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Identification
YMDB IDYMDB00681
Namepalmitoleic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPalmitoleic acid, also known as (Z)-9-hexadecenoate or palmitoleate, 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. Palmitoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
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
  • cis-Δ(9)-hexadecenoate
  • cis-Δ(9)-hexadecenoic acid
  • (9Z)-Hexadec-9-enoic acid
  • (9Z)-Hexadecenoate
  • Hexadecenoate (N-C16:1)
  • Palmitoleic acid, (Z)-isomer
  • Palmitoleic acid, sodium salt, (Z)-isomer
  • Palmitoleic acid, (e)-isomer
  • Palmitoleic acid, potassium salt, (Z)-isomer
  • C16:1 trans-9
  • Palmitelaidic acid
CAS number373-49-9
WeightAverage: 254.4082
Monoisotopic: 254.224580204
InChI KeySECPZKHBENQXJG-FPLPWBNLSA-N
InChIInChI=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 Namepalmitoleic acid
Chemical FormulaC16H30O2
SMILESCCCCCC\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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-0.1 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00045 g/LALOGPS
logP6.71ALOGPS
logP5.89ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.2 m³·mol⁻¹ChemAxon
Polarizability32.87 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cell Envelope
  • Cytoplasm
  • Endoplasmic Reticulum
  • Extracellular
  • Lipid Particle
  • Mitochondrion
  • Peroxisome
Organoleptic PropertiesNot Available
SMPDB Pathways
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid biosynthesisec00061 Map00061
SMPDB ReactionsNot Available
KEGG Reactions
hydron + myristic acid + malonyl-CoA + oxygen + NADPHNADP + Carbon dioxide + Coenzyme A + palmitoleic acid + water
Adenosine triphosphate + Coenzyme A + palmitoleic acidAdenosine monophosphate + Pyrophosphate + hexadec-2-enoyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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:
ResourceLink
CHEBI ID28716
HMDB IDHMDB03229
Pubchem Compound ID5282745
Kegg IDC08362
ChemSpider ID393216
FOODB IDFDB011675
WikipediaPalmitoleic_acid
BioCyc IDCPD-724

Enzymes

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.
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.
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.
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).
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.
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.