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Record Information
Version1.0
Creation Date2016-10-03 18:38:51 UTC
Update Date2020-04-22 15:50:27 UTC
BMDB IDBMDB0012453
Secondary Accession Numbers
  • BMDB12453
Metabolite Identification
Common Name3 beta-Hydroxy-5-cholestenoate
DescriptionPS(16:1(9Z)/18:1(9Z)) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PS(16:1(9Z)/18:1(9Z)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 9Z-octadecenoyl to the C-2 atom. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.
Structure
Thumb
Synonyms
ValueSource
1-Palmitoleoyl-2-oleoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(16:1/18:1)HMDB
Phosphatidylserine(16:1n7/18:1n9)HMDB
Phosphatidylserine(16:1W7/18:1W9)HMDB
Phosphatidylserine(34:2)HMDB
PS(16:1/18:1)HMDB
PS(16:1N7/18:1N9)HMDB
PS(16:1W7/18:1W9)HMDB
PS(34:2)HMDB
pSer(16:1/18:1)HMDB
pSer(16:1n7/18:1n9)HMDB
pSer(16:1W7/18:1W9)HMDB
pSer(34:2)HMDB
1-(9Z-Hexadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoserineHMDB
(3beta)-3-Hydroxy-cholest-5-en-26-OateHMDB
(3beta)-3-Hydroxy-cholest-5-en-26-Oic acidHMDB
3 beta-Hydroxycholest-5-en-27-OateHMDB
3 beta-Hydroxycholest-5-en-27-Oic acidHMDB
3-HCOAHMDB, MeSH
3-Hydroxy-5-cholesten-26-OateHMDB
3-Hydroxy-5-cholesten-26-Oic acidHMDB, MeSH
3-Hydroxy-5-cholestenoateHMDB
3-Hydroxy-5-cholestenoic acidHMDB, MeSH
3beta-Hydroxy-5-cholesten-26-OateHMDB
3beta-Hydroxy-5-cholesten-26-Oic acidHMDB
3beta-Hydroxy-5-cholestenoateHMDB
3beta-Hydroxy-5-cholestenoic acidHMDB
3 b-Hydroxy-5-cholestenoateGenerator
3 b-Hydroxy-5-cholestenoic acidGenerator
3 beta-Hydroxy-5-cholestenoic acidGenerator
3 Β-hydroxy-5-cholestenoateGenerator
3 Β-hydroxy-5-cholestenoic acidGenerator
3-Hydroxy-5-cholestenoic acid, (3beta,25S)-isomerMeSH
3-Hydroxy-5-cholestenoic acid, 26-14(C)-labeledMeSH
3-Hydroxycholest-5-en-26-Oic acidMeSH
3 beta-Hydroxy-5-cholesten-26-Oic acidMeSH
3-Hydroxy-5-cholestenoic acid, (3beta,25R)-isomerMeSH
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(6R)-6-[(2R,5S,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid
Traditional Name(6R)-6-[(2R,5S,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid
CAS Registry Number6561-58-6
SMILES
C[C@H](CCCC(C)C(O)=O)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C27H44O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3,(H,29,30)/t17-,18?,20+,21?,22?,23?,24?,26+,27-/m1/s1
InChI KeyWVXOMPRLWLXFAP-UBJAGWMESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoserines
Direct ParentPhosphatidylserines
Alternative Parents
Substituents
  • Diacyl-glycerol-3-phosphoserine
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organic oxide
  • Primary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.57ALOGPS
logP6.05ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.31 m³·mol⁻¹ChemAxon
Polarizability50.2 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg0-0119200000-cf2f89654276410539c7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1111490000-662961a4e7c28f9be860View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009300000-7b08fcb4326612280404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fxt-1009000000-b2577c5e07feec9d9fcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfs-3139000000-76e577fa5177fe93c8a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0003900000-4457a23048f590acbbe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gi0-0009400000-39ee1cce45f0c6abaa3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-7009000000-58516d19e994795057aeView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012368
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028986
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52926009
PDB IDNot Available
ChEBI ID90032
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available