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Showing NP-Card for Asparagusic acid (NP0045425)

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Record Information
Version2.0
Created at2022-03-17 19:19:45 UTC
Updated at2022-03-17 19:19:45 UTC
NP-MRD IDNP0045425
Secondary Accession NumbersNone
Natural Product Identification
Common NameAsparagusic acid
DescriptionAsparagusic acid, also known as asparagusate or AACOCF3, belongs to the class of organic compounds known as 1,2-dithiolane-4-carboxylic acids. These are organic compounds containing a 1,2-dithiolane ring that bears a carboxylic acid group at the 4-position. Asparagusic acid is a weakly acidic compound (based on its pKa). Asparagusic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Asparagusic acid has been detected, but not quantified in, asparagus and green vegetables. This could make asparagusic acid a potential biomarker for the consumption of these foods. Small-scale studies noted that the "asparagus urine" odour was not produced by all individuals and estimates as to the proportion of the population who are excretors (reporting a noticeable asparagus urine odour after eating asparagus) has ranged from about 40% to as high as 79% In a 91 subject population study 82 participants (90%) reported "asparagus urine" odour. The (R)-(+)-enantiomer of α-lipoic acid is a cofactor in the pyruvate dehydrogenase complex and is essential for aerobic metabolism. Biosynthetic studies revealed that asparagusic acid is derived from isobutyric acid. More recent research has attributed the odour to a mixture of sulfur-containing metabolites of asparagusic acid which have been detected in urine; these include methanethiol and span at least seven distinct functional groups, as shown in the table below. Similar transformations of asparagusic acid would lead to metabolites like this detected in asparagus urine. The molecule consists of a heterocyclic disulfide functional group (a 1,2-dithiolane) with a carboxylic acid side chain. In the small minority of people who do not produce these metabolites after consuming asparagus, the reason may be as simple as asparagusic acid not being taken into the body from the digestive tract or that these individuals metabolise it in such a way as to minimise the release of volatile sulfur-containing products.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045425 (Asparagusic acid)


  Mrv1652309172021042D          

  8  8  0  0  0  0            999 V2000
   -0.3571    3.0566    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245    2.5716    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696    1.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0553    1.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102    2.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5402    1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2047    0.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    1.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  1  2  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for NP0045425 (Asparagusic acid)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    0.7093    1.1044    1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781    0.4938    0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678    0.0411    0.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0402    0.2248   -0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447   -1.2590   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3010   -1.7906    1.1014 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5147   -0.0824    1.6563 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3773    0.7397    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9196    0.6805   -0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636    0.7507   -1.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0791   -1.5911   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7684   -1.6227   -1.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137    0.4949   -0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2361    1.8161    0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
  8 13  1  0
  8 14  1  0
M  END
Download

3D SDF for NP0045425 (Asparagusic acid)


  Mrv1652309172021042D          

  8  8  0  0  0  0            999 V2000
   -0.3571    3.0566    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245    2.5716    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696    1.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0553    1.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102    2.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5402    1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2047    0.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    1.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  1  2  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1CSSC1

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O2S2/c5-4(6)3-1-7-8-2-3/h3H,1-2H2,(H,5,6)

> <INCHI_KEY>
AYGMEFRECNWRJC-UHFFFAOYSA-N

> <FORMULA>
C4H6O2S2

> <MOLECULAR_WEIGHT>
150.219

> <EXACT_MASS>
149.980920816

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
13.571807684822605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2-dithiolane-4-carboxylic acid

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.7943954316666666

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9831958714241305

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
35.9635

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asparagusic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045425 (Asparagusic acid)

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PDB for NP0045425 (Asparagusic acid)
HEADER    PROTEIN                                 17-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-20         0                                  
HETATM    1  S   UNK     0      -0.667   5.706   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      -1.912   4.800   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -1.437   3.336   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.103   3.336   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.579   4.800   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.008   2.090   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.382   0.683   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.540   2.251   0.000  0.00  0.00           O+0
CONECT    1    5    2                                                       
CONECT    2    3    1                                                       
CONECT    3    4    2                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0045425 (Asparagusic acid)
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SMILES for NP0045425 (Asparagusic acid)
OC(=O)C1CSSC1
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INCHI for NP0045425 (Asparagusic acid)
InChI=1S/C4H6O2S2/c5-4(6)3-1-7-8-2-3/h3H,1-2H2,(H,5,6)
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View in JSmol
Synonyms
ValueSource
AsparagusateChEBI
1,2-Dithiolane-4-carboxylic acidMeSH
1,2-Dithiacyclopentane-4-carboxylic acidHMDB
Asparagusic acidHMDB
Chemical FormulaC4H6O2S2
Average Mass150.2190 Da
Monoisotopic Mass149.98092 Da
IUPAC Name1,2-dithiolane-4-carboxylic acid
Traditional Nameasparagusic acid
CAS Registry Number2224-02-4
SMILES
OC(=O)C1CSSC1
InChI Identifier
InChI=1S/C4H6O2S2/c5-4(6)3-1-7-8-2-3/h3H,1-2H2,(H,5,6)
InChI KeyAYGMEFRECNWRJC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Asparagus officinalisFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-dithiolane-4-carboxylic acids. These are organic compounds containing a 1,2-dithiolane ring that bears a carboxylic acid group at the 4-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDithiolanes  
Sub ClassDithiolanecarboxylic acids  
Direct Parent1,2-dithiolane-4-carboxylic acids  
Alternative Parents
Substituents
  • 1,2-dithiolane-4-carboxylic acid
    • 

  • 1,2-dithiolane
    • 

  • Organic disulfide
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.51ALOGPS
logP0.79ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)3.98ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.96 m³·mol⁻¹ChemAxon
Polarizability13.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029611  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000778  
KNApSAcK IDC00000304  
Chemspider ID15819  
KEGG Compound IDC01892  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAsparagusic acid  
METLIN IDNot Available
PubChem Compound16682  
PDB IDNot Available
ChEBI ID18091  
Good Scents IDNot Available
References
General ReferencesNot Available