NPASS Compound

Natural Product: NPC470451

Natural Product ID	NPC470451
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Methoxyquercetin-3-O-(2,4-Di-O-Acetyl)-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	[(2S,3R,4R,5R,6R)-5-acetyloxy-6-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-2-methyloxan-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2037054
PubChem CID	57408284
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 91 0 0 0 0 0 0 0 0999 V2000 7.0214 1.6870 -0.3253 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7539 1.4467 0.4913 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0217 0.7175 1.7525 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9977 -0.2811 2.1857 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1274 -0.7722 1.0562 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6837 0.4462 0.2840 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8021 0.9446 -0.3461 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7189 0.1702 -0.6565 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5793 0.9206 -0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5960 0.4768 -1.6081 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3142 -0.9979 -1.4950 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4245 -1.4310 -2.7480 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3024 -0.2963 -3.1427 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6998 0.5486 -1.9397 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5510 1.2105 -1.4955 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3077 -0.1196 -0.8903 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6398 -0.1051 -0.5090 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1602 0.7931 0.3670 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4663 0.7135 0.6427 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2450 -0.1774 0.1184 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7753 -1.1232 -0.7765 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4371 -1.0658 -1.0816 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0108 -1.9395 -1.9000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5865 -2.0856 -1.3479 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9171 -2.1118 -1.0197 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4191 -1.1793 -0.1278 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6085 -0.2251 0.4371 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7811 -1.2439 0.1772 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7610 -3.0667 -1.5755 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9118 -4.2943 -0.8680 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0159 -2.9805 -2.2273 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4100 1.8619 1.0533 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0677 1.8781 1.1993 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3917 2.9299 1.8077 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0996 3.9903 2.2806 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4850 3.9834 2.1369 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1301 2.9338 1.5317 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4209 5.0402 2.8883 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0012 2.8762 1.9211 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3341 -0.6557 -3.9103 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0574 -2.6407 -2.6276 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5201 -1.7043 -1.3735 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9502 -1.6126 0.2536 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7189 -2.9527 0.0952 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7221 -3.4335 0.7035 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6119 -3.7608 -0.7518 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2358 0.3078 3.2129 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3302 1.6412 2.7877 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5834 1.6451 3.3494 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5064 0.8497 2.9867 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8436 2.6370 4.4306 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6892 2.4158 0.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7758 2.1077 -1.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6154 0.7323 -0.4005 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4084 2.4857 0.7737 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9656 0.1174 1.5804 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4710 -1.1875 2.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2948 -1.3353 1.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3474 1.2474 0.9978 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8155 1.9903 -0.7215 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0862 0.8469 0.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0262 0.6722 -2.6304 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3158 -1.1780 -0.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3614 -1.5381 -3.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6822 0.4462 -3.7650 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3913 1.3021 -2.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9870 0.5083 1.1352 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4057 -1.4950 -0.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9876 -4.5752 -0.3276 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2360 -5.1109 -1.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7390 -4.2026 -0.1051 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8302 -3.9272 -1.9105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4788 1.0619 0.8862 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0238 4.8492 2.5299 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2210 2.9766 1.4430 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4923 5.9517 2.4333 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5944 3.5592 1.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3760 -0.2880 -4.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7343 -3.3258 -3.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4660 -2.2461 -0.5620 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3099 -3.0841 -1.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0602 -4.3471 -1.5167 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1882 -4.4387 -0.0669 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4856 -0.0638 4.0882 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4430 2.2376 5.3874 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3450 3.5826 4.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9288 2.8592 4.4989 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 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 21 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 25 29 1 0 29 30 1 0 24 31 1 0 18 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 35 38 1 0 34 39 1 0 13 40 1 0 12 41 1 0 11 42 1 0 5 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 4 47 1 0 3 48 1 0 48 49 1 0 49 50 2 0 49 51 1 0 7 2 1 0 15 10 1 0 22 17 1 0 27 20 1 0 37 32 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 0 3 56 1 0 4 57 1 0 5 58 1 0 6 59 1 0 9 60 1 0 9 61 1 0 10 62 1 0 11 63 1 0 12 64 1 0 13 65 1 0 14 66 1 0 27 67 1 0 28 68 1 0 30 69 1 0 30 70 1 0 30 71 1 0 31 72 1 0 33 73 1 0 36 74 1 0 37 75 1 0 38 76 1 0 39 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 46 81 1 0 46 82 1 0 46 83 1 0 47 84 1 0 51 85 1 0 51 86 1 0 51 87 1 0 M END

Standard InCHIKey	HBEXKXGYZHGIHZ-ASGGTIEFSA-N
Standard InCHI	InChI=1S/C32H36O19/c1-10-26(47-11(2)33)25(43)30(48-12(3)34)32(46-10)45-9-18-20(38)23(41)24(42)31(50-18)51-29-22(40)19-17(8-16(37)28(44-4)21(19)39)49-27(29)13-5-6-14(35)15(36)7-13/h5-8,10,18,20,23-26,30-32,35-39,41-43H,9H2,1-4H3/t10-,18+,20+,23-,24+,25+,26-,30+,31-,32+/m0/s1
SMILES	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=C(C3=O)C(=C(C(=C4)O)OC)O)C5=CC(=C(C=C5)O)O)O)O)O)OC(=O)C)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	724.19	Volume:	659.895 ? Van der Waals volume.
Dense:	1.097	LogP:	0.403 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.009 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.225 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	32.0
TPSA:	290.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.102	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.074	Fsp³:	0.469
MCE-18:	130.17 ? 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:	1
Colloidal aggregators:	0.28	Fluc inhibitor:	0.031 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.915 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.795 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.128	Promiscuous compounds:	0.27

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.135	MDCK Permeability:	-5.332
Pgp-inhibitor:	0.0	Pgp-substrate:	0.784
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):	0.75
20% Bioavailability (F20%):	0.4	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.992
Plasma Protein Binding (PPB):	68.842%	Volume Distribution (VD):	-0.182
Fu:	30.891% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.007
OATP1B3 inhibitor:	0.977	BCRP inhibitor:	0.384
BSEP inhibitor:	0.048

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.536 ? 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):

2.204

Half-life (T1/2):

3.061

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.424
Human Hepatotoxicity (H-HT):	0.373	Drug-induced Liver Injury (DILI):	0.877
AMES Toxicity:	0.763	Rat Oral Acute Toxicity:	0.407
Maximum Recommended Daily Dose:	0.511	Skin Sensitization:	0.747
Carcinogencity:	0.076	Eye Corrosion:	0.0
Eye Irritation:	0.019	Respiratory Toxicity:	0.031
Drug-induced Neurotoxicity:	0.029	Ototoxicity:	0.975
Hematotoxicity:	0.015	Drug-induced Nephrotoxicity:	0.012
Genotoxicity:	0.903	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.417	Hek293 Cytotoxicity:	0.655
BCF:	0.464 ? 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:	3.169 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.002 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.117 ? 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
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	Flowers	Santana do Riacho, State Minas Gerais, Brazil	n.a.	PMID[22506638]
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Activity	1

Activity Type	# Activity
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	1.214	mM	PMID[22506638]

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 NPC470451 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	16657
0.1-0.2	29819
0.2-0.3	2585
0.3-0.4	436
0.4-0.5	249
0.5-0.6	91
0.6-0.7	9
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8478	Intermediate Similarity	NPC470445
0.8191	Intermediate Similarity	NPC470446
0.7604	Intermediate Similarity	NPC470447
0.7374	Intermediate Similarity	NPC470455
0.7368	Intermediate Similarity	NPC126784
0.7368	Intermediate Similarity	NPC241423
0.7347	Intermediate Similarity	NPC470449
0.7188	Intermediate Similarity	NPC488073
0.7188	Intermediate Similarity	NPC488074
0.6813	Remote Similarity	NPC305811
0.6566	Remote Similarity	NPC473571
0.6566	Remote Similarity	NPC110941
0.6559	Remote Similarity	NPC42773
0.6559	Remote Similarity	NPC45522
0.6392	Remote Similarity	NPC116864
0.6392	Remote Similarity	NPC244776
0.6117	Remote Similarity	NPC483415
0.6038	Remote Similarity	NPC36138
0.5981	Remote Similarity	NPC470450
0.598	Remote Similarity	NPC203259
0.598	Remote Similarity	NPC33054
0.598	Remote Similarity	NPC176740
0.598	Remote Similarity	NPC471725
0.598	Remote Similarity	NPC134532
0.598	Remote Similarity	NPC602582
0.5943	Remote Similarity	NPC471669
0.5882	Remote Similarity	NPC67326
0.5865	Remote Similarity	NPC153755
0.5825	Remote Similarity	NPC156869
0.5818	Remote Similarity	NPC470416
0.581	Remote Similarity	NPC470443
0.581	Remote Similarity	NPC483414
0.5794	Remote Similarity	NPC483412
0.5773	Remote Similarity	NPC488080
0.5773	Remote Similarity	NPC169977
0.5755	Remote Similarity	NPC473327
0.5648	Remote Similarity	NPC473073
0.5648	Remote Similarity	NPC483413
0.5625	Remote Similarity	NPC292019
0.5625	Remote Similarity	NPC202908
0.5612	Remote Similarity	NPC27640
0.5607	Remote Similarity	NPC483416
0.56	Remote Similarity	NPC101026
0.56	Remote Similarity	NPC488077
0.5545	Remote Similarity	NPC223426
0.5505	Remote Similarity	NPC476472
0.5505	Remote Similarity	NPC294815
0.5505	Remote Similarity	NPC16194
0.5505	Remote Similarity	NPC89127
0.55	Remote Similarity	NPC175107
0.5495	Remote Similarity	NPC81042
0.5481	Remote Similarity	NPC609888
0.5463	Remote Similarity	NPC37668
0.5455	Remote Similarity	NPC271692
0.5446	Remote Similarity	NPC259957
0.5429	Remote Similarity	NPC173582
0.5429	Remote Similarity	NPC265885
0.5429	Remote Similarity	NPC181465
0.5429	Remote Similarity	NPC215710
0.5429	Remote Similarity	NPC473438
0.5429	Remote Similarity	NPC253788
0.5413	Remote Similarity	NPC486577
0.5408	Remote Similarity	NPC127546
0.5408	Remote Similarity	NPC57625
0.5408	Remote Similarity	NPC173637
0.5408	Remote Similarity	NPC317489
0.5408	Remote Similarity	NPC223424
0.5408	Remote Similarity	NPC600591
0.5392	Remote Similarity	NPC209023
0.5377	Remote Similarity	NPC65563
0.5377	Remote Similarity	NPC470949
0.5347	Remote Similarity	NPC159579
0.5347	Remote Similarity	NPC488071
0.5333	Remote Similarity	NPC471079
0.5294	Remote Similarity	NPC484158
0.5283	Remote Similarity	NPC39834
0.525	Remote Similarity	NPC488078
0.5248	Remote Similarity	NPC599850
0.5238	Remote Similarity	NPC254540
0.5229	Remote Similarity	NPC480471
0.5229	Remote Similarity	NPC488076
0.52	Remote Similarity	NPC145038
0.52	Remote Similarity	NPC56077
0.52	Remote Similarity	NPC281131
0.52	Remote Similarity	NPC253662
0.52	Remote Similarity	NPC179950
0.52	Remote Similarity	NPC88789
0.52	Remote Similarity	NPC491374
0.5196	Remote Similarity	NPC182121
0.5196	Remote Similarity	NPC219904
0.514	Remote Similarity	NPC471748
0.513	Remote Similarity	NPC488075
0.513	Remote Similarity	NPC189564
0.5114	Remote Similarity	NPC163524
0.5098	Remote Similarity	NPC59534
0.5093	Remote Similarity	NPC233994
0.5089	Remote Similarity	NPC85751
0.5089	Remote Similarity	NPC19240
0.5088	Remote Similarity	NPC214621
0.5088	Remote Similarity	NPC34267
0.5086	Remote Similarity	NPC173837
0.5086	Remote Similarity	NPC477895
0.5085	Remote Similarity	NPC139571
0.5046	Remote Similarity	NPC129264
0.5046	Remote Similarity	NPC186816
0.5045	Remote Similarity	NPC122467
0.5045	Remote Similarity	NPC270448
0.5043	Remote Similarity	NPC121703
0.5043	Remote Similarity	NPC217520

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5091
0.1-0.2	4013
0.2-0.3	37
0.3-0.4	4
0.4-0.5	3
0.5-0.6	2
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
0.598	Remote Similarity	NPD6797	Phase 2
0.5364	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