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Showing NP-Card for Galanolactone (NP0048822)

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Record Information
Version2.0
Created at2022-03-17 21:02:43 UTC
Updated at2022-03-17 21:02:43 UTC
NP-MRD IDNP0048822
Secondary Accession NumbersNone
Natural Product Identification
Common NameGalanolactone
DescriptionGalanolactone 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. Galanolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Galanolactone has been detected, but not quantified in, gingers and herbs and spices. This could make galanolactone a potential biomarker for the consumption of these foods. Galanolactone is found in Aframomum alboviolaceum, Aframomum zambesiacum (Baker) K.Schum. and Alpinia galanga . Galanolactone is a diterpenoid lactone first isolated from ginger.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048822 (Galanolactone)


  Mrv0541 05061309502D          

 23 26  0  0  0  0            999 V2000
    5.3522    1.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    1.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -0.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8929   -1.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6870   -1.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976    0.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229   -2.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2730   -0.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2753   -1.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5035    0.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9764   -3.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7239   -0.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -2.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8882    0.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165   -3.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6824    0.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -0.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999   -0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398   -3.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759   -3.8397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5004    0.0944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  4  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 14  5  2  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 16  6  1  0  0  0  0
 17 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19 10  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 11  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  2  0  0  0  0
 22 12  1  0  0  0  0
 22 17  1  0  0  0  0
 23 13  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
Download

3D MOL for NP0048822 (Galanolactone)

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3D SDF for NP0048822 (Galanolactone)

  Mrv0541 05061309502D          

 23 26  0  0  0  0            999 V2000
    5.3522    1.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    1.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -0.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8929   -1.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6870   -1.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976    0.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229   -2.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2730   -0.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2753   -1.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5035    0.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9764   -3.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7239   -0.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -2.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8882    0.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165   -3.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6824    0.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -0.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999   -0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398   -3.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759   -3.8397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5004    0.0944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  4  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 14  5  2  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 16  6  1  0  0  0  0
 17 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19 10  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 11  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  2  0  0  0  0
 22 12  1  0  0  0  0
 22 17  1  0  0  0  0
 23 13  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-18(2)9-4-10-19(3)15(18)7-11-20(13-23-20)16(19)6-5-14-8-12-22-17(14)21/h5,15-16H,4,6-13H2,1-3H3/b14-5-

> <INCHI_KEY>
MBPTXJNHCBXMBP-RZNTYIFUSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.60155335786483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-3-(2-{5,5,8a-trimethyl-octahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
4.240132235

> <ALOGPS_LOGS>
-5.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.203803826241783

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
90.371

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.96e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-(2-{5,5,8a-trimethyl-hexahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048822 (Galanolactone)
Download
PDB for NP0048822 (Galanolactone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.991   1.947   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.072   2.435   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.498  -2.354   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.463  -1.520   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.533  -3.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.016  -2.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.156   1.706   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.723  -5.251   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.843  -0.027   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.981  -1.937   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.673   1.289   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.823  -6.788   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.218  -1.306   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.154  -4.681   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.258   0.631   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.396  -1.279   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.137  -5.865   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.740   1.048   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.878  -0.862   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.293  -0.204   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.674  -5.766   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.315  -7.167   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.801   0.176   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    9   10                                                       
CONECT    5    6   14                                                       
CONECT    6    5   16                                                       
CONECT    7   11   15                                                       
CONECT    8   12   14                                                       
CONECT    9    4   18                                                       
CONECT   10    4   19                                                       
CONECT   11    7   20                                                       
CONECT   12    8   22                                                       
CONECT   13   20   23                                                       
CONECT   14    5    8   17                                                  
CONECT   15    7   18   19                                                  
CONECT   16    6   19   20                                                  
CONECT   17   14   21   22                                                  
CONECT   18    1    2    9   15                                             
CONECT   19    3   10   15   16                                             
CONECT   20   11   13   16   23                                             
CONECT   21   17                                                            
CONECT   22   12   17                                                       
CONECT   23   13   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

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3D PDB for NP0048822 (Galanolactone)
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SMILES for NP0048822 (Galanolactone)
CC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12
Download
INCHI for NP0048822 (Galanolactone)
InChI=1S/C20H30O3/c1-18(2)9-4-10-19(3)15(18)7-11-20(13-23-20)16(19)6-5-14-8-12-22-17(14)21/h5,15-16H,4,6-13H2,1-3H3/b14-5-
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H30O3
Average Mass318.4504 Da
Monoisotopic Mass318.21949 Da
IUPAC Name(3Z)-3-(2-{5,5,8a-trimethyl-octahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one
Traditional Name(3Z)-3-(2-{5,5,8a-trimethyl-hexahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one
CAS Registry Number115753-79-2
SMILES
CC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12
InChI Identifier
InChI=1S/C20H30O3/c1-18(2)9-4-10-19(3)15(18)7-11-20(13-23-20)16(19)6-5-14-8-12-22-17(14)21/h5,15-16H,4,6-13H2,1-3H3/b14-5-
InChI KeyMBPTXJNHCBXMBP-RZNTYIFUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aframomum alboviolaceumLOTUS Database
Aframomum zambesiacum (Baker) K.Schum.Plant
Alpinia galangaPlant
Zingiber officinaleFooDB
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
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Dialkyl ether
    • 

  • Oxirane
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP3.81ALOGPS
logP4.24ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.37 m³·mol⁻¹ChemAxon
Polarizability36.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037523  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016604  
KNApSAcK IDC00034848  
Chemspider IDNot Available
KEGG Compound IDC17498  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGalanolactone  
METLIN IDNot Available
PubChem Compound57457805  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available