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Showing NP-Card for Erythronic acid gamma-lactone (NP0083939)

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Record Information
Version1.0
Created at2022-04-29 04:49:30 UTC
Updated at2022-04-29 04:49:30 UTC
NP-MRD IDNP0083939
Secondary Accession NumbersNone
Natural Product Identification
Common NameErythronic acid gamma-lactone
DescriptionErythrono-1,4-lactone, also known as erythronate g-lactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Erythronic acid gamma-lactone is found in Averrhoa carambola . It was first documented in 1975 (PMID: 1192581). Erythrono-1,4-lactone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083939 (Erythronic acid gamma-lactone)


  Mrv0541 02231218282D          

  8  8  0  0  1  0            999 V2000
   15.6628  -15.0213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5601  -16.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7655  -16.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2108  -15.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0753  -16.2907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2502  -16.2907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3302  -15.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9955  -15.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  5  2  1  1  0  0  0
  6  3  1  1  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for NP0083939 (Erythronic acid gamma-lactone)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    1.9335   -1.6540    0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8808   -1.0870    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3683   -1.6488   -0.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745   -0.6657   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557    0.6561    0.0789 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6815    1.0023    1.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385    0.3167   -0.4260 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7072    1.1582    0.0474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7410   -0.6141   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1888   -0.8530    0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128    1.4660   -0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972    0.3887    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707    0.2706   -1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    1.2641   -0.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2  7  1  0
  7  8  1  0
  7  5  1  0
  6 12  1  0
  5 11  1  6
  4  9  1  0
  4 10  1  0
  7 13  1  6
  8 14  1  0
M  END
Download

3D SDF for NP0083939 (Erythronic acid gamma-lactone)


  Mrv0541 02231218282D          

  8  8  0  0  1  0            999 V2000
   15.6628  -15.0213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5601  -16.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7655  -16.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2108  -15.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0753  -16.2907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2502  -16.2907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3302  -15.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9955  -15.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  5  2  1  1  0  0  0
  6  3  1  1  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1COC(=O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1

> <INCHI_KEY>
SGMJBNSHAZVGMC-PWNYCUMCSA-N

> <FORMULA>
C4H6O4

> <MOLECULAR_WEIGHT>
118.088

> <EXACT_MASS>
118.02660868

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
9.837678905951314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R)-3,4-dihydroxyoxolan-2-one

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-1.484603302

> <ALOGPS_LOGS>
1.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.000796211703818

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.66159827209987

> <JCHEM_PKA_STRONGEST_BASIC>
-3.608833819644188

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
22.8538

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erythrono-1,4-lactone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0083939 (Erythronic acid gamma-lactone)

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PDB for NP0083939 (Erythronic acid gamma-lactone)
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      29.237 -28.040   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.912 -31.655   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      27.562 -31.655   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      26.527 -28.469   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      30.007 -30.409   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.467 -30.409   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.483 -28.945   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.992 -28.945   0.000  0.00  0.00           C+0
CONECT    1    7    8                                                       
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    8                                                            
CONECT    5    2    6    7                                                  
CONECT    6    3    5    8                                                  
CONECT    7    1    5                                                       
CONECT    8    1    4    6                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0083939 (Erythronic acid gamma-lactone)
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SMILES for NP0083939 (Erythronic acid gamma-lactone)
O[C@@H]1COC(=O)[C@@H]1O
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INCHI for NP0083939 (Erythronic acid gamma-lactone)
InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1
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View in JSmol
Synonyms
ValueSource
D-ErythronolactoneChEBI
Erythronic acid gamma-lactoneChEBI
Erythronate g-lactoneGenerator
Erythronate gamma-lactoneGenerator
Erythronate γ-lactoneGenerator
Erythronic acid g-lactoneGenerator
Erythronic acid γ-lactoneGenerator
(3R,4R)-Dihydro-3,4-dihydroxy-threono-1,4-lactone 2(3H)-furanoneHMDB
(3R,4R)-Rel-dihydro-3,4-dihydroxy-2(3H)-furanoneHMDB
3,4-Dihydroxydihydro-2(3H)-furanoneHMDB
D-Erythronic acid gamma-lactoneHMDB
delta-Erythronic acid gamma-lactoneHMDB
Dihydro-3,4-dihydroxy-cis-2(3H)-furanoneHMDB
Chemical FormulaC4H6O4
Average Mass118.0880 Da
Monoisotopic Mass118.02661 Da
IUPAC Name(3R,4R)-3,4-dihydroxyoxolan-2-one
Traditional Nameerythrono-1,4-lactone
CAS Registry NumberNot Available
SMILES
O[C@@H]1COC(=O)[C@@H]1O
InChI Identifier
InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1
InChI KeySGMJBNSHAZVGMC-PWNYCUMCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Averrhoa carambolaPlant
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassGamma butyrolactones  
Direct ParentGamma butyrolactones  
Alternative Parents
Substituents
  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • 1,2-diol
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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-1.7ALOGPS
logP-1.5ChemAxon
logS1.02ALOGPS
pKa (Strongest Acidic)11.66ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.85 m³·mol⁻¹ChemAxon
Polarizability9.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000349  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021972  
KNApSAcK IDNot Available
Chemspider ID4483398  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5338  
PubChem Compound5325915  
PDB IDNot Available
ChEBI ID87625  
Good Scents IDNot Available
References
General References
  1. Thompson JA, Markey SP, Fennessey PV: Gas-chromatographic/mass-spectrometric identification and quantitation of tetronic and deoxytetronic acids in urine from normal adults and neonates. Clin Chem. 1975 Dec;21(13):1892-8. [PubMed:1192581  ]