Milk Composition Database: Showing metabocard for Undecanoic acid (BMDB0000947)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:39:00 UTC

Update Date

2020-06-04 19:29:40 UTC

MCDB ID

BMDB0000947

Secondary Accession Numbers

BMDB00947

Metabolite Identification

Common Name

Undecanoic acid

Description

Undecanoic acid, also known as N-undecylic acid or N-undecanoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Undecanoic acid exists in all eukaryotes, ranging from yeast to humans. Undecanoic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Decanecarboxylic acid	ChEBI
CH3-[CH2]9-COOH	ChEBI
Hendecanoic acid	ChEBI
N-Undecanoic acid	ChEBI
N-Undecoic acid	ChEBI
N-Undecylic acid	ChEBI
UDA	ChEBI
Undecoic acid	ChEBI
Undecylic acid	ChEBI
Undekansaeure	ChEBI
1-Decanecarboxylate	Generator
Hendecanoate	Generator
N-Undecanoate	Generator
N-Undecoate	Generator
N-Undecylate	Generator
Undecoate	Generator
Undecylate	Generator
Undecanoate	Generator
1N-Undecoic acid	HMDB
FA(11:0)	HMDB
Undecanoic acid	MeSH

Chemical Formula

C₁₁H₂₂O₂

Average Molecular Weight

186.2912

Monoisotopic Molecular Weight

186.161979948

IUPAC Name

undecanoic acid

Traditional Name

undecanoic acid

CAS Registry Number

112-37-8

SMILES

CCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)

InChI Key

ZDPHROOEEOARMN-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-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

medium-chain fatty acid (CHEBI:32368 )
straight-chain saturated fatty acid (CHEBI:32368 )
Straight chain fatty acids (C17715 )
Straight chain fatty acids (LMFA01010011 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	28.6 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.052 mg/mL	Not Available
LogP	4.42	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	4.49	ALOGPS
logP	4.03	ChemAxon
logS	-3.9	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	9	ChemAxon
Refractivity	54.08 m³·mol⁻¹	ChemAxon
Polarizability	23.73 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2910000000-722a87fa01fa27b58b07	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0706-9000000000-d7f6a00a2bcfd58539f5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2910000000-722a87fa01fa27b58b07	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r6-9400000000-c452aa611294afd4b227	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00du-9310000000-90668bb3fcf413ecc767	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0900000000-4e46062530f2b87127f2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-001i-2900000000-1bd11599567676fd18b8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0019-3900000000-3ed16e9aae084b8128f7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0706-9000000000-f0f2855ce0a7d3e0e44c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-70bc980554bccc2d565f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-0900000000-1923c2ee9004b1a4f217	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-0900000000-818107787c04dbc613be	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-01t9-9000000000-da3c8186be5724d14262	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-052f-9000000000-4a1e2f342d24eb6ec79e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-03di-0090000000-2dadd8baad50427686a7	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-03di-0090000000-2dadd8baad50427686a7	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0900000000-d09512035285f332d56c	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0900000000-fca225c5971e85f0f121	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0900000000-0fabd46bd1eaa73e5af0	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0900000000-d09512035285f332d56c	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-70bc980554bccc2d565f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-1923c2ee9004b1a4f217	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-f871962b32a5d16913f8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-01t9-9000000000-f75b1abf45a6ce1d1e16	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0900000000-5e1b204d52a76537f6dd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-4900000000-4156178f661bac3b8785	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-8f8e8441132607db272a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-36794ad067903d2b6624	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-1900000000-157dc43c0ad4ff0f5509	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-95af6ebcd3a0e83715bd	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-074l-9100000000-e152e90785434b58612c	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, 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, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	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: 5409465	details
Detected but not Quantified	Not Applicable		PMID: 11913692	details
Detected but not Quantified	Not Applicable		PMID: 14168161	details
Detected but not Quantified	Not Applicable		PMID: 19038946	details
Detected and Quantified	0.38 +/- 0.01 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	0.51 +/- 0.01 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	0.516 +/- 0.014 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	0.45 +/- 0.02 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000947

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Undecylic_acid

METLIN ID

5894

PubChem Compound

8180

PDB ID

Not Available

ChEBI ID

32368

References

Synthesis Reference

Schreyer, Gerd; Schwarze, Werner; Weigert, Wolfgang. Carboxylic acids by oxidation of vicinal diols. Ger. Offen. (1972), 10 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
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 Undecanoic acid (BMDB0000947)

Structure for BMDB0000947 (Undecanoic acid)