Showing metabocard for Lathosterol (BMDB0001170)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:41:59 UTC
Update Date2020-05-21 16:28:43 UTC
BMDB IDBMDB0001170
Secondary Accession Numbers
  • BMDB01170
Metabolite Identification
Common NameLathosterol
DescriptionLathosterol, also known as gamma-cholesterol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, lathosterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on Lathosterol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
gamma-CholesterolChEBI
5alpha-Cholest-7-en-3beta-olKegg
g-CholesterolGenerator
Γ-cholesterolGenerator
5a-Cholest-7-en-3b-olGenerator
5Α-cholest-7-en-3β-olGenerator
(3beta)-Cholest-7-en-3-olHMDB
(3beta,5alpha)-Cholest-7-en-3-olHMDB
(3beta,alpha)-Cholest-7-en-3-olHMDB
(7)-CholestenolHMDB
3b-Hydroxy-5-cholesteneHMDB
3beta-Hydroxy-5alpha-cholest-7-eneHMDB
5-a-Cholest-7-en-3-beta-olHMDB
5-alpha-Cholest-7-en-3-beta-olHMDB
7-Cholesten-3-beta-olHMDB
7-CholestenolHMDB
7-CholesterolHMDB
Cholest-7-en-3-olHMDB
Cholest-7-en-3beta-olHMDB
Cholest-7-en-olHMDB
Cholesterol - syntheticHMDB
Cholesterol extra pureHMDB
Cholesterol GRHMDB
Cholesterol pharmaHMDB
Cholesterol,NF gradeHMDB
delta(7)-CholestenolHMDB
DELTA7-Cholesten-3beta-olHMDB
DELTA7-CholestenolHMDB
gamma-CholestenolHMDB
LathosterolChEBI
Chemical FormulaC27H46O
Average Molecular Weight386.6535
Monoisotopic Molecular Weight386.354866094
IUPAC Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry Number80-99-9
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H46O/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/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1
InChI KeyIZVFFXVYBHFIHY-SKCNUYALSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholesterol
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point122.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.4ALOGPS
logP7.11ChemAxon
logS-7ALOGPS
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 Count5ChemAxon
Refractivity120.62 m³·mol⁻¹ChemAxon
Polarizability50.52 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, Positivesplash10-0ab9-1019000000-45e8f26aff61be3d325aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-3004900000-efe936a9ed1a83aa429cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-88fe25051d65e99ecb32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3149000000-d25373f7179ed89b61dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c00-6359000000-8bff83f3efe22597deabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-82b1527837d67c6be40aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-e2badd995ee41a69b18fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1009000000-96f6e67651380e1c959eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-178681247f5078239898View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avu-9233000000-247b9ee1da8d484a4da6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9710000000-8ebbaf147cf1232af879View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-fbd8e8ecfb898bb732a5View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Myelin sheath
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Ovary
  • Pancreas
  • Placenta
  • Platelet
  • Prostate Tissue
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Adrenal MedullaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Eye LensExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
OvaryExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001170
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022463
KNApSAcK IDC00023744
Chemspider ID59151
KEGG Compound IDC01189
BioCyc IDNot Available
BiGG ID37036
Wikipedia LinkLathosterol
METLIN ID6052
PubChem Compound65728
PDB IDNot Available
ChEBI ID17168
References
Synthesis ReferenceFieser, Louis F. Cholesterol and companions. III. Cholestanol, lathosterol, and ketone 104. Journal of the American Chemical Society (1953), 75 4395-403.
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
Lathosterol → 5a-Cholest-8-en-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
Enzyme Details
3. Sterol-C5-desaturase
General function:
Not Available
Specific function:
Not Available
Gene Name:
SC5D
Uniprot ID:
Q3SYX8
Molecular weight:
23318.0
Reactions
Lathosterol + NADPH + Oxygen → 7-Dehydrocholesterol + NADP +2 Waterdetails