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Showing metabocard for Leprapinic acid (HMDB0341171)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 19:29:15 UTC
Update Date2022-09-22 18:35:04 UTC
HMDB IDHMDB0341171
Secondary Accession NumbersNone
Metabolite Identification
Common NameLeprapinic acid
DescriptionLeprapic acid, also known as leprapate, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Leprapic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for HMDB0341171 (Leprapinic acid)


  Mrv1652305152111552D          

 26 28  0  0  0  0            999 V2000
    1.0992    0.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    5.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0580    3.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449    4.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    3.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4262    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    1.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6603    4.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    2.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8131    3.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4700    1.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888    3.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284    2.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1431    1.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846    3.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131    4.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    4.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262    4.6567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    1.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    1.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715    4.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    2.2581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 21 17  1  0  0  0  0
 22 19  2  0  0  0  0
 23 20  2  0  0  0  0
 24  1  1  0  0  0  0
 24 14  1  0  0  0  0
 25  2  1  0  0  0  0
 25 19  1  0  0  0  0
 26 18  1  0  0  0  0
 26 20  1  0  0  0  0
M  END
Download

3D MOL for HMDB0341171 (Leprapinic acid)

Download
3D SDF for HMDB0341171 (Leprapinic acid)

  Mrv1652305152111552D          

 26 28  0  0  0  0            999 V2000
    1.0992    0.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    5.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0580    3.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449    4.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    3.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4262    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    1.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6603    4.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    2.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8131    3.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4700    1.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888    3.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284    2.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1431    1.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846    3.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131    4.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    4.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262    4.6567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    1.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    1.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715    4.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    2.2581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 21 17  1  0  0  0  0
 22 19  2  0  0  0  0
 23 20  2  0  0  0  0
 24  1  1  0  0  0  0
 24 14  1  0  0  0  0
 25  2  1  0  0  0  0
 25 19  1  0  0  0  0
 26 18  1  0  0  0  0
 26 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341171

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C(=C1\OC(=O)C(=C1O)C1=CC=CC=C1)\C1=CC=CC=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O6/c1-24-14-11-7-6-10-13(14)16(19(22)25-2)18-17(21)15(20(23)26-18)12-8-4-3-5-9-12/h3-11,21H,1-2H3/b18-16+

> <INCHI_KEY>
IWYVMUDIEOXASM-FBMGVBCBSA-N

> <FORMULA>
C20H16O6

> <MOLECULAR_WEIGHT>
352.342

> <EXACT_MASS>
352.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.8877974160267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(2E)-3-hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene]-2-(2-methoxyphenyl)acetate

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
3.0698446020000003

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.934212078069298

> <JCHEM_PKA_STRONGEST_BASIC>
-4.854382072823377

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
95.3545

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(2E)-3-hydroxy-5-oxo-4-phenylfuran-2-ylidene](2-methoxyphenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0341171 (Leprapinic acid)
Download
PDB for HMDB0341171 (Leprapinic acid)
HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       2.052   1.637   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.014   9.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.442   7.107   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.297   8.138   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.121   5.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.662   4.571   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.342   3.064   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.833   7.662   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.657   5.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.518   5.601   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.877   2.588   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.512   6.156   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.053   5.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.267   3.619   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.048   5.680   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.091   6.156   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.802   6.585   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.556   5.680   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.771   7.662   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.572   4.215   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.802   8.125   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.916   8.693   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.477   2.969   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.732   3.143   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.693   8.138   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.032   4.215   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   25                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3    9                                                       
CONECT    6    7   10                                                       
CONECT    7    6   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   12                                                       
CONECT   10    6   13                                                       
CONECT   11    7   14                                                       
CONECT   12    8    9   15                                                  
CONECT   13   10   14   16                                                  
CONECT   14   11   13   24                                                  
CONECT   15   12   17   20                                                  
CONECT   16   13   18   19                                                  
CONECT   17   15   18   21                                                  
CONECT   18   16   17   26                                                  
CONECT   19   16   22   25                                                  
CONECT   20   15   23   26                                                  
CONECT   21   17                                                            
CONECT   22   19                                                            
CONECT   23   20                                                            
CONECT   24    1   14                                                       
CONECT   25    2   19                                                       
CONECT   26   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Download
3D PDB for HMDB0341171 (Leprapinic acid)
Download
SMILES for HMDB0341171 (Leprapinic acid)
COC(=O)C(=C1\OC(=O)C(=C1O)C1=CC=CC=C1)\C1=CC=CC=C1OC
Download
INCHI for HMDB0341171 (Leprapinic acid)
InChI=1S/C20H16O6/c1-24-14-11-7-6-10-13(14)16(19(22)25-2)18-17(21)15(20(23)26-18)12-8-4-3-5-9-12/h3-11,21H,1-2H3/b18-16+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
LeprapateGenerator
Chemical FormulaC20H16O6
Average Molecular Weight352.342
Monoisotopic Molecular Weight352.094688235
IUPAC Namemethyl 2-[(2E)-3-hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene]-2-(2-methoxyphenyl)acetate
Traditional Namemethyl [(2E)-3-hydroxy-5-oxo-4-phenylfuran-2-ylidene](2-methoxyphenyl)acetate
CAS Registry NumberNot Available
SMILES
COC(=O)C(=C1\OC(=O)C(=C1O)C1=CC=CC=C1)\C1=CC=CC=C1OC
InChI Identifier
InChI=1S/C20H16O6/c1-24-14-11-7-6-10-13(14)16(19(22)25-2)18-17(21)15(20(23)26-18)12-8-4-3-5-9-12/h3-11,21H,1-2H3/b18-16+
InChI KeyIWYVMUDIEOXASM-FBMGVBCBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenol ethers  
Sub ClassAnisoles  
Direct ParentAnisoles  
Alternative Parents
Substituents
  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • 2-furanone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Vinylogous acid
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Methyl ester
    • 

  • Dihydrofuran
    • 

  • Enol ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Enol
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.97ALOGPS
logP3.07ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)5.93ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.35 m³·mol⁻¹ChemAxon
Polarizability35.89 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Predicted Kovats Retention Indices
Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal  details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal  details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID20125048  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54707104  
PDB IDNot Available
ChEBI ID144167  
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864  ]