palmitoleic acid (YMDB00681)

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Identification

YMDB ID

YMDB00681

Name

palmitoleic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Palmitoleic acid, also known as palmitoleate or (9Z)-hexadecenoate, 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. Based on a literature review a significant number of articles have been published on Palmitoleic acid.

Structure

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

Synonyms

(9E)-9-Hexadecenoic acid
(9Z)-Hexadecenoic acid
(Z)-9-Hexadecenoate
(Z)-9-Hexadecenoic acid
(Z)-Hexadec-9-enoate
(Z)-Hexadec-9-enoic acid
(Z)-Palmitoleic acid
16:1Delta9
9-cis-Hexadecenoate
9-cis-Hexadecenoic acid
9-Hexadecenoate
9-Hexadecenoic acid
9-Hexadecenoic acid, (Z)-
cis-9-Hexadecenoate
cis-9-Hexadecenoic acid
cis-9-palmitoleic acid
cis-delta-9-Hexadecenoate
cis-delta-9-Hexadecenoic acid
cis-Delta(9)-hexadecenoate
cis-Delta(9)-hexadecenoic acid
cis-Hexadec-9-enoic acid
cis-Palmitoleate
cis-Palmitoleic acid
Hexadecenoate
Hexadecenoic acid
Oleopalmitate
Oleopalmitic acid
Palmitoleate
Palmitoleic acid
palmitolinoleate
palmitolinoleic acid
zoomarate
zoomaric acid
Zoomerate
Zoomeric acid
(9Z)-Hexadec-9-enoate
(9Z)-Hexadecenoate
cis-9-Palmitoleate
cis-Δ-9-hexadecenoate
cis-Δ-9-hexadecenoic acid
cis-Δ(9)-hexadecenoate
cis-Δ(9)-hexadecenoic acid
(9Z)-Hexadec-9-enoic acid
Hexadecenoate (N-C16:1)
Palmitoleic acid, (Z)-isomer
Palmitoleic acid, (e)-isomer
C16:1 trans-9
Palmitelaidic acid
(9Z)-9-Hexadecenoic acid
9Z-Hexadecenoic acid
C16:1
FA(16:1(9Z))
FA(16:1n7)
cis-delta9-Hexadecenoic acid
cis-Δ9-hexadecenoic acid

CAS number

373-49-9

Weight

Average: 254.4082
Monoisotopic: 254.224580204

InChI Key

SECPZKHBENQXJG-FPLPWBNLSA-N

InChI

InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-

IUPAC Name

(9Z)-hexadec-9-enoic acid

Traditional IUPAC Name

palmitoleic acid

Chemical Formula

C₁₆H₃₀O₂

SMILES

CCCCCC\C=C/CCCCCCCC(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
Unsaturated 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

hexadec-9-enoic acid (CHEBI:28716 )
Unsaturated fatty acids (C08362 )
Monounsaturated fatty acids (C08362 )
Unsaturated fatty acids (LMFA01030056 )

Physical Properties

State

Liquid

Charge

Melting point

-0.1 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.00045 g/L	ALOGPS
logP	6.71	ALOGPS
logP	5.89	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.99	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	78.2 m³·mol⁻¹	ChemAxon
Polarizability	32.87 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

Cell Envelope
Cytoplasm
Endoplasmic Reticulum
Extracellular
Lipid Particle
Mitochondrion
Peroxisome

Organoleptic Properties

Not Available

SMPDB Pathways

Fatty acid biosynthesis

PW002458

KEGG Pathways

Fatty acid biosynthesis

ec00061

SMPDB Reactions

Not Available

KEGG Reactions

hydron + myristic acid + malonyl-CoA + oxygen + NADPH → NADP + Carbon dioxide + Coenzyme A + palmitoleic acid + water

Adenosine triphosphate + Coenzyme A + palmitoleic acid ↔ Adenosine monophosphate + Pyrophosphate + hexadec-2-enoyl-CoA

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00nb-5900000000-90ab9a21246ad658bda0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-2900000000-6683cd8579813b4f1ebb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00nb-5900000000-90ab9a21246ad658bda0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00nb-5900000000-90ab9a21246ad658bda0	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8910000000-20fcd1fc2d9e095b2c24	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9630000000-7eda678c0ecd65b2e479	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0090000000-993c95f96e1ca69a41c0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0090000000-e72ac58f23bacbf37344	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0090000000-d1585cc46cbce84a0506	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0091000000-fd89101236e85a2d9154	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-35027c88ff732ff74b4c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-3cac469ac1efde0a3543	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-e5833c7aa4795570bdc4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-9090000000-909ebad9120d01bf8e79	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004j-9000000000-fb5a2e21c48a7d72aac8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-0090000000-09c91b61deabc72625f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0udi-0090000000-993c95f96e1ca69a41c0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0udi-0090000000-e72ac58f23bacbf37344	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 17V, positive	splash10-000i-0490000000-472e6cf8ba7a80f708b8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0a4i-0090000000-3c6c13dcd5649fd90845	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0a4i-0090000000-e5cccbc8340bb0dce9d3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0a4i-2490000000-1dbd141e66d6e7a165ae	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0090000000-202819132f83589a248b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-7790000000-ff129e0c7cc2a7e4cf19	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-749f09fec19d95c21683	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-5005f244d7d1c3502c3e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zg0-1090000000-cac7fce9a75b0f1abd63	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-2e782c63ccf72afe9be9	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Petschnigg, J., Wolinski, H., Kolb, D., Zellnig, G., Kurat, C. F., Natter, K., Kohlwein, S. D. (2009). "Good fat, essential cellular requirements for triacylglycerol synthesis to maintain membrane homeostasis in yeast." J Biol Chem 284:30981-30993.19608739
Fakas, S., Qiu, Y., Dixon, J. L., Han, G. S., Ruggles, K. V., Garbarino, J., Sturley, S. L., Carman, G. M. (2011). "Phosphatidate Phosphatase Activity Plays Key Role in Protection against Fatty Acid-induced Toxicity in Yeast." J Biol Chem 286:29074-29085.21708942
Aguilera, F., Peinado, R. A., Millan, C., Ortega, J. M., Mauricio, J. C. (2006). "Relationship between ethanol tolerance, H+ -ATPase activity and the lipid composition of the plasma membrane in different wine yeast strains." Int J Food Microbiol 110:34-42.16690148
You, K. M., Rosenfield, C. L., Knipple, D. C. (2003). "Ethanol tolerance in the yeast Saccharomyces cerevisiae is dependent on cellular oleic acid content." Appl Environ Microbiol 69:1499-1503.12620835
Schneiter, R., Tatzer, V., Gogg, G., Leitner, E., Kohlwein, S. D. (2000). "Elo1p-dependent carboxy-terminal elongation of C14:1Delta(9) to C16:1Delta(11) fatty acids in Saccharomyces cerevisiae." J Bacteriol 182:3655-3660.10850979
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Xu, Huashun; Luo, Yuping; Li, Siguang. Palmitoleic acid production by fermentation with yeast. Zhongguo Youzhi (1999), 24(6), 53-55.

External Links:

Resource	Link
CHEBI ID	28716
HMDB ID	HMDB03229
Pubchem Compound ID	5282745
Kegg ID	C08362
ChemSpider ID	393216
FOODB ID	FDB031085
Wikipedia	Palmitoleic_acid
BioCyc ID	CPD-724

Enzymes

Protein Details

1. Long-chain-fatty-acid--CoA ligase 4

General function:: Involved in catalytic activity
Specific function:: Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Contributes, with FAA1, to the activation of imported myristate
Gene Name:: FAA4
Uniprot ID:: P47912
Molecular weight:: 77266.5

Reactions

ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.

Protein Details

2. Long-chain-fatty-acid--CoA ligase 1

General function:: Involved in catalytic activity
Specific function:: Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It may supplement intracellular myristoyl-CoA pools from exogenous myristate. Preferentially acts on C12:0-C16:0 fatty acids with myristic and pentadecanic acid (C15:0) having the highest activities
Gene Name:: FAA1
Uniprot ID:: P30624
Molecular weight:: 77865.79688

Reactions

ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.

Protein Details

3. Long-chain-fatty-acid--CoA ligase 3

General function:: Involved in catalytic activity
Specific function:: Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. This enzyme acts preferentially on C16 and C18 fatty acids with a cis-double bond at C-9-C-10
Gene Name:: FAA3
Uniprot ID:: P39002
Molecular weight:: 77946.0

Reactions

ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.

Protein Details

4. Elongation of fatty acids protein 1

General function:: Involved in fatty acid elongase activity
Specific function:: May be a membrane bound enzyme involved in the highly specific elongation of saturated 14-carbon fatty acids (14:0) to 16-carbon species (16:0)
Gene Name:: ELO1
Uniprot ID:: P39540
Molecular weight:: 36233.60156

Reactions

Acyl-CoA + malonyl-CoA → 3-oxoacyl-CoA + CoA + CO(2).

Protein Details

5. Long-chain-fatty-acid--CoA ligase 2

General function:: Involved in catalytic activity
Specific function:: Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Preferentially acts on C9:0-C13:0 fatty acids although C7:0-C17:0 fatty acids are tolerated
Gene Name:: FAA2
Uniprot ID:: P39518
Molecular weight:: 83437.10156

Reactions

ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.

Protein Details

6. Fatty acid synthase subunit beta

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long- chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. The beta subunit contains domains for:[acyl-carrier-protein] acetyltransferase and malonyltransferase, S-acyl fatty acid synthase thioesterase, enoyl-[acyl-carrier-protein] reductase, and 3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase
Gene Name:: FAS1
Uniprot ID:: P07149
Molecular weight:: 228689.0

Reactions

Acetyl-CoA + n malonyl-CoA + 2n NADH + 2n NADPH → long-chain-acyl-CoA + n CoA + n CO(2) + 2n NAD(+) + 2n NADP(+).
Acetyl-CoA + [acyl-carrier-protein] → CoA + acetyl-[acyl-carrier-protein].
Malonyl-CoA + [acyl-carrier-protein] → CoA + malonyl-[acyl-carrier-protein].
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] → hexadec-2-enoyl-[acyl-carrier-protein] + H(2)O.
Acyl-[acyl-carrier-protein] + NAD(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH.
Oleoyl-[acyl-carrier-protein] + H(2)O → [acyl-carrier-protein] + oleate.

Structure for #<Compound:0xa6b9da38>

Enzymes

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