Natural Product: NPC215875

Natural Product IDNPC215875
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Mallotojaponin
IUPAC Name 1-[3-[[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-2,6-dihydroxy-4-methoxy-5-methylphenyl]ethanone
Synonyms Mallotojaponin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL487405
PubChem CID 122659
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000369] Diphenylmethanes

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey GEWBQPFQVFANET-UHFFFAOYSA-N
Standard InCHI InChI=1S/C24H28O8/c1-10(2)7-8-14-20(28)15(22(30)18(13(5)26)21(14)29)9-16-23(31)17(12(4)25)19(27)11(3)24(16)32-6/h7,27-31H,8-9H2,1-6H3
SMILES COc1c(Cc2c(O)c(CC=C(C)C)c(c(c2O)C(=O)C)O)c(O)c(c(c1C)O)C(=O)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   444.18 Volume:   453.141
?
Van der Waals volume.
Dense:   0.98 LogP:   2.613
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.669
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.161
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   7.0 Rigid Bonds:   15.0
TPSA:   144.52
?
Topological Polar Surface Area.
 H-Bond Acceptor:   8.0
H-Bond Donor:   5.0 Rings:   2.0
Heavy Atoms:   8.0

MedChem Properties

QED Drug-Likeness Score:   0.318 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.212 Fsp3:   0.333
MCE-18:   21.0
?
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:   1
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.39 Fluc inhibitor:   0.075
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.707
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.35
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.641 Promiscuous compounds:   0.203

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.22 MDCK Permeability:   -4.877
Pgp-inhibitor:   0.06 Pgp-substrate:   0.006
PAMPA:   0.941
?
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):   0.257
20% Bioavailability (F20%):   0.497 30% Bioavailability (F30%):   0.761
50% Bioavailability (F50%):   0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.002 MRP1:   0.989
Plasma Protein Binding (PPB):   95.947% Volume Distribution (VD):   0.04
Fu: 5.608%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.998
OATP1B3 inhibitor:   0.994 BCRP inhibitor:   0.024
BSEP inhibitor:   0.142

ADMET: Metabolism

CYP1A2-inhibitor:   0.389 CYP1A2-substrate:   0.059
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.924
CYP2C9-inhibitor:   0.177 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.0
CYP3A4-inhibitor:   1.0 CYP3A4-substrate:   0.008
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   1.0
?
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):  1.962 Half-life (T1/2):  1.442

ADMET: Toxicity

hERG Blockers:  0.016 hERG Blockers (10um):  0.504
Human Hepatotoxicity (H-HT):  0.55 Drug-induced Liver Injury (DILI):  0.326
AMES Toxicity:  0.545 Rat Oral Acute Toxicity:  0.373
Maximum Recommended Daily Dose:  0.403 Skin Sensitization:  0.886
Carcinogencity:  0.177 Eye Corrosion:  0.0
Eye Irritation:  0.848 Respiratory Toxicity:  0.977
Drug-induced Neurotoxicity:  0.078 Ototoxicity:  0.365
Hematotoxicity:  0.301 Drug-induced Nephrotoxicity:  0.445
Genotoxicity:  0.832 RPMI-8226 Immunitoxicity:  0.243
A549 Cytotoxicity:  0.691 Hek293 Cytotoxicity:  0.622
BCF:   1.573
?
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:   4.633
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   6.087
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.582
?
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
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10757709]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. leaf n.a. PMID[10830513]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. twig n.a. PMID[10830513]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. PMID[10830513]
NPO26880 Mallotus japonicus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[12193039]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. leaf n.a. PMID[17685627]
NPO26880 Mallotus japonicus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[1800639]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota rhizomes n.a. n.a. PMID[21353549]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21510636]
NPO25715 Senna siamea Species Fabaceae Eukaryota Stems n.a. n.a. PMID[23078294]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[23210623]
NPO26880 Mallotus japonicus Species Euphorbiaceae Eukaryota n.a. pericarp n.a. PMID[2347013]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23513740]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[30379546]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[31596079]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[32092041]
NPO26880 Mallotus japonicus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[3210017]
NPO26880 Mallotus japonicus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[3734813]
NPO26880 Mallotus japonicus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[4040956]
NPO26880 Mallotus japonicus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14615 Streptomyces paulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO6179 Aframomum amaniense Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14504 Alectoria divergens Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14200 Aristolochia zollingeriana Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3199 Balanophora involucrata Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1661 Bartramia pomiformis Species Bartramiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7752 Beilschmiedia anacardioides Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13076 Cephalaria grossheimii Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12754 Cerinthe minor Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21498 Coccus ilicis Species Coccidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12585 Craspidospermum verticillatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9669 Dictyopteris acrostichoides Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12069 Isaria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12910 Ixeris stolonifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12061 Justicia paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12234 Khaya ivorensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10389 Larix cajanderi Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3458 Lupinus verbasciformis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13701 Melaleuca rhaphiophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7169 Nama hispidum Species Namaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12414 Penicillium paxilli Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14289 Pieris napi Species Pieridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10865 Sextonia rubra Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10012 Triaenophora rupestris Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26880 Mallotus japonicus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26880 Mallotus japonicus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3199 Balanophora involucrata Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21498 Coccus ilicis Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9669 Dictyopteris acrostichoides Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3199 Balanophora involucrata Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13701 Melaleuca rhaphiophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12069 Isaria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1661 Bartramia pomiformis Species Bartramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12910 Ixeris stolonifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14200 Aristolochia zollingeriana Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14504 Alectoria divergens Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12754 Cerinthe minor Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14289 Pieris napi Species Pieridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10012 Triaenophora rupestris Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7169 Nama hispidum Species Namaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7752 Beilschmiedia anacardioides Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12414 Penicillium paxilli Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10389 Larix cajanderi Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10865 Sextonia rubra Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3458 Lupinus verbasciformis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14615 Streptomyces paulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12234 Khaya ivorensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13076 Cephalaria grossheimii Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12061 Justicia paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12585 Craspidospermum verticillatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6179 Aframomum amaniense Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26880 Mallotus japonicus Species Euphorbiaceae 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

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
NPT91 Cell line KB Homo sapiens ED50 = 0.58 ug ml-1 PMID[3734813]
NPT1864 Cell line L5178Y Mus musculus ED50 = 0.74 ug ml-1 PMID[3734813]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 100.0 % PMID[1800639]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 85.8 % PMID[1800639]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Activity = 0.59 g PMID[3734813]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Activity = 0.93 g PMID[3734813]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. T/C = 49.5 % PMID[3734813]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. T/C = 78.1 % PMID[3734813]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. MST = 14.0 day PMID[3734813]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. MST = 20.0 day PMID[3734813]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. ID50 = 1.0 ug ml-1 PMID[1800639]
NPT2 Others Unspecified n.a. Inhibition = 90.0 % PMID[20137956]

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
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 NPC215875 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.717 Intermediate Similarity NPC483796
0.7 Intermediate Similarity NPC15834
0.6444 Remote Similarity NPC186628
0.6333 Remote Similarity NPC483785
0.6 Remote Similarity NPC16197
0.5667 Remote Similarity NPC483787
0.55 Remote Similarity NPC248995
0.541 Remote Similarity NPC483786
0.5192 Remote Similarity NPC279566
0.5172 Remote Similarity NPC254168
0.5156 Remote Similarity NPC240305
0.5156 Remote Similarity NPC470981
0.5143 Remote Similarity NPC228779
0.5143 Remote Similarity NPC483811
0.5094 Remote Similarity NPC479738
0.5085 Remote Similarity NPC112749

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC215875 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  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