NPASS Compound

Natural Product: NPC298171

Natural Product ID	NPC298171
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Apigenin 7-O-Alpha-L-2,3-Di-O-Acetylrhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	[(2S,3S,4R,5R,6R)-5-acetyloxy-3-hydroxy-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]oxan-4-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451831
PubChem CID	11787166
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 81 85 0 0 0 0 0 0 0 0999 V2000 -0.3281 0.1985 3.5936 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0070 0.1919 2.9357 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9988 -0.3183 3.5176 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2239 0.7341 1.6759 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4945 0.7290 1.0401 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3981 -0.1455 -0.1820 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4822 -0.9475 -0.3675 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3991 -2.2583 -0.5261 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8754 -3.0849 0.6591 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6415 -2.7017 0.9838 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5640 -3.5096 0.9315 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5594 -2.9319 0.6137 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7039 -2.4358 0.3136 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8661 -3.2346 0.1914 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0697 -2.7145 -0.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2347 -3.4961 -0.2445 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1787 -1.3551 -0.3257 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0932 -0.5187 -0.2224 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8744 -1.0580 0.0925 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1990 0.7943 -0.4180 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3422 1.3689 -0.7210 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4603 0.5801 -0.8401 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3969 -0.7775 -0.6465 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3963 -1.5416 -0.7455 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3471 2.8201 -0.9074 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4666 3.5065 -1.2844 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4620 4.8965 -1.4336 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3279 5.6060 -1.2040 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1930 4.9236 -0.8232 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1950 3.5665 -0.6770 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2297 6.9920 -1.3287 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8540 -4.6376 -0.1225 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0185 -5.4194 0.4701 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2047 -4.5250 0.4150 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2083 -4.9447 1.3073 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2169 -6.5393 -0.3230 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2757 -5.3898 -0.2463 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2397 0.6899 -1.3424 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5197 1.2129 -1.6271 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0796 1.9004 -0.4101 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9772 2.0773 0.6544 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9420 2.7826 -0.0214 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6610 4.1046 0.3587 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3595 4.5873 1.2908 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 4.8565 -0.3286 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0316 1.0632 0.1614 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3669 2.2063 -2.7358 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7592 -0.7925 3.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0555 0.8145 2.9919 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1932 0.6515 4.5974 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2641 0.2505 1.6918 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4737 -0.7204 -0.1549 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8409 -2.6026 -1.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4499 -2.6580 -0.7036 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5563 -2.7918 1.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4694 -4.2060 1.8615 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7748 -4.3073 0.3560 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4890 -3.7078 -1.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9952 -0.3996 0.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4007 1.0420 -1.0904 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3907 2.9944 -1.4863 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3690 5.3858 -1.7329 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2481 5.4568 -0.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3014 3.0408 -0.3793 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7954 7.5622 -0.7185 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1795 -4.1338 -1.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7815 -5.7564 1.5109 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6045 -4.6193 -0.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8588 -5.7092 1.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1925 -6.2656 -1.2774 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0920 -6.3642 -0.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1601 0.3896 -1.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5696 2.8555 -0.6439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4254 2.6875 1.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2147 4.1835 -0.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1638 5.6506 0.3250 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0026 5.3883 -1.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9596 1.3286 -0.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3761 1.7120 -3.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4106 2.7749 -2.6082 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1849 2.9619 -2.6872 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 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 15 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 21 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 28 31 1 0 11 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 6 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 40 46 1 0 39 47 1 0 41 5 1 0 34 9 1 0 19 13 1 0 30 25 1 0 23 17 1 0 1 48 1 0 1 49 1 0 1 50 1 0 5 51 1 1 6 52 1 1 8 53 1 0 8 54 1 0 9 55 1 1 11 56 1 1 14 57 1 0 16 58 1 0 19 59 1 0 22 60 1 0 26 61 1 0 27 62 1 0 29 63 1 0 30 64 1 0 31 65 1 0 32 66 1 6 33 67 1 1 34 68 1 6 35 69 1 0 36 70 1 0 37 71 1 0 39 72 1 6 40 73 1 6 41 74 1 1 45 75 1 0 45 76 1 0 45 77 1 0 46 78 1 0 47 79 1 0 47 80 1 0 47 81 1 0 M END

Standard InCHIKey	YSOYXQCUOHSLOS-XHDIWSJJSA-N
Standard InCHI	InChI=1S/C31H34O16/c1-12-24(37)28(43-13(2)32)29(44-14(3)33)31(42-12)41-11-22-25(38)26(39)27(40)30(47-22)45-17-8-18(35)23-19(36)10-20(46-21(23)9-17)15-4-6-16(34)7-5-15/h4-10,12,22,24-31,34-35,37-40H,11H2,1-3H3/t12-,22+,24-,25+,26-,27+,28+,29+,30+,31+/m0/s1
SMILES	CC(=O)O[C@H]1[C@H](OC[C@H]2O[C@@H](Oc3cc(O)c4c(c3)oc(cc4=O)c3ccc(cc3)O)[C@@H]([C@H]([C@@H]2O)O)O)O[C@H]([C@@H]([C@H]1OC(=O)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	662.18	Volume:	616.229 ? Van der Waals volume.
Dense:	1.075	LogP:	0.975 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.439 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.428 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	32.0
TPSA:	241.11 ? 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:	0.175	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.804	Fsp³:	0.452
MCE-18:	120.556 ? 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:	0.693	Fluc inhibitor:	0.42 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.922 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.612 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.087	Promiscuous compounds:	0.37

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.212	MDCK Permeability:	-5.075
Pgp-inhibitor:	0.001	Pgp-substrate:	0.889
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):	0.552
20% Bioavailability (F20%):	0.713	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.614
Plasma Protein Binding (PPB):	80.705%	Volume Distribution (VD):	-0.042
Fu:	18.75% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.373
BSEP inhibitor:	0.044

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.009	CYP2C9-substrate:	0.238
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.977
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.315 ? 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):

1.926

Half-life (T1/2):

3.546

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.211
Human Hepatotoxicity (H-HT):	0.456	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.828	Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.098	Skin Sensitization:	0.884
Carcinogencity:	0.112	Eye Corrosion:	0.0
Eye Irritation:	0.468	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.728
Hematotoxicity:	0.062	Drug-induced Nephrotoxicity:	0.521
Genotoxicity:	0.883	RPMI-8226 Immunitoxicity:	0.118
A549 Cytotoxicity:	0.263	Hek293 Cytotoxicity:	0.426
BCF:	0.514 ? 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:	3.252 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.643 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.929 ? 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
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880314]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1294695]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104516]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	leaves and twigs	Taiwan	n.a.	PMID[1659612]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	aerial parts	Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China	2012-OCT	PMID[24955889]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	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
Activity	1

Activity Type	# Activity
Cell line	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
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	14.9	%	PubChem BioAssay data set

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 NPC298171 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	18188
0.1-0.2	28129
0.2-0.3	2614
0.3-0.4	584
0.4-0.5	244
0.5-0.6	68
0.6-0.7	26
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
0.7849	Intermediate Similarity	NPC101636
0.7556	Intermediate Similarity	NPC44931
0.6977	Remote Similarity	NPC331652
0.6947	Remote Similarity	NPC64051
0.6907	Remote Similarity	NPC488089
0.6737	Remote Similarity	NPC22062
0.6737	Remote Similarity	NPC473634
0.6737	Remote Similarity	NPC210073
0.6737	Remote Similarity	NPC138811
0.6735	Remote Similarity	NPC270675
0.6735	Remote Similarity	NPC195685
0.6667	Remote Similarity	NPC27942
0.6535	Remote Similarity	NPC472994
0.6517	Remote Similarity	NPC39360
0.6517	Remote Similarity	NPC29763
0.6517	Remote Similarity	NPC210003
0.6471	Remote Similarity	NPC470455
0.6316	Remote Similarity	NPC172807
0.63	Remote Similarity	NPC473623
0.63	Remote Similarity	NPC209296
0.63	Remote Similarity	NPC229409
0.6286	Remote Similarity	NPC472993
0.62	Remote Similarity	NPC65711
0.6154	Remote Similarity	NPC19709
0.61	Remote Similarity	NPC46202
0.6058	Remote Similarity	NPC179862
0.6042	Remote Similarity	NPC190003
0.6	Remote Similarity	NPC186816
0.5946	Remote Similarity	NPC298666
0.5851	Remote Similarity	NPC181712
0.5826	Remote Similarity	NPC262222
0.5745	Remote Similarity	NPC95090
0.5745	Remote Similarity	NPC27408
0.5745	Remote Similarity	NPC189142
0.5745	Remote Similarity	NPC77660
0.5714	Remote Similarity	NPC488086
0.5699	Remote Similarity	NPC473043
0.5676	Remote Similarity	NPC488087
0.5657	Remote Similarity	NPC211594
0.5648	Remote Similarity	NPC11468
0.5644	Remote Similarity	NPC67105
0.5638	Remote Similarity	NPC108831
0.5638	Remote Similarity	NPC182634
0.56	Remote Similarity	NPC254540
0.5588	Remote Similarity	NPC473512
0.5588	Remote Similarity	NPC65003
0.5588	Remote Similarity	NPC129827
0.5566	Remote Similarity	NPC80068
0.5536	Remote Similarity	NPC488083
0.5534	Remote Similarity	NPC204693
0.551	Remote Similarity	NPC601144
0.5474	Remote Similarity	NPC261866
0.5474	Remote Similarity	NPC249281
0.5455	Remote Similarity	NPC311830
0.5408	Remote Similarity	NPC282169
0.5405	Remote Similarity	NPC473278
0.54	Remote Similarity	NPC276377
0.5361	Remote Similarity	NPC46420
0.5354	Remote Similarity	NPC22832
0.5354	Remote Similarity	NPC243930
0.5351	Remote Similarity	NPC488088
0.5321	Remote Similarity	NPC135358
0.531	Remote Similarity	NPC311850
0.5304	Remote Similarity	NPC68592
0.53	Remote Similarity	NPC220169
0.53	Remote Similarity	NPC607707
0.5288	Remote Similarity	NPC303913
0.5278	Remote Similarity	NPC470447
0.5278	Remote Similarity	NPC475382
0.5278	Remote Similarity	NPC479765
0.5278	Remote Similarity	NPC477629
0.5258	Remote Similarity	NPC146792
0.5258	Remote Similarity	NPC323593
0.5258	Remote Similarity	NPC203500
0.5238	Remote Similarity	NPC122809
0.5234	Remote Similarity	NPC210961
0.5234	Remote Similarity	NPC72016
0.5225	Remote Similarity	NPC121703
0.5221	Remote Similarity	NPC473644
0.52	Remote Similarity	NPC80188
0.5196	Remote Similarity	NPC477848
0.5192	Remote Similarity	NPC227508
0.5189	Remote Similarity	NPC64425
0.5185	Remote Similarity	NPC479766
0.5176	Remote Similarity	NPC234133
0.5155	Remote Similarity	NPC238376
0.5149	Remote Similarity	NPC116458
0.5149	Remote Similarity	NPC246943
0.5143	Remote Similarity	NPC150164
0.5138	Remote Similarity	NPC188815
0.5133	Remote Similarity	NPC480796
0.5102	Remote Similarity	NPC93337
0.5102	Remote Similarity	NPC297987
0.5093	Remote Similarity	NPC483707
0.5088	Remote Similarity	NPC25523
0.5051	Remote Similarity	NPC105025

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC298171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5083
0.1-0.2	4001
0.2-0.3	56
0.3-0.4	5
0.4-0.5	3
0.5-0.6	1
0.6-0.7	1
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
0.63	Remote Similarity	NPD7054	Phase 4
0.5138	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