NPASS Compound

Natural Product: NPC471030

Natural Product ID	NPC471030
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2R,3R,4S,5R,6S)-3,5-Dihydroxy-6-[5-Hydroxy-2-(4-Hydroxy-3-Methoxyphenyl)-4-Oxochromen-7-Yl]Oxy-4-[(E)-3-(4-Hydroxyphenyl)Prop-2-Enoyl]Oxyoxan-2-Yl]Methyl (E)-3-Phenylprop-2-Enoate
IUPAC Name	[(2R,3R,4S,5R,6S)-3,5-dihydroxy-6-[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-phenylprop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL233697
PubChem CID	44429744
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 88 93 0 0 0 0 0 0 0 0999 V2000 7.7598 2.8122 -1.9479 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1205 2.3607 -1.9937 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3917 1.1455 -1.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6373 0.6149 -1.2384 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8948 -0.5757 -0.5759 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8216 -1.2529 0.0323 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5630 -0.7425 -0.0340 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3645 0.4583 -0.7103 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3838 -1.4382 0.5282 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4515 -2.6513 1.1578 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3227 -3.2646 1.6566 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3487 -4.3848 2.2438 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1154 -2.6464 1.5186 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9563 -3.1982 1.9796 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7553 -2.5579 1.8237 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6743 -1.3301 1.1949 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8837 -0.7753 0.7235 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0941 -1.4070 0.8706 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2005 -0.8678 0.4144 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5822 -0.6948 1.0206 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3710 -0.1985 0.8860 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6779 -0.9244 1.8040 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0174 -0.4566 1.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0059 0.6869 0.4717 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9927 1.6924 0.9458 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2621 1.1730 1.0107 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9395 2.9391 0.1036 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1747 3.5440 -0.1025 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2816 4.7038 -0.8254 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1859 5.2090 -1.2834 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5275 5.4144 -1.1215 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6928 4.9474 -0.6873 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9199 5.6424 -0.9785 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9585 6.8132 -1.6736 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2040 7.4155 -1.9328 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3559 6.8155 -1.4825 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3457 5.6188 -0.7678 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1143 5.0577 -0.5326 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2876 1.2781 0.3952 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9275 -1.4590 1.0537 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0900 -1.7325 1.7396 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3576 -1.0794 2.7613 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9528 -2.7825 1.2232 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6693 -3.4696 0.1450 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5055 -4.5201 -0.3928 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0462 -5.1821 -1.5319 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7452 -6.2020 -2.1361 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9735 -6.5925 -1.5824 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4395 -5.9587 -0.4695 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6902 -4.9318 0.1018 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6732 -7.6251 -2.1986 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3429 -0.8031 3.1262 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9955 -4.4430 2.6253 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7237 1.2599 -1.8307 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5351 3.1483 -0.9400 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1262 1.9911 -2.3130 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7093 3.6550 -2.6998 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8991 -0.9449 -0.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0071 -2.1758 0.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3728 0.8379 -0.7371 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4022 -3.1543 1.2751 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8497 -3.0114 2.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8905 0.1784 0.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0303 -0.4874 -0.1544 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4880 -2.0061 1.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4766 -0.0159 2.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7513 0.3962 -0.5626 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3365 2.0121 1.9625 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4006 2.7808 -0.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2941 3.6585 0.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4660 6.3153 -1.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6792 4.0185 -0.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0798 7.3182 -2.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2312 8.3446 -2.4854 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3014 7.3022 -1.6986 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2631 5.1869 -0.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0651 4.1196 0.0275 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5326 1.4267 -0.5354 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8607 -3.0011 1.7577 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7498 -3.2178 -0.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0846 -4.8928 -1.9759 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4115 -6.7285 -3.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4043 -6.2728 -0.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0909 -4.4479 0.9879 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3128 -8.5776 -2.2197 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5829 -1.6526 3.5858 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2618 -4.3796 3.6128 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2608 0.8222 -2.5605 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 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 16 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 3 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 24 39 1 0 23 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 2 3 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 48 51 1 0 22 52 1 0 14 53 1 0 4 54 1 0 8 3 1 0 19 9 1 0 18 13 1 0 26 21 1 0 38 33 1 0 50 45 1 0 1 55 1 0 1 56 1 0 1 57 1 0 5 58 1 0 6 59 1 0 8 60 1 0 10 61 1 0 15 62 1 0 17 63 1 0 21 64 1 0 22 65 1 0 23 66 1 0 24 67 1 0 25 68 1 0 27 69 1 0 27 70 1 0 31 71 1 0 32 72 1 0 34 73 1 0 35 74 1 0 36 75 1 0 37 76 1 0 38 77 1 0 39 78 1 0 43 79 1 0 44 80 1 0 46 81 1 0 47 82 1 0 49 83 1 0 50 84 1 0 51 85 1 0 52 86 1 0 53 87 1 0 54 88 1 0 M END

Standard InCHIKey	RZLBGVNPBMPJNW-KXNNMBPQSA-N
Standard InCHI	InChI=1S/C40H34O14/c1-49-31-17-24(11-14-27(31)42)30-20-29(44)36-28(43)18-26(19-32(36)52-30)51-40-38(48)39(54-35(46)16-10-23-7-12-25(41)13-8-23)37(47)33(53-40)21-50-34(45)15-9-22-5-3-2-4-6-22/h2-20,33,37-43,47-48H,21H2,1H3/b15-9+,16-10+/t33-,37-,38-,39+,40-/m1/s1
SMILES	COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)COC(=O)C=CC5=CC=CC=C5)O)OC(=O)C=CC6=CC=C(C=C6)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	738.19	Volume:	724.664 ? Van der Waals volume.
Dense:	1.019	LogP:	3.579 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.994 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.529 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	40.0
TPSA:	211.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.095	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.451	Fsp³:	0.175
MCE-18:	118.872 ? 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:	1.0	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.986 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.987 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.199	Promiscuous compounds:	0.835

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.021	MDCK Permeability:	-5.232
Pgp-inhibitor:	0.064	Pgp-substrate:	0.051
PAMPA:	0.963 ? 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):	0.247
20% Bioavailability (F20%):	0.959	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.76
Plasma Protein Binding (PPB):	95.673%	Volume Distribution (VD):	-0.045
Fu:	3.892% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.516
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.304
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.925
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

1.951

Half-life (T1/2):

2.42

ADMET: Toxicity

hERG Blockers:	0.17	hERG Blockers (10um):	0.743
Human Hepatotoxicity (H-HT):	0.362	Drug-induced Liver Injury (DILI):	0.862
AMES Toxicity:	0.85	Rat Oral Acute Toxicity:	0.342
Maximum Recommended Daily Dose:	0.955	Skin Sensitization:	0.997
Carcinogencity:	0.173	Eye Corrosion:	0.0
Eye Irritation:	0.043	Respiratory Toxicity:	0.165
Drug-induced Neurotoxicity:	0.217	Ototoxicity:	0.628
Hematotoxicity:	0.004	Drug-induced Nephrotoxicity:	0.3
Genotoxicity:	0.736	RPMI-8226 Immunitoxicity:	0.174
A549 Cytotoxicity:	0.797	Hek293 Cytotoxicity:	0.991
BCF:	1.01 ? 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:	4.339 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.239 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.04 ? 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
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17287127]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6536	Marrubium velutinum	Species	Lamiaceae	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

Activity Type	# Activity
Inhibition	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Inhibition	=	15.59	%	DrugMatrix in vitro pharmacology data

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 NPC471030 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	16784
0.1-0.2	28687
0.2-0.3	3684
0.3-0.4	540
0.4-0.5	130
0.5-0.6	20
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8866	High Similarity	NPC473278
0.7048	Intermediate Similarity	NPC472994
0.699	Remote Similarity	NPC210961
0.6789	Remote Similarity	NPC472993
0.6762	Remote Similarity	NPC270675
0.6762	Remote Similarity	NPC195685
0.6207	Remote Similarity	NPC474093
0.6207	Remote Similarity	NPC104910
0.6071	Remote Similarity	NPC96605
0.6071	Remote Similarity	NPC280642
0.5946	Remote Similarity	NPC479765
0.5806	Remote Similarity	NPC35924
0.5804	Remote Similarity	NPC80068
0.5776	Remote Similarity	NPC480796
0.5526	Remote Similarity	NPC477629
0.5478	Remote Similarity	NPC260504
0.5478	Remote Similarity	NPC89809
0.5476	Remote Similarity	NPC199172
0.5462	Remote Similarity	NPC217520
0.5421	Remote Similarity	NPC311830
0.5373	Remote Similarity	NPC475179
0.5372	Remote Similarity	NPC470716
0.5345	Remote Similarity	NPC101636
0.5299	Remote Similarity	NPC484301
0.5278	Remote Similarity	NPC220169
0.5263	Remote Similarity	NPC137062
0.5175	Remote Similarity	NPC64051
0.5128	Remote Similarity	NPC188815
0.5086	Remote Similarity	NPC139060
0.5046	Remote Similarity	NPC601144

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3785
0.1-0.2	5281
0.2-0.3	77
0.3-0.4	6
0.4-0.5	1
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