NPASS Compound

Natural Product: NPC490398

Natural Product ID	NPC490398
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6''-Malonyldaidzin
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 58 61 0 0 0 0 0 0 0 0999 V2000 -4.3668 -4.2680 -0.5805 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4393 -3.3609 -1.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0645 -2.1389 -1.6781 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2824 -2.5868 -2.2385 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3494 -1.0549 -0.6766 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6800 0.2244 -1.4099 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0740 1.2659 -0.5597 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1533 1.2437 0.2871 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8684 0.2054 0.3206 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5494 2.3641 1.1794 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6290 3.5174 1.0379 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8218 4.6535 1.7757 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6774 3.4339 0.2358 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3193 -0.8008 0.1914 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1539 -1.4882 -0.1735 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1152 -1.1751 0.6937 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1531 -0.7773 0.3560 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0379 -0.5136 1.4133 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3224 -0.1112 1.1190 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7540 0.0367 -0.1810 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8750 -0.2255 -1.2050 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5608 -0.6367 -0.9475 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0666 0.4475 -0.4360 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4519 0.5797 -1.6048 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9245 0.7031 0.6131 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4146 0.5311 1.8831 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1757 0.1437 2.0911 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3145 1.1372 0.4025 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6347 2.1097 -0.5113 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9477 2.4979 -0.6881 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9429 1.8916 0.0708 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2770 2.2551 -0.0782 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6101 0.9176 0.9840 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3044 0.5545 1.1372 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4927 -2.9675 0.0809 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1333 -3.0914 1.3254 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1969 -5.1650 -0.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8313 -3.8549 -1.8323 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4533 -1.7919 -2.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8993 -2.7067 -1.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2191 -1.4033 -0.0672 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4431 0.0188 -2.2097 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7702 0.5481 -1.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5845 2.7247 0.9727 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5734 1.9639 2.2177 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1611 5.4279 1.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9308 -1.4042 -1.2344 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6871 -0.6336 2.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2213 -0.1069 -2.2186 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1106 -0.8365 -1.7865 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0732 0.7268 2.7363 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8608 2.5918 -1.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2715 3.2504 -1.3831 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9841 1.5295 0.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4194 0.4570 1.5692 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0515 -0.2114 1.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5868 -3.5744 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4058 -3.0669 2.0244 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 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 11 13 2 0 5 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 25 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 31 33 1 0 33 34 2 0 15 35 1 0 35 36 1 0 35 2 1 0 22 17 1 0 34 28 1 0 27 19 1 0 1 37 1 0 2 38 1 0 3 39 1 0 4 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 10 44 1 0 10 45 1 0 12 46 1 0 15 47 1 0 18 48 1 0 21 49 1 0 22 50 1 0 26 51 1 0 29 52 1 0 30 53 1 0 32 54 1 0 33 55 1 0 34 56 1 0 35 57 1 0 36 58 1 0 M END

Standard InCHIKey	MTXMHWSVSZKYBT-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C24H22O12/c25-12-3-1-11(2-4-12)15-9-33-16-7-13(5-6-14(16)20(15)29)35-24-23(32)22(31)21(30)17(36-24)10-34-19(28)8-18(26)27/h1-7,9,17,21-25,30-32H,8,10H2,(H,26,27)
SMILES	OC1C(O)C(COC(=O)CC(O)=O)OC(OC2=CC3=C(C=C2)C(=O)C(=CO3)C2=CC=C(O)C=C2)C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	502.11	Volume:	468.552 ? Van der Waals volume.
Dense:	1.072	LogP:	-0.688 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.922 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.28 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	26.0
TPSA:	193.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.22	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.897	Fsp³:	0.292
MCE-18:	86.387 ? 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:	0.15	Fluc inhibitor:	0.187 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.951 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.809 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.105	Promiscuous compounds:	0.053

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.198	MDCK Permeability:	-5.15
Pgp-inhibitor:	0.0	Pgp-substrate:	0.016
PAMPA:	1.0 ? 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):	0.268
20% Bioavailability (F20%):	0.117	30% Bioavailability (F30%):	0.248
50% Bioavailability (F50%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.715
Plasma Protein Binding (PPB):	70.22%	Volume Distribution (VD):	-0.267
Fu:	27.845% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.441
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.002
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.115	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.089
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
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):

1.474

Half-life (T1/2):

2.056

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.104
Human Hepatotoxicity (H-HT):	0.423	Drug-induced Liver Injury (DILI):	0.893
AMES Toxicity:	0.403	Rat Oral Acute Toxicity:	0.384
Maximum Recommended Daily Dose:	0.417	Skin Sensitization:	0.14
Carcinogencity:	0.407	Eye Corrosion:	0.0
Eye Irritation:	0.116	Respiratory Toxicity:	0.078
Drug-induced Neurotoxicity:	0.096	Ototoxicity:	0.898
Hematotoxicity:	0.122	Drug-induced Nephrotoxicity:	0.453
Genotoxicity:	0.81	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.004	Hek293 Cytotoxicity:	0.221
BCF:	0.279 ? 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:	2.881 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.468 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.652 ? 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.	5.339999994	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7635	Glycine max	Dried Or Powder	n.a.	100.6033306	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7635	Glycine max	Raw	n.a.	10.7338891	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7635	Glycine max	Raw	n.a.	4.64307697	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7635	Glycine max	n.a.	n.a.	1.465000004	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 NPC490398 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	15726
0.1-0.2	30635
0.2-0.3	2684
0.3-0.4	666
0.4-0.5	120
0.5-0.6	21
0.6-0.7	4
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	Natural Product ID
0.7108	Intermediate Similarity	NPC211014
0.7024	Intermediate Similarity	NPC161749
0.6495	Remote Similarity	NPC231194
0.6421	Remote Similarity	NPC64051
0.6289	Remote Similarity	NPC51326
0.6047	Remote Similarity	NPC25547
0.5941	Remote Similarity	NPC235575
0.5918	Remote Similarity	NPC46202
0.5876	Remote Similarity	NPC479405
0.5876	Remote Similarity	NPC303913
0.5843	Remote Similarity	NPC45165
0.5816	Remote Similarity	NPC479404
0.58	Remote Similarity	NPC229409
0.5638	Remote Similarity	NPC229729
0.5604	Remote Similarity	NPC259070
0.5543	Remote Similarity	NPC105511
0.5543	Remote Similarity	NPC258035
0.5474	Remote Similarity	NPC43761
0.5435	Remote Similarity	NPC348541
0.5432	Remote Similarity	NPC181124
0.5376	Remote Similarity	NPC197896
0.5376	Remote Similarity	NPC313163
0.5312	Remote Similarity	NPC601607
0.5312	Remote Similarity	NPC610187
0.5263	Remote Similarity	NPC100720
0.5185	Remote Similarity	NPC121703
0.5104	Remote Similarity	NPC205076

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC490398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3314
0.1-0.2	5698
0.2-0.3	125
0.3-0.4	9
0.4-0.5	2
0.5-0.6	0
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
0.7024	Intermediate Similarity	NPD4381	Clinical (unspecified phase)

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