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Showing NP-Card for (+)-(R)-3-Hydroxy-.gamma.-butyrolactone (NP0070680)

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Record Information
Version1.0
Created at2022-04-28 16:08:29 UTC
Updated at2022-04-28 16:08:29 UTC
NP-MRD IDNP0070680
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-(R)-3-Hydroxy-.gamma.-butyrolactone
Description58081-05-3 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. (+)-(R)-3-Hydroxy-.gamma.-butyrolactone is found in Anoectochilus formosanus. Based on a literature review very few articles have been published on 58081-05-3.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0070680 ((+)-(R)-3-Hydroxy-.gamma.-butyrolactone)


  Mrv1652304282218082D          

  7  7  0  0  1  0            999 V2000
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  1  0  0  0
M  END
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3D MOL for NP0070680 ((+)-(R)-3-Hydroxy-.gamma.-butyrolactone)

     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
   -0.9706    2.6303    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    1.5640    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7539    0.3861   -0.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257   -0.7105    0.2128 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0899   -1.9225   -0.4156 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524   -0.0774    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    1.2618    0.7344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224    0.2583   -0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1917    0.3933   -1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6352   -0.7187    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7641   -2.5225    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7433    0.0062   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -0.5483    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  6  1  0
  6  7  1  0
  7  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  5 11  1  0
  4 10  1  1
  6 12  1  0
  6 13  1  0
  3  8  1  0
  3  9  1  0
M  END
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3D SDF for NP0070680 ((+)-(R)-3-Hydroxy-.gamma.-butyrolactone)


  Mrv1652304282218082D          

  7  7  0  0  1  0            999 V2000
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0070680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1COC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O3/c5-3-1-4(6)7-2-3/h3,5H,1-2H2/t3-/m1/s1

> <INCHI_KEY>
FUDDLSHBRSNCBV-GSVOUGTGSA-N

> <FORMULA>
C4H6O3

> <MOLECULAR_WEIGHT>
102.089

> <EXACT_MASS>
102.031694053

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.075206879473496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-4-hydroxyoxolan-2-one

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-0.7694448413333334

> <ALOGPS_LOGS>
1.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.181664640858479

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1567398860885003

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
21.5156

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-hydroxyoxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0070680 ((+)-(R)-3-Hydroxy-.gamma.-butyrolactone)

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PDB for NP0070680 ((+)-(R)-3-Hydroxy-.gamma.-butyrolactone)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
CONECT    1    2    3    6                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0070680 ((+)-(R)-3-Hydroxy-.gamma.-butyrolactone)
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SMILES for NP0070680 ((+)-(R)-3-Hydroxy-.gamma.-butyrolactone)
O[C@H]1COC(=O)C1
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INCHI for NP0070680 ((+)-(R)-3-Hydroxy-.gamma.-butyrolactone)
InChI=1S/C4H6O3/c5-3-1-4(6)7-2-3/h3,5H,1-2H2/t3-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC4H6O3
Average Mass102.0890 Da
Monoisotopic Mass102.03169 Da
IUPAC Name(4R)-4-hydroxyoxolan-2-one
Traditional Name(4R)-4-hydroxyoxolan-2-one
CAS Registry NumberNot Available
SMILES
O[C@H]1COC(=O)C1
InChI Identifier
InChI=1S/C4H6O3/c5-3-1-4(6)7-2-3/h3,5H,1-2H2/t3-/m1/s1
InChI KeyFUDDLSHBRSNCBV-GSVOUGTGSA-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
Anoectochilus formosanusPlant
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
    • 

  • Oxolane
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • 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-0.96ALOGPS
logP-0.77ChemAxon
logS1.04ALOGPS
pKa (Strongest Acidic)14.18ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.52 m³·mol⁻¹ChemAxon
Polarizability9.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00029343  
Chemspider ID5416576  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7060520  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available