Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-05-01 17:29:28 UTC
Update Date2020-02-26 16:25:52 UTC
HMDB IDHMDB0060038
Secondary Accession Numbers
  • HMDB0062542
  • HMDB60038
  • HMDB62542
Metabolite Identification
Common Name10Z-Heptadecenoic acid
Description10Z-Heptadecenoic acid is a monounsaturated fatty acid with an unsaturated double bond at the 10th carbon. Heptadecanoic acid, or margaric acid, is a saturated fatty acid. Its molecular formula is CH3(CH2)15COOH. It occurs as a trace component of the fat and milkfat of ruminants, but it does not occur in any natural animal or vegetable fat at concentrations over half a percent. Salts and esters of heptadecanoic acid are called heptadecanoates.
Structure
Data?1574702173
Synonyms
ValueSource
(10Z)-10-Heptadecenoic acidChEBI
(10Z)-Heptadec-10-enoic acidChEBI
17:1 N-7 cisChEBI
C17:1 N-7 cisChEBI
cis-10-Heptadecenoic acidChEBI
cis-Tetradec-10-enoic acidChEBI
(10Z)-10-HeptadecenoateGenerator
(10Z)-Heptadec-10-enoateGenerator
cis-10-HeptadecenoateGenerator
cis-Tetradec-10-enoateGenerator
10Z-HeptadecenoateGenerator
(Z)-10-Heptadecenoic acidHMDB
10-cis-Heptadecenoic acidHMDB
10-Heptadecenoate (17:1n7)HMDB
FA(17:1(10Z))HMDB
10Z-Heptadecenoic acidChEBI
10-HeptadecenoateHMDB
FA(17:1n7)HMDB
(10Z)-HeptadecenoateGenerator
Chemical FormulaC17H32O2
Average Molecular Weight268.4348
Monoisotopic Molecular Weight268.240230268
IUPAC Name(10Z)-heptadec-10-enoic acid
Traditional Name(10Z)-heptadec-10-enoic acid
CAS Registry Number29743-97-3
SMILES
CCCCCC\C=C/CCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h7-8H,2-6,9-16H2,1H3,(H,18,19)/b8-7-
InChI KeyGDTXICBNEOEPAZ-FPLPWBNLSA-N
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00023 g/LALOGPS
logP7.21ALOGPS
logP6.34ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)5.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity82.8 m³·mol⁻¹ChemAxon
Polarizability34.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.28231661259
DarkChem[M-H]-174.02231661259
DeepCCS[M+H]+175.70630932474
DeepCCS[M-H]-171.68630932474
DeepCCS[M-2H]-208.79430932474
DeepCCS[M+Na]+184.74530932474
AllCCS[M+H]+174.832859911
AllCCS[M+H-H2O]+171.732859911
AllCCS[M+NH4]+177.732859911
AllCCS[M+Na]+178.532859911
AllCCS[M-H]-175.532859911
AllCCS[M+Na-2H]-177.032859911
AllCCS[M+HCOO]-178.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
10Z-Heptadecenoic acidCCCCCC\C=C/CCCCCCCCC(O)=O3024.7Standard polar33892256
10Z-Heptadecenoic acidCCCCCC\C=C/CCCCCCCCC(O)=O1997.5Standard non polar33892256
10Z-Heptadecenoic acidCCCCCC\C=C/CCCCCCCCC(O)=O2054.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
10Z-Heptadecenoic acid,1TMS,isomer #1CCCCCC/C=C\CCCCCCCCC(=O)O[Si](C)(C)C2119.9Semi standard non polar33892256
10Z-Heptadecenoic acid,1TBDMS,isomer #1CCCCCC/C=C\CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2373.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 10Z-Heptadecenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9820000000-28c2fa1855cfbbc9c2142017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10Z-Heptadecenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9541000000-2c0c2ca243bec9498af22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10Z-Heptadecenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 10V, Positive-QTOFsplash10-0udi-0090000000-8d22fb8ea6a1dbd0555b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 20V, Positive-QTOFsplash10-0kmj-5590000000-4e674ed8993cc4f6adfc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 40V, Positive-QTOFsplash10-052f-9710000000-4cc9451aa48db2e103362017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 10V, Negative-QTOFsplash10-014i-0090000000-ad4ddb899eecac37200a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 20V, Negative-QTOFsplash10-01ba-0090000000-6a19ff0f71cf55a086ee2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 40V, Negative-QTOFsplash10-0a4l-9230000000-b126ed98ee26be5341362017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 10V, Positive-QTOFsplash10-0gb9-5490000000-7203ce5b9705a0093dbc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 20V, Positive-QTOFsplash10-0apj-9310000000-327c20c9869bbb1c50452021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 40V, Positive-QTOFsplash10-0api-9000000000-15e2fa1b8da2e785503c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 10V, Negative-QTOFsplash10-014i-0090000000-36c0d9e881e1f25aa9bd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 20V, Negative-QTOFsplash10-014j-0090000000-3bf7120436a89b8151252021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10Z-Heptadecenoic acid 40V, Negative-QTOFsplash10-0006-9310000000-c3ed7c93efc443a799032021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.03 +/- 0.057 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4471860
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312435
PDB IDNot Available
ChEBI ID75094
Food Biomarker OntologyNot Available
VMH IDM00003
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.