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Human Metabolome Database Version 2.5

 

Showing metabocard for 22b-Hydroxycholesterol (HMDB04035)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 10:27:14
Update Date 2010-04-28 13:20:44
Accession Number HMDB04035
Secondary Accession Numbers Not Available
Common Name 22b-Hydroxycholesterol
Description 22beta-Hydroxycholesterol is a substrate for DCC-interacting protein 13 beta.
Synonyms
  1. (3beta,22R)-Cholest-5-ene-3,22-diol
  2. 22R-hydroxycholesterol
  3. cholest-5-en-3beta,22R-diol
  4. 22beta-Hydroxycholesterol
  5. (R)-mevalonate
Chemical IUPAC Name (3S,8S,9S,10R,13R,14S,17R)-17-[(2S,3R)-3-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
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)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILES CC(C)CCC(O)C(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C
KEGG Compound ID C05502 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04035 Link Image
Metagene Link HMDB04035 Link Image
METLIN ID 7006 Link Image
PubChem Compound 167685 Link Image
PubChem Substance 7855 Link Image
ChEBI ID Not Available
CAS Registry Number 22348-64-7
InChI Identifier InChI=1/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25+,26-,27+/m0/s1
Synthesis Reference Koreeda, Masato; Ricca, Daniel J. Chirality transfer in stereoselective synthesis. A highly stereocontrolled synthesis of 22-hydroxylated steroid side chains via the [2,3]-Wittig rearrangement. Journal of Organic Chemistry (1986), 51(21), 4090-2.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 6.53e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.69 [Predicted by ALOGPS]; 6.5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
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)
Biofluid Location Not Available
Tissue Location
Tissue References
Adrenal Cortex —
Epidermis —
Fibroblasts —
Neuron —
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 Link Image map00140 Link Image
General References
  1. Haidar B, Denis M, Marcil M, Krimbou L, Genest J Jr: Apolipoprotein A-I activates cellular cAMP signaling through the ABCA1 transporter. J Biol Chem. 2004 Mar 12;279(11):9963-9. Epub 2003 Dec 29. [PubMed Link Image]
  2. Yao ZX, Brown RC, Teper G, Greeson J, Papadopoulos V: 22R-Hydroxycholesterol protects neuronal cells from beta-amyloid-induced cytotoxicity by binding to beta-amyloid peptide. J Neurochem. 2002 Dec;83(5):1110-9. [PubMed Link Image]
  3. Matsuzaki J, Tsuji T, Imazeki I, Ikeda H, Nishimura T: Immunosteroid as a regulator for Th1/Th2 balance: its possible role in autoimmune diseases. Autoimmunity. 2005 Aug;38(5):369-75. [PubMed Link Image]
  4. Tuckey RC: Cholesterol side-chain cleavage by mitochondria from the human placenta. Studies using hydroxycholesterols as substrates. J Steroid Biochem Mol Biol. 1992 Sep;42(8):883-90. [PubMed Link Image]
  5. Hanley K, Ng DC, He SS, Lau P, Min K, Elias PM, Bikle DD, Mangelsdorf DJ, Williams ML, Feingold KR: Oxysterols induce differentiation in human keratinocytes and increase Ap-1-dependent involucrin transcription. J Invest Dermatol. 2000 Mar;114(3):545-53. [PubMed Link Image]
Metabolic Enzymes
  1. cDNA FLJ76435, highly similar to Homo sapiens cytochrome P450, family 11, subfamily A, polypeptide 1
Enzyme 1 [top]
Enzyme 1 ID 13012
Enzyme 1 Name cDNA FLJ76435, highly similar to Homo sapiens cytochrome P450, family 11, subfamily A, polypeptide 1
Enzyme 1 Synonyms
  1. CYP11A1, mRNA
  2. Cytochrome P450, family 11, subfamily A, polypeptide 1, isoform CRA_b
Enzyme 1 Gene Name CYP11A1
Enzyme 1 Protein Sequence >cDNA FLJ76435, highly similar to Homo sapiens cytochrome P450, family 11, subfamily A, polypeptide 1 
MLAKGLPPRSVLVKGCQTFLSAPREGLGRLRVPTGEGAGISTRSPRPFNEIPSPGDNGWL
NLYHFWRETGTHKVHLHHVQNFQKYGPIYREKLGNVESVYVIDPEDVALLFKSEGPNPER
FLIPPWVAYHQYYQRPIGVLLKKSAAWKKDRVALNQEVMAPEATKNFLPLLDAVSRDFVS
VLHRRIKKAGSGNYSGDISDDLFRFAFESITNVIFGERQGMLEEVVNPEAQRFIDAIYQM
FHTSVPMLNLPPDLFRLFRTKTWKDHVAAWDVIFSKADIYTQNFYWELRQKGSVHHDYRG
ILYRLLGDSKMSFEDIKANVTEMLAGGVDTTSMTLQWHLYEMARNLKVQDMLRAEVLAAR
HQAQGDMATMLQLVPLLKASIKETLRLHPISVTLQRYLVNDLVLRDYMIPAKTLVQVAIY
ALGREPTFFFDPENFDPTRWLSKDKNITYFRNLGFGWGVRQCLGRRIAELEMTIFLINML
ENFRVEIQHLSDVGTTFNLILMPEKPISFTFWPFNQEATQQ
Enzyme 1 Number of Residues 521
Enzyme 1 Molecular Weight 60103
Enzyme 1 Theoretical pI 9.18
Enzyme 1 GO Classification Not Available
Enzyme 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Enzyme 1 Specific Function Not Available
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function Not Available
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 158258032 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID A8K8D5 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name A8K8D5_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence Not Available
Enzyme 1 GenBank Gene ID AK292300 Link Image
Enzyme 1 GeneCard ID A8K8D5 Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available