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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:48 UTC
HMDB IDHMDB0001170
Secondary Accession Numbers
  • HMDB01170
Metabolite Identification
Common NameLathosterol
DescriptionLathosterol is a a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438 ). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID: 8777839 ). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O.
Structure
Thumb
Synonyms
ValueSource
gamma-CholesterolChEBI
g-CholesterolGenerator
γ-cholesterolGenerator
(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
5alpha-Cholest-7-en-3beta-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
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Traditional Name7-cholesterol
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
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These 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
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

    Endocrine gland:

  Cell and elements:

    Cell:

    Element:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Multicellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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
Water Solubility3.5e-05 g/LALOGPS
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
Polarizability50.6 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
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 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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Feces
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Eye Lens
  • Fetus
  • Fibroblasts
  • Gonads
  • Gut
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Skin
Pathways
NameSMPDB/PathwhizKEGG
Alendronate pathwayPw000137Pw000137 greyscalePw000137 simpleNot Available
Atorvastatin PathwayPw000275Pw000275 greyscalePw000275 simpleNot Available
CHILD SyndromePw000096Pw000096 greyscalePw000096 simpleNot Available
Cerivastatin PathwayPw000271Pw000271 greyscalePw000271 simpleNot Available
Cholesteryl ester storage diseasePw000484Pw000484 greyscalePw000484 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.9 +/- 7.0 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified5.38 +/- 0.038 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.43 +/- 0.048 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified67.5 +/- 58.4 uMAdult (>18 years old)Both
Cerebrotendinous xanthomatosis (CTX)
details
BloodDetected and Quantified9.6 (5.4-13.5) uMAdult (>18 years old)Female
Cirrhosis
details
Associated Disorders and Diseases
Disease References
Cerebrotendinous xanthomatosis
  1. Halperin G, Elisaf M, Leitersdorf E, Harats D: A new method for determination of serum cholestanol by high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):345-52. [PubMed:10901139 ]
Cirrhosis
  1. Halperin G, Elisaf M, Leitersdorf E, Harats D: A new method for determination of serum cholestanol by high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):345-52. [PubMed:10901139 ]
Associated OMIM IDs
  • 213700 (Cerebrotendinous xanthomatosis)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022463
KNApSAcK IDNot Available
Chemspider ID59151
KEGG Compound IDC01189
BioCyc IDCPD-4186
BiGG ID37036
Wikipedia LinkNot Available
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)Download (PDF)
General References
  1. Brunetti-Pierri N, Corso G, Rossi M, Ferrari P, Balli F, Rivasi F, Annunziata I, Ballabio A, Russo AD, Andria G, Parenti G: Lathosterolosis, a novel multiple-malformation/mental retardation syndrome due to deficiency of 3beta-hydroxysteroid-delta5-desaturase. Am J Hum Genet. 2002 Oct;71(4):952-8. Epub 2002 Aug 20. [PubMed:12189593 ]
  2. Nikkila K, Hockerstedt K, Miettinen TA: Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels. Clin Chim Acta. 1992 Jun 30;208(3):205-18. [PubMed:1499139 ]
  3. Paiva H, Thelen KM, Van Coster R, Smet J, De Paepe B, Mattila KM, Laakso J, Lehtimaki T, von Bergmann K, Lutjohann D, Laaksonen R: High-dose statins and skeletal muscle metabolism in humans: a randomized, controlled trial. Clin Pharmacol Ther. 2005 Jul;78(1):60-8. [PubMed:16003294 ]
  4. Rioux FM, Innis SM: Cholesterol and fatty acid metabolism in piglets fed sow milk or infant formula with or without addition of cholesterol. Metabolism. 1993 Dec;42(12):1552-9. [PubMed:8246769 ]
  5. Laaksonen R, Thelen KM, Paiva H, Matinheikki J, Vesalainen R, Janatuinen T, Knuuti J, Rontu R, von Bergmann K, Lutjohann D, Lehtimaki T: Genetic variant of the SREBF-1 gene is significantly related to cholesterol synthesis in man. Atherosclerosis. 2006 Mar;185(1):206-9. Epub 2005 Jul 11. [PubMed:16005884 ]
  6. Lutjohann D, Harzer K, Gieselmann V, Eckhardt M: Reduced brain cholesterol content in arylsulfatase A-deficient mice. Biochem Biophys Res Commun. 2006 Jun 2;344(2):647-50. Epub 2006 Apr 7. [PubMed:16630546 ]
  7. Hamilton JJ, Synnes A, Innis SM: Plasma cholesterol and lathosterol levels in term infants in the early neonatal period. Pediatr Res. 1992 Apr;31(4 Pt 1):396-400. [PubMed:1570206 ]
  8. Boomsma DI, Princen HM, Frants RR, Gevers Leuven JA, Kempen HJ: Genetic analysis of indicators of cholesterol synthesis and absorption: lathosterol and phytosterols in Dutch twins and their parents. Twin Res. 2003 Aug;6(4):307-14. [PubMed:14511438 ]
  9. Farkkila MA, Kairemo KJ, Taavitsainen MJ, Strandberg TA, Miettinen TA: Plasma lathosterol as a screening test for bile acid malabsorption due to ileal resection: correlation with 75SeHCAT test and faecal bile acid excretion. Clin Sci (Lond). 1996 Apr;90(4):315-9. [PubMed:8777839 ]

Enzymes

General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
SC5DL
Uniprot ID:
O75845
Molecular weight:
35300.55
Reactions
Lathosterol + NAD(P)H + Oxygen → 7-Dehydrocholesterol + NAD(P)(+) + Waterdetails
Lathosterol + NADH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NAD + Waterdetails
Lathosterol + NADPH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NADP + Waterdetails
General function:
Involved in iron ion binding
Specific function:
Not Available
Gene Name:
MSMO1
Uniprot ID:
Q15800
Molecular weight:
19470.325
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
Not Available
Gene Name:
NSDHL
Uniprot ID:
Q15738
Molecular weight:
41899.99
General function:
Involved in oxidoreductase activity
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:
HSD17B7
Uniprot ID:
P56937
Molecular weight:
38205.77
General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615
Reactions
Lathosterol → 5-alpha-cholest-8-en-3-beta-oldetails
Lathosterol → 5a-Cholest-8-en-3b-oldetails
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
Lathosterol + NADP → 5-alpha-Cholesta-7,24-dien-3-beta-ol + NADPHdetails
Lathosterol + NADP → 5a-Cholesta-7,24-dien-3b-ol + NADPH + Hydrogen Iondetails