Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2021-06-22 17:26:44 UTC
Updated at2021-08-20 00:00:46 UTC
NP-MRD IDNP0043870
Secondary Accession NumbersNone
Natural Product Identification
Common NameEsculin
DescriptionAesculin, also known as esculoside or venoplant, belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Aesculin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Esculin is found in Actinidia chinensis, Afraegle paniculata, Althaea officinalis, Arabidopsis thaliana, Artemisia absinthium, Artemisia jacutica, Artemisia tridentata, Artemisia vulgaris, Cistus creticus, Crataegus monogyna, Cynara cornigera, Fraxinus angustifolia, Fraxinus chinensis, Fraxinus floribunda, Fraxinus insularis, Gundelia tournefortii, Hordeum vulgare, Hydrophyllum tenuipes, Ixeridium laevigatum, Koelpinia linearis, Lithospermum erythrorhizon, Lupinus angustifolius, Manihot esculenta, Morus alba, Myrtus communis, Ocimum tenuiflorum, Olea europaea, Ostericum grosseserratum, Peucedanum japonicum, Phaseolus vulgaris, Rhododendron groenlandicum, Solanum aethiopicum, Taraxacum officinale and Vitis vinifera. It was first documented in 2013 (PMID: 22564167). Based on a literature review a significant number of articles have been published on Aesculin (PMID: 23497098) (PMID: 23499166) (PMID: 34315523) (PMID: 34059101).
Structure
Thumb
Synonyms
ValueSource
6,7-Dihydroxycoumarin 6-glucosideChEBI
6,7-Dihydroxycoumarin-6-O-glucosideChEBI
6-(beta-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-oneChEBI
6-(beta-D-Glucopyranosyloxy)-7-hydroxy-cumarinChEBI
7-Hydroxy-6-glucosyloxy-2H-chromeneChEBI
Esculetin 6-beta-D-glucosideChEBI
Esculetin 6-O-glucosideChEBI
EsculosideChEBI
6-(b-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-oneGenerator
6-(Β-D-glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-oneGenerator
6-(b-D-Glucopyranosyloxy)-7-hydroxy-cumarinGenerator
6-(Β-D-glucopyranosyloxy)-7-hydroxy-cumarinGenerator
Esculetin 6-b-D-glucosideGenerator
Esculetin 6-β-D-glucosideGenerator
VenoplantHMDB
(-)-EsculinHMDB
6-(beta-D-Glucopyranosyloxy)-7-hydroxycoumarinHMDB
6-(Β-D-glucopyranosyloxy)-7-hydroxycoumarinHMDB
EsculinHMDB
EsculineHMDB
AesculinChEBI, MeSH
Chemical FormulaC15H16O9
Average Mass340.2840 Da
Monoisotopic Mass340.07943 Da
IUPAC Name7-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
Traditional Name(-)-esculin
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=C(O)C=C3OC(=O)C=CC3=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1
InChI KeyXHCADAYNFIFUHF-TVKJYDDYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Actinidia chinensisLOTUS Database
Aesculus hippocastanumKNApSAcK Database
Afraegle paniculataLOTUS Database
Althaea officinalisLOTUS Database
Arabidopsis thalianaLOTUS Database
Artemisia absinthiumLOTUS Database
Artemisia jacuticaLOTUS Database
Artemisia tridentataLOTUS Database
Artemisia vulgarisLOTUS Database
Bursaria spinosaKNApSAcK Database
Cichorium intybusKNApSAcK Database
Cistus creticusLOTUS Database
Crataegus monogynaLOTUS Database
Crataegus oxyacanthaKNApSAcK Database
Cynara cornigeraLOTUS Database
Datura stramoniumKNApSAcK Database
Euphorbia lathyrisKNApSAcK Database
Ficus septicaKNApSAcK Database
Fraxinus angustifoliaLOTUS Database
Fraxinus bungeanaKNApSAcK Database
Fraxinus chinensisLOTUS Database
Fraxinus floribundaLOTUS Database
Fraxinus insularisLOTUS Database
Fraxinus mandshuricaKNApSAcK Database
Fraxinus ornusKNApSAcK Database
Fraxinus paxianaKNApSAcK Database
Fraxinus rhynchophyllaKNApSAcK Database
Fraxinus spp.KNApSAcK Database
Fraxinus stylosaKNApSAcK Database
Fraxinus szaboanaKNApSAcK Database
Gundelia tournefortiiLOTUS Database
Hordeum vulgareLOTUS Database
Hydrophyllum tenuipesLOTUS Database
Hymenodictyon excelsumKNApSAcK Database
Ixeridium laevigatumLOTUS Database
Koelpinia linearisLOTUS Database
Lithospermum erythrorhizonLOTUS Database
Lupinus angustifoliusLOTUS Database
Manihot esculentaLOTUS Database
Melilotus suaveolensKNApSAcK Database
Morus albaLOTUS Database
Myrtus communisLOTUS Database
Ocimum tenuiflorumLOTUS Database
Olea europaeaLOTUS Database
Ostericum grosseserratumLOTUS Database
Peucedanum japonicumLOTUS Database
Phaseolus vulgarisLOTUS Database
Rhododendron groenlandicumLOTUS Database
Solanum aethiopicumLOTUS Database
Taraxacum officinaleLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassCoumarin glycosides
Direct ParentCoumarin glycosides
Alternative Parents
Substituents
  • Coumarin o-glycoside
  • Coumarin-6-o-glycoside
  • Phenolic glycoside
  • 7-hydroxycoumarin
  • Hydroxycoumarin
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point205.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point697.65 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility206000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-1.307 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP-0.53ALOGPS
logP-1.1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.12ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.65 m³·mol⁻¹ChemAxon
Polarizability31.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0030820
DrugBank IDDB13155
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002776
KNApSAcK IDC00002472
Chemspider ID4444765
KEGG Compound IDC09264
BioCyc ID14461
BiGG IDNot Available
Wikipedia LinkAesculin
METLIN IDNot Available
PubChem Compound5281417
PDB IDNot Available
ChEBI ID4853
Good Scents IDrw1242871
References
General References
  1. Ohadi R MS, Alvari A, Samim M, Abdin MZ: Plant bio-transformable HMG-CoA reductase gene loaded calcium phosphate nanoparticle: in vitro characterization and stability study. Curr Drug Discov Technol. 2013 Mar;10(1):25-34. doi: 10.2174/1570163811310010005. [PubMed:22564167 ]
  2. Pandey S, Sree A, Dash SS, Sethi DP: A novel method for screening beta-glucosidase inhibitors. BMC Microbiol. 2013 Mar 8;13:55. doi: 10.1186/1471-2180-13-55. [PubMed:23497098 ]
  3. Barbic M, Willer EA, Rothenhofer M, Heilmann J, Furst R, Jurgenliemk G: Spirostanol saponins and esculin from Rusci rhizoma reduce the thrombin-induced hyperpermeability of endothelial cells. Phytochemistry. 2013 Jun;90:106-13. doi: 10.1016/j.phytochem.2013.02.004. Epub 2013 Mar 13. [PubMed:23499166 ]
  4. Lather A, Sharma S, Khatkar A: Aesculin based glucosamine-6-phosphate synthase inhibitors as novel preservatives for food and pharmaceutical products: in-silico studies, antioxidant, antimicrobial and preservative efficacy evaluation. BMC Chem. 2021 Jul 27;15(1):45. doi: 10.1186/s13065-021-00769-8. [PubMed:34315523 ]
  5. Yu Y, Chen J, Zhang X, Wang Y, Wang S, Zhao L, Wang Y: Identification of anti-inflammatory compounds from Zhongjing formulae by knowledge mining and high-content screening in a zebrafish model of inflammatory bowel diseases. Chin Med. 2021 May 31;16(1):42. doi: 10.1186/s13020-021-00452-z. [PubMed:34059101 ]
  6. Aleksandra Owczarek, Arkadiusz Kłys, Monika A.Olszewska (2019). Aleksandra Owczarek, Arkadiusz Kłys, Monika A.Olszewska A validated 1H qNMR method for direct and simultaneous quantification of esculin, fraxin and (–)-epicatechin in Hippocastani cortex. Talanta Volume 192, 15 January 2019, Pages 263-269. DOI: 10.1016/j.talanta.2018.09.036. Talanta.