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Showing NP-Card for Glycerol trihexanoate (NP0337073)

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Record Information
Version2.0
Created at2024-09-11 09:09:20 UTC
Updated at2024-09-11 09:09:20 UTC
NP-MRD IDNP0337073
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlycerol trihexanoate
DescriptionGlycerol trihexanoate, also known as glycerol tricaproic acid or 1,2,3-tricaproylglycerol, 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. A triglyceride obtained by condensation of each of the three hydroxy groups of glycerol with hexanoic (caproic) acid. It was first documented in 1972 (PMID: 5031847). Glycerol trihexanoate is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 10917917) (PMID: 3146344) (PMID: 6612095) (PMID: 7040975).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337073 (Glycerol trihexanoate)


  Mrv0541 05061305442D          

 27 26  0  0  0  0            999 V2000
   -6.0770   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3546   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5046    1.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5046    0.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6480   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901    0.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9336   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2112   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901   -0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5046   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -1.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5046   -4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901   -2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0677   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -2.3349    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
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 19  2  0  0  0  0
 23 20  2  0  0  0  0
 24 21  2  0  0  0  0
 25 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 26 20  1  0  0  0  0
 27 18  1  0  0  0  0
 27 21  1  0  0  0  0
M  END
Download

3D MOL for NP0337073 (Glycerol trihexanoate)

Download
3D SDF for NP0337073 (Glycerol trihexanoate)

  Mrv0541 05061305442D          

 27 26  0  0  0  0            999 V2000
   -6.0770   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3546   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5046    1.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5046    0.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6480   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901    0.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9336   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2112   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901   -0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5046   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -1.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5046   -4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901   -2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0677   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -2.3349    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
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 19  2  0  0  0  0
 23 20  2  0  0  0  0
 24 21  2  0  0  0  0
 25 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 26 20  1  0  0  0  0
 27 18  1  0  0  0  0
 27 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)OCC(COC(=O)CCCCC)OC(=O)CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C21H38O6/c1-4-7-10-13-19(22)25-16-18(27-21(24)15-12-9-6-3)17-26-20(23)14-11-8-5-2/h18H,4-17H2,1-3H3

> <INCHI_KEY>
MAYCICSNZYXLHB-UHFFFAOYSA-N

> <FORMULA>
C21H38O6

> <MOLECULAR_WEIGHT>
386.5228

> <EXACT_MASS>
386.266838948

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
45.192392367876565

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-bis(hexanoyloxy)propan-2-yl hexanoate

> <ALOGPS_LOGP>
5.17

> <JCHEM_LOGP>
5.587087734333333

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.565867972254278

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
103.26029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tricaproin

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0337073 (Glycerol trihexanoate)
Download
PDB for NP0337073 (Glycerol trihexanoate)
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     -11.344  -5.898   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.995  -5.898   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.675   2.572   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.010  -6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.662  -6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.675   1.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.676  -5.898   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.328  -5.898   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.342   0.262   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.343  -6.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.994  -6.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.342  -1.278   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.009  -5.898   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.661  -5.898   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.008  -2.048   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.008  -6.668   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.659  -6.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.674  -5.898   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.675  -6.668   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.327  -6.668   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.008  -3.588   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.675  -8.208   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.327  -8.208   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.342  -4.358   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.342  -5.898   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.993  -5.898   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.674  -4.358   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10                                                       
CONECT    8    5   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   19                                                       
CONECT   14   11   20                                                       
CONECT   15   12   21                                                       
CONECT   16   18   25                                                       
CONECT   17   18   26                                                       
CONECT   18   16   17   27                                                  
CONECT   19   13   22   25                                                  
CONECT   20   14   23   26                                                  
CONECT   21   15   24   27                                                  
CONECT   22   19                                                            
CONECT   23   20                                                            
CONECT   24   21                                                            
CONECT   25   16   19                                                       
CONECT   26   17   20                                                       
CONECT   27   18   21                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

Download
3D PDB for NP0337073 (Glycerol trihexanoate)
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SMILES for NP0337073 (Glycerol trihexanoate)
CCCCCC(=O)OCC(COC(=O)CCCCC)OC(=O)CCCCC
Download
INCHI for NP0337073 (Glycerol trihexanoate)
InChI=1S/C21H38O6/c1-4-7-10-13-19(22)25-16-18(27-21(24)15-12-9-6-3)17-26-20(23)14-11-8-5-2/h18H,4-17H2,1-3H3
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Synonyms
ValueSource
1,2,3-Propanetriyl hexanoateChEBI
1,2,3-TricaproylglycerolChEBI
1,2,3-TrihexanoylglycerolChEBI
Caproic triglycerideChEBI
Glycerol tricaproateChEBI
Glycerol tricapronateChEBI
Glyceryl tricaproateChEBI
Hexanoic acid, 1,2,3-propanetriyl esterChEBI
Propane-1,2,3-triyl tricaproateChEBI
TG 6:0/6:0/6:0ChEBI
TricaproylglycerolChEBI
TrihexanoinChEBI
Trihexanoyl glycerolChEBI
TrihexanoylglycerolChEBI
1,2,3-Propanetriyl hexanoic acidGenerator
Glycerol tricaproic acidGenerator
Glycerol tricapronic acidGenerator
Glyceryl tricaproic acidGenerator
Hexanoate, 1,2,3-propanetriyl esterGenerator
Propane-1,2,3-triyl tricaproic acidGenerator
Glycerol trihexanoic acidGenerator
1,2,3-Propanetriyl hexanoate, 9ciHMDB
2,3-Bis(hexanoyloxy)propyl hexanoateHMDB
Hexanoic acid, 1,1',1''-(1,2,3-propanetriyl) esterHMDB
Hexanoin, tri- (6ci,7ci,8ci)HMDB
Palmitic acid triglycerideHMDB
Tri-hexanoinHMDB
Tri-N-caproinHMDB
TricaproinHMDB
TricaproninHMDB
Glycerol trihexanoateChEBI
Chemical FormulaC21H38O6
Average Mass386.5228 Da
Monoisotopic Mass386.26684 Da
IUPAC Name1,3-bis(hexanoyloxy)propan-2-yl hexanoate
Traditional Nametricaproin
CAS Registry NumberNot Available
SMILES
CCCCCC(=O)OCC(COC(=O)CCCCC)OC(=O)CCCCC
InChI Identifier
InChI=1S/C21H38O6/c1-4-7-10-13-19(22)25-16-18(27-21(24)15-12-9-6-3)17-26-20(23)14-11-8-5-2/h18H,4-17H2,1-3H3
InChI KeyMAYCICSNZYXLHB-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
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • 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 Descriptors
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
logP5.17ALOGPS
logP5.59ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity103.26 m³·mol⁻¹ChemAxon
Polarizability45.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031125  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003136  
KNApSAcK IDNot Available
Chemspider ID11633  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12131  
PDB IDNot Available
ChEBI ID77386  
Good Scents IDNot Available
References
General References
  1. Fontagne S, Corraze G, Bergot P: Tricaproin, tricaprin and trilaurin are utilized more efficiently than tricaprylin by carp (Cyprinus carpio L.) larvae. J Nutr. 2000 Aug;130(8):2009-15. doi: 10.1093/jn/130.8.2009. [PubMed:10917917  ] 
  2. Aurousseau B: Effects of substitution of tricaproin for tallow and of protein concentration in milk substitutes on nitrogen and energy balance in the preruminant lamb. Br J Nutr. 1988 Nov;60(3):525-38. doi: 10.1079/bjn19880125. [PubMed:3146344  ] 
  3. Letellier PR, Nawar WW: Recombination products from the radiolysis of tricaproin. J Am Oil Chem Soc. 1972 Apr;49(4):259-63. doi: 10.1007/BF02582589. [PubMed:5031847  ] 
  4. Aurousseau B, Vermorel M, Bouvier JC: [Effect on energy and nitrogen balances of replacing part of the tallow in a milk replacer for preruminant calves by tricaproin or coconut oil: effect of previous feeding level]. Reprod Nutr Dev (1980). 1983;23(3):587-97. [PubMed:6612095  ] 
  5. Ogundero VW: Hydrolysis of vegetable oils and triglycerides by thermotolerant and zoopathogenic species of Aspergillus from Nigerian palm produce. Mycopathologia. 1982 Jan 15;77(1):43-6. doi: 10.1007/BF00588656. [PubMed:7040975  ]