NPASS Compound

Natural Product: NPC490009

Natural Product ID	NPC490009
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6''-Acetyldaidzin
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid 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 55 58 0 0 0 0 0 0 0 0999 V2000 -7.5605 2.1508 -2.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6959 0.9531 -2.2997 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7212 0.2033 -3.3080 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8063 0.6161 -1.2897 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9511 -0.5268 -1.3747 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1436 -0.5771 -0.1283 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2708 -1.6421 -0.0845 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3526 -1.4900 0.9535 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4467 -0.4597 0.7143 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0895 -0.5104 0.5437 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6002 0.6854 0.3130 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9771 0.6713 0.1355 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6912 -0.4997 0.1805 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0323 -1.6926 0.4068 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6494 -1.6573 0.5826 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0526 -0.4650 -0.0007 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7072 -1.5131 0.0376 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7248 0.7082 -0.2264 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9261 1.8496 -0.2569 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6313 1.7938 -0.0818 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1295 0.7911 -0.4189 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6736 1.5660 -1.4306 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0347 1.6604 -1.6349 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9141 0.9680 -0.8165 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2826 1.0425 -0.9964 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3975 0.1879 0.1999 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0330 0.1069 0.3876 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0239 -1.3527 2.2977 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2896 -2.6046 2.8626 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2551 -0.5255 2.2858 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9584 0.8371 2.3346 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1039 -0.7603 1.0466 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4876 -2.0834 1.0557 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1010 2.9362 -1.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5481 1.9062 -1.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7648 2.6045 -3.1548 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3490 -0.4946 -2.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6209 -1.4092 -1.3945 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5607 0.3536 0.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8041 -2.4477 0.9950 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0852 1.6119 0.2709 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5873 -2.5964 0.4411 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1393 -2.5947 0.7594 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4090 2.8168 -0.4336 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0369 2.1316 -2.1042 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4774 2.2565 -2.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7920 1.9131 -0.9169 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0337 -0.3698 0.8636 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5836 -0.4864 1.1642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2814 -0.8636 2.9789 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4882 -3.2100 2.0819 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8648 -0.7690 3.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9844 0.9551 2.1361 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9485 -0.0782 1.0138 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1290 -2.5972 0.2801 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 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 13 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 18 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 24 26 1 0 26 27 2 0 8 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 6 1 0 15 10 1 0 27 21 1 0 20 12 1 0 1 34 1 0 1 35 1 0 1 36 1 0 5 37 1 0 5 38 1 0 6 39 1 0 8 40 1 0 11 41 1 0 14 42 1 0 15 43 1 0 19 44 1 0 22 45 1 0 23 46 1 0 25 47 1 0 26 48 1 0 27 49 1 0 28 50 1 0 29 51 1 0 30 52 1 0 31 53 1 0 32 54 1 0 33 55 1 0 M END

Standard InCHIKey	ZMOZJTDOTOZVRT-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C23H22O10/c1-11(24)30-10-18-20(27)21(28)22(29)23(33-18)32-14-6-7-15-17(8-14)31-9-16(19(15)26)12-2-4-13(25)5-3-12/h2-9,18,20-23,25,27-29H,10H2,1H3
SMILES	CC(=O)OCC1OC(OC2=CC3=C(C=C2)C(=O)C(=CO3)C2=CC=C(O)C=C2)C(O)C(O)C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	458.12	Volume:	436.312 ? Van der Waals volume.
Dense:	1.05	LogP:	0.137 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.95 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.566 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	25.0
TPSA:	155.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.405	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.749	Fsp³:	0.304
MCE-18:	83.333 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.232	Fluc inhibitor:	0.169 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.942 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.846 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.086	Promiscuous compounds:	0.312

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.108	MDCK Permeability:	-5.16
Pgp-inhibitor:	0.001	Pgp-substrate:	0.256
PAMPA:	0.999 ? 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):	0.871
20% Bioavailability (F20%):	0.891	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.472
Plasma Protein Binding (PPB):	74.613%	Volume Distribution (VD):	-0.209
Fu:	27.773% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.674
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.044
BSEP inhibitor:	0.697

ADMET: Metabolism

CYP1A2-inhibitor:	0.009	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.66	CYP2C9-substrate:	0.665
CYP2D6-inhibitor:	0.493	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.478
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):

2.66

Half-life (T1/2):

1.842

ADMET: Toxicity

hERG Blockers:	0.138	hERG Blockers (10um):	0.488
Human Hepatotoxicity (H-HT):	0.462	Drug-induced Liver Injury (DILI):	0.789
AMES Toxicity:	0.765	Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.452	Skin Sensitization:	0.128
Carcinogencity:	0.609	Eye Corrosion:	0.0
Eye Irritation:	0.184	Respiratory Toxicity:	0.047
Drug-induced Neurotoxicity:	0.289	Ototoxicity:	0.783
Hematotoxicity:	0.085	Drug-induced Nephrotoxicity:	0.165
Genotoxicity:	0.686	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.068	Hek293 Cytotoxicity:	0.608
BCF:	0.57 ? 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:	3.274 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.921 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.161 ? 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
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	WrocÃ…â€šaw, Poland	2004Ã¢â‚¬â€œ2005	DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003Ã¢â‚¬â€œ2005	DOI[10.1016/j.jfca.2006.05.007]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0021-9258(18)90865-3]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(02)00136-X]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(02)00136-X]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf950732o]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1023/A:1024390522259]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775096]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[1622242]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16659156]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16668466]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20963508]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	Tekirdag, Turkey		PMID[24499198]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25053043]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070365]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Hypocotyl	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7635	Glycine max	Species	Fabaceae	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
NPO7635	Glycine max	Cooked	n.a.	38.26000134	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7635	Glycine max	Dried Or Powder	n.a.	5.346666733	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7635	Glycine max	n.a.	n.a.	1.383750021	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7635	Glycine max	n.a.	n.a.	0.534999996	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7635	Glycine max	n.a.	n.a.	34.13999939	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

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

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

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 NPC490009 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	13065
0.1-0.2	32352
0.2-0.3	3420
0.3-0.4	784
0.4-0.5	198
0.5-0.6	22
0.6-0.7	13
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8108	Intermediate Similarity	NPC211014
0.7763	Intermediate Similarity	NPC161749
0.7079	Intermediate Similarity	NPC231194
0.6883	Remote Similarity	NPC25547
0.6854	Remote Similarity	NPC51326
0.6591	Remote Similarity	NPC303913
0.6548	Remote Similarity	NPC43761
0.6452	Remote Similarity	NPC235575
0.642	Remote Similarity	NPC45165
0.6404	Remote Similarity	NPC479405
0.6341	Remote Similarity	NPC259070
0.6333	Remote Similarity	NPC479404
0.6163	Remote Similarity	NPC229729
0.6145	Remote Similarity	NPC348541
0.6071	Remote Similarity	NPC105511
0.6027	Remote Similarity	NPC181124
0.5882	Remote Similarity	NPC197896
0.5882	Remote Similarity	NPC258035
0.5882	Remote Similarity	NPC313163
0.5795	Remote Similarity	NPC226722
0.5795	Remote Similarity	NPC601607
0.5778	Remote Similarity	NPC172807
0.5747	Remote Similarity	NPC100720
0.5568	Remote Similarity	NPC205076
0.5529	Remote Similarity	NPC487214
0.5479	Remote Similarity	NPC192229
0.5465	Remote Similarity	NPC160515
0.5435	Remote Similarity	NPC211594
0.5435	Remote Similarity	NPC477848
0.5368	Remote Similarity	NPC475155
0.5361	Remote Similarity	NPC479403
0.5326	Remote Similarity	NPC53587
0.5287	Remote Similarity	NPC135345
0.5281	Remote Similarity	NPC73511
0.5213	Remote Similarity	NPC254540
0.5102	Remote Similarity	NPC64051
0.51	Remote Similarity	NPC270675
0.51	Remote Similarity	NPC195685

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC490009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3748
0.1-0.2	5286
0.2-0.3	102
0.3-0.4	5
0.4-0.5	7
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7763	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.5465	Remote Similarity	NPD3818	Discontinued

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