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Showing NP-Card for l-threitol (NP0292117)

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Record Information
Version2.0
Created at2022-09-09 23:29:47 UTC
Updated at2022-09-09 23:29:48 UTC
NP-MRD IDNP0292117
Secondary Accession NumbersNone
Natural Product Identification
Common Namel-threitol
DescriptionD-Treitol, also known as L-threo-tetritol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. D-Treitol is an extremely weak basic (essentially neutral) compound (based on its pKa). l-threitol is found in Chlamydomonas reinhardtii. l-threitol was first documented in 1994 (PMID: 7925706). The L-enantiomer of threitol (PMID: 16901854) (PMID: 15639248) (PMID: 16671745).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0292117 (l-threitol)


  Mrv0541 02231216502D          

  8  7  0  0  1  0            999 V2000
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    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  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0292117 (l-threitol)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
   -0.9559    1.8163    0.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3170    1.0685   -0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8702   -0.3542   -0.3520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4104   -0.9883    0.7615 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5840   -0.5945   -0.5434 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0419    0.0736   -1.6614 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4463   -0.3864    0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910    0.9715    0.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919    1.2831    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4385    1.0815   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0127    1.5810   -1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3644   -0.8639   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6238   -1.9406    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710   -1.6967   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -0.4868   -2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921   -0.6906    0.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1319   -0.9884    1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303    1.1149    1.9060 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  3 12  1  6
  4 13  1  0
  5 14  1  6
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
M  END
Download

3D SDF for NP0292117 (l-threitol)


  Mrv0541 02231216502D          

  8  7  0  0  1  0            999 V2000
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    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  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292117

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H](O)[C@@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m0/s1

> <INCHI_KEY>
UNXHWFMMPAWVPI-IMJSIDKUSA-N

> <FORMULA>
C4H10O4

> <MOLECULAR_WEIGHT>
122.1198

> <EXACT_MASS>
122.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
11.624074279377824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-butane-1,2,3,4-tetrol

> <ALOGPS_LOGP>
-2.03

> <JCHEM_LOGP>
-2.4693489646666666

> <ALOGPS_LOGS>
0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.285181811808233

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.044993073077713

> <JCHEM_PKA_STRONGEST_BASIC>
-2.973906601202132

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
26.478599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-threitol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0292117 (l-threitol)

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PDB for NP0292117 (l-threitol)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.310  -0.206   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0292117 (l-threitol)
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SMILES for NP0292117 (l-threitol)
OC[C@H](O)[C@@H](O)CO
Download
INCHI for NP0292117 (l-threitol)
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m0/s1
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View in JSmol
Synonyms
ValueSource
L-Threo-tetritolChEBI
D-TREITOLChEBI
Chemical FormulaC4H10O4
Average Mass122.1198 Da
Monoisotopic Mass122.05791 Da
IUPAC Name(2S,3S)-butane-1,2,3,4-tetrol
Traditional NameL-threitol
CAS Registry NumberNot Available
SMILES
OC[C@H](O)[C@@H](O)CO
InChI Identifier
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m0/s1
InChI KeyUNXHWFMMPAWVPI-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 Origin
Species NameSourceReference
Chlamydomonas reinhardtiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentSugar alcohols  
Alternative Parents
Substituents
  • Sugar alcohol
    • 

  • Secondary alcohol
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Alcohol
    • 

  • 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
logP-2ALOGPS
logP-2.5ChemAxon
logS0.98ALOGPS
pKa (Strongest Acidic)13.04ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.48 m³·mol⁻¹ChemAxon
Polarizability11.62 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB03278  
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 LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID42090  
Good Scents IDNot Available
References
General References
  1. Sreenath K, Prabhasankar P, Venkatesh YP: Generation of an antibody specific to erythritol, a non-immunogenic food additive. Food Addit Contam. 2006 Sep;23(9):861-9. doi: 10.1080/02652030600722353. [PubMed:16901854  ] 
  2. Jesus AJ, Tome LI, Rosado MT, Leitao ML, Redinha JS: Conformational study of erythritol and threitol in the gas state by density functional theory calculations. Carbohydr Res. 2005 Feb 7;340(2):283-91. doi: 10.1016/j.carres.2004.11.018. [PubMed:15639248  ] 
  3. Lopes Jesus AJ, Tome LI, Eusebio ME, Redinha JS: Determination of the enthalpy of solute-solvent interaction from the enthalpy of solution: aqueous solutions of erythritol and L-threitol. J Phys Chem B. 2006 May 11;110(18):9280-5. doi: 10.1021/jp0561221. [PubMed:16671745  ] 
  4. Ortwerth BJ, Speaker JA, Prabhakaram M, Lopez MG, Li EY, Feather MS: Ascorbic acid glycation: the reactions of L-threose in lens tissue. Exp Eye Res. 1994 Jun;58(6):665-74. doi: 10.1006/exer.1994.1064. [PubMed:7925706  ] 
  5. LOTUS database [Link]