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Showing NP-Card for DL-Homocysteic acid (NP0137242)

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Record Information
Version2.0
Created at2022-05-30 16:46:20 UTC
Updated at2022-05-30 16:46:20 UTC
NP-MRD IDNP0137242
Secondary Accession NumbersNone
Natural Product Identification
Common NameDL-Homocysteic acid
DescriptionHomocysteic acid, also known as homocysteate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group has benn oxidised to the corresponding sulfonic acid. DL-Homocysteic acid was first documented in 2016 (PMID: 26335909). Homocysteic acid is a very strong basic compound (based on its pKa) (PMID: 27225950).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0137242 (DL-Homocysteic acid)


  Mrv1533004241500332D          

 11 10  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 O   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
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
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3D MOL for NP0137242 (DL-Homocysteic acid)

     RDKit          3D

 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.1665   -1.1440    0.6735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063   -0.4838   -0.2923 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0897   -0.5475    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    0.0958   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468   -0.0087    0.1644 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.7571    0.6744   -0.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1397   -1.4449    0.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7624    0.7686    1.6480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940    0.8991   -0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821    1.7351   -1.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844    1.3205    0.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2240   -0.4941    1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7748   -2.0654    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417   -1.0019   -1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404   -0.1064    1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3412   -1.6365    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151   -0.3701   -1.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893    1.1925   -0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    1.7295    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772    0.8878    0.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  8  1  0
  5  6  2  0
  5  7  2  0
  2  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  8 19  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0137242 (DL-Homocysteic acid)


  Mrv1533004241500332D          

 11 10  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 O   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
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137242

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCS(O)(=O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)

> <INCHI_KEY>
VBOQYPQEPHKASR-UHFFFAOYSA-N

> <FORMULA>
C4H9NO5S

> <MOLECULAR_WEIGHT>
183.18

> <EXACT_MASS>
183.020143568

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.69281173455363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-sulfobutanoic acid

> <ALOGPS_LOGP>
-2.35

> <JCHEM_LOGP>
-2.90591122812339

> <ALOGPS_LOGS>
-0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.3892367160594725

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.2525954713848684

> <JCHEM_PKA_STRONGEST_BASIC>
9.511223417279629

> <JCHEM_POLAR_SURFACE_AREA>
117.69000000000001

> <JCHEM_REFRACTIVITY>
35.3004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-sulfobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0137242 (DL-Homocysteic acid)

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PDB for NP0137242 (DL-Homocysteic acid)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  N   UNK     0       3.850   1.334   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0       1.540   5.335   0.000  0.00  0.00           S+0
HETATM    6  O   UNK     0       0.770   6.668   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.206   4.565   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.874   6.105   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0137242 (DL-Homocysteic acid)
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SMILES for NP0137242 (DL-Homocysteic acid)
NC(CCS(O)(=O)=O)C(O)=O
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INCHI for NP0137242 (DL-Homocysteic acid)
InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)
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View in JSmol
Synonyms
ValueSource
2-Amino-4-sulfobutyric acidChEBI
2-Amino-4-sulfobutyrateGenerator
2-Amino-4-sulphobutyrateGenerator
2-Amino-4-sulphobutyric acidGenerator
HomocysteateGenerator
DL-HomocysteateGenerator
Homocysteic acidMeSH
Homocysteic acid, (DL)-isomerMeSH
Homocysteic acid, monosodium saltMeSH
Homocysteic acid, sodium salt, (+-)-isomerMeSH
Homocysteic acid, monosodium salt, (+-)-isomerMeSH
2-Amino-4-sulfobutanoic acidMeSH
Homocysteic acid, (D)-isomerMeSH
(DL)-Homocysteic acidMeSH
Homocysteic acid, (L)-isomerMeSH
Chemical FormulaC4H9NO5S
Average Mass183.1800 Da
Monoisotopic Mass183.02014 Da
IUPAC Name2-amino-4-sulfobutanoic acid
Traditional Name2-amino-4-sulfobutanoic acid
CAS Registry NumberNot Available
SMILES
NC(CCS(O)(=O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)
InChI KeyVBOQYPQEPHKASR-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • Thia fatty acid
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • Organic sulfonic acid or derivatives
    • 

  • Organosulfonic acid or derivatives
    • 

  • Organosulfonic acid
    • 

  • Sulfonyl
    • 

  • Alkanesulfonic acid
    • 

  • Amino acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Primary amine
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP-2.4ALOGPS
logP-2.9ChemAxon
logS-0.45ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability15.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHomocysteic acid  
METLIN IDNot Available
PubChem Compound92117  
PDB IDNot Available
ChEBI ID90324  
Good Scents IDNot Available
References
General References
  1. Harasawa I, Johansen JP, Fields HL, Porreca F, Meng ID: Alterations in the rostral ventromedial medulla after the selective ablation of mu-opioid receptor expressing neurons. Pain. 2016 Jan;157(1):166-173. doi: 10.1097/j.pain.0000000000000344. [PubMed:26335909  ] 
  2. Guo ZL, Longhurst JC, Tjen-A-Looi SC, Fu LW: elPBN neurons regulate rVLM activity through elPBN-rVLM projections during activation of cardiac sympathetic afferent nerves. Am J Physiol Regul Integr Comp Physiol. 2016 Aug 1;311(2):R410-25. doi: 10.1152/ajpregu.00127.2016. Epub 2016 May 25. [PubMed:27225950  ]