Showing metabocard for 5a-Cholesta-7,24-dien-3b-ol (BMDB0006842)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:26:41 UTC
Update Date2020-05-21 16:27:03 UTC
BMDB IDBMDB0006842
Secondary Accession Numbers
  • BMDB06842
Metabolite Identification
Common 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
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
Traditional 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
CAS Registry Number651-54-7
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
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-1019000000-626e97645b632a1ff077View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-002f-3005900000-d8ed9d20e09e9fa8cc7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-7a6c3d9d9c76b57c466dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-3149000000-c495f8dafd8943c3d42eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdi-4359000000-ad675d67e0ffcf298cfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-8ff4cced50a3c638abbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-7c6022da576a7535f88dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-1019000000-d3fac15fb12cab1c814fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0008279
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779048
PDB IDNot Available
ChEBI ID74970
References
Synthesis ReferenceMoreau, Jacques P.; Aberhart, Donald J.; Caspi, Eliahu. Synthesis of 5a-cholesta-7,24-dien-3b-ol and cholesta-5,7,24-trien-3b-ol. Journal of Organic Chemistry (1974), 39(14), 2018-23.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. EBP cholestenol delta-isomerase
General function:
Involved in C-8 sterol isomerase activity
Specific function:
Not Available
Gene Name:
EBP
Uniprot ID:
Q3ZBT8
Molecular weight:
26480.0
Reactions
Zymosterol intermediate 2 → 5a-Cholesta-7,24-dien-3b-oldetails
Enzyme Details
2. 24-dehydrocholesterol reductase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
DHCR24
Uniprot ID:
A6QR14
Molecular weight:
60173.0
Reactions
5a-Cholesta-7,24-dien-3b-ol + NADPH → Lathosterol + NADPdetails