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Showing NP-Card for 3-mercaptopropionic acid (NP0292354)

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Record Information
Version2.0
Created at2022-09-09 23:50:33 UTC
Updated at2022-09-09 23:50:33 UTC
NP-MRD IDNP0292354
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-mercaptopropionic acid
Description3-Mercaptopropanoic acid, also known as 3-thiolpropanoate or 3-thiohydracrylic 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. 3-Mercaptopropanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Mercaptopropanoic acid exists in all living organisms, ranging from bacteria to humans. 3-Mercaptopropanoic acid is a roasted and sulfurous tasting compound. Outside of the human body,. 3-mercaptopropionic acid is found in Synechococcus elongatus. 3-mercaptopropionic acid was first documented in 1987 (PMID: 3600189). A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3 (PMID: 19885720).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0292354 (3-mercaptopropionic acid)

Structure #1
  Mrv0541 02241207092D          

  6  5  0  0  0  0            999 V2000
    1.2375   -0.7145    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
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
M  END
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3D MOL for NP0292354 (3-mercaptopropionic acid)

     RDKit          3D

 12 11  0  0  0  0  0  0  0  0999 V2000
    0.2528    1.8385   -0.1243 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194    0.7873    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761    0.9645    0.2715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850   -0.5726   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -0.6549   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0626    0.1826    0.9666 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9400    0.1750    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9095   -1.0868   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573   -1.1256    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120   -1.7160   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3932   -0.2722   -1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850    1.4801    0.5944 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
  3  7  1  0
  4  8  1  0
  4  9  1  0
  5 10  1  0
  5 11  1  0
  6 12  1  0
M  END
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3D SDF for NP0292354 (3-mercaptopropionic acid)

Structure #1
  Mrv0541 02241207092D          

  6  5  0  0  0  0            999 V2000
    1.2375   -0.7145    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
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCS

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O2S/c4-3(5)1-2-6/h6H,1-2H2,(H,4,5)

> <INCHI_KEY>
DKIDEFUBRARXTE-UHFFFAOYSA-N

> <FORMULA>
C3H6O2S

> <MOLECULAR_WEIGHT>
106.144

> <EXACT_MASS>
106.008850126

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
10.202464668863485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-sulfanylpropanoic acid

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
0.44778837199999993

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.207254896328308

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5650648839009635

> <JCHEM_PKA_STRONGEST_BASIC>
-9.578019909528756

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
25.073900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-mercaptopropionic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0292354 (3-mercaptopropionic acid)

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PDB for NP0292354 (3-mercaptopropionic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.310  -1.334   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       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.620  -2.667   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.620   0.000   0.000  0.00  0.00           O+0
HETATM    6  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0292354 (3-mercaptopropionic acid)
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SMILES for NP0292354 (3-mercaptopropionic acid)
OC(=O)CCS
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INCHI for NP0292354 (3-mercaptopropionic acid)
InChI=1S/C3H6O2S/c4-3(5)1-2-6/h6H,1-2H2,(H,4,5)
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Synonyms
ValueSource
2-Mercaptoethanecarboxylic acidChEBI
3-Mercaptopropionic acidChEBI
3-Thiohydracrylic acidChEBI
3-Thiolpropanoic acidChEBI
3-Thiopropanoic acidChEBI
3-Thiopropionic acidChEBI
3MPAChEBI
beta-Mercaptopropionic acidChEBI
beta-Thiopropionic acidChEBI
2-MercaptoethanecarboxylateGenerator
3-MercaptopropionateGenerator
3-ThiohydracrylateGenerator
3-ThiolpropanoateGenerator
3-ThiopropanoateGenerator
3-ThiopropionateGenerator
b-MercaptopropionateGenerator
b-Mercaptopropionic acidGenerator
beta-MercaptopropionateGenerator
Β-mercaptopropionateGenerator
Β-mercaptopropionic acidGenerator
b-ThiopropionateGenerator
b-Thiopropionic acidGenerator
beta-ThiopropionateGenerator
Β-thiopropionateGenerator
Β-thiopropionic acidGenerator
3-MercaptopropanoateGenerator
3-Mercaptopropanoic acid, 9ciHMDB
Thiohydracrylic acidHMDB
3 Mercaptopropanoic acidHMDB
Acid, 3-mercaptopropionicHMDB
3 Mercaptopropionic acidHMDB
Acid, 3-mercaptopropanoicHMDB
beta MercaptopropionateHMDB
Chemical FormulaC3H6O2S
Average Mass106.1440 Da
Monoisotopic Mass106.00885 Da
IUPAC Name3-sulfanylpropanoic acid
Traditional Name3-mercaptopropionic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCS
InChI Identifier
InChI=1S/C3H6O2S/c4-3(5)1-2-6/h6H,1-2H2,(H,4,5)
InChI KeyDKIDEFUBRARXTE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Synechococcus elongatusLOTUS Database
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
logP0.34ALOGPS
logP0.45ChemAxon
logS-0.84ALOGPS
pKa (Strongest Acidic)4.57ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.07 m³·mol⁻¹ChemAxon
Polarizability10.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041604  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021759  
KNApSAcK IDNot Available
Chemspider ID6267  
KEGG Compound IDNot Available
BioCyc IDCPD-7673  
BiGG IDNot Available
Wikipedia Link3-Mercaptopropionic acid  
METLIN IDNot Available
PubChem Compound6514  
PDB IDMPT  
ChEBI ID44111  
Good Scents IDNot Available
References
General References
  1. Magafa V, Borovickova L, Slaninova J, Cordopatis P: Synthesis and biological activity of oxytocin analogues containing unnatural amino acids in position 9: structure activity study. Amino Acids. 2010 May;38(5):1549-59. doi: 10.1007/s00726-009-0372-2. Epub 2009  Nov 3. [PubMed:19885720  ] 
  2. Kushner L, Schulz H: Inhibition of mammalian pyruvate dehydrogenase complex by metabolites of 3-mercaptopropanoic acid. Life Sci. 1987 Jul 27;41(4):485-90. doi: 10.1016/0024-3205(87)90225-6. [PubMed:3600189  ] 
  3. LOTUS database [Link]