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Showing metabocard for 7alpha-Hydroxycholesterol (HMDB0001496)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-10-09 21:01:49 UTC
HMDB IDHMDB0001496
Secondary Accession Numbers
  • HMDB01496
Metabolite Identification
Common Name7alpha-Hydroxycholesterol
Description7alpha-Hydroxycholesterol is an oxysterol and can serve as a biomarker for lipid peroxidation (PMID: 17386651 ). Products of cholesterol oxidation accumulate within atherosclerotic plaque and have been proposed to contribute to inflammatory signalling in the diseased artery (PMID: 17364953 ). 7alpha-Hydroxycholesterol is a cholesterol oxide that has been described as a biomarker of oxidative stress in subjects with impaired glucose tolerance and diabetes (PMID: 16634125 ). 7alpha-Hydroxycholesterol has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1582752205
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7alpha-Hydroxy-cholesterolChEBI
Cholest-5-ene-3beta,7alpha-diolChEBI
7a-Hydroxy-cholesterolGenerator
7Α-hydroxy-cholesterolGenerator
Cholest-5-ene-3b,7a-diolGenerator
Cholest-5-ene-3β,7α-diolGenerator
7a-HydroxycholesterolGenerator
7Α-hydroxycholesterolGenerator
7 alpha-HydroxycholesterolMeSH
Cholest-5-en-3 beta,7 alpha-diolMeSH
(3beta,7alpha)-Cholest-5-ene-3,7-diolHMDB
(3β,7α)-Cholest-5-ene-3,7-diolHMDB
7alpha-Hydroxycholest-5-en-3beta-olHMDB
7alpha-HydroxycholesterolHMDB
7alphaOHCholHMDB
7α-Hydroxycholest-5-en-3β-olHMDB
7αOHCholHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.663
Monoisotopic Molecular Weight402.349780721
IUPAC Name(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol
Traditional Name(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol
CAS Registry Number566-26-7
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI KeyOYXZMSRRJOYLLO-RVOWOUOISA-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
  • Cholesterol-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 7-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00048 g/LALOGPS
logP5.61ALOGPS
logP5.96ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.06 m³·mol⁻¹ChemAxon
Polarizability51.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.18 +/- 0.047 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.335 +/- 0.068 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.012 +/- 0.002 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.004 +/- 0.0016 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.054 +/- 0.019 uMAdult (>18 years old)Both
Cirrhosis		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.005 +/- 0.0021 uMAdult (>18 years old)Not SpecifiedMultiple Sclerosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Hahn C, Reichel C, von Bergmann K: Serum concentration of 7 alpha-hydroxycholesterol as an indicator of bile acid synthesis in humans. J Lipid Res. 1995 Sep;36(9):2059-66. [PubMed:8558093 ]
Multiple sclerosis
  1. Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. Epub 2004 Dec 1. [PubMed:15576852 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  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 IDFDB022655
KNApSAcK IDNot Available
Chemspider ID96891
KEGG Compound IDC03594
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link7α-Hydroxycholesterol
METLIN IDNot Available
PubChem Compound107722
PDB IDNot Available
ChEBI ID17500
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000333
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kitano S, Yoshida Y, Kawano K, Hibi N, Niki E: Oxidative status of human low density lipoprotein isolated by anion-exchange high-performance liquid chromatography--assessment by total hydroxyoctadecadienoic acid, 7-hydroxycholesterol, and 8-iso-prostaglandin F(2alpha). Anal Chim Acta. 2007 Feb 28;585(1):86-93. Epub 2006 Dec 23. [PubMed:17386651 ]
  2. Erridge C, Webb DJ, Spickett CM: 25-Hydroxycholesterol, 7beta-hydroxycholesterol and 7-ketocholesterol upregulate interleukin-8 expression independently of Toll-like receptor 1, 2, 4 or 6 signalling in human macrophages. Free Radic Res. 2007 Mar;41(3):260-6. [PubMed:17364953 ]
  3. Ferderbar S, Pereira EC, Apolinario E, Bertolami MC, Faludi A, Monte O, Calliari LE, Sales JE, Gagliardi AR, Xavier HT, Abdalla DS: Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes Metab Res Rev. 2007 Jan;23(1):35-42. [PubMed:16634125 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details
1. Cholesterol 7-alpha-monooxygenase
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:
CYP7A1
Uniprot ID:
P22680
Molecular weight:
57660.155
Reactions
Cholesterol + NADPH + Oxygen → 7alpha-Hydroxycholesterol + NADP + Waterdetails
Cholesterol + Oxygen + NADPH + Hydrogen Ion → 7alpha-Hydroxycholesterol + NADP + Waterdetails
Enzyme Details
2. 3 beta-hydroxysteroid dehydrogenase type 7
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:
HSD3B7
Uniprot ID:
Q9H2F3
Molecular weight:
21322.265
Reactions
7alpha-Hydroxycholesterol + NAD → 7a-Hydroxy-cholestene-3-one + NADH + Hydrogen Iondetails