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Showing NP-Card for Glycerol tripropanoate (NP0337753)

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Record Information
Version2.0
Created at2024-09-11 12:15:35 UTC
Updated at2024-09-11 12:15:36 UTC
NP-MRD IDNP0337753
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlycerol tripropanoate
DescriptionGlycerol tripropanoate, also known as glycerol tripropionic acid or tri-propionin, belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Glycerol tripropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycerol tripropanoate is a bitter, chemical, and oily tasting compound. Outside of the human body,. Glycerol tripropanoate was first documented in 1980 (PMID: 7439178). A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by propionic acid (PMID: 11750885) (PMID: 12216836) (PMID: 9822688).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337753 (Glycerol tripropanoate)


  Mrv0541 05061306452D          

 18 17  0  0  0  0            999 V2000
   -4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7177    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0033    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2888    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5743    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5743    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 15 12  2  0  0  0  0
 16  7  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
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3D MOL for NP0337753 (Glycerol tripropanoate)

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3D SDF for NP0337753 (Glycerol tripropanoate)

  Mrv0541 05061306452D          

 18 17  0  0  0  0            999 V2000
   -4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7177    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0033    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2888    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5743    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5743    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 15 12  2  0  0  0  0
 16  7  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337753

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OCC(COC(=O)CC)OC(=O)CC

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O6/c1-4-10(13)16-7-9(18-12(15)6-3)8-17-11(14)5-2/h9H,4-8H2,1-3H3

> <INCHI_KEY>
YZWRNSARCRTXDS-UHFFFAOYSA-N

> <FORMULA>
C12H20O6

> <MOLECULAR_WEIGHT>
260.2836

> <EXACT_MASS>
260.125988372

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.12171044956935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-bis(propanoyloxy)propan-2-yl propanoate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.5859697493333336

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.562815685863429

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
61.85130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tripropionin

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337753 (Glycerol tripropanoate)
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PDB for NP0337753 (Glycerol tripropanoate)
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      -8.264   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.073   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.595  -0.619   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.930   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.739   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.262   0.151   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.929   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.262   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.595   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.596   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.406   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.262   1.691   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.596   6.311   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.406   6.311   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.072   2.461   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.263   4.001   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.072   4.001   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.595   2.461   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1   10                                                       
CONECT    5    2   11                                                       
CONECT    6    3   12                                                       
CONECT    7    9   16                                                       
CONECT    8    9   17                                                       
CONECT    9    7    8   18                                                  
CONECT   10    4   13   16                                                  
CONECT   11    5   14   17                                                  
CONECT   12    6   15   18                                                  
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15   12                                                            
CONECT   16    7   10                                                       
CONECT   17    8   11                                                       
CONECT   18    9   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

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3D PDB for NP0337753 (Glycerol tripropanoate)
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SMILES for NP0337753 (Glycerol tripropanoate)
CCC(=O)OCC(COC(=O)CC)OC(=O)CC
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INCHI for NP0337753 (Glycerol tripropanoate)
InChI=1S/C12H20O6/c1-4-10(13)16-7-9(18-12(15)6-3)8-17-11(14)5-2/h9H,4-8H2,1-3H3
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Synonyms
ValueSource
1,2,3-Propanetriol tripropanoateChEBI
1,2,3-TripropanoylglycerolChEBI
2,3-Di(propanoyloxy)propyl propanoateChEBI
Glycerine tripropionateChEBI
Glycerol tripropionateChEBI
Glyceryl tripropanoateChEBI
Glyceryl tripropionateChEBI
TripropionylglycerolChEBI
1,2,3-Propanetriol tripropanoic acidGenerator
2,3-Di(propanoyloxy)propyl propanoic acidGenerator
Glycerine tripropionic acidGenerator
Glycerol tripropionic acidGenerator
Glyceryl tripropanoic acidGenerator
Glyceryl tripropionic acidGenerator
Glycerol tripropanoic acidGenerator
1,2,3-Propanetriol tripropanoate, 9ciHMDB
1,2,3-Propanetriol, 1,2,3-tripropanoateHMDB
1,2,3-Propanetriol, tripropanoateHMDB
1,2,3-Propanetriol, tripropionateHMDB
2,3-Bis(propionyloxy)propyl propionateHMDB
FEMA 3286HMDB
Propionic acid triglycerideHMDB
Propionin, tri- (8ci)HMDB
Tri-propioninHMDB
TripropioninHMDB
Tripropionin, 8ciHMDB
TripropionineHMDB
Chemical FormulaC12H20O6
Average Mass260.2836 Da
Monoisotopic Mass260.12599 Da
IUPAC Name1,3-bis(propanoyloxy)propan-2-yl propanoate
Traditional Nametripropionin
CAS Registry NumberNot Available
SMILES
CCC(=O)OCC(COC(=O)CC)OC(=O)CC
InChI Identifier
InChI=1S/C12H20O6/c1-4-10(13)16-7-9(18-12(15)6-3)8-17-11(14)5-2/h9H,4-8H2,1-3H3
InChI KeyYZWRNSARCRTXDS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassGlycerolipids  
Sub ClassTriradylcglycerols  
Direct ParentTriacylglycerols  
Alternative Parents
Substituents
  • Triacyl-sn-glycerol
    • 

  • Tricarboxylic acid or derivatives
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP1.69ALOGPS
logP1.59ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity61.85 m³·mol⁻¹ChemAxon
Polarizability27.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032857  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010834  
KNApSAcK IDNot Available
Chemspider ID8433  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8763  
PDB IDNot Available
ChEBI ID88153  
Good Scents IDNot Available
References
General References
  1. Nini L, Sarda L, Comeau LC, Boitard E, Dubes JP, Chahinian H: Lipase-catalysed hydrolysis of short-chain substrates in solution and in emulsion: a kinetic study. Biochim Biophys Acta. 2001 Nov 30;1534(1):34-44. doi:  10.1016/s1388-1981(01)00172-x. [PubMed:11750885  ] 
  2. Chahinian H, Nini L, Boitard E, Dubes JP, Comeau LC, Sarda L: Distinction between esterases and lipases: a kinetic study with vinyl esters and TAG. Lipids. 2002 Jul;37(7):653-62. doi: 10.1007/s11745-002-0946-7. [PubMed:12216836  ] 
  3. Granon S, Semeriva M: Effect of taurodeoxycholate, colipase and temperature on the interfacial inactivation of porcine pancreatic lipase. Eur J Biochem. 1980 Oct;111(1):117-24. doi: 10.1111/j.1432-1033.1980.tb06082.x. [PubMed:7439178  ] 
  4. Roussel A, Yang Y, Ferrato F, Verger R, Cambillau C, Lowe M: Structure and activity of rat pancreatic lipase-related protein 2. J Biol Chem. 1998 Nov 27;273(48):32121-8. doi: 10.1074/jbc.273.48.32121. [PubMed:9822688  ]