NP-MRD: Showing NP-Card for Glycerol tributanoate (NP0333402)

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Record Information

Version

2.0

Created at

2024-06-10 18:48:02 UTC

Updated at

2024-09-03 04:22:15 UTC

NP-MRD ID

NP0333402

Natural Product DOI

https://doi.org/10.57994/2794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycerol tributanoate

Description

Glycerol tributanoate, also known as butyrin or glycerol tributyric acid, 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 tributanoate is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycerol tributanoate is a bitter, cheese, and creamy tasting compound. Outside of the human body, Glycerol tributanoate has been detected, but not quantified in, several different foods, such as tree ferns, strawberry guava, dandelions, black-eyed pea, and roman camomiles. This could make glycerol tributanoate a potential biomarker for the consumption of these foods. Glycerol tributanoate was first documented in 2013 (PMID: 23568954). TriGlycerol tributanoate has been used in trials studying the treatment of Prostate Cancer and Unspecified Adult Solid Tumor, Protocol Specific (PMID: 23630018) (PMID: 23887917) (PMID: 24121865) (PMID: 24302446).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08271307202D          

 21 20  0  0  0  0            999 V2000
   -4.8395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816    0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1618   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816   -1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -1.6204    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
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  2  0  0  0  0
 18 15  2  0  0  0  0
 19 10  1  0  0  0  0
 19 13  1  0  0  0  0
 20 11  1  0  0  0  0
 20 14  1  0  0  0  0
 21 12  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333402

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O6/c1-4-7-13(16)19-10-12(21-15(18)9-6-3)11-20-14(17)8-5-2/h12H,4-11H2,1-3H3

> <INCHI_KEY>
UYXTWWCETRIEDR-UHFFFAOYSA-N

> <FORMULA>
C15H26O6

> <MOLECULAR_WEIGHT>
302.3633

> <EXACT_MASS>
302.172938564

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.967592969103634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-bis(butanoyloxy)propan-2-yl butanoate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.9196757443333334

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.565759760414948

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
75.65429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tributyrin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-AUG-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-AUG-13         0                                  
HETATM    1  C   UNK     0      -9.034  -4.565   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.971  -4.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.699   1.595   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.700  -5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.637  -5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.699   0.055   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.366  -4.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.303  -4.565   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.365  -0.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.365  -5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.302  -5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.032  -4.565   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.033  -5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.969  -5.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.365  -2.255   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.033  -6.875   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.969  -6.875   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.699  -3.025   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.699  -4.565   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.636  -4.565   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.032  -3.025   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   13                                                       
CONECT    8    5   14                                                       
CONECT    9    6   15                                                       
CONECT   10   12   19                                                       
CONECT   11   12   20                                                       
CONECT   12   10   11   21                                                  
CONECT   13    7   16   19                                                  
CONECT   14    8   17   20                                                  
CONECT   15    9   18   21                                                  
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19   10   13                                                       
CONECT   20   11   14                                                       
CONECT   21   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
1,2,3-Propanetriol, tributyrate	ChEBI
1,2,3-Propanetriyl tributanoate	ChEBI
1,2,3-Tributanoylglycerol	ChEBI
1,2,3-Tributyrylglycerol	ChEBI
2,3-Bis(butyryloxy)propyl butyrate	ChEBI
Butanoic acid, 1,2,3-propanetriyl ester	ChEBI
Butyrin	ChEBI
Butyryl triglyceride	ChEBI
Glycerin tributyrate	ChEBI
Glycerol tributyrate	ChEBI
Glyceroltributyrin	ChEBI
Glyceryl tributyrate	ChEBI
Propane-1,2,3-triyl tributyrate	ChEBI
Tri-N-butyrin	ChEBI
Tributin	ChEBI
Tributyryl glyceride	ChEBI
1,2,3-Propanetriol, tributyric acid	Generator
1,2,3-Propanetriyl tributanoic acid	Generator
2,3-Bis(butyryloxy)propyl butyric acid	Generator
Butanoate, 1,2,3-propanetriyl ester	Generator
Glycerin tributyric acid	Generator
Glycerol tributyric acid	Generator
Glyceryl tributyric acid	Generator
Propane-1,2,3-triyl tributyric acid	Generator
Glycerol tributanoic acid	Generator
Butyric acid triester with glycerin	HMDB
FEMA 2223	HMDB
Kodaflex	HMDB
NSC 661583	HMDB
Tri-butyrin	HMDB
Tributyrin	HMDB
Tributyrinine	HMDB
Tributyrl glyceride	HMDB
Tributyroin	HMDB
Tributyrylglycerol	MeSH
Glycerol tributanoate	ChEBI

Chemical Formula

C₁₅H₂₆O₆

Average Mass

302.3633 Da

Monoisotopic Mass

302.17294 Da

IUPAC Name

1,3-bis(butanoyloxy)propan-2-yl butanoate

Traditional Name

tributyrin

CAS Registry Number

Not Available

SMILES

CCCC(=O)OCC(COC(=O)CCC)OC(=O)CCC

InChI Identifier

InChI=1S/C15H26O6/c1-4-7-13(16)19-10-12(21-15(18)9-6-3)11-20-14(17)8-5-2/h12H,4-11H2,1-3H3

InChI Key

UYXTWWCETRIEDR-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum

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

butyrate ester (CHEBI:35020 )
triglyceride (CHEBI:35020 )
Triacylglycerols (C13870 )
a triacylglycerol (CPD-13014 )

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	2.71	ALOGPS
logP	2.92	ChemAxon
logS	-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	14	ChemAxon
Refractivity	75.65 m³·mol⁻¹	ChemAxon
Polarizability	32.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031094

DrugBank ID

DB12709

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003099

KNApSAcK ID

Not Available

Chemspider ID

13849665

KEGG Compound ID

C13870

BioCyc ID

CPD-13014

BiGG ID

Not Available

Wikipedia Link

Butyrin

METLIN ID

Not Available

PubChem Compound

6050

PDB ID

Not Available

ChEBI ID

35020

Good Scents ID

Not Available

References

General References

de Conti A, Tryndyak V, Koturbash I, Heidor R, Kuroiwa-Trzmielina J, Ong TP, Beland FA, Moreno FS, Pogribny IP: The chemopreventive activity of the butyric acid prodrug tributyrin in experimental rat hepatocarcinogenesis is associated with p53 acetylation and activation of the p53 apoptotic signaling pathway. Carcinogenesis. 2013 Aug;34(8):1900-6. doi: 10.1093/carcin/bgt124. Epub 2013 Apr 8. [PubMed:23568954 ]
Cresci G, Nagy LE, Ganapathy V: Lactobacillus GG and tributyrin supplementation reduce antibiotic-induced intestinal injury. JPEN J Parenter Enteral Nutr. 2013 Nov;37(6):763-74. doi: 10.1177/0148607113486809. Epub 2013 Apr 29. [PubMed:23630018 ]
Song P, Xu X, Jiang L, Zhang R, Wang J, Xu Q, Li S: Genome Sequence of Bacillus subtilis SPZ1, an Evolved Strain for Higher Uptake Rate of Tributyrin. Genome Announc. 2013 Jul 25;1(4):e00511-13. doi: 10.1128/genomeA.00511-13. [PubMed:23887917 ]
Sanguansri L, Day L, Shen Z, Fagan P, Weerakkody R, Cheng LJ, Rusli J, Augustin MA: Encapsulation of mixtures of tuna oil, tributyrin and resveratrol in a spray dried powder formulation. Food Funct. 2013 Dec;4(12):1794-802. doi: 10.1039/c3fo60197h. Epub 2013 Oct 11. [PubMed:24121865 ]
Guariento AH, Furtado KS, de Conti A, Campos A, Purgatto E, Carrilho J, Shinohara EM, Tryndyak V, Han T, Fuscoe JC, Ross SA, Beland FA, Pogribny IP, Moreno FS: Transcriptomic responses provide a new mechanistic basis for the chemopreventive effects of folic acid and tributyrin in rat liver carcinogenesis. Int J Cancer. 2014 Jul 1;135(1):7-18. doi: 10.1002/ijc.28642. Epub 2014 Feb 22. [PubMed:24302446 ]

Showing NP-Card for Glycerol tributanoate (NP0333402)

MOL for NP0333402 (Glycerol tributanoate)

3D MOL for NP0333402 (Glycerol tributanoate)

3D SDF for NP0333402 (Glycerol tributanoate)

3D-SDF for NP0333402 (Glycerol tributanoate)

PDB for NP0333402 (Glycerol tributanoate)

3D PDB for NP0333402 (Glycerol tributanoate)

SMILES for NP0333402 (Glycerol tributanoate)

INCHI for NP0333402 (Glycerol tributanoate)

Structure for NP0333402 (Glycerol tributanoate)

3D Structure for NP0333402 (Glycerol tributanoate)