You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00677
Namecapric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCapric acid, also known as decanoate or 10:0, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Capric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Capric acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1-decanoic acid
  • 1-Nonanecarboxylate
  • 1-Nonanecarboxylic acid
  • 15-(4-Iodophenyl)-3(R,S)-methylpentadecanoic acid (123I)
  • 15-(p-Iodophenyl)-3-methylpentadecanoic acid (123I)
  • C10:0
  • Caprate
  • Capric acid
  • Caprinate
  • Caprinic acid
  • Caprynate
  • Caprynic acid
  • CH3-[CH2]8-COOH
  • Decanoate
  • Decanoic acid
  • Decanoic acid (capric acid)
  • Decoate
  • Decoic acid
  • Decylate
  • Decylic acid
  • Dekansaeure
  • Kaprinsaeure
  • n-Caprate
  • n-Capric acid
  • n-Decanoate
  • n-Decanoic acid
  • n-Decoate
  • n-Decoic acid
  • n-Decylate
  • n-Decylic acid
  • Nonane-1-carboxylic acid
  • 10:0
  • Emery 659
  • Lunac 10-95
  • Lunac 10-98
  • Prifac 2906
  • Prifac 296
  • Decanoic acid, sodium salt
  • Sodium caprate
  • Sodium decanoate
  • FA(10:0)
CAS number334-48-5
WeightAverage: 172.2646
Monoisotopic: 172.146329884
InChI KeyGHVNFZFCNZKVNT-UHFFFAOYSA-N
InChIInChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)
IUPAC Namedecanoic acid
Traditional IUPAC Namecapric acid
Chemical FormulaC10H20O2
SMILESCCCCCCCCCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point31.9 °C
Experimental Properties
PropertyValueReference
Water Solubility0.0618 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP4.09 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.095 g/LALOGPS
logP3.93ALOGPS
logP3.59ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.48 m³·mol⁻¹ChemAxon
Polarizability21.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cell envelope
  • mitochondrion
  • endoplasmic reticulum
  • lipid particle
  • peroxisome
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
CitrusFDB012027
FatFDB012027
FattyFDB012027
RancidFDB012027
SourFDB012027
UnpleasantFDB012027
SMPDB Pathways
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid biosynthesisec00061 Map00061
SMPDB Reactions
capric acid + Malonate3-Oxododecanoic acid
trans-Dec-2-enoic acidcapric acid
KEGG Reactions
malonyl-CoA + Caprylic acid + hydron + NADPHcapric acid + Carbon dioxide + NADP + water + Coenzyme A
capric acid + malonyl-CoA + hydron + NADPHlauric acid + Carbon dioxide + NADP + water + Coenzyme A
capric acid + Adenosine triphosphate + Coenzyme AAdenosine monophosphate + Pyrophosphate + decanoyl-CoA
decanoyl-CoA + watercapric acid + hydron + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017i-2920000000-7f6721f01b80a790d544JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-076u-9000000000-96a2e9e00e464db3c086JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017i-2920000000-7f6721f01b80a790d544JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-016r-1910000000-1cc1026f6f325d994ab4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-9200000000-71a57b0e200e46fb66edJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9300000000-c615f39c0b907a00f67cJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-771e7907916bf05e6b10JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-f1e000384728ee06f802JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-1900000000-42a901bb54546da030daJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-83e77de04461ded1c4bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-f3190b828218d04d3cc7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0000000910-e82208ed71b4a3735258JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-00di-0900000000-8c6cdf0491f51ba6ef26JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-00di-0900000000-3afa642872e4450f0c49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-771e7907916bf05e6b10JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-f1e000384728ee06f802JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-d5dbc60c65c1a7d34e2fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-83e77de04461ded1c4bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-f3190b828218d04d3cc7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-00di-0900000000-53ea38eb25eaea66d22aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0900000000-8c6cdf0491f51ba6ef26JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0900000000-3afa642872e4450f0c49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-0a7f944302bce161f7e5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00b9-1900000000-b68efbceecf3433a9995JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-005a-9600000000-f2a54ed1a56ee9b7af77JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-076u-9000000000-96a2e9e00e464db3c086JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kf-0900100000-28cc3e7dc24d4208e159JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0900000000-3eb3455ff5fbfa8a3a2cJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-074l-9100000000-bf788cb34c09c6af56bfJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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
  • Furukawa, K., Yamada, T., Mizoguchi, H., Hara, S. (2003). "Increased ethyl caproate production by inositol limitation in Saccharomyces cerevisiae." J Biosci Bioeng 95:448-454.16233438
  • Jones, J. M., Nau, K., Geraghty, M. T., Erdmann, R., Gould, S. J. (1999). "Identification of peroxisomal acyl-CoA thioesterases in yeast and humans." J Biol Chem 274:9216-9223.10092594
  • Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
  • Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
Synthesis Reference:Wang, Qin; Ni, Xindi; Shi, Jianying. Manufacturing technology of capric acid and hydroxyalkyl amide from Litsea cubeba nucleolus oil. Huaxue Shijie (1993), 34(2), 84-7.
External Links:
ResourceLink
CHEBI ID30813
HMDB IDHMDB00511
Pubchem Compound ID2969
Kegg IDC01571
ChemSpider ID2863
FOODB IDFDB012027
WikipediaDecanoic_acid
BioCyc ID3-OXODODECANOATE

Enzymes

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.
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH
Gene Name:
TES1
Uniprot ID:
P41903
Molecular weight:
40259.39844
Reactions
Palmitoyl-CoA + H(2)O → CoA + palmitate.