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Showing NP-Card for (+)-Gentiolactone (NP0057648)

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Record Information
Version2.0
Created at2022-04-28 03:03:11 UTC
Updated at2022-04-28 03:03:11 UTC
NP-MRD IDNP0057648
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Gentiolactone
Description(R)-(?)-Gentiolactone belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. (+)-Gentiolactone is found in Gentiana lutea and Gentiana purpurea . Based on a literature review very few articles have been published on (R)-(?)-Gentiolactone.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0057648 ((+)-Gentiolactone)


  Mrv1652304282205032D          

 15 16  0  0  1  0            999 V2000
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
M  END
Download

3D MOL for NP0057648 ((+)-Gentiolactone)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -3.0171   -0.8754   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4959   -1.0031   -0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095    0.1065    0.3088 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3865   -0.1032    1.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4190    1.3817   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5790    1.7491    0.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216    2.1665   -1.0384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652    2.1462   -0.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    0.9143   -0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5582    0.0528    0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639   -0.9562    1.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -1.5229    0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048   -0.4468    0.1215 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523    0.6938   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823    1.4990   -1.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4104   -0.1637   -1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5100   -1.8590   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3116   -0.4945    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -0.9339   -1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385   -2.0030   -0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    0.7876    2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2270    2.2373   -1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1071    3.0299   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7194   -0.4133    2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140   -1.7695    1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -1.8745   -0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9203   -2.3456    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  1
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 10  3  1  0
 14  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  8 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
M  END
Download

3D SDF for NP0057648 ((+)-Gentiolactone)


  Mrv1652304282205032D          

 15 16  0  0  1  0            999 V2000
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]1(O)C(=O)OCC2=C1CCOC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5/c1-2-10(13)7-3-4-14-8(11)6(7)5-15-9(10)12/h13H,2-5H2,1H3/t10-/m1/s1

> <INCHI_KEY>
YOWUDEPRYODFBZ-SNVBAGLBSA-N

> <FORMULA>
C10H12O5

> <MOLECULAR_WEIGHT>
212.201

> <EXACT_MASS>
212.068473486

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.97730026553964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-5-ethyl-5-hydroxy-1H,3H,4H,5H,6H,8H-pyrano[3,4-c]pyran-1,6-dione

> <ALOGPS_LOGP>
-0.07

> <JCHEM_LOGP>
0.2123452430000002

> <ALOGPS_LOGS>
-0.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.750825317528019

> <JCHEM_PKA_STRONGEST_BASIC>
-4.219989006113242

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
49.7659

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.76e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-ethyl-5-hydroxy-3H,4H,8H-pyrano[3,4-c]pyran-1,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0057648 ((+)-Gentiolactone)

Download
PDB for NP0057648 ((+)-Gentiolactone)
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      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.390  -4.440   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.405  -4.493   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    1                                                       
CONECT    8    3    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    2   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

Download
3D PDB for NP0057648 ((+)-Gentiolactone)
Download
SMILES for NP0057648 ((+)-Gentiolactone)
CC[C@]1(O)C(=O)OCC2=C1CCOC2=O
Download
INCHI for NP0057648 ((+)-Gentiolactone)
InChI=1S/C10H12O5/c1-2-10(13)7-3-4-14-8(11)6(7)5-15-9(10)12/h13H,2-5H2,1H3/t10-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H12O5
Average Mass212.2010 Da
Monoisotopic Mass212.06847 Da
IUPAC Name(5R)-5-ethyl-5-hydroxy-1H,3H,4H,5H,6H,8H-pyrano[3,4-c]pyran-1,6-dione
Traditional Name(5R)-5-ethyl-5-hydroxy-3H,4H,8H-pyrano[3,4-c]pyran-1,6-dione
CAS Registry NumberNot Available
SMILES
CC[C@]1(O)C(=O)OCC2=C1CCOC2=O
InChI Identifier
InChI=1S/C10H12O5/c1-2-10(13)7-3-4-14-8(11)6(7)5-15-9(10)12/h13H,2-5H2,1H3/t10-/m1/s1
InChI KeyYOWUDEPRYODFBZ-SNVBAGLBSA-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
Gentiana luteaPlant
Gentiana purpureaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentDihydropyranones  
Alternative Parents
Substituents
  • Dihydropyranone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tertiary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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-0.07ALOGPS
logP0.21ChemAxon
logS-0.44ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.77 m³·mol⁻¹ChemAxon
Polarizability19.98 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9206313  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11031139  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References