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Showing NP-Card for l-dithiothreitol (NP0296734)

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Record Information
Version2.0
Created at2022-09-10 06:29:54 UTC
Updated at2022-09-10 06:29:54 UTC
NP-MRD IDNP0296734
Secondary Accession NumbersNone
Natural Product Identification
Common Namel-dithiothreitol
Description1,4-Dithiothreitol, also known as clelands reagent or reagent, cleland's, belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions. 1,4-Dithiothreitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Dimerization greatly lowers the efficiency of subsequent coupling reactions such as DNA immobilization on gold in biosensors. 1,4-Dithiothreitol exists in all living organisms, ranging from bacteria to humans. DTT is frequently used to reduce the disulfide bonds of proteins and, more generally, to prevent intramolecular and intermolecular disulfide bonds from forming between cysteine residues of proteins. 1,4-Dithiothreitol can be converted into oxidized dithiothreitol; which is catalyzed by the enzyme vitamin K epoxide reductase complex subunit 1. In humans, 1,4-dithiothreitol is involved in vitamin k metabolism. Its principal advantage is that effectively no mixed-disulfide species are populated, in contrast to other agents such as glutathione. In very rare cases, a DTT adduct may be formed, i.E., The two sulfur atoms of DTT may form disulfide bonds to different sulfur atoms; in such cases, DTT cannot cyclize since it has no remaining free thiols. Dithiothreitol (DTT) is the common name for a small-molecule redox reagent known as Cleland's reagent.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0296734 (l-dithiothreitol)


  Mrv1652303102016522D          

  8  7  0  0  1  0            999 V2000
    5.2408   -8.5347    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553   -8.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6698   -8.5347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3843   -8.1222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0988   -8.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8133   -8.1222    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6698   -9.3597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3843   -7.2972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  3  7  1  1  0  0  0
  4  8  1  1  0  0  0
M  END
Download

3D MOL for NP0296734 (l-dithiothreitol)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
   -0.5179    1.0249   -0.5789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908    0.2254    0.5637 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8401   -0.4061    0.7224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    0.9431    0.8918 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.8023    0.4691 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3827   -1.5993   -0.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677   -0.1502    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0166    0.9017   -1.1041 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501    0.6031   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3247    0.8969    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8927   -1.0842    1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.9725   -0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7494    1.9981    0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -1.4621    1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.0109   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523    0.5401    1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7465   -0.9208    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3401    1.2750   -1.3642 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
  2  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  1  9  1  0
  2 10  1  1
  3 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  1
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
M  END
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3D SDF for NP0296734 (l-dithiothreitol)


  Mrv1652303102016522D          

  8  7  0  0  1  0            999 V2000
    5.2408   -8.5347    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553   -8.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6698   -8.5347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3843   -8.1222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0988   -8.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8133   -8.1222    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6698   -9.3597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3843   -7.2972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  3  7  1  1  0  0  0
  4  8  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0296734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H](CS)[C@@H](O)CS

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m0/s1

> <INCHI_KEY>
VHJLVAABSRFDPM-IMJSIDKUSA-N

> <FORMULA>
C4H10O2S2

> <MOLECULAR_WEIGHT>
154.251

> <EXACT_MASS>
154.012220944

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.681480052396674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-1,4-disulfanylbutane-2,3-diol

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
-0.27842509266666665

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.219099376080758

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.616219832236466

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2867962949581777

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
38.8438

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-dithiothreitol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0296734 (l-dithiothreitol)

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PDB for NP0296734 (l-dithiothreitol)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  S   UNK     0       9.783 -15.931   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0      11.117 -15.161   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.450 -15.931   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.784 -15.161   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.118 -15.931   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      16.451 -15.161   0.000  0.00  0.00           S+0
HETATM    7  O   UNK     0      12.450 -17.471   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      13.784 -13.621   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    3                                                            
CONECT    8    4                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0296734 (l-dithiothreitol)
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SMILES for NP0296734 (l-dithiothreitol)
O[C@@H](CS)[C@@H](O)CS
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INCHI for NP0296734 (l-dithiothreitol)
InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m0/s1
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View in JSmol
Synonyms
ValueSource
(2R,3R)-1,4-Dimercaptobutane-2,3-diolChEBI
2,3-DIHYDROXY-1,4-dithiobutaneChEBI
DL-Threo-1,4-dimercapto-2,3-butanediolChEBI
L-DithiothreitolChEBI
L-DTTChEBI
L-Threo-1,4-dimercapto-2,3-butanediolChEBI
Threo-1,4-dimercapto-2,3-butanediolChEBI
DithiothreitolHMDB
SputolysinHMDB
Clelands reagentHMDB
Cleland reagentHMDB
Cleland's reagentHMDB
Reagent, clelandHMDB
Reagent, cleland'sHMDB
Chemical FormulaC4H10O2S2
Average Mass154.2510 Da
Monoisotopic Mass154.01222 Da
IUPAC Name(2R,3R)-1,4-disulfanylbutane-2,3-diol
Traditional NameL-dithiothreitol
CAS Registry NumberNot Available
SMILES
O[C@@H](CS)[C@@H](O)CS
InChI Identifier
InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m0/s1
InChI KeyVHJLVAABSRFDPM-IMJSIDKUSA-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 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct Parent1,2-diols  
Alternative Parents
Substituents
  • Secondary alcohol
    • 

  • 1,2-diol
    • 

  • Alkylthiol
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • 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
logP0.18ALOGPS
logP-0.28ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)9.62ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.84 m³·mol⁻¹ChemAxon
Polarizability15.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013593  
DrugBank IDDB04447  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029593  
KNApSAcK IDNot Available
Chemspider ID388336  
KEGG Compound IDC00265  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDithiothreitol  
METLIN IDNot Available
PubChem Compound439196  
PDB IDDTT  
ChEBI ID42106  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]