NPASS Compound

Natural Product: NPC89809

Natural Product ID	NPC89809
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Apigenin-4'-O-(2'',6''-Di-O-P-Coumaroyl)-Beta-D-Glucoside
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4-dihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL499941
PubChem CID	21721975
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 2D 85 90 0 0 0 0 0 0 0 0999 V2000 -0.4472 -6.8300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7077 -8.3073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4414 -9.2714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 -8.7584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4095 -8.3073 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6700 -9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5209 -10.7487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1114 -10.2356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 -11.7128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6700 -11.7128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0796 -9.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4891 -8.7584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7496 -7.2812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6005 -6.3170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1591 -6.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3082 -7.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7177 -7.2193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8668 -8.1835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2763 -7.6705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5368 -6.1933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3877 -5.2291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9782 -5.7421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.9463 -5.6802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1172 -8.8203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2663 -7.8561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6758 -8.3691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9363 -9.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3458 -10.3594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4949 -9.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2344 -7.9180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8249 -7.4050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9044 -9.9082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1009 -7.4594 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 -6.8300 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4200 -11.0835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7709 -12.0477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6114 -10.2356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4414 -12.2259 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4095 -13.1900 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5665 -7.8619 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5926 -10.6810 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4196 -5.2910 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0477 -9.2096 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6063 -9.6607 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4254 -8.6347 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6482 -3.7519 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8291 -4.7779 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.2068 -4.2030 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3777 -10.2975 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0058 -6.3789 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7872 -10.8105 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6063 -11.8366 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3835 -6.9538 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5644 -5.9277 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0535 -8.9440 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 10 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 21 25 1 0 5 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 41 44 1 0 2 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 50 53 1 0 29 4 1 0 43 38 1 0 52 47 1 0 12 7 1 0 19 13 1 0 23 17 1 0 4 54 1 6 5 55 1 1 8 56 1 0 9 57 1 0 11 58 1 0 12 59 1 0 14 60 1 0 20 61 1 0 22 62 1 0 24 63 1 0 25 64 1 0 27 65 1 1 28 66 1 6 29 67 1 1 30 68 1 0 31 69 1 0 32 70 1 0 32 71 1 0 36 72 1 0 37 73 1 0 39 74 1 0 40 75 1 0 42 76 1 0 43 77 1 0 44 78 1 0 45 79 1 0 46 80 1 0 48 81 1 0 49 82 1 0 51 83 1 0 52 84 1 0 53 85 1 0 M END

Standard InCHIKey	CGRSWPSYXURRMV-IGNRUKHTSA-N
Standard InCHI	InChI=1S/C39H32O14/c40-24-9-1-21(2-10-24)5-15-33(45)49-20-32-36(47)37(48)38(53-34(46)16-6-22-3-11-25(41)12-4-22)39(52-32)50-27-13-7-23(8-14-27)30-19-29(44)35-28(43)17-26(42)18-31(35)51-30/h1-19,32,36-43,47-48H,20H2/b15-5+,16-6+/t32-,36-,37+,38-,39-/m1/s1
SMILES	O=C(O[C@H]1[C@H](Oc2ccc(cc2)c2cc(=O)c3c(o2)cc(cc3O)O)O[C@@H]([C@H]([C@@H]1O)O)COC(=O)/C=C/c1ccc(cc1)O)/C=C/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	724.18	Volume:	707.368 ? Van der Waals volume.
Dense:	1.024	LogP:	3.059 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.548 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.973 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	40.0
TPSA:	222.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.429	Fsp³:	0.154
MCE-18:	119.222 ? 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:	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:	0.949 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.986 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.348	Promiscuous compounds:	0.649

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.307	MDCK Permeability:	-5.181
Pgp-inhibitor:	0.028	Pgp-substrate:	0.014
PAMPA:	0.829 ? 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):	0.012
20% Bioavailability (F20%):	0.993	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	96.361%	Volume Distribution (VD):	-0.193
Fu:	4.714% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.058
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.829
CYP2D6-inhibitor:	0.063	CYP2D6-substrate:	0.987
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.74 ? 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):

2.245

Half-life (T1/2):

2.67

ADMET: Toxicity

hERG Blockers:	0.256	hERG Blockers (10um):	0.678
Human Hepatotoxicity (H-HT):	0.528	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.86	Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.951	Skin Sensitization:	0.99
Carcinogencity:	0.303	Eye Corrosion:	0.0
Eye Irritation:	0.78	Respiratory Toxicity:	0.071
Drug-induced Neurotoxicity:	0.05	Ototoxicity:	0.226
Hematotoxicity:	0.008	Drug-induced Nephrotoxicity:	0.319
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.129
A549 Cytotoxicity:	0.634	Hek293 Cytotoxicity:	0.989
BCF:	0.883 ? 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:	4.499 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.394 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.24 ? 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
NPO29769	Lycopodium cernuum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141856]
NPO29769	Lycopodium cernuum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29769	Lycopodium cernuum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29769	Lycopodium cernuum	Species	Lycopodiaceae	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	1

Activity Type	# Activity
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
NPT2	Others	Unspecified	n.a.	IC50	=	8.4	ug.mL-1	PMID[19884373]

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 NPC89809 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	14324
0.1-0.2	30989
0.2-0.3	3541
0.3-0.4	716
0.4-0.5	218
0.5-0.6	49
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC260504
0.8202	Intermediate Similarity	NPC477628
0.8132	Intermediate Similarity	NPC477629
0.7766	Intermediate Similarity	NPC218161
0.6429	Remote Similarity	NPC472992
0.64	Remote Similarity	NPC270675
0.64	Remote Similarity	NPC195685
0.633	Remote Similarity	NPC162394
0.6226	Remote Similarity	NPC470712
0.6176	Remote Similarity	NPC85751
0.6176	Remote Similarity	NPC19240
0.6078	Remote Similarity	NPC472991
0.6058	Remote Similarity	NPC223426
0.6058	Remote Similarity	NPC472994
0.6	Remote Similarity	NPC96605
0.6	Remote Similarity	NPC280642
0.5981	Remote Similarity	NPC473278
0.5981	Remote Similarity	NPC477895
0.5905	Remote Similarity	NPC483767
0.5905	Remote Similarity	NPC483769
0.5905	Remote Similarity	NPC483768
0.5905	Remote Similarity	NPC483766
0.5833	Remote Similarity	NPC472993
0.5818	Remote Similarity	NPC470718
0.578	Remote Similarity	NPC217520
0.5769	Remote Similarity	NPC221288
0.5769	Remote Similarity	NPC194836
0.5769	Remote Similarity	NPC91493
0.5769	Remote Similarity	NPC605081
0.5702	Remote Similarity	NPC249560
0.5701	Remote Similarity	NPC214621
0.5701	Remote Similarity	NPC34267
0.5673	Remote Similarity	NPC139060
0.5575	Remote Similarity	NPC474093
0.5575	Remote Similarity	NPC104910
0.5556	Remote Similarity	NPC478277
0.5556	Remote Similarity	NPC483765
0.5556	Remote Similarity	NPC478276
0.5556	Remote Similarity	NPC478275
0.5556	Remote Similarity	NPC92815
0.5556	Remote Similarity	NPC81042
0.5526	Remote Similarity	NPC470713
0.5508	Remote Similarity	NPC25946
0.5492	Remote Similarity	NPC487502
0.5478	Remote Similarity	NPC471030
0.5474	Remote Similarity	NPC143851
0.5472	Remote Similarity	NPC479766
0.5426	Remote Similarity	NPC138915
0.5421	Remote Similarity	NPC80068
0.5377	Remote Similarity	NPC210961
0.5377	Remote Similarity	NPC104883
0.5377	Remote Similarity	NPC488679
0.5372	Remote Similarity	NPC473554
0.5333	Remote Similarity	NPC21359
0.5333	Remote Similarity	NPC460984
0.5327	Remote Similarity	NPC101399
0.5327	Remote Similarity	NPC217822
0.5327	Remote Similarity	NPC11847
0.5327	Remote Similarity	NPC198938
0.5263	Remote Similarity	NPC139571
0.525	Remote Similarity	NPC199172
0.5229	Remote Similarity	NPC36138
0.5221	Remote Similarity	NPC470715
0.5185	Remote Similarity	NPC205824
0.504	Remote Similarity	NPC72554

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC89809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3968
0.1-0.2	5095
0.2-0.3	77
0.3-0.4	8
0.4-0.5	2
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