978 1.5448 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5644 1.3554 -2.3722 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5378 1.3764 -3.3701 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6477 2.6790 -1.6490 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0661 3.7155 -2.3733 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9790 2.5393 -0.2755 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9419 2.3064 0.7112 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0773 0.3318 0.4751 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6383 -1.0490 0.5009 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4442 -1.5287 0.9234 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0994 -2.8806 0.8588 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9926 -3.7967 0.3482 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6939 -5.1514 0.2640 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4259 -5.5746 0.7246 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2164 -3.3471 -0.0897 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1043 -4.2887 -0.6012 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5284 -2.0084 -0.0142 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4036 0.5478 0.3428 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9413 1.7240 0.3104 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3176 1.8932 0.1709 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8370 4.6217 -0.1998 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2001 5.2268 -0.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5041 5.0969 0.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4304 5.2836 0.2282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6377 5.6094 1.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6177 1.5734 -1.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6979 0.6405 -0.7427 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0854 -0.8408 -2.6235 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3796 -1.3127 -2.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0511 -0.7807 -0.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5431 -3.4552 0.9627 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0897 -4.1172 -0.7113 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0334 -2.5468 -1.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8778 -2.6647 0.0228 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9905 -0.5983 -0.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2105 -2.1849 1.9748 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3834 0.0612 1.4275 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4327 -0.5067 3.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6400 -2.9005 1.4456 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4906 -0.7706 2.2849 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5964 1.1850 -2.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4133 0.6642 -4.0374 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7136 2.8935 -1.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6096 4.5382 -2.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5269 3.4996 -0.0707 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5511 1.7183 1.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7312 -0.8617 1.3576 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1309 -3.1977 1.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3417 -5.4551 1.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3256 -4.9236 0.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2431 -6.6410 0.4988 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6382 -4.1351 -1.4299 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4984 -1.7071 -0.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9680 1.0375 0.0860 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 5 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 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 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 14 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 10 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 37 40 1 0 40 41 1 0 40 42 2 0 33 43 1 0 43 44 1 0 44 45 2 0 45 3 1 0 44 7 1 0 31 12 1 0 42 34 1 0 25 17 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 6 50 1 0 12 51 1 6 14 52 1 1 15 53 1 0 15 54 1 0 17 55 1 1 19 56 1 1 20 57 1 0 20 58 1 0 20 59 1 0 21 60 1 6 22 61 1 0 23 62 1 1 24 63 1 0 25 64 1 1 26 65 1 0 27 66 1 6 28 67 1 0 29 68 1 1 30 69 1 0 31 70 1 1 32 71 1 0 35 72 1 0 36 73 1 0 39 74 1 0 39 75 1 0 39 76 1 0 41 77 1 0 42 78 1 0 45 79 1 0 M END

Standard InCHIKey	VVSFMIXQNYRGMG-AADHHPFFSA-N
Standard InCHI	InChI=1S/C29H34O16/c1-10-19(32)22(35)24(37)28(42-10)41-9-17-20(33)23(36)25(38)29(44-17)45-27-21(34)18-14(31)7-12(39-2)8-16(18)43-26(27)11-4-5-15(40-3)13(30)6-11/h4-8,10,17,19-20,22-25,28-33,35-38H,9H2,1-3H3/t10-,17-,19-,20-,22-,23+,24+,25-,28+,29-/m0/s1
SMILES	COC1=CC(O)=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(O)=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.18	Volume:	586.91 ? Van der Waals volume.
Dense:	1.087	LogP:	0.991 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.522 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.11 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	247.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.73	Fsp³:	0.483
MCE-18:	121.279 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.626	Fluc inhibitor:	0.284 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.859 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.68 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.051	Promiscuous compounds:	0.407

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.232	MDCK Permeability:	-5.403
Pgp-inhibitor:	0.001	Pgp-substrate:	0.82
PAMPA:	0.998 ? 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):	0.968
20% Bioavailability (F20%):	0.192	30% Bioavailability (F30%):	0.951
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.084
Plasma Protein Binding (PPB):	82.055%	Volume Distribution (VD):	-0.115
Fu:	17.403% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.833
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.598	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.929
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.945 ? 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):

1.194

Half-life (T1/2):

3.023

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.149
Human Hepatotoxicity (H-HT):	0.601	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.96	Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.048	Skin Sensitization:	0.999
Carcinogencity:	0.148	Eye Corrosion:	0.0
Eye Irritation:	0.421	Respiratory Toxicity:	0.051
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.855
Hematotoxicity:	0.329	Drug-induced Nephrotoxicity:	0.645
Genotoxicity:	0.697	RPMI-8226 Immunitoxicity:	0.303
A549 Cytotoxicity:	0.858	Hek293 Cytotoxicity:	0.542
BCF:	0.443 ? 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:	3.142 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.683 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.908 ? 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
NPO22702	Phytolacca dioica	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21962	Flyriella parryi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26811	Gynostemma yixingense	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO49134	Erythroxylum spp.	Genus	Erythroxylaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50109	Gynostemon pentaphyllum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26811	Gynostemma yixingense	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22702	Phytolacca dioica	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26811	Gynostemma yixingense	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21962	Flyriella parryi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO22702	Phytolacca dioica	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21962	Flyriella parryi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26811	Gynostemma yixingense	Species	Cucurbitaceae	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 NPC515326 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	17722
0.1-0.2	27962
0.2-0.3	3142
0.3-0.4	539
0.4-0.5	275
0.5-0.6	137
0.6-0.7	49
0.7-0.8	2
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8276	Intermediate Similarity	NPC473327
0.8148	Intermediate Similarity	NPC611303
0.8068	Intermediate Similarity	NPC209296
0.7931	Intermediate Similarity	NPC186816
0.7363	Intermediate Similarity	NPC470443
0.7283	Intermediate Similarity	NPC606657
0.7222	Intermediate Similarity	NPC22062
0.7222	Intermediate Similarity	NPC473634
0.7222	Intermediate Similarity	NPC138811
0.7079	Intermediate Similarity	NPC251417
0.7065	Intermediate Similarity	NPC126784
0.7065	Intermediate Similarity	NPC241423
0.7059	Intermediate Similarity	NPC271692
0.7021	Intermediate Similarity	NPC142142
0.6947	Remote Similarity	NPC476472
0.6947	Remote Similarity	NPC294815
0.6947	Remote Similarity	NPC16194
0.686	Remote Similarity	NPC46420
0.6848	Remote Similarity	NPC203259
0.6848	Remote Similarity	NPC33054
0.6848	Remote Similarity	NPC176740
0.6848	Remote Similarity	NPC471725
0.6848	Remote Similarity	NPC134532
0.6848	Remote Similarity	NPC602582
0.68	Remote Similarity	NPC480441
0.6774	Remote Similarity	NPC473571
0.6774	Remote Similarity	NPC110941
0.6744	Remote Similarity	NPC158674
0.6739	Remote Similarity	NPC173582
0.6739	Remote Similarity	NPC265885
0.6739	Remote Similarity	NPC181465
0.6739	Remote Similarity	NPC215710
0.6739	Remote Similarity	NPC67105
0.6739	Remote Similarity	NPC473438
0.6739	Remote Similarity	NPC253788
0.6705	Remote Similarity	NPC219904
0.6667	Remote Similarity	NPC210073
0.6634	Remote Similarity	NPC25523
0.6598	Remote Similarity	NPC473073
0.6559	Remote Similarity	NPC44931
0.6559	Remote Similarity	NPC39834
0.6559	Remote Similarity	NPC227508
0.6437	Remote Similarity	NPC249281
0.6327	Remote Similarity	NPC486577
0.6316	Remote Similarity	NPC65563
0.6316	Remote Similarity	NPC470949
0.6304	Remote Similarity	NPC276377
0.625	Remote Similarity	NPC204693
0.6196	Remote Similarity	NPC605784
0.6186	Remote Similarity	NPC488073
0.6176	Remote Similarity	NPC121703
0.6168	Remote Similarity	NPC198199
0.6095	Remote Similarity	NPC277532
0.6078	Remote Similarity	NPC14187
0.6067	Remote Similarity	NPC289667
0.6061	Remote Similarity	NPC473623
0.604	Remote Similarity	NPC470445
0.6022	Remote Similarity	NPC116458
0.6022	Remote Similarity	NPC246943
0.602	Remote Similarity	NPC240306
0.602	Remote Similarity	NPC488074
0.6	Remote Similarity	NPC120952
0.6	Remote Similarity	NPC488089
0.598	Remote Similarity	NPC470446
0.598	Remote Similarity	NPC135358
0.5979	Remote Similarity	NPC303913
0.5979	Remote Similarity	NPC150164
0.5979	Remote Similarity	NPC156869
0.5938	Remote Similarity	NPC187379
0.5914	Remote Similarity	NPC120099
0.5905	Remote Similarity	NPC173837
0.59	Remote Similarity	NPC32641
0.59	Remote Similarity	NPC256188
0.59	Remote Similarity	NPC72016
0.5876	Remote Similarity	NPC67326
0.5875	Remote Similarity	NPC270620
0.5865	Remote Similarity	NPC89052
0.5865	Remote Similarity	NPC11468
0.5859	Remote Similarity	NPC153755
0.5856	Remote Similarity	NPC209550
0.5824	Remote Similarity	NPC136042
0.5784	Remote Similarity	NPC470447
0.5784	Remote Similarity	NPC89127
0.5773	Remote Similarity	NPC471079
0.5773	Remote Similarity	NPC609888
0.5761	Remote Similarity	NPC84362
0.5761	Remote Similarity	NPC27640
0.5745	Remote Similarity	NPC22832
0.5745	Remote Similarity	NPC21666
0.5745	Remote Similarity	NPC486578
0.5743	Remote Similarity	NPC122467
0.5743	Remote Similarity	NPC35119
0.5729	Remote Similarity	NPC116864
0.5729	Remote Similarity	NPC244776
0.5728	Remote Similarity	NPC470449
0.5714	Remote Similarity	NPC275454
0.57	Remote Similarity	NPC475366
0.5699	Remote Similarity	NPC59534
0.5652	Remote Similarity	NPC297987
0.5652	Remote Similarity	NPC265530
0.5644	Remote Similarity	NPC12013
0.5644	Remote Similarity	NPC11432
0.5644	Remote Similarity	NPC477613
0.5607	Remote Similarity	NPC292019
0.5607	Remote Similarity	NPC202908
0.5591	Remote Similarity	NPC305811
0.5577	Remote Similarity	NPC101636
0.5567	Remote Similarity	NPC265115
0.5556	Remote Similarity	NPC473644
0.5545	Remote Similarity	NPC46202
0.5521	Remote Similarity	NPC223747
0.5514	Remote Similarity	NPC470451
0.5514	Remote Similarity	NPC189564
0.5505	Remote Similarity	NPC311850
0.549	Remote Similarity	NPC483414
0.5474	Remote Similarity	NPC60735
0.5474	Remote Similarity	NPC26230
0.5474	Remote Similarity	NPC285197
0.5429	Remote Similarity	NPC221342
0.5429	Remote Similarity	NPC476470
0.5426	Remote Similarity	NPC349108
0.5421	Remote Similarity	NPC203145
0.5417	Remote Similarity	NPC609478
0.5398	Remote Similarity	NPC470719
0.5392	Remote Similarity	NPC64425
0.5391	Remote Similarity	NPC192539
0.5391	Remote Similarity	NPC175429
0.5377	Remote Similarity	NPC602448
0.5376	Remote Similarity	NPC127546
0.5376	Remote Similarity	NPC57625
0.5376	Remote Similarity	NPC173637
0.5376	Remote Similarity	NPC317489
0.5376	Remote Similarity	NPC238376
0.5376	Remote Similarity	NPC223424
0.5376	Remote Similarity	NPC600591
0.5357	Remote Similarity	NPC68592
0.5347	Remote Similarity	NPC475155
0.534	Remote Similarity	NPC65711
0.534	Remote Similarity	NPC483415
0.5327	Remote Similarity	NPC470455
0.5306	Remote Similarity	NPC355481
0.5304	Remote Similarity	NPC138990
0.5304	Remote Similarity	NPC241781
0.5294	Remote Similarity	NPC473554
0.5288	Remote Similarity	NPC483416
0.5288	Remote Similarity	NPC51326
0.5273	Remote Similarity	NPC303694
0.5269	Remote Similarity	NPC111929
0.5269	Remote Similarity	NPC320283
0.5269	Remote Similarity	NPC41121
0.5263	Remote Similarity	NPC162394
0.5213	Remote Similarity	NPC108831
0.5213	Remote Similarity	NPC19709
0.5213	Remote Similarity	NPC182634
0.5208	Remote Similarity	NPC472459
0.5204	Remote Similarity	NPC99957
0.5196	Remote Similarity	NPC479405
0.5189	Remote Similarity	NPC475382
0.5189	Remote Similarity	NPC471669
0.5182	Remote Similarity	NPC477895
0.5172	Remote Similarity	NPC469622
0.5149	Remote Similarity	NPC480466
0.5146	Remote Similarity	NPC479404
0.5143	Remote Similarity	NPC483707
0.5143	Remote Similarity	NPC229409
0.514	Remote Similarity	NPC298171
0.5135	Remote Similarity	NPC217520
0.513	Remote Similarity	NPC156785
0.5106	Remote Similarity	NPC473043
0.5106	Remote Similarity	NPC135599
0.5106	Remote Similarity	NPC73855
0.5106	Remote Similarity	NPC331652
0.5106	Remote Similarity	NPC113968
0.5106	Remote Similarity	NPC328940
0.5106	Remote Similarity	NPC277174
0.5106	Remote Similarity	NPC606877
0.5104	Remote Similarity	NPC181712
0.5102	Remote Similarity	NPC181616
0.51	Remote Similarity	NPC211594
0.5098	Remote Similarity	NPC267680
0.5096	Remote Similarity	NPC64051
0.5093	Remote Similarity	NPC223426
0.5093	Remote Similarity	NPC470450
0.5088	Remote Similarity	NPC488086
0.5088	Remote Similarity	NPC295625
0.5086	Remote Similarity	NPC470720
0.5086	Remote Similarity	NPC488078
0.5085	Remote Similarity	NPC262222
0.5078	Remote Similarity	NPC482520
0.5078	Remote Similarity	NPC482519
0.505	Remote Similarity	NPC278419
0.505	Remote Similarity	NPC179198
0.5049	Remote Similarity	NPC605592
0.5048	Remote Similarity	NPC479403
0.5047	Remote Similarity	NPC85751
0.5047	Remote Similarity	NPC19240
0.5046	Remote Similarity	NPC244875
0.5046	Remote Similarity	NPC81042
0.5045	Remote Similarity	NPC480796
0.5045	Remote Similarity	NPC472993

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC515326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4764
0.1-0.2	4314
0.2-0.3	61
0.3-0.4	4
0.4-0.5	2
0.5-0.6	0
0.6-0.7	2
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8068	Intermediate Similarity	NPD7054	Phase 4
0.7692	Intermediate Similarity	NPD7251	Phase 2
0.7553	Intermediate Similarity	NPD7808	Phase 3
0.6848	Remote Similarity	NPD6797	Phase 2
0.65	Remote Similarity	NPD7472	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