Milk Composition Database: Showing metabocard for Pentadecanoic acid (BMDB0000826)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:37:11 UTC

Update Date

2020-06-04 22:26:03 UTC

MCDB ID

BMDB0000826

Secondary Accession Numbers

BMDB00826

Metabolite Identification

Common Name

Pentadecanoic acid

Description

Pentadecanoic acid, also known as C15 or N-pentadecanoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Pentadecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Pentadecanoic acid is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
15:00	ChEBI
C15	ChEBI
C15:0	ChEBI
N-Pentadecanoic acid	ChEBI
Pentadecylic acid	ChEBI
N-Pentadecanoate	Generator
Pentadecylate	Generator
Pentadecanoate	Generator
N-Pentadecylate	HMDB
N-Pentadecylic acid	HMDB
Pentadecyclate	HMDB
Pentadecyclic acid	HMDB
FA(15:0)	HMDB
Pentadecanoic acid	MeSH
14FA	PhytoBank

Chemical Formula

C₁₅H₃₀O₂

Average Molecular Weight

242.3975

Monoisotopic Molecular Weight

242.224580204

IUPAC Name

pentadecanoic acid

Traditional Name

pentadecanoic acid

CAS Registry Number

1002-84-2

SMILES

CCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17/h2-14H2,1H3,(H,16,17)

InChI Key

WQEPLUUGTLDZJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

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

long-chain fatty acid (CHEBI:42504 )
straight-chain saturated fatty acid (CHEBI:42504 )
Straight chain fatty acids (C16537 )
Straight chain fatty acids (LMFA01010015 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	52.3 °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	6.65	ALOGPS
logP	5.81	ChemAxon
logS	-5.9	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	13	ChemAxon
Refractivity	72.48 m³·mol⁻¹	ChemAxon
Polarizability	32.23 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)	splash10-015a-2910000000-7f0113961bc4f281b68d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-015a-2910000000-7f0113961bc4f281b68d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1900000000-d69aa674fba2ef153294	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9700000000-5fdb791c98a3d1afb3f2	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ds-9440000000-c48712b46200e1d92783	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 - ESI-TOF 20V, Negative	splash10-00di-0900000000-6ec01ce9b8fdc68d94a9	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-00di-0900000000-6ec01ce9b8fdc68d94a9	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-00di-0900000000-6ec01ce9b8fdc68d94a9	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0006-0090000000-e497b3530081726e5ced	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0006-0090000000-15d18c0525685af6dade	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0006-0090000000-72b33052a241e98e015e	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0006-0090000000-e497b3530081726e5ced	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0006-0090000000-15d18c0525685af6dade	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0006-0090000000-72b33052a241e98e015e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-1416cf4e0892e7961cf5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9100000000-7afbfa184267e53ce724	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9550000000-66ce9961a17feae488d9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-066r-9000000000-d53184bd1b3b6d6a3eb5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0090000000-cb5c25c7dcdbbb67eb60	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0090000000-30f81c19c47194f754c5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9100000000-250dbe37e10809fe3616	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-bf26bddfb84b56f5d5ef	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002f-0290000000-e7342714318939c2be52	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002e-4930000000-0b5a7be5eba92f894517	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9500000000-4a20037c0dd6bfa5cd45	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0190000000-af3122f573a9dcce9040	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-1590000000-76597eec59d238b7eb31	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9400000000-5852258bf4f39de4722e	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06xx-9100000000-5bd17e6ee11dac1f2a7f	2014-09-20	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, 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

Concentrations

Status	Value		Reference	Details
Detected and Quantified	1650 +/- 413 uM	Total fatty acid	PMID: 16899705	details
Detected but not Quantified	Not Applicable		PMID: 1779072	details
Detected but not Quantified	Not Applicable		PMID: 11913692	details
Detected but not Quantified	Not Applicable		Lawrence K. Cream...	details
Detected but not Quantified	Not Applicable		Lawrence K. Cream...	details
Detected and Quantified	1526 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1444 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	454 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	825 uM	Total fatty acid	Fooddata+, T...	details

External Links

HMDB ID

HMDB0000826

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

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

42504

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
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 ]
Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
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 ]
van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
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 ]
Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.

Showing metabocard for Pentadecanoic acid (BMDB0000826)

Structure for BMDB0000826 (Pentadecanoic acid)