ECMDB: Margaric acid (ECMDB21506) (M2MDB001901)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)Transporters (1)XML

Proteins (5)

Record Information

Version

2.0

Creation Date

2012-08-09 09:25:11 -0600

Update Date

2015-09-13 12:56:17 -0600

Secondary Accession Numbers

ECMDB21506

Identification

Name:

Margaric acid

Description

Margaric acid, also known as heptadecanoic acid, is a saturated fatty acid with a 17-carbon chain. Exogenous propionate can be incorporated by Escherichia coli as a primer to produce lipids with fatty acids of odd chain lengths.

Structure

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

Synonyms:

17:0
CH31[CH2]151COOH
Heptadecanoate
Heptadecanoate (ACD/Name 4.0)
Heptadecanoic acid
Heptadecanoic acid (ACD/Name 4.0)
Heptadecoate
Heptadecoic acid
Heptadecylate
Heptadecylic acid
Margarate
Margaric acid
Margarinate
Margarinic acid
Margarinsaure
Margaroate
Margaroic acid
N-Heptadecanoate
N-Heptadecanoic acid
N-Heptadecoate
N-Heptadecoic acid
N-Heptadecylate
N-Heptadecylic acid
Normal-heptadecanoate
Normal-heptadecanoic acid

Chemical Formula:

C₁₇H₃₄O₂

Weight:

Average: 270.4507
Monoisotopic: 270.255880332

InChI Key:

KEMQGTRYUADPNZ-UHFFFAOYSA-N

InChI:

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)

CAS number:

506-12-7

IUPAC Name:

heptadecanoic acid

Traditional IUPAC Name:

heptadecanoic acid

SMILES:

CCCCCCCCCCCCCCCCC(O)=O

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

Charge:

-1

Melting point:

61.3 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
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	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Membrane

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-017i-0900000000-ebd7708ca40db1f69377	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-017i-1900000000-140a09beb5b6859644fd	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-017i-0900000000-ebd7708ca40db1f69377	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-017i-1900000000-140a09beb5b6859644fd	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-016r-0900000000-a9975b7f916df9242d31	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9620000000-2e104e4843f27f81734a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00bi-9350000000-8e55b03dd2c18c1e3ca7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0a4i-0019000000-83d961b9674b7b1b2a65	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0019000000-83d961b9674b7b1b2a65	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-1e57778151b8b2a05362	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014i-0090000000-1e57778151b8b2a05362	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-233b71c471008bbed61b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-94bee87e459e47f84a4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-1e57778151b8b2a05362	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0090000000-433ed2666c0e94078147	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014i-0900000000-1e14b3fcd14dfdf48cbd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0uxr-0090000000-de66caaa914ba0366a3d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-233b71c471008bbed61b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-94bee87e459e47f84a4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-433ed2666c0e94078147	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0900000000-1e14b3fcd14dfdf48cbd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-0006-0190000000-0d9a873b65555a15a62e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-0390000000-c2f846ea7246884b09ed	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0090000000-7aadc5ba2a6acb7162cf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-1e14b3fcd14dfdf48cbd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-3452bef1d9fd1091e354	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fi0-4590000000-727243a3559dd7ed991f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9710000000-f50bf2fb7778841f9f16	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-98c6dcf5eaea4132deb7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gdi-1090000000-e7ed55db02f1210fe7e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9230000000-24fa7a34c1095502e707	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-05fu-9210000000-099bddb00b5e5f57a591	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Hvid-Jacobsen K, Nielsen SL, Jensen VJ, Thomsen HS: Demonstration of the thoracic duct by 123I heptadecanoic acid. Report of a case. Acta Radiol. 1987 Nov-Dec;28(6):783-4. Pubmed: 2962620
Mertens J, Vanryckeghem W, Bossuyt A: Fast, low-temperature preparation of carrier-free 17-123I-heptadecanoic acid applied for liver and heart scintigraphy. Eur J Nucl Med. 1986;11(9):361-2. Pubmed: 3956529
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
Steer P, Basu S, Lithell H, Vessby B, Berne C, Lind L: Acute elevations of medium- and long-chain fatty acid have different impacts on endothelium-dependent vasodilation in humans. Lipids. 2003 Jan;38(1):15-9. Pubmed: 12669814
Takala TO, Nuutila P, Pulkki K, Oikonen V, Gronroos T, Savunen T, Vahasilta T, Luotolahti M, Kallajoki M, Bergman J, Forsback S, Knuuti J: 14(R,S)-[18F]Fluoro-6-thia-heptadecanoic acid as a tracer of free fatty acid uptake and oxidation in myocardium and skeletal muscle. Eur J Nucl Med Mol Imaging. 2002 Dec;29(12):1617-22. Epub 2002 Oct 3. Pubmed: 12458396
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Van Roosmalen PB, Drummond I: Simultaneous determination by gas chromatography of the major metabolites in urine of toluene, xylenes and styrene. Br J Ind Med. 1978 Feb;35(1):56-60. Pubmed: 629890
Wolk A, Vessby B, Ljung H, Barrefors P: Evaluation of a biological marker of dairy fat intake. Am J Clin Nutr. 1998 Aug;68(2):291-5. Pubmed: 9701185
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	32365
HMDB ID	HMDB02259
Pubchem Compound ID	10465
Kegg ID	Not Available
ChemSpider ID	10033
Wikipedia	Margaric_acid
BioCyc ID	Not Available

Enzymes

Protein Details

1. 3-oxoacyl-[acyl-carrier-protein] synthase 3

General function:: Involved in 3-oxoacyl-[acyl-carrier-protein] synthase activity
Specific function:: Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Catalyzes the first condensation reaction which initiates fatty acid synthesis and may therefore play a role in governing the total rate of fatty acid production. Possesses both acetoacetyl-ACP synthase and acetyl transacylase activities. Has some substrate specificity for acetyl-CoA. Its substrate specificity determines the biosynthesis of straight-chain of fatty acids instead of branched-chain
Gene Name:: fabH
Uniprot ID:: P0A6R0
Molecular weight:: 33515

Reactions

Acetyl-CoA + malonyl-[acyl-carrier-protein] = acetoacetyl-[acyl-carrier-protein] + CoA + CO(2).

Protein Details

2. 3-oxoacyl-[acyl-carrier-protein] synthase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Has a preference for short chain acid substrates and may function to supply the octanoic substrates for lipoic acid biosynthesis
Gene Name:: fabF
Uniprot ID:: P0AAI5
Molecular weight:: 43045

Reactions

(Z)-hexadec-11-enoyl-[acyl-carrier-protein] + malonyl-[acyl-carrier-protein] = (Z)-3-oxooctadec-13-enoyl-[acyl-carrier-protein] + CO(2) + [acyl-carrier-protein].

Protein Details

3. 3-oxoacyl-[acyl-carrier-protein] reductase

General function:: Involved in 3-oxoacyl-[acyl-carrier-protein] reductase (NADPH) activity
Specific function:: (3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP(+) = 3-oxoacyl-[acyl-carrier-protein] + NADPH
Gene Name:: fabG
Uniprot ID:: P0AEK2
Molecular weight:: 25560

Reactions

(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP(+) = 3-oxoacyl-[acyl-carrier-protein] + NADPH.

Protein Details

4. Acyl carrier protein

General function:: Involved in fatty acid biosynthetic process
Specific function:: Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:: acpP
Uniprot ID:: P0A6A8
Molecular weight:: 8640

Transporters

Protein Details

1. Long-chain fatty acid transport protein

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids across the outer membrane. It is a receptor for the bacteriophage T2. FadL may form a specific channel
Gene Name:: fadL
Uniprot ID:: P10384
Molecular weight:: 48541

Margaric acid (ECMDB21506) (M2MDB001901)

Structure for #<Compound:0xac82f6ac>

Enzymes

Reactions

Reactions

Reactions

Transporters