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Human Metabolome Database Version 2.5

 

Showing metabocard for 7a-Hydroxycholesterol (HMDB01496)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:48
Accession Number HMDB01496
Secondary Accession Numbers Not Available
Common Name 7a-Hydroxycholesterol
Description 7alpha-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 biomarker of oxidative stress in subjects with impaired glucose tolerance and diabetes. (PMID: 16634125)
Synonyms
  1. 7alpha-Hydroxycholesterol
  2. 7 alpha-Hydroxycholesterol
  3. Cholest-5-ene-3beta,7alpha-diol
  4. 7-alpha-hydroxycholesterol
  5. 7-a-Hydroxycholesterol
Chemical IUPAC Name 10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Chemical Formula C27H46O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Dihydroxy steroids
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • alkene
Biofunction
  • Hormones, Membrane component
Application
—
Source
  • Endogenous
Average Molecular Weight 402.653
Monoisotopic Molecular Weight 402.349792
Isomeric SMILES CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILES CC(C)CCCC(C)C1CCC2C3C(O)C=C4CC(O)CCC4(C)C3CCC12C
KEGG Compound ID C03594 Link Image
BioCyc ID CPD-266 Link Image
BiGG ID 42155 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB01496 Link Image
Metagene Link HMDB01496 Link Image
METLIN ID 6280 Link Image
PubChem Compound 405 Link Image
PubChem Substance 2363 Link Image
ChEBI ID 17500 Link Image
CAS Registry Number Not Available
InChI Identifier InChI=1/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
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 4.76e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.61 [Predicted by ALOGPS]; 6.8 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
  • endoplasmic reticulum
Biofluid Location
  • Blood
  • Cerebrospinal Fluid
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.18 +/- 0.047 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.004 +/- 0.0016 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 0.054 +/- 0.019 uM
Age Adult:>18 yrs old
Sex Both
Condition Cirrhosis
Comments Advanced liver disease and biopsy-proven cirrhosis
References
  • 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 Link Image]
Biofluid CSF
Value 0.005 +/- 0.0021 uM
Age Adult:>18 yrs old
Sex N/A
Condition Multiple sclerosis
Comments Not Available
References
  • 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 Link Image]
Associated Disorders
Condition References
Cirrhosis
  • 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 Link Image]
Multiple sclerosis
  • 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 Link Image]
OMIM ID
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 Link Image map00120 Link Image
General References Not Available
Metabolic Enzymes
  1. Cytochrome P450 7A1
Enzyme 1 [top]
Enzyme 1 ID 5749
Enzyme 1 Name Cytochrome P450 7A1
Enzyme 1 Synonyms
  1. Cholesterol 7-alpha-monooxygenase
  2. CYPVII
  3. Cholesterol 7-alpha-hydroxylase
Enzyme 1 Gene Name CYP7A1
Enzyme 1 Protein Sequence >Cytochrome P450 7A1 
MMTTSLIWGIAIAACCCLWLILGIRRRQTGEPPLENGLIPYLGCALQFGANPLEFLRANQ
RKHGHVFTCKLMGKYVHFITNPLSYHKVLCHGKYFDWKKFHFATSAKAFGHRSIDPMDGN
TTENINDTFIKTLQGHALNSLTESMMENLQRIMRPPVSSNSKTAAWVTEGMYSFCYRVMF
EAGYLTIFGRDLTRRDTQKAHILNNLDNFKQFDKVFPALVAGLPIHMFRTAHNAREKLAE
SLRHENLQKRESISELISLRMFLNDTLSTFDDLEKAKTHLVVLWASQANTIPATFWSLFQ
MIRNPEAMKAATEEVKRTLENAGQKVSLEGNPICLSQAELNDLPVLDSIIKESLRLSSAS
LNIRTAKEDFTLHLEDGSYNIRKDDIIALYPQLMHLDPEIYPDPLTFKYDRYLDENGKTK
TTFYCNGLKLKYYYMPFGSGATICPGRLFAIHEIKQFLILMLSYFELELIEGQAKCPPLD
QSRAGLGILPPLNDIEFKYKFKHL
Enzyme 1 Number of Residues 504
Enzyme 1 Molecular Weight 57661
Enzyme 1 Theoretical pI 8.34
Enzyme 1 GO Classification
Function
  • binding
  • catalytic activity
  • cation binding
  • heme binding
  • ion binding
  • iron ion binding
  • monooxygenase activity
  • oxidoreductase activity
  • tetrapyrrole binding
  • transition metal ion binding
Process
  • cellular metabolism
  • electron transport
  • generation of precursor metabolites and energy
  • metabolism
  • physiological process
Component
—
Enzyme 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Enzyme 1 Specific Function Cholesterol + NADPH + O(2) = 7-alpha- hydroxycholesterol + NADP(+) + H(2)O
Enzyme 1 Pathways
Enzyme 1 Reactions
  • cholesterol + NADPH + H+ + O2 = 7alpha-hydroxycholesterol + NADP+ + H2O
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • 1-23
Enzyme 1 Transmembrane Regions Not Available
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 23909 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P22680 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name CP7A1_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1515 bp 
ATGATGACCACATCTTTGATTTGGGGGATTGCTATAGCAGCATGCTGTTGTCTATGGCTT
ATTCTTGGAATTAGGAGAAGGCAAACGGGTGAACCACCTCTAGAGAATGGATTAATTCCA
TACCTGGGCTGTGCTCTGCAATTTGGTGCCAATCCTCTTGAGTTCCTCAGAGCAAATCAA
AGGAAACATGGTCATGTTTTTACCTGCAAACTAATGGGAAAATATGTCCATTTCATCACA
AATCCCTTGTCATACCATAAGGTGTTGTGCCACGGAAAATATTTTGATTGGAAAAAATTT
CACTTTGCTACTTCTGCGAAGGCATTTGGGCACAGAAGCATTGACCCGATGGATGGAAAT
ACCACTGAAAACATAAACGACACTTTCATCAAAACCCTGCAGGGCCATGCCTTGAATTCC
CTCACGGAAAGCATGATGGAAAACCTCCAACGTATCATGAGACCTCCAGTCTCCTCTAAC
TCAAAGACCGCTGCCTGGGTGACAGAAGGGATGTATTCTTTCTGCTACCGAGTGATGTTT
GAAGCTGGGTATTTAACTATCTTTGGCAGAGATCTTACAAGGCGGGACACACAGAAAGCA
CATATTCTAAACAATCTTGACAACTTCAAGCAATTCGACAAAGTCTTTCCAGCCCTGGTA
GCAGGCCTCCCCATTCACATGTTCAGGACTGCGCACAATGCCCGGGAGAAACTGGCAGAG
AGCTTGAGGCACGAGAACCTCCAAAAGAGGGAAAGCATCTCAGAACTGATCAGCCTGCGC
ATGTTTCTCAATGACACTTTGTCCACCTTTGATGATCTGGAGAAGGCCAAGACACACCTC
GTGGTCCTCTGGGCATCGCAAGCAAACACCATTCCAGCGACTTTCTGGAGTTTATTTCAA
ATGATTAGGAACCCAGAAGCAATGAAAGCAGCTACTGAAGAAGTGAAAAGAACATTAGAG
AATGCTGGTCAAAAAGTCAGCTTGGAAGGCAATCCTATTTGTTTGAGTCAAGCAGAACTG
AATGACCTGCCAGTATTAAATAGTATAATCAAGGAATCGCTGAGGCTTTCCAGTGCCTCC
CTCAACATCCGGACAGCTAAGGAGGATTTCACTTTGCACCTTGAGGACGGTTCCTACAAC
ATCCGAAAAGATAGCATCATAGCTCTTTACCCACAGTTAATGCACTTAGATCCAGAAATC
TACCCAGACCCTTTGACTTTTAAATATGATAGGTATCTTGATGAAAACGGGAAGACAAAG
ACTACCTTCTATTGTAATGGACTCAAGTTAAAGTATTACTACATGCCCTTTGGATCGGGA
GCTACAATATGTCCTGGAAGATTGTTCGCTATCCACGAAATCAAGCAATTTTTGATTCTG
ATGCTTTCTTATTTTGAATTGGAGCTTATAGAGGGCCAAGCTAAATGTCCACCTTTGGAC
CAGTCCCGGGCAGGCTTGGGCATTTTGCCGCCATTGAATGATATTGAATTTAAATATAAA
TTCAAGCATTTGTGA
Enzyme 1 GenBank Gene ID X56088 Link Image
Enzyme 1 GeneCard ID CYP7A1 Link Image
Enzyme 1 GenAtlas ID CYP7A1 Link Image
Enzyme 1 HGNC ID HGNC:2651 Link Image
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Nishimoto M, Noshiro M, Okuda K: Structure of the gene encoding human liver cholesterol 7 alpha-hydroxylase. Biochim Biophys Acta. 1993 Feb 20;1172(1-2):147-50. [PubMed Link Image]
  2. Noshiro M, Okuda K: Molecular cloning and sequence analysis of cDNA encoding human cholesterol 7 alpha-hydroxylase. FEBS Lett. 1990 Jul 30;268(1):137-40. [PubMed Link Image]
  3. Karam WG, Chiang JY: Polymorphisms of human cholesterol 7 alpha-hydroxylase. Biochem Biophys Res Commun. 1992 Jun 15;185(2):588-95. [PubMed Link Image]
  4. Wang DP, Chiang JY: Structure and nucleotide sequences of the human cholesterol 7 alpha-hydroxylase gene (CYP7). Genomics. 1994 Mar 15;20(2):320-3. [PubMed Link Image]
  5. Molowa DT, Chen WS, Cimis GM, Tan CP: Transcriptional regulation of the human cholesterol 7 alpha-hydroxylase gene. Biochemistry. 1992 Mar 10;31(9):2539-44. [PubMed Link Image]
  6. Saito S, Iida A, Sekine A, Kawauchi S, Higuchi S, Ogawa C, Nakamura Y: Catalog of 680 variations among eight cytochrome p450 ( CYP) genes, nine esterase genes, and two other genes in the Japanese population. J Hum Genet. 2003;48(5):249-70. Epub 2003 Apr 29. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available