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Showing Compound 3beta-Hydroxy-5-cholestenoate (FDB029069)

Record Information
Version1.0
Creation date2011-09-21 01:49:39 UTC
Update date2015-07-21 06:59:37 UTC
Primary IDFDB029069
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3beta-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.
CAS Number6561-58-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
(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-Hydroxy-5-cholesten-26-oatehmdb
3-Hydroxy-5-cholesten-26-oic acidhmdb
3beta-Hydroxy-5-cholesten-26-oatehmdb
3beta-Hydroxy-5-cholesten-26-oic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00048 g/LALOGPS
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
Chemical FormulaC27H44O3
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
InChI IdentifierInChI=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
Isomeric SMILESC[C@H](CCCC(C)C(O)=O)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3beta-Hydroxy-5-cholestenoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zg0-0119200000-cf2f89654276410539c7Spectrum
Predicted GC-MS3beta-Hydroxy-5-cholestenoate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-1111490000-662961a4e7c28f9be860Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009300000-7b08fcb43266122804042016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fxt-1009000000-b2577c5e07feec9d9fcd2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfs-3139000000-76e577fa5177fe93c8a82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0003900000-4457a23048f590acbbe22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gi0-0009400000-39ee1cce45f0c6abaa3b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-7009000000-58516d19e994795057ae2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC17333
Pubchem Compound ID53481407
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12453
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference