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Showing metabocard for Asparagusic acid (HMDB0029611)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:27 UTC
Update Date2023-12-12 16:14:14 UTC
HMDB IDHMDB0029611
Secondary Accession Numbers
  • HMDB29611
Metabolite Identification
Common NameAsparagusic acid
Description
Structure
Data?1676999932
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029611 (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
Download

3D MOL for HMDB0029611 (Asparagusic acid)

HMDB0029611
     RDKit          3D
Asparagusic acid
 14 14  0  0  0  0  0  0  0  0999 V2000
    0.3896   -2.1861    0.6162 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7912   -1.1544    0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928   -1.0535   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1396   -0.0329   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4173    1.1655    0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482    2.4903    0.3243 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125    1.1057    0.2635 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690   -0.3957    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8428   -0.6406    0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1202    0.1510   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2868    1.5175   -0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404    0.9905    1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9362   -1.1102   -0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354   -0.8470    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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 HMDB0029611 (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>
HMDB0029611

> <DATABASE_NAME>
hmdb

> <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 HMDB0029611 (Asparagusic acid)

HMDB0029611
     RDKit          3D
Asparagusic acid
 14 14  0  0  0  0  0  0  0  0999 V2000
    0.3896   -2.1861    0.6162 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7912   -1.1544    0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928   -1.0535   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1396   -0.0329   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4173    1.1655    0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482    2.4903    0.3243 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125    1.1057    0.2635 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690   -0.3957    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8428   -0.6406    0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1202    0.1510   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2868    1.5175   -0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404    0.9905    1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9362   -1.1102   -0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354   -0.8470    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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
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PDB for HMDB0029611 (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 HMDB0029611 (Asparagusic acid)

COMPND    HMDB0029611
HETATM    1  O1  UNL     1       0.390  -2.186   0.616  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.791  -1.154   0.042  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.093  -1.054  -0.362  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.140  -0.033  -0.207  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.417   1.166   0.508  1.00  0.00           C  
HETATM    6  S1  UNL     1      -0.848   2.490   0.324  1.00  0.00           S  
HETATM    7  S2  UNL     1      -2.512   1.106   0.263  1.00  0.00           S  
HETATM    8  C4  UNL     1      -1.469  -0.396   0.325  1.00  0.00           C  
HETATM    9  H1  UNL     1       2.843  -0.641   0.192  1.00  0.00           H  
HETATM   10  H2  UNL     1      -0.120   0.151  -1.299  1.00  0.00           H  
HETATM   11  H3  UNL     1       1.287   1.518  -0.082  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.640   0.990   1.560  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.936  -1.110  -0.382  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.435  -0.847   1.310  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5    8   10
CONECT    5    6   11   12
CONECT    6    7
CONECT    7    8
CONECT    8   13   14
END
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SMILES for HMDB0029611 (Asparagusic acid)

OC(=O)C1CSSC1
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INCHI for HMDB0029611 (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 JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
AsparagusateChEBI
1,2-Dithiolane-4-carboxylateKegg
1,2-Dithiolane-4-carboxylic acidGenerator
1,2-Dithiacyclopentane-4-carboxylic acidHMDB
Asparagusic acidHMDB
Chemical FormulaC4H6O2S2
Average Molecular Weight150.219
Monoisotopic Molecular Weight149.980920816
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point75.7 - 76.5 °CNot Available
Boiling Point232.00 to 234.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility11230 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.480 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1387631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mitchell SC, Waring RH: Asparagusic acid. Phytochemistry. 2014 Jan;97:5-10. doi: 10.1016/j.phytochem.2013.09.014. Epub 2013 Oct 4. [PubMed:24099657 ]
  2. Pegiou E, Mumm R, Acharya P, de Vos RCH, Hall RD: Green and White Asparagus (Asparagus officinalis): A Source of Developmental, Chemical and Urinary Intrigue. Metabolites. 2019 Dec 25;10(1):17. doi: 10.3390/metabo10010017. [PubMed:31881716 ]
  3. Pelchat ML, Bykowski C, Duke FF, Reed DR: Excretion and perception of a characteristic odor in urine after asparagus ingestion: a psychophysical and genetic study. Chem Senses. 2011 Jan;36(1):9-17. doi: 10.1093/chemse/bjq081. Epub 2010 Sep 27. [PubMed:20876394 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .