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Heptadecenoic acid (M2MDB001933)

Record Information
Version2.0
Creation Date2012-08-09 09:25:22 -0600
Update Date2015-06-03 17:21:44 -0600
Secondary Accession Numbers
  • ECMDB21538
Identification
Name:Heptadecenoic acid
DescriptionHeptadecenoic acid is a member of the chemical class known as Unsaturated Fatty Acids. These are fatty acids whose chain contains at least one CC double bond. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (E)-Heptadec-9-enoate
  • (E)-Heptadec-9-enoic acid
  • 9E-Heptadecenoate
  • 9E-Heptadecenoic acid
  • Heptadecenoate
Chemical Formula:C17H32O2
Weight:Average: 268.4348
Monoisotopic: 268.240230268
InChI Key:GEHPRJRWZDWFBJ-FOCLMDBBSA-N
InChI:InChI=1S/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h15-16H,2-14H2,1H3,(H,18,19)/b16-15+
CAS number:26265-99-6
IUPAC Name:(2E)-heptadec-2-enoic acid
Traditional IUPAC Name:2-heptadecylenic acid
SMILES:[H]\C(CCCCCCCCCCCCCC)=C(\[H])C(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
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00013 g/LALOGPS
logP7.65ALOGPS
logP6.7ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)5.03ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity82.78 m³·mol⁻¹ChemAxon
Polarizability35.88 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-6d82979388c980b71ff4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-4390000000-1dd1acb86b8755a56405View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-8910000000-0fc3d6af279de990c553View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-9f1c4c32c5a19023f739View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0090000000-9b53c9dc12390b9203e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9460000000-166a216dfa69c7b2db71View in MoNA
References
References:
  • 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
  • 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)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID5282747
Kegg IDC16536
ChemSpider ID4445874
Wikipedia IDNot Available
BioCyc IDNot 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