Milk Composition Database: Showing metabocard for Tricosanoic acid (BMDB0001160)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:41:47 UTC

Update Date

2020-04-22 15:06:53 UTC

MCDB ID

BMDB0001160

Secondary Accession Numbers

BMDB01160

Metabolite Identification

Common Name

Tricosanoic acid

Description

Tricosanoic acid, also known as N-tricosanoate or 22FA, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tricosanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Tricosanoic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Tricosanoic acid	ChEBI
N-Tricosanoate	Generator
Tricosanoate	Generator
22FA	HMDB
F23	HMDB
Tricosanoic acid, aluminum salt	MeSH, HMDB
Tricosanoic acid, calcium salt	MeSH, HMDB
Tricosanoic acid, lead salt	MeSH, HMDB
Tricosylate	Generator, HMDB
Tricosanoic acid	MeSH
23FA	PhytoBank
Tricosylic acid	PhytoBank
FA(23:0)	PhytoBank

Chemical Formula

C₂₃H₄₆O₂

Average Molecular Weight

354.6101

Monoisotopic Molecular Weight

354.349780716

IUPAC Name

tricosanoic acid

Traditional Name

tricosanoic acid

CAS Registry Number

2433-96-7

SMILES

CCCCCCCCCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C23H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(24)25/h2-22H2,1H3,(H,24,25)

InChI Key

XEZVDURJDFGERA-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

very long-chain fatty acid (CHEBI:42394 )
straight-chain saturated fatty acid (CHEBI:42394 )
Straight chain fatty acids (LMFA01010023 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	77.0 - 79.0 °C	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	9.39	ALOGPS
logP	9.37	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	109.29 m³·mol⁻¹	ChemAxon
Polarizability	49.4 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 - GC-MS (1 TMS)	splash10-0159-2900000000-90925cf3c5c344889a87	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2900000000-90925cf3c5c344889a87	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8790000000-189d993955590b247b04	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00g0-9541000000-22eb85c1b6ca5b727ec2	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0pvr-0298000000-80b9daf5924525f32b70	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-3390000000-ac935102623d865e251d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00l6-4980000000-ff160222688e5c3a5eba	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-05fr-0590000000-455d8ab1313a61d90f8c	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0udi-0009000000-6cab4a327eae32b5f787	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0029000000-37d069e8e40dc2126055	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0009000000-32d4687abf7d5b474472	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0009000000-0756d3aa19109128f075	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-05fr-0590000000-455d8ab1313a61d90f8c	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0019000000-f057f22a9f1ae508491f	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-4698000000-93353ef0bd573ddf3856	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-5890000000-a4664c743314ab26742e	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-e7720ae2787f40cc1c41	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-1009000000-972e00d6c61341c05ce8	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9122000000-1a4a94c95b1a24167584	2017-07-26	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0596-9201000000-4c4b474aedf9d85a53e1	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Not Available	2021-10-10	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: 14168161	details
Detected but not Quantified	Not Applicable		PMID: 19038946	details

External Links

HMDB ID

HMDB0001160

DrugBank ID

DB03500

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002894

KNApSAcK ID

C00053866

Chemspider ID

16170

KEGG Compound ID

Not Available

BioCyc ID

CPD-7834

BiGG ID

Not Available

Wikipedia Link

Tricosylic acid

METLIN ID

4211

PubChem Compound

17085

PDB ID

Not Available

ChEBI ID

42394

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]

Showing metabocard for Tricosanoic acid (BMDB0001160)

Structure for BMDB0001160 (Tricosanoic acid)