Np mrd loader

Showing NP-Card for Aesculetin (NP0000027)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2012-09-11 17:39:14 UTC
Updated at2024-09-15 13:56:06 UTC
NP-MRD IDNP0000027
Natural Product DOIhttps://doi.org/10.57994/1711
Secondary Accession NumbersNone
Natural Product Identification
Common NameAesculetin
DescriptionAesculetin, also known as cichorigenin or cichoriin aglucon, belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively. Aesculetin is found, on average, in the highest concentration within sherries. Aesculetin has also been detected, but not quantified, in several different foods, such as horseradish, carrots, dandelions, grape wines, and highbush blueberries. This could make aesculetin a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0000027 (Aesculetin)

Esculetin
  Mrv1652305201900042D          

 13 14  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
M  END
Download

3D MOL for NP0000027 (Aesculetin)

Download
3D SDF for NP0000027 (Aesculetin)
Esculetin
  Mrv1652305201900042D          

 13 14  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000027

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C=C2C=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H

> <INCHI_KEY>
ILEDWLMCKZNDJK-UHFFFAOYSA-N

> <FORMULA>
C9H6O4

> <MOLECULAR_WEIGHT>
178.143

> <EXACT_MASS>
178.026608673

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
16.30902135502844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,7-dihydroxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.1762289719999999

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.273221654598073

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.9149077763827895

> <JCHEM_PKA_STRONGEST_BASIC>
-6.2656901008042505

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
45.510400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
esculetin

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0000027 (Aesculetin)
Download
PDB for NP0000027 (Aesculetin)
HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Esculetin                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    2                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Download
3D PDB for NP0000027 (Aesculetin)
Download
SMILES for NP0000027 (Aesculetin)
OC1=C(O)C=C2C=CC(=O)OC2=C1
Download
INCHI for NP0000027 (Aesculetin)
InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
Download
View in JSmol
Synonyms
ValueSource
6,7-Dihydroxy-2H-1-benzopyran-2-oneChEBI
6,7-DihydroxycoumarinChEBI
CichorigeninChEBI
Cichoriin agluconChEBI
Cichoriin aglyconChEBI
Esculin agluconChEBI
Esculin aglyconChEBI
2H-1-Benzopyran-2-one, 6,7-dihydroxy- (9ci)HMDB
6,7-Dihydroxy-2-benzopyroneHMDB
6,7-Dihydroxy-2H-chromen-2-oneHMDB
6,7-Dihydroxy-coumarinHMDB
6,7-Dihydroxycoumarin, 8ciHMDB
Aesculetin (cichorigeninHMDB
AsculetineHMDB
Coumarin, 6,7-dihydroxy- esculetinHMDB
EsculetinHMDB
EsculetolHMDB
Esculetol)HMDB
AesculetinChEBI
Chemical FormulaC9H6O4
Average Mass178.1430 Da
Monoisotopic Mass178.02661 Da
IUPAC Name6,7-dihydroxy-2H-chromen-2-one
Traditional Nameesculetin
CAS Registry Number305-01-1
SMILES
OC1=C(O)C=C2C=CC(=O)OC2=C1
InChI Identifier
InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
InChI KeyILEDWLMCKZNDJK-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea filipendulina
Achillea grandifolia
Aesculus hippocastanumPlant
Aesculus turbinataPlant
Allium ampeloprasumFooDB
Aloe arborescens
Althaea officinalis
Anethum graveolensFooDB
Anisodus tanguticusPlant
Anthriscus cerefolium
Arabidopsis thaliana
Arachis hypogaeaFooDB
Aralia fargesiiPlant
Armoracia rusticanaFooDB
Artemisia capillaris
Artemisia dracunculusFooDB
Artemisia eriopoda
Artemisia jacutica
Artemisia mongolica
Artemisia montana
Artemisia tridentata
Artemisia vulgarisFooDB
Artemisia xerophytica
Asphodeline damascena
Asphodeline globiferaPlant
Berberis vulgaris
Bidens tripartitaPlant
Bupleurum fruticosum
Cacalia hastata
Calendula officinalis
Campanula rotundifolia
Caragana frutex
Cedrelopsis grevei
Ceratostigma willmottianumPlant
Chondrilla juncea
Chrysanthemum segetum
Cichorium glandulosum
Cichorium intybusFooDB
Cichorium pumilum
Citrus limonPlant
Citrus limoniaPlant
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dictamnus albus
Erica vagansPlant
Euphorbia decipiens
Euphorbia lagascae
Euphorbia lanataPlant
Euphorbia lathyrisPlant
Euphorbia lunulataPlant
Euphorbia petiolata
Fraxinus angustifolia
Fraxinus bungeanaPlant
Fraxinus chinensisPlant
Fraxinus excelsior
Fraxinus floribunda
Fraxinus insularis
Fraxinus mandshuricaPlant
Fraxinus ornusPlant
Fraxinus paxianaPlant
Fraxinus rhynchophyllaPlant
Fraxinus spp.Plant
Fraxinus stylosaPlant
Fraxinus szaboanaPlant
Galinsoga quadriradiata
Geum rivale
Ginkgo bilobaPlant
Gymnophyton isatidicarpum
Haplopappus foliosusPlant
Haplopappus multifolius
Helichrysum italicum
Helichrysum maracandicum
Hordeum vulgareFooDB
Hydrophyllum virginianum
Hylotelephium ewersii
Isodon eriocalyx
Ixeridium laevigatum
Khaya ivorensisPlant
Khaya senegalensis L.Plant
Koelpinia linearisPlant
Lepidaploa remotiflora
Ligularia amplexicaulis
Ligularia sagitta
Ligustrum japonicum
Lonicera bournei Hemsl.
Lonicera gracilipes var. glandulosaPlant
Lupinus angustifolius
Manihot esculenta
Matricaria chamomilla
Medicago sativaPlant
Meehania urticifoliaPlant
Melilotus suaveolensPlant
Myrtus communis
Nervilia fordii
Notoseris henryi
Notoseris macilenta
Ocimum basilicumFooDB
Ocimum tenuiflorum
Olea europaeaFooDB
Passiflora menispermifolia
Perilla frutescens
Periploca graecaPlant
Phaseolus vulgarisFooDB
Phellodendron amurensePlant
Phellodendron japonicum MAXIMPlant
Potentilla erecta
Prunella vulgaris
Pterocaulon polystachyum
Quercus faginea
Quercus suber
Ranunculus sieboldii
Rhododendron hypoleucum
Rosa laevigata
Salvia euphraticaPlant
Salvia verticillata
Santolina oblongifolia
Scorzonera laciniata
Sedum ewersiiPlant
Sedum kamtschaticumPlant
Sedum selskianum
Skimmia laureola
Solanum dasyphyllum
Solanum virginianumPlant
Sonchus asper
Sonchus hierrensis (Pit.) Boulos
Syringa vulgaris
Tagetes lucida
Taraxacum formosanumPlant
Taraxacum mongolicum
Taraxacum officinaleFooDB
Theobroma cacaoFooDB
Trifolium pratensePlant
Vaccinium corymbosumFooDB
Viburnum cylindricum
Vicia sativa
Viola mandshurica
Vitis vinifera
Withania somnifera
Xenophyllum dactylophyllum
Zanthoxylum piasezkii
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassHydroxycoumarins  
Direct Parent6,7-dihydroxycoumarins  
Alternative Parents
Substituents
  • 6,7-dihydroxycoumarin
    • 

  • 7-hydroxycoumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.6 g/LALOGPS
logP1.38ALOGPS
logP1.18ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.91ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.51 m³·mol⁻¹ChemAxon
Polarizability16.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0030819  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002775  
KNApSAcK IDC00002471  
Chemspider ID4444764  
KEGG Compound IDC09263  
BioCyc IDCPD-8097  
BiGG IDNot Available
Wikipedia LinkAesculetin  
METLIN IDNot Available
PubChem Compound5281416  
PDB IDNot Available
ChEBI ID490095  
Good Scents IDNot Available
References
General References
  1. Riveiro ME, Moglioni A, Vazquez R, Gomez N, Facorro G, Piehl L, de Celis ER, Shayo C, Davio C: Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells. Bioorg Med Chem. 2008 Mar 1;16(5):2665-75. doi: 10.1016/j.bmc.2007.11.038. Epub 2007 Nov 19. [PubMed:18060791  ] 
  2. Park C, Jin CY, Kwon HJ, Hwang HJ, Kim GY, Choi IW, Kwon TK, Kim BW, Kim WJ, Choi YH: Induction of apoptosis by esculetin in human leukemia U937 cells: roles of Bcl-2 and extracellular-regulated kinase signaling. Toxicol In Vitro. 2010 Mar;24(2):486-94. doi: 10.1016/j.tiv.2009.09.017. Epub 2009 Sep 26. [PubMed:19786087  ] 
  3. Witaicenis A, Seito LN, Di Stasi LC: Intestinal anti-inflammatory activity of esculetin and 4-methylesculetin in the trinitrobenzenesulphonic acid model of rat colitis. Chem Biol Interact. 2010 Jul 30;186(2):211-8. doi: 10.1016/j.cbi.2010.03.045. Epub 2010 Apr 7. [PubMed:20380826  ] 
  4.  (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .