NPASS Compound

Natural Product: NPC117478

Natural Product ID	NPC117478
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Astragalin Heptaacetate
IUPAC Name	[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[5,7-diacetyloxy-2-(4-acetyloxyphenyl)-4-oxochromen-3-yl]oxyoxan-2-yl]methyl acetate
Synonyms	Astragalin Heptaacetate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1774168
PubChem CID	12900986
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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 87 90 0 0 0 0 0 0 0 0999 V2000 -6.2597 -3.6122 0.8836 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9102 -3.0720 1.2238 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6412 -2.5249 2.3006 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9199 -3.2023 0.2647 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6041 -2.7638 0.3901 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4944 -1.2794 0.5969 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1080 -0.5134 -0.5836 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2173 0.8894 -0.0331 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7945 1.4080 0.0710 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8368 0.4160 0.5350 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2321 -0.8731 0.7164 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2182 0.2914 -0.4921 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4419 -0.2165 -0.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5341 -1.6148 -0.1381 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5712 -2.3303 -0.5086 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7135 -2.1957 0.2428 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8008 -3.5789 0.2059 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9870 -4.1934 0.5896 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0467 -3.4118 0.9970 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9355 -2.0399 1.0248 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7559 -1.3860 0.6453 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6552 -0.0933 0.6730 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5153 0.5165 0.3055 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5608 1.9648 0.3873 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6244 2.7739 -0.1596 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7278 4.1696 -0.0116 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7554 4.7415 0.6750 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7082 3.9325 1.2320 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5961 2.5740 1.0804 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8266 6.1454 0.8036 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4850 6.8801 -0.1518 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0031 6.2476 -1.1156 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5685 8.3540 -0.0312 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2462 -3.9913 1.3869 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2505 -4.2194 0.4399 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0131 -3.8830 -0.7357 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5457 -4.8314 0.7929 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -4.3230 -0.2119 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5739 -4.6767 -1.5353 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4647 -4.3083 -2.3438 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4390 -5.4707 -2.0764 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7859 2.6441 0.7758 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6290 3.8685 0.1983 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4861 3.8756 -1.0674 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6273 5.0967 0.9997 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0102 1.7214 -0.8501 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1735 2.3082 -0.3808 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5035 2.0752 0.8044 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9722 3.1744 -1.2791 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3376 -1.0519 -0.9699 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4573 -1.5294 -2.2703 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4837 -1.4804 -3.0847 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7266 -2.1223 -2.7793 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0949 -4.5710 0.3446 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8752 -3.7682 1.7929 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7221 -2.8857 0.1844 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0603 -3.1029 -0.5055 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1636 -3.2476 1.2827 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1185 -0.9925 1.4712 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3398 -0.5252 -1.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6591 0.7929 0.9791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5612 1.7137 -0.9985 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2866 0.6695 1.5007 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0599 -5.2663 0.5629 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7679 -1.4095 1.3459 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7925 2.3955 -0.7306 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9825 4.8323 -0.4554 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5396 4.3300 1.7849 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3467 1.9482 1.5214 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8969 8.8646 -0.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6293 8.6521 -0.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2592 8.6528 0.9764 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3449 -5.6751 1.5072 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9943 -5.2439 -0.1304 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2192 -4.1297 1.3329 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1950 -5.9114 -1.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8953 -6.3074 -2.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1121 -4.8201 -2.7860 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6550 5.2737 1.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7983 5.9512 0.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4062 5.0734 1.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8783 2.6551 -1.6595 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3823 3.5536 -2.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3155 4.0482 -0.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7690 -3.2079 -2.5615 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6145 -1.6051 -2.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7808 -2.0168 -3.8940 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 27 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 19 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 17 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 9 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 8 46 1 0 46 47 1 0 47 48 2 0 47 49 1 0 7 50 1 0 50 51 1 0 51 52 2 0 51 53 1 0 11 6 1 0 23 13 2 0 29 24 1 0 21 16 1 0 1 54 1 0 1 55 1 0 1 56 1 0 5 57 1 0 5 58 1 0 6 59 1 1 7 60 1 6 8 61 1 1 9 62 1 6 10 63 1 1 18 64 1 0 20 65 1 0 25 66 1 0 26 67 1 0 28 68 1 0 29 69 1 0 33 70 1 0 33 71 1 0 33 72 1 0 37 73 1 0 37 74 1 0 37 75 1 0 41 76 1 0 41 77 1 0 41 78 1 0 45 79 1 0 45 80 1 0 45 81 1 0 49 82 1 0 49 83 1 0 49 84 1 0 53 85 1 0 53 86 1 0 53 87 1 0 M END

Standard InCHIKey	XNIDEUYQVRRKJJ-FZPNTLRJSA-N
Standard InCHI	InChI=1S/C35H34O18/c1-15(36)44-14-27-31(48-19(5)40)33(49-20(6)41)34(50-21(7)42)35(52-27)53-32-29(43)28-25(47-18(4)39)12-24(46-17(3)38)13-26(28)51-30(32)22-8-10-23(11-9-22)45-16(2)37/h8-13,27,31,33-35H,14H2,1-7H3/t27-,31-,33+,34-,35+/m1/s1
SMILES	CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	742.17	Volume:	698.367 ? Van der Waals volume.
Dense:	1.063	LogP:	1.28 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.608 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.523 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	31.0
TPSA:	232.77 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.477	Fsp³:	0.371
MCE-18:	105.875 ? 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:	0.524	Fluc inhibitor:	0.324 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.964 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.358 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.236	Promiscuous compounds:	0.466

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.264	MDCK Permeability:	-4.588
Pgp-inhibitor:	0.998	Pgp-substrate:	0.732
PAMPA:	0.894 ? 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):	0.003
20% Bioavailability (F20%):	0.031	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.969
Plasma Protein Binding (PPB):	65.194%	Volume Distribution (VD):	-0.237
Fu:	25.588% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

1.425

Half-life (T1/2):

0.978

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.388	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.702	Rat Oral Acute Toxicity:	0.233
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	0.999
Carcinogencity:	0.081	Eye Corrosion:	0.013
Eye Irritation:	0.291	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.114
Hematotoxicity:	0.677	Drug-induced Nephrotoxicity:	0.089
Genotoxicity:	0.986	RPMI-8226 Immunitoxicity:	0.015
A549 Cytotoxicity:	0.378	Hek293 Cytotoxicity:	0.023
BCF:	0.506 ? 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:	3.417 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.994 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.597 ? 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
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[10978212]
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21466157]
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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
IC50	2
Ratio IC50	1
Inhibition	1
Activity	2

Activity Type	# Activity
Cell line	1
Organism	4
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
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	164000.0	nM	PMID[21466157]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	800.0	nM	PMID[21466157]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Inhibition	=	91.0	%	PMID[21466157]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	95.0	%	PMID[21466157]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	23.0	%	PMID[21466157]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	205.0	n.a.	PMID[21466157]

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 NPC117478 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	22451
0.1-0.2	25828
0.2-0.3	1268
0.3-0.4	283
0.4-0.5	12
0.5-0.6	8
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC321478
0.8571	High Similarity	NPC475214
0.7821	Intermediate Similarity	NPC481404
0.7683	Intermediate Similarity	NPC473516
0.7412	Intermediate Similarity	NPC476180
0.6778	Remote Similarity	NPC475434
0.6628	Remote Similarity	NPC414831
0.6286	Remote Similarity	NPC474037
0.589	Remote Similarity	NPC605569
0.5256	Remote Similarity	NPC177839
0.5125	Remote Similarity	NPC472535
0.5104	Remote Similarity	NPC473862
0.5098	Remote Similarity	NPC478277
0.5098	Remote Similarity	NPC478276
0.5098	Remote Similarity	NPC478275
0.5098	Remote Similarity	NPC92815

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC117478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5089
0.1-0.2	4014
0.2-0.3	41
0.3-0.4	6
0.4-0.5	0
0.5-0.6	0
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
		NPD

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