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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:29:15 UTC

Update Date

2022-09-22 18:35:04 UTC

HMDB ID

HMDB0341171

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Leprapinic acid

Description

Leprapinic acid, also known as leprapinate, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Based on a literature review a significant number of articles have been published on Leprapinic acid.

Structure

MOL SDF PDB SMILES InChI

  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

  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

$$$$

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Leprapinate	Generator
Leprapate	HMDB

Chemical Formula

C₂₀H₁₆O₆

Average Molecular Weight

352.342

Monoisotopic Molecular Weight

352.094688235

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not 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 Key

IWYVMUDIEOXASM-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.97	ALOGPS
logP	3.07	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	5.93	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.35 m³·mol⁻¹	ChemAxon
Polarizability	35.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20125048

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54707104

PDB ID

Not Available

ChEBI ID

144167

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for Leprapinic acid (HMDB0341171)

MOL for HMDB0341171 (Leprapinic acid)

3D MOL for HMDB0341171 (Leprapinic acid)

3D SDF for HMDB0341171 (Leprapinic acid)

3D-SDF for HMDB0341171 (Leprapinic acid)

PDB for HMDB0341171 (Leprapinic acid)

3D PDB for HMDB0341171 (Leprapinic acid)

SMILES for HMDB0341171 (Leprapinic acid)

INCHI for HMDB0341171 (Leprapinic acid)

Structure for HMDB0341171 (Leprapinic acid)

3D Structure for HMDB0341171 (Leprapinic acid)

Predicted Kovats Retention Indices