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Showing NP-Card for 2-Methylerythritol (NP0334797)

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Record Information
Version2.0
Created at2024-09-10 20:00:32 UTC
Updated at2024-09-10 20:00:32 UTC
NP-MRD IDNP0334797
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Methylerythritol
Description2-Methylerythritol 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. 2-Methylerythritol is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methylerythritol was first documented in 2004 (PMID: 15384409). A tetritol that is erythritol substituted by a methyl group at position 2.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334797 (2-Methylerythritol)


  Mrv0541 02241201492D          

  9  8  0  0  1  0            999 V2000
   10.1286   -7.1765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9536   -7.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3661   -7.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1911   -7.8910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6036   -8.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4286   -8.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9536   -8.6054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7329   -7.3057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -6.8982    0.0000 C   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  6  0  0  0
  4  8  1  1  0  0  0
  3  9  1  1  0  0  0
M  END
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3D MOL for NP0334797 (2-Methylerythritol)

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3D SDF for NP0334797 (2-Methylerythritol)

  Mrv0541 02241201492D          

  9  8  0  0  1  0            999 V2000
   10.1286   -7.1765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9536   -7.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3661   -7.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1911   -7.8910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6036   -8.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4286   -8.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9536   -8.6054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7329   -7.3057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -6.8982    0.0000 C   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  6  0  0  0
  4  8  1  1  0  0  0
  3  9  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334797

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H12O4/c1-5(9,3-7)4(8)2-6/h4,6-9H,2-3H2,1H3/t4-,5+/m0/s1

> <INCHI_KEY>
HGVJFBSSLICXEM-CRCLSJGQSA-N

> <FORMULA>
C5H12O4

> <MOLECULAR_WEIGHT>
136.1464

> <EXACT_MASS>
136.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
13.345309394881504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.84

> <JCHEM_LOGP>
-2.188772296333333

> <ALOGPS_LOGS>
0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.098447823363575

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.8859950940716

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9777325528655147

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
31.116799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.42e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-2-methylbutane-1,2,3,4-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334797 (2-Methylerythritol)
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PDB for NP0334797 (2-Methylerythritol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      18.907 -13.396   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      20.447 -13.396   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.217 -14.730   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.757 -14.730   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.527 -16.063   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      25.067 -16.064   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      20.447 -16.063   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      23.768 -13.637   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      21.578 -12.877   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    7    9                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    3                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0334797 (2-Methylerythritol)
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SMILES for NP0334797 (2-Methylerythritol)
CC(O)(CO)[C@@H](O)CO
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INCHI for NP0334797 (2-Methylerythritol)
InChI=1S/C5H12O4/c1-5(9,3-7)4(8)2-6/h4,6-9H,2-3H2,1H3/t4-,5+/m0/s1
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Synonyms
ValueSource
(2R,3S)-2-Methyl-1,2,3,4-butanetetrolHMDB
2-C-Methyl-D-erythritolHMDB
2-C-MethylerythritolHMDB
3-MethylerythritolHMDB
[S-(R,S)]-2-Methyl-1,2,3,4-butanetetrolHMDB
3-C-MethylerythritolHMDB
2-MethylerythritolMeSH, HMDB
Chemical FormulaC5H12O4
Average Mass136.1464 Da
Monoisotopic Mass136.07356 Da
IUPAC Name(3S)-2-methylbutane-1,2,3,4-tetrol
Traditional Name(3S)-2-methylbutane-1,2,3,4-tetrol
CAS Registry NumberNot Available
SMILES
CC(O)(CO)[C@@H](O)CO
InChI Identifier
InChI=1S/C5H12O4/c1-5(9,3-7)4(8)2-6/h4,6-9H,2-3H2,1H3/t4-,5+/m0/s1
InChI KeyHGVJFBSSLICXEM-CRCLSJGQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • Tertiary 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-1.8ALOGPS
logP-2.2ChemAxon
logS0.74ALOGPS
pKa (Strongest Acidic)12.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.12 m³·mol⁻¹ChemAxon
Polarizability13.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011659  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028350  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481015  
PDB IDNot Available
ChEBI ID86367  
Good Scents IDNot Available
References
General References
  1. Enomoto H, Kohata K, Nakayama M, Yamaguchi Y, Ichimura K: 2-C-methyl-D-erythritol is a major carbohydrate in petals of Phlox subulata possibly involved in flower development. J Plant Physiol. 2004 Aug;161(8):977-80. doi: 10.1016/j.jplph.2004.01.009. [PubMed:15384409  ]