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Showing metabocard for Aesculetin (HMDB0030819)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:14 UTC
Update Date2023-02-21 17:19:42 UTC
HMDB IDHMDB0030819
Secondary Accession Numbers
  • HMDB30819
Metabolite 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
Data?1676999982
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030819 (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 HMDB0030819 (Aesculetin)

HMDB0030819
     RDKit          3D
Aesculetin
 19 20  0  0  0  0  0  0  0  0999 V2000
    3.9201   -1.5027   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410   -0.8433   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8806    0.4580    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161    1.1518    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5233    0.4975    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804    1.1179    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8561    0.4346    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0613    1.0687    0.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8800   -0.8722   -0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781   -1.5552   -0.5849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6654   -1.5010   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207   -0.8098   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6736   -1.3914   -0.4383 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322    0.9459    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7414    2.1946    0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664    2.1495    0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1653    2.0261    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9463   -1.0611   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6495   -2.5077   -0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13  2  1  0
 12  5  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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3D SDF for HMDB0030819 (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>
HMDB0030819

> <DATABASE_NAME>
hmdb

> <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 HMDB0030819 (Aesculetin)

HMDB0030819
     RDKit          3D
Aesculetin
 19 20  0  0  0  0  0  0  0  0999 V2000
    3.9201   -1.5027   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410   -0.8433   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8806    0.4580    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161    1.1518    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5233    0.4975    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804    1.1179    0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8561    0.4346    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0613    1.0687    0.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8800   -0.8722   -0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781   -1.5552   -0.5849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6654   -1.5010   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207   -0.8098   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6736   -1.3914   -0.4383 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322    0.9459    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7414    2.1946    0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664    2.1495    0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1653    2.0261    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9463   -1.0611   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6495   -2.5077   -0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13  2  1  0
 12  5  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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PDB for HMDB0030819 (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
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3D PDB for HMDB0030819 (Aesculetin)

COMPND    HMDB0030819
HETATM    1  O1  UNL     1       3.920  -1.503  -0.433  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.841  -0.843  -0.231  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.881   0.458   0.210  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.716   1.152   0.422  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.523   0.497   0.178  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.680   1.118   0.365  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.856   0.435   0.111  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.061   1.069   0.303  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.880  -0.872  -0.331  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.078  -1.555  -0.585  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.665  -1.501  -0.520  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.521  -0.810  -0.264  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.674  -1.391  -0.438  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.832   0.946   0.393  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.741   2.195   0.775  1.00  0.00           H  
HETATM   16  H3  UNL     1      -0.666   2.149   0.714  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.165   2.026   0.624  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.946  -1.061  -0.434  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.650  -2.508  -0.860  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   14
CONECT    4    5   15
CONECT    5    6    6   12
CONECT    6    7   16
CONECT    7    8    9    9
CONECT    8   17
CONECT    9   10   11
CONECT   10   18
CONECT   11   12   12   19
CONECT   12   13
END
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SMILES for HMDB0030819 (Aesculetin)

OC1=C(O)C=C2C=CC(=O)OC2=C1
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INCHI for HMDB0030819 (Aesculetin)

InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC9H6O4
Average Molecular Weight178.143
Monoisotopic Molecular Weight178.026608673
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling Point469.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility72130 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.980 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available129.461http://allccs.zhulab.cn/database/detail?ID=AllCCS00001458
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1242861
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Aesculetin → 3,4,5-trihydroxy-6-[(7-hydroxy-2-oxo-2H-chromen-6-yl)oxy]oxane-2-carboxylic aciddetails
Aesculetin → 3,4,5-trihydroxy-6-[(6-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic aciddetails