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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-22 19:16:51 UTC
Update Date2021-09-16 15:27:36 UTC
HMDB IDHMDB0006247
Secondary Accession Numbers
  • HMDB06247
Metabolite Identification
Common Name25-Hydroxycholesterol
Description25-Hydroxycholesterol is steroid derivative that suppresses the cleavage of sterol regulatory element binding proteins (SREBPs). It also induces apoptosis through down-regulation of Bcl-2 expression and activation of caspases. 25-Hydroxycholesterol also enhances Interleukin-1 beta (IL-1beta-induced) IL-8 production.(PMID: 17086498 ). 25-hydroxycholesterol is endogenously produced from cholesterol at early time intervals after cholesterol ingestion. It inhibits HMG-CoA reductase and so it also plays a significant role in the in vivo regulation of cholesterol biosynthesis after an acute dietary cholesterol challenge.
Structure
Data?1582752377
Synonyms
ValueSource
(beta)-Cholest-5-ene-3-25-diolHMDB
25-Hydroxy-cholesterolHMDB
25-Hydroxycholest-5-en-3-olHMDB
5-Cholestene-3beta-25-diolHMDB
Cholest-5-en-3beta-25-diolHMDB
Cholest-5-ene-3-b,25-diolHMDB
Cholest-5-ene-3-beta,25-diolHMDB
Cholest-5-ene-3beta-25-diolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name(2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
CAS Registry Number2140-46-7
SMILES
[H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23?,24?,26+,27-/m1/s1
InChI KeyINBGSXNNRGWLJU-POAVOMIWSA-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
  • 25-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Delta-5-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point172 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M-H]-MetCCS_train_neg202.80830932474
AllCCS[M-H]-Not Available202.808http://allccs.zhulab.cn/database/detail?ID=AllCCS00000276
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP10(5.95) g/LALOGPS
logP10(5.64) g/LChemAxon
logS10(-6.2) g/LALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.45 m³·mol⁻¹ChemAxon
Polarizability50.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.99531661259
DarkChem[M-H]-191.60731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
25-Hydroxycholesterol,1TMS,#1C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C3381.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
25-Hydroxycholesterol,1TMS,#2C[C@H](CCCC(C)(C)O)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C3342.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
25-Hydroxycholesterol,2TMS,#1C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C3403.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
25-Hydroxycholesterol,1TBDMS,#1C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C3616.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
25-Hydroxycholesterol,1TBDMS,#2C[C@H](CCCC(C)(C)O)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C3559.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
25-Hydroxycholesterol,2TBDMS,#1C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C3841.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 25-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-059l-1009000000-cec357bcbaf7149e29f52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positivesplash10-001i-2211390000-0527cfa38749e09bd2b62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Hydroxycholesterol 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 - 25-Hydroxycholesterol 10V, Positive-QTOFsplash10-00kr-0009100000-9e729aebf6add28b22e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Positive-QTOFsplash10-0170-1109000000-3349124bb19a8fd2ee082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Positive-QTOFsplash10-02di-2239000000-7a23aff71704f1c442ac2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0003900000-bc39f53a2f47d9e530b42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Negative-QTOFsplash10-0ue9-0009600000-14eb751b01166860ee822017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Negative-QTOFsplash10-00kr-1019000000-981e4ae54c86fe2b7d182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Negative-QTOFsplash10-0udi-0001900000-25ec6288bc3521fc5e322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Negative-QTOFsplash10-0udj-0039300000-b49af36b609e46ef37012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Positive-QTOFsplash10-00kr-0309000000-94663290c06fb4528adf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Positive-QTOFsplash10-014i-8669100000-8343de835a906d68edec2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Positive-QTOFsplash10-0a4i-5952000000-e7e8f0bed73a8187daa32021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.02 +/- 0.003 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.001 +/- 0.0001 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023859
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15519
BioCyc IDNot Available
BiGG ID2197441
Wikipedia LinkNot Available
METLIN ID3899
PubChem Compound53477807
PDB IDNot Available
ChEBI ID37616
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRyer, August I.; Gebert, Wm. H. Steroids. (1954), US 2673206 19540323 CAN 49:8565 AN 1955:8565
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bai B, Yamamoto K, Sato H, Sugiura H, Tanaka T: Combined effect of 25-hydroxycholesterol and IL-1beta on IL-8 production in human colon carcinoma cell line (Caco-2). Inflammation. 2005 Dec;29(4-6):141-6. [PubMed:17086498 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
Reactions
25-Hydroxycholesterol + NADPH + Oxygen → 7-a,25-Dihydroxycholesterol + NADP + Waterdetails
25-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,25-Dihydroxycholesterol + NADP + Waterdetails
General function:
Involved in steroid metabolic process
Specific function:
Binds cholesterol and a range of oxysterols. Cholesterol binding promotes the formation of a complex with PP2A and a tyrosine phosphatase which dephosphorylate ERK1/2, whereas 25- hydroxycholesterol causes its disassembly. Regulates cholesterol efflux by decreasing ABCA1 stability
Gene Name:
OSBP
Uniprot ID:
P22059
Molecular weight:
89419.9
General function:
Involved in iron ion binding
Specific function:
Catalyzes the formation of 25-hydroxycholesterol from cholesterol, leading to repress cholesterol biosynthetic enzymes. May play an important role in regulating lipid metabolism by synthesizing a corepressor that blocks sterol regulatory element binding protein (SREBP) processing. In testis, production of 25-hydroxycholesterol by macrophages may play a role in Leydig cell differentiation.
Gene Name:
CH25H
Uniprot ID:
O95992
Molecular weight:
31744.755
Reactions
Cholesterol + AH(2) + Oxygen → 25-Hydroxycholesterol + A + Waterdetails
Cholesterol + Reduced acceptor + Oxygen → 25-Hydroxycholesterol + Acceptor + Waterdetails