NP-MRD: Showing NP-Card for Glycerol trihexanoate (NP0337073)

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Record Information

Version

2.0

Created at

2024-09-11 09:09:20 UTC

Updated at

2024-09-11 09:09:20 UTC

NP-MRD ID

NP0337073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycerol trihexanoate

Description

Glycerol 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. Glycerol trihexanoate 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

MOL SDF PDB SMILES InChI


  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


  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

$$$$

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

View in JSmol

Synonyms

Value	Source
1,2,3-Propanetriyl hexanoate	ChEBI
1,2,3-Tricaproylglycerol	ChEBI
1,2,3-Trihexanoylglycerol	ChEBI
Caproic triglyceride	ChEBI
Glycerol tricaproate	ChEBI
Glycerol tricapronate	ChEBI
Glyceryl tricaproate	ChEBI
Hexanoic acid, 1,2,3-propanetriyl ester	ChEBI
Propane-1,2,3-triyl tricaproate	ChEBI
TG 6:0/6:0/6:0	ChEBI
Tricaproylglycerol	ChEBI
Trihexanoin	ChEBI
Trihexanoyl glycerol	ChEBI
Trihexanoylglycerol	ChEBI
1,2,3-Propanetriyl hexanoic acid	Generator
Glycerol tricaproic acid	Generator
Glycerol tricapronic acid	Generator
Glyceryl tricaproic acid	Generator
Hexanoate, 1,2,3-propanetriyl ester	Generator
Propane-1,2,3-triyl tricaproic acid	Generator
Glycerol trihexanoic acid	Generator
1,2,3-Propanetriyl hexanoate, 9ci	HMDB
2,3-Bis(hexanoyloxy)propyl hexanoate	HMDB
Hexanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester	HMDB
Hexanoin, tri- (6ci,7ci,8ci)	HMDB
Palmitic acid triglyceride	HMDB
Tri-hexanoin	HMDB
Tri-N-caproin	HMDB
Tricaproin	HMDB
Tricapronin	HMDB
Glycerol trihexanoate	ChEBI

Chemical Formula

C₂₁H₃₈O₆

Average Mass

386.5228 Da

Monoisotopic Mass

386.26684 Da

IUPAC Name

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

Traditional Name

tricaproin

CAS Registry Number

Not 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 Key

MAYCICSNZYXLHB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not 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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Triradylcglycerols

Direct Parent

Triacylglycerols

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 Framework

Aliphatic acyclic compounds

External Descriptors

triglyceride (CHEBI:77386 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.17	ALOGPS
logP	5.59	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	103.26 m³·mol⁻¹	ChemAxon
Polarizability	45.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031125

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003136

KNApSAcK ID

Not Available

Chemspider ID

11633

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12131

PDB ID

Not Available

ChEBI ID

77386

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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 ]
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 ]
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 ]

Showing NP-Card for Glycerol trihexanoate (NP0337073)

MOL for NP0337073 (Glycerol trihexanoate)

3D MOL for NP0337073 (Glycerol trihexanoate)

3D SDF for NP0337073 (Glycerol trihexanoate)

3D-SDF for NP0337073 (Glycerol trihexanoate)

PDB for NP0337073 (Glycerol trihexanoate)

3D PDB for NP0337073 (Glycerol trihexanoate)

SMILES for NP0337073 (Glycerol trihexanoate)

INCHI for NP0337073 (Glycerol trihexanoate)

Structure for NP0337073 (Glycerol trihexanoate)

3D Structure for NP0337073 (Glycerol trihexanoate)