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Showing Compound 5a-Cholesta-7,24-dien-3b-ol (FDB024115)

Record Information
Version1.0
Creation date2011-09-21 00:40:06 UTC
Update date2020-09-17 15:42:04 UTC
Primary IDFDB024115
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5a-Cholesta-7,24-dien-3b-ol
DescriptionPC(20:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(20:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one eicosanoyl chain to the C-1 atom, and one 5Z,8Z,11Z,14Z-eicosatetraenoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
CAS Number651-54-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-Arachidoyl-2-arachidonoyl-sn-glycero-3-phosphocholineChEBI
1-C20:0-2-C20:4(Omega-6)-phosphatidylcholineChEBI
1-Eicosanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineChEBI
1-Eicosanoyl-2-arachidonoyl-sn-glycero-3-phosphocholineChEBI
1-Icosanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholineChEBI
PC(20:0/20:4)ChEBI
PC(20:0/20:4omega6)ChEBI
PC(40:4)ChEBI
Phosphatidylcholine(20:0/20:4)ChEBI
Phosphatidylcholine(20:0/20:4omega6)ChEBI
Phosphatidylcholine(40:4)ChEBI
1-Arachidonyl-2-arachidonoyl-sn-glycero-3-phosphocholineHMDB
GPCho(20:0/20:4)HMDB
LecithinHMDB
GPCho(40:4)HMDB
1-Eicosanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineHMDB
5 alpha-Cholesta-7,24-dien-3beta-olHMDB
5alpha-Cholesta-7,24-dien-3beta-olHMDB
5 alpha-Cholesta-7,24-dien-3 beta-olMeSH, HMDB
Cholesta-7,24-dien-3-olMeSH, HMDB
Cholesta-7,24-dien-3-ol, (3beta)-isomerMeSH, HMDB
5 alpha-cholesta-7,24-dien-3beta-olhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00016 g/LALOGPS
logP7.4ALOGPS
logP6.71ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity121.47 m³·mol⁻¹ChemAxon
Polarizability49.74 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H44O
IUPAC name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
InChI IdentifierInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,10,19-21,23-25,28H,6,8-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25?,26+,27-/m1/s1
InChI KeyPKEPPDGGTSZLBL-FZAJRYLSSA-N
Isomeric SMILES[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
Classification
Description Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

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-MS5a-Cholesta-7,24-dien-3b-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aor-1019000000-626e97645b632a1ff077Spectrum
Predicted GC-MS5a-Cholesta-7,24-dien-3b-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-3005900000-d8ed9d20e09e9fa8cc7dSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-7a6c3d9d9c76b57c466d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-3149000000-c495f8dafd8943c3d42e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdi-4359000000-ad675d67e0ffcf298cfd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-8ff4cced50a3c638abba2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-7c6022da576a7535f88d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-1019000000-d3fac15fb12cab1c814f2017-09-01View Spectrum
NMRNot Available
ChemSpider ID389550
ChEMBL IDNot Available
KEGG Compound IDC05439
Pubchem Compound ID440670
Pubchem Substance IDNot Available
ChEBI ID16290
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06842
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID45811
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
Steroid BiosynthesisSMP00023 map00100
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference