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Showing NP-Card for Dihydroasparagusic acid (NP0048301)

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Record Information
Version2.0
Created at2022-03-17 20:54:17 UTC
Updated at2022-03-17 20:54:17 UTC
NP-MRD IDNP0048301
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydroasparagusic acid
DescriptionDihydroasparagusic acid belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. A sulfur-containing carboxylic acid consisting of isobutyric acid having mercapto substituents on both beta-carbons. Dihydroasparagusic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dihydroasparagusic acid has been detected, but not quantified in, asparagus and green vegetables. This could make dihydroasparagusic acid a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048301 (Dihydroasparagusic acid)


  Mrv0541 05061308402D          

  8  7  0  0  0  0            999 V2000
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
M  END
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3D MOL for NP0048301 (Dihydroasparagusic acid)

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3D SDF for NP0048301 (Dihydroasparagusic acid)

  Mrv0541 05061308402D          

  8  7  0  0  0  0            999 V2000
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(CS)CS

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2S2/c5-4(6)3(1-7)2-8/h3,7-8H,1-2H2,(H,5,6)

> <INCHI_KEY>
KRHAHEQEKNJCSD-UHFFFAOYSA-N

> <FORMULA>
C4H8O2S2

> <MOLECULAR_WEIGHT>
152.235

> <EXACT_MASS>
151.99657088

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
14.94678811599962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-sulfanyl-2-(sulfanylmethyl)propanoic acid

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
0.9613728896666665

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.870697586064733

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.555286814531032

> <JCHEM_PKA_STRONGEST_BASIC>
-9.58887847715804

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
37.4517

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-sulfanyl-2-(sulfanylmethyl)propanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048301 (Dihydroasparagusic acid)
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PDB for NP0048301 (Dihydroasparagusic acid)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.207   3.080   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.540   3.080   0.000  0.00  0.00           O+0
HETATM    7  S   UNK     0       5.541   0.770   0.000  0.00  0.00           S+0
HETATM    8  S   UNK     0       0.206   0.770   0.000  0.00  0.00           S+0
CONECT    1    3    7                                                       
CONECT    2    3    8                                                       
CONECT    3    1    2    4                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1                                                            
CONECT    8    2                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0048301 (Dihydroasparagusic acid)
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SMILES for NP0048301 (Dihydroasparagusic acid)
OC(=O)C(CS)CS
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INCHI for NP0048301 (Dihydroasparagusic acid)
InChI=1S/C4H8O2S2/c5-4(6)3(1-7)2-8/h3,7-8H,1-2H2,(H,5,6)
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Synonyms
ValueSource
3-Mercapto-2-mercaptomethylpropanoateChEBI
3-Mercapto-2-mercaptomethylpropanoic acidGenerator
DihydroasparagusateGenerator
3-Mercapto-2-(mercaptomethyl)-propanoic acidHMDB
3-Mercapto-2-[mercaptomethyl]propionic acidHMDB
3-Sulfanyl-2-(sulfanylmethyl)propanoic acidHMDB
b,B'-dimercaptoisobutyric acidHMDB
Dihydroasparagusic acidMeSH
Chemical FormulaC4H8O2S2
Average Mass152.2350 Da
Monoisotopic Mass151.99657 Da
IUPAC Name3-sulfanyl-2-(sulfanylmethyl)propanoic acid
Traditional Name3-sulfanyl-2-(sulfanylmethyl)propanoic acid
CAS Registry Number7634-96-0
SMILES
OC(=O)C(CS)CS
InChI Identifier
InChI=1S/C4H8O2S2/c5-4(6)3(1-7)2-8/h3,7-8H,1-2H2,(H,5,6)
InChI KeyKRHAHEQEKNJCSD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
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 carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassCarboxylic acids  
Direct ParentCarboxylic acids  
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Alkylthiol
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP0.63ALOGPS
logP0.96ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.45 m³·mol⁻¹ChemAxon
Polarizability14.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035716  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014440  
KNApSAcK IDC00000305  
Chemspider ID389286  
KEGG Compound IDC04371  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440312  
PDB IDNot Available
ChEBI ID17919  
Good Scents IDNot Available
References
General ReferencesNot Available