Milk Composition Database: Showing metabocard for Heptadecanoic acid (BMDB0002259)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:53:14 UTC

Update Date

2020-06-04 22:40:23 UTC

MCDB ID

BMDB0002259

Secondary Accession Numbers

BMDB02259

Metabolite Identification

Common Name

Heptadecanoic acid

Description

Heptadecanoic acid, also known as 17:0 or heptadecoate, 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. Heptadecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Heptadecanoic acid exists in all living species, ranging from bacteria to humans. In cattle, heptadecanoic acid is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(8:0/17:0/17:0) pathway. Heptadecanoic acid is a potentially toxic compound.

Structure

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

Synonyms

Value	Source
17:0	ChEBI
C17:0	ChEBI
CH3-[CH2]15-COOH	ChEBI
Heptadecoic acid	ChEBI
Heptadecylic acid	ChEBI
Margaric acid	ChEBI
Margarinic acid	ChEBI
Margarinsaeure	ChEBI
N-Heptadecanoic acid	ChEBI
N-Heptadecoic acid	ChEBI
N-Heptadecylic acid	ChEBI
Heptadecoate	Generator
Heptadecylate	Generator
Margarate	Generator
Margarinate	Generator
N-Heptadecanoate	Generator
N-Heptadecoate	Generator
N-Heptadecylate	Generator
Heptadecanoate	Generator
Margaroate	HMDB
Margaroic acid	HMDB
Normal-heptadecanoate	HMDB
Normal-heptadecanoic acid	HMDB
Margaric acid, 1-(11)C-labeled	MeSH, HMDB
Margaric acid, nickel (2+) salt	MeSH, HMDB
Omega I-123 heptadecanoic acid	MeSH, HMDB
Margaric acid, potassium salt	MeSH, HMDB
Margaric acid, sodium salt	MeSH, HMDB
FA(17:0)	HMDB
Heptadecanoic acid	MeSH

Chemical Formula

C₁₇H₃₄O₂

Average Molecular Weight

270.4507

Monoisotopic Molecular Weight

270.255880332

IUPAC Name

heptadecanoic acid

Traditional Name

heptadecanoic acid

CAS Registry Number

506-12-7

SMILES

CCCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)

InChI Key

KEMQGTRYUADPNZ-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:32365 )
straight-chain saturated fatty acid (CHEBI:32365 )
Straight chain fatty acids (LMFA01010017 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	61.3 °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	7.66	ALOGPS
logP	6.7	ChemAxon
logS	-6.2	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	15	ChemAxon
Refractivity	81.68 m³·mol⁻¹	ChemAxon
Polarizability	36.49 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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-017i-0900000000-ebd7708ca40db1f69377	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-017i-1900000000-140a09beb5b6859644fd	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-017i-0900000000-ebd7708ca40db1f69377	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-017i-1900000000-140a09beb5b6859644fd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-016r-0900000000-a9975b7f916df9242d31	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9620000000-2e104e4843f27f81734a	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00bi-9350000000-8e55b03dd2c18c1e3ca7	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 - ESI-TOF 20V, Negative	splash10-0a4i-0019000000-83d961b9674b7b1b2a65	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0019000000-83d961b9674b7b1b2a65	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 10V, 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 20V, Negative	splash10-014i-0090000000-233b71c471008bbed61b	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-94bee87e459e47f84a4d	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-1e57778151b8b2a05362	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0090000000-433ed2666c0e94078147	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014i-0900000000-1e14b3fcd14dfdf48cbd	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0uxr-0090000000-de66caaa914ba0366a3d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-233b71c471008bbed61b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-94bee87e459e47f84a4d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-433ed2666c0e94078147	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0900000000-1e14b3fcd14dfdf48cbd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-0006-0190000000-0d9a873b65555a15a62e	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-0390000000-c2f846ea7246884b09ed	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0090000000-7aadc5ba2a6acb7162cf	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-1e14b3fcd14dfdf48cbd	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-3452bef1d9fd1091e354	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fi0-4590000000-727243a3559dd7ed991f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9710000000-f50bf2fb7778841f9f16	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-98c6dcf5eaea4132deb7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gdi-1090000000-e7ed55db02f1210fe7e1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9230000000-24fa7a34c1095502e707	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05fu-9210000000-099bddb00b5e5f57a591	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	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	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-23	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: 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	5176 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	5916 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	6656 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	7025 uM	Total fatty acid	M.J. Abarghuei, Y...	details

External Links

HMDB ID

HMDB0002259

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB004676

KNApSAcK ID

C00007426

Chemspider ID

10033

KEGG Compound ID

Not Available

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

32365

References

Synthesis Reference

Heiduschka, A.; Ripper, J. Heptadecylic acid. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1923), 56B 1736-9.

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 ]
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 ]
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 ]
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.
M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.

Showing metabocard for Heptadecanoic acid (BMDB0002259)

Structure for BMDB0002259 (Heptadecanoic acid)