Milk Composition Database: Showing metabocard for TG(10:0/10:0/10:0)[iso] (BMDB0000548)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-09-30 22:32:35 UTC

Update Date

2020-04-21 18:15:55 UTC

MCDB ID

BMDB0000548

Secondary Accession Numbers

BMDB00548

Metabolite Identification

Common Name

TG(10:0/10:0/10:0)[iso]

Description

TG(10:0/10:0/10:0), also known as caprin or glycerol tridecanoate, 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. Thus, TG(10:0/10:0/10:0) is considered to be a triradylglycerol lipid molecule. TG(10:0/10:0/10:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. TG(10:0/10:0/10:0) exists in all eukaryotes, ranging from yeast to humans. TG(10:0/10:0/10:0) can be biosynthesized from DG(10:0/10:0/0:0) and decanoyl-CoA; which is catalyzed by the enzyme diacylglycerol O-acyltransferase. In cattle, TG(10:0/10:0/10:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(10:0/10:0/10:0) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2,3-Propanol tridecanoate	ChEBI
1,2,3-Tridecanoylglycerol	ChEBI
Capric acid triglyceride	ChEBI
Capric triglyceride	ChEBI
Caprin	ChEBI
Decanoic acid, 1,2,3-propanetriyl ester	ChEBI
Glycerin tridecanoate	ChEBI
Glycerol tricaprate	ChEBI
Glycerol tridecanoate	ChEBI
Glyceryl tricaprate	ChEBI
Glyceryl tridecanoate	ChEBI
TG 10:0/10:0/10:0	ChEBI
Tri-N-caprin	ChEBI
Tricapric glyceride	ChEBI
Tridecanoin	ChEBI
Tridecanoylglycerol	ChEBI
1,2,3-Propanol tridecanoic acid	Generator
Caprate triglyceride	Generator
Decanoate, 1,2,3-propanetriyl ester	Generator
Glycerin tridecanoic acid	Generator
Glycerol tricapric acid	Generator
Glycerol tridecanoic acid	Generator
Glyceryl tricapric acid	Generator
Glyceryl tridecanoic acid	Generator
1-Animal fats-2-animal fats-3-animal fats-glycerol	HMDB
1-Decanoic acid-2-decanoic acid-3-decanoic acid-glycerol	HMDB
TAG(10:0/10:0/10:0)	HMDB
Triacylglycerol	HMDB
Tracylglycerol(30:0)	HMDB
Triglyceride	HMDB
Tracylglycerol(10:0/10:0/10:0)	HMDB
TAG(30:0)	HMDB
TG(30:0)	HMDB
1,2, 3-Propanetriyl-decanoate	HMDB
1,2, 3-Propanetriyl-decanoic acid	HMDB
2,3-Bis(decanoyloxy)propyl decanoate	HMDB
2,3-Bis(decanoyloxy)propyl decanoate (acd/name 4.0)	HMDB
2,3-Bis(decanoyloxy)propyl decanoic acid	HMDB
Glycerol tricaprin	HMDB
Tri-decanoin	HMDB
Tricaprin	HMDB
TG(10:0/10:0/10:0)	Lipid Annotator, ChEBI

Chemical Formula

C₃₃H₆₂O₆

Average Molecular Weight

554.853

Monoisotopic Molecular Weight

554.454639716

IUPAC Name

1,3-bis(decanoyloxy)propan-2-yl decanoate

Traditional Name

tricaprin

CAS Registry Number

621-71-6

SMILES

[H]C(COC(=O)CCCCCCCCC)(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC

InChI Identifier

InChI=1S/C33H62O6/c1-4-7-10-13-16-19-22-25-31(34)37-28-30(39-33(36)27-24-21-18-15-12-9-6-3)29-38-32(35)26-23-20-17-14-11-8-5-2/h30H,4-29H2,1-3H3

InChI Key

LADGBHLMCUINGV-UHFFFAOYSA-N

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:77388 )
Triacylglycerols (LMGL03012617 )

Physical Properties

State

Solid

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	8.78	ALOGPS
logP	10.92	ChemAxon
logS	-7.5	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	32	ChemAxon
Refractivity	158.47 m³·mol⁻¹	ChemAxon
Polarizability	70.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a59-3958000000-f57192615ab610f32def	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a59-3958000000-f57192615ab610f32def	2018-05-18	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0000190000-62ceec1552f50a5d7886	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-0175090000-8c7de03a1649bbcb9482	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0089-9010000000-4e7483739c7dcb61b0bc	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0a59-3958000000-f57192615ab610f32def	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000090000-ce340e48f0c1c82582ea	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000090000-ce340e48f0c1c82582ea	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-0009070000-2c86bfc78962fbd6aa8d	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000090000-2a5a4f209f02f40b110f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000090000-2a5a4f209f02f40b110f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ii-0909090000-c6a9641978779d1182b0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ue9-0527090000-00cdfe845f15d4b6a661	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000t-0933010000-de250ac1d1f0d8fcdca2	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dj-0912000000-3aa31014b1eb3b307c92	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000090000-add7d9098153c7a00e9a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000090000-add7d9098153c7a00e9a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0000090000-add7d9098153c7a00e9a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0102090000-747370baaa832594f1b2	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-5727790000-91d904d103a37903b33b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bu0-3591100000-2da6107e763a64b2df76	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000090000-d6cd7cf63c9fb0b8a266	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000090000-d6cd7cf63c9fb0b8a266	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-0109070000-6b4138a13a27d3e87308	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 11556330	details

External Links

HMDB ID

HMDB0000548

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003134

KNApSAcK ID

Not Available

Chemspider ID

62521

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5532

PubChem Compound

69310

PDB ID

Not Available

ChEBI ID

77388

References

Synthesis Reference

Selmi, B.; Gontier, E.; Ergan, F.; Thomas, D. Effects of fatty acid chain length and unsaturation number on triglyceride synthesis catalyzed by immobilized lipase in solvent-free medium. Enzyme and Microbial Technology (1998), 23(3/4), 182-186.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mottram HR, Evershed RP: Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2001 Aug 17;926(2):239-53. [PubMed:11556330 ]

Showing metabocard for TG(10:0/10:0/10:0)[iso] (BMDB0000548)

Structure for BMDB0000548 (TG(10:0/10:0/10:0)[iso])