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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 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
Data?1582752181
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
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point122.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability50.52 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.45631661259
DarkChem[M-H]-194.73131661259
AllCCS[M+H]+204.01632859911
AllCCS[M-H]-202.19132859911
DeepCCS[M-2H]-242.03530932474
DeepCCS[M+Na]+216.24530932474
AllCCS[M+H]+204.032859911
AllCCS[M+H-H2O]+201.932859911
AllCCS[M+NH4]+205.932859911
AllCCS[M+Na]+206.532859911
AllCCS[M-H]-202.232859911
AllCCS[M+Na-2H]-204.032859911
AllCCS[M+HCOO]-206.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lathosterol[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)C2649.1Standard polar33892256
Lathosterol[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)C3200.1Standard non polar33892256
Lathosterol[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)C3200.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lathosterol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3244.0Semi standard non polar33892256
Lathosterol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3472.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lathosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1019000000-45e8f26aff61be3d325a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lathosterol GC-MS (1 TMS) - 70eV, Positivesplash10-0006-3004900000-efe936a9ed1a83aa429c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lathosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 10V, Positive-QTOFsplash10-014r-0009000000-88fe25051d65e99ecb322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 20V, Positive-QTOFsplash10-05p9-3149000000-d25373f7179ed89b61dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 40V, Positive-QTOFsplash10-0c00-6359000000-8bff83f3efe22597deab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 10V, Negative-QTOFsplash10-000i-0009000000-82b1527837d67c6be40a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 20V, Negative-QTOFsplash10-000i-0009000000-e2badd995ee41a69b18f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 40V, Negative-QTOFsplash10-0ldi-1009000000-96f6e67651380e1c959e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 10V, Positive-QTOFsplash10-000i-0009000000-178681247f50782398982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 20V, Positive-QTOFsplash10-0avu-9233000000-247b9ee1da8d484a4da62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 40V, Positive-QTOFsplash10-0a4l-9710000000-8ebbaf147cf1232af8792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 10V, Negative-QTOFsplash10-000i-0009000000-c037f2d2f217e99b79ac2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 20V, Negative-QTOFsplash10-000i-0009000000-c037f2d2f217e99b79ac2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lathosterol 40V, Negative-QTOFsplash10-001i-0009000000-fbd8e8ecfb898bb732a52021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Ovary
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected and Quantified<18 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified<0.000129 uMNewborn (0-30 days old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected and Quantified81.6 uMChildren (1-13 years old)MaleLathosterolosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
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 ]
Lathosterolosis
  1. Ho AC, Fung CW, Siu TS, Ma OC, Lam CW, Tam S, Wong VC: Lathosterolosis: a disorder of cholesterol biosynthesis resembling smith-lemli-opitz syndrome. JIMD Rep. 2014;12:129-34. doi: 10.1007/8904_2013_255. Epub 2013 Oct 20. [PubMed:24142275 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDLTHSTRL
MarkerDB IDMDB00000305
Good Scents IDNot Available
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 → 5alpha-Cholest-8-en-3beta-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 → 5alpha-Cholesta-7,24-dien-3beta-ol + NADPH + Hydrogen Iondetails