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Showing NP-Card for L-Tartaric acid (NP0002638)

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Record Information
Version1.0
Created at2020-11-23 18:25:48 UTC
Updated at2021-08-19 23:59:14 UTC
NP-MRD IDNP0002638
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Tartaric acid
Provided ByBMRBBMRB logo
DescriptionD-tartaric acid is also known as erythraric acid or mesoweinsaeure. L-Tartaric acid is found in Parasenecio hastatus, Laetiporus sulphureus, Plantago major and Scutellaria baicalensis. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on D-tartaric acid (PMID: 33433553) (PMID: 34378325) (PMID: 34352583) (PMID: 33492931).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002638 (L-Tartaric acid)


     RDKit          2D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.2647   -1.2005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6678    0.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8262    1.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2633    0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412    1.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -1.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678   -0.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647    1.2005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262   -1.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2307    0.6021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7899    2.1068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3874    2.7085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7899   -2.1068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -2.7085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307   -0.6021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  6
  5 13  1  0
  6 14  1  1
  7 15  1  0
 10 16  1  0
M  END
Download

3D MOL for NP0002638 (L-Tartaric acid)

NP0002638
     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
    1.9386   -0.1038    1.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6154   -0.0811    0.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4787    0.4031   -0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958   -0.5768    0.3910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4401   -1.0274    1.4823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    0.5595   -0.3373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4484    0.9147   -1.3983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6929    0.2228   -0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9585    0.2664   -2.0886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834   -0.1615    0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0524   -0.1487   -0.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3847   -1.4339   -0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0350   -0.8919    2.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878    1.4247    0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446    0.0848   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2477    0.5490    0.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  6
  5 13  1  0
  6 14  1  1
  7 15  1  0
 10 16  1  0
M  END
Download

3D SDF for NP0002638 (L-Tartaric acid)


     RDKit          2D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.2647   -1.2005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6678    0.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8262    1.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2633    0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412    1.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -1.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678   -0.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647    1.2005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262   -1.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2307    0.6021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7899    2.1068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3874    2.7085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7899   -2.1068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -2.7085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307   -0.6021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  6
  5 13  1  0
  6 14  1  1
  7 15  1  0
 10 16  1  0
M  END
> <DATABASE_ID>
NP0002638

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2+

> <INCHI_KEY>
FEWJPZIEWOKRBE-XIXRPRMCSA-N

> <FORMULA>
C4H6O6

> <MOLECULAR_WEIGHT>
150.0868

> <EXACT_MASS>
150.016437924

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
11.694464646180473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-2,3-dihydroxybutanedioic acid

> <ALOGPS_LOGP>
-1.27

> <JCHEM_LOGP>
-1.8287998886666665

> <ALOGPS_LOGS>
0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.792876457889946

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7190410038171646

> <JCHEM_PKA_STRONGEST_BASIC>
-4.330574673439462

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
26.213400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-tartaric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002638 (L-Tartaric acid)

NP0002638
     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
    1.9386   -0.1038    1.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6154   -0.0811    0.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4787    0.4031   -0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958   -0.5768    0.3910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4401   -1.0274    1.4823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    0.5595   -0.3373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4484    0.9147   -1.3983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6929    0.2228   -0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9585    0.2664   -2.0886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834   -0.1615    0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0524   -0.1487   -0.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3847   -1.4339   -0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0350   -0.8919    2.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878    1.4247    0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446    0.0848   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2477    0.5490    0.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  6
  5 13  1  0
  6 14  1  1
  7 15  1  0
 10 16  1  0
M  END
Download

PDB for NP0002638 (L-Tartaric acid)

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       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.644   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       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0002638 (L-Tartaric acid)

COMPND    NP0002638
HETATM    1  O1  UNL     1       1.939  -0.104   1.997  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.615  -0.081   0.803  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.479   0.403  -0.141  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.296  -0.577   0.391  1.00  0.00           C  
HETATM    5  O3  UNL     1      -0.440  -1.027   1.482  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.383   0.560  -0.337  1.00  0.00           C  
HETATM    7  O4  UNL     1       0.448   0.915  -1.398  1.00  0.00           O  
HETATM    8  C4  UNL     1      -1.693   0.223  -0.871  1.00  0.00           C  
HETATM    9  O5  UNL     1      -1.958   0.266  -2.089  1.00  0.00           O  
HETATM   10  O6  UNL     1      -2.683  -0.161   0.009  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.052  -0.149  -0.762  1.00  0.00           H  
HETATM   12  H2  UNL     1       0.385  -1.434  -0.327  1.00  0.00           H  
HETATM   13  H3  UNL     1       0.035  -0.892   2.348  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.388   1.425   0.356  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.545   0.085  -1.951  1.00  0.00           H  
HETATM   16  H6  UNL     1      -3.248   0.549   0.491  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    6   12
CONECT    5   13
CONECT    6    7    8   14
CONECT    7   15
CONECT    8    9    9   10
CONECT   10   16
END
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SMILES for NP0002638 (L-Tartaric acid)

O[C@@H]([C@@H](O)C(O)=O)C(O)=O
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INCHI for NP0002638 (L-Tartaric acid)

InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2+
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View in JSmol
Synonyms
ValueSource
(2R,3S)-2,3-Dihydroxysuccinic acidChEBI
(2R,3S)-Rel-2,3-dihydroxybutanedioic acidChEBI
(2R,3S)-Tartaric acidChEBI
(R*,s*)-2,3-dihydroxybutanedioic acidChEBI
Erythraric acidChEBI
Internally compensated tartaric acidChEBI
m-Tartaric acidChEBI
Mesotartaric acidChEBI
MesoweinsaeureChEBI
S,R MESO-tartarIC ACIDChEBI
Unresolvable tartaric acidChEBI
Meso-tartrateKegg
(2R,3S)-2,3-DihydroxysuccinateGenerator
(2R,3S)-Rel-2,3-dihydroxybutanedioateGenerator
(2R,3S)-TartarateGenerator
(R*,s*)-2,3-dihydroxybutanedioateGenerator
ErythrarateGenerator
Internally compensated tartarateGenerator
m-TartarateGenerator
MesotartarateGenerator
S,R MESO-tartarateGenerator
Unresolvable tartarateGenerator
Meso-tartric acidGenerator
D-TartarateGenerator
Chemical FormulaC4H6O6
Average Mass150.0868 Da
Monoisotopic Mass150.01644 Da
IUPAC Name(2R,3S)-2,3-dihydroxybutanedioic acid
Traditional Name(-)-tartaric acid
CAS Registry NumberNot Available
SMILES
O[C@@H]([C@@H](O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2+
InChI KeyFEWJPZIEWOKRBE-XIXRPRMCSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cacalia hastataLOTUS Database
Laetiporus sulphureusLOTUS Database
Plantago majorLOTUS Database
Scutellaria baicalensisLOTUS Database
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Sugar acid
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Fatty acid
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point147.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling PointNot AvailableNot Available
Water Solubility560000 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.3ALOGPS
logP-1.8ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.21 m³·mol⁻¹ChemAxon
Polarizability11.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB01694
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID394447
KEGG Compound IDC00552
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTartaric acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15673
Good Scents IDrw1345931
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Das S, Dalal A, Gholap SL: Stereoselective total syntheses of (-)-hygrophorone A(12), 4-O-acetyl-hygrophorone A(12) and (+)-hygrophorone B(12). Org Biomol Chem. 2021 Feb 11;19(5):1100-1108. doi: 10.1039/d0ob02303e. [PubMed:33433553 ]
  3. Song G, Kim KM, Lee S, Jeong KS: Subtle Modification of Imine-linked Helical Receptors to Significantly Alter their Binding Affinities and Selectivities for Chiral Guests. Chem Asian J. 2021 Oct 4;16(19):2958-2966. doi: 10.1002/asia.202100768. Epub 2021 Aug 18. [PubMed:34378325 ]
  4. Huang HY, Ren QQ, Lai YH, Peng MY, Zhang J, Yang LT, Huang ZR, Chen LS: Metabolomics combined with physiology and transcriptomics reveals how Citrus grandis leaves cope with copper-toxicity. Ecotoxicol Environ Saf. 2021 Oct 15;223:112579. doi: 10.1016/j.ecoenv.2021.112579. Epub 2021 Aug 2. [PubMed:34352583 ]
  5. Liu J, Wang D, Xu X, Li H, Zhao J, Chen L: Multi-Nuclear Rare-Earth-Implanted Tartaric Acid-Functionalized Selenotungstates and Their Fluorescent and Magnetic Properties. Inorg Chem. 2021 Feb 15;60(4):2533-2541. doi: 10.1021/acs.inorgchem.0c03443. Epub 2021 Jan 25. [PubMed:33492931 ]