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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-08 15:00:03 UTC
Update Date2020-02-26 21:43:08 UTC
HMDB IDHMDB0029216
Secondary Accession Numbers
  • HMDB29216
Metabolite Identification
Common NameSM C16:1
DescriptionSm c16:1 is classified as a member of the phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. Sm c16:1 is considered to be a practically insoluble (in water) and a moderately acidic compound. Sm c16:1 can be found in blood and urine. Within a cell, Sm c16:1 is primarily located near the membrane (predicted from logp).
Structure
Data?1582753388
SynonymsNot Available
Chemical FormulaC40H80N2O6P
Average Molecular Weight716.0468
Monoisotopic Molecular Weight715.575399814
IUPAC Name{[(2S,3R,11E)-2-[(9E)-hexadec-9-enamido]-3-hydroxynonadec-11-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid
Traditional Name[(2S,3R,11E)-2-[(9E)-hexadec-9-enamido]-3-hydroxynonadec-11-en-1-yl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
CCCCCCC\C=C\CCCCCCC[C@@H](O)[C@H](COP(O)(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCC\C=C\CCCCCC
InChI Identifier
InChI=1S/C40H79N2O6P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-39(43)38(37-48-49(45,46)47-36-35-42(3,4)5)41-40(44)34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h17-20,38-39,43H,6-16,21-37H2,1-5H3,(H-,41,44,45,46)/p+1/b19-17+,20-18+/t38-,39+/m0/s1
InChI KeyZKIVREDSEABFBU-NDBDZNEVSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentPhosphocholines
Alternative Parents
Substituents
  • Phosphocholine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty amide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Amine
  • Alcohol
  • Organic oxide
  • Organic salt
  • Hydrocarbon derivative
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.5e-05 g/LALOGPS
logP4.99ALOGPS
logP6.9ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.09 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity220.94 m³·mol⁻¹ChemAxon
Polarizability90.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q1-6030394100-0921e5cc77015b10667aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02a2-2170190000-45451da024085f9209cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001a-6090011000-8bf200d1cd2fcfe48fa4Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified16.6 +/- 3.36 uMAdult (>18 years old)BothNormal details
FecesDetected and Quantified0.1 +/- 0.12 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.09 +/- 0.1 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0009 (0.0004-0.0023) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.455 (10.081) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified18.125 (15.986) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified20.316 (4.306) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified31.102 (6.468) uMAdult (>18 years old)FemalePregnancy details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031404
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124202091
PDB IDNot Available
ChEBI ID89104
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available