Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:09:08 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006280
Secondary Accession Numbers
  • HMDB06280
Metabolite Identification
Common Name7-a,25-Dihydroxycholesterol
Description7 alpha-hydroxylation is not directly involved, positively or negatively, in the action of 25- or 27-hydroxycholesterol as suppressors of HMG-CoA reductase activity. Human diploid fibroblasts (HDF) and the human melanoma cell line SK-MEL-2 converted 25-hydroxycholesterol into 7 alpha,25-dihydroxycholesterol and 7 alpha,25-dihydroxy-4-cholesten-3-one while the virus-transformed fibroblast line 90VA-VI, the colon carcinoma cell line WiDr and the breast cancer cell line MDA-231 did not express 7 alpha-hydroxylase activity. The 7 alpha-hydroxylation of 25-hydroxycholesterol in HDF could be stimulated by dexamethasone and cortisol and inhibited by metyrapone. An unidentified, possibly 4-hydroxylated, metabolite was formed by 90VA-VI cells and a polar, probably conjugated, metabolite was formed by WiDr cells. The 7 alpha-hydroxylated metabolites of 25-hydroxycholesterol suppressed the activity of HMG-CoA reductase to a similar extent as 25-hydroxycholesterol in HDF but not in 90VA-VI cells, while the 7 alpha-hydroxylated metabolites of 27-hydroxycholesterol suppressed the activity of HMG-CoA reductase also in 90VA-VI cells. (PMID: 9059514 ).
Structure
Data?1582752379
Synonyms
ValueSource
3beta,7alpha,25-Trihydroxycholest-5-eneChEBI
5-Cholesten-3beta,7alpha,25-triolChEBI
Cholest-5-ene-3beta,7alpha,25-triolChEBI
7alpha,25-DihydroxycholesterolKegg
3b,7a,25-Trihydroxycholest-5-eneGenerator
3Β,7α,25-trihydroxycholest-5-eneGenerator
5-Cholesten-3b,7a,25-triolGenerator
5-Cholesten-3β,7α,25-triolGenerator
Cholest-5-ene-3b,7a,25-triolGenerator
Cholest-5-ene-3β,7α,25-triolGenerator
7a,25-DihydroxycholesterolGenerator
7Α,25-dihydroxycholesterolGenerator
7-alpha,25-DihydroxycholesterolHMDB
Cholest-5-ene-3-b,7-a,25-triolHMDB
Cholest-5-ene-3-beta,7-alpha,25-triolHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name7α,25-dihydroxycholesterol
CAS Registry Number64907-22-8
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1
InChI KeyBQMSKLCEWBSPPY-IKVTXIKFSA-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-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0051 g/LALOGPS
logP4.54ALOGPS
logP4.49ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.89 m³·mol⁻¹ChemAxon
Polarizability52.17 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.92731661259
DarkChem[M-H]-193.66731661259
DeepCCS[M-2H]-249.45330932474
DeepCCS[M+Na]+224.57130932474
AllCCS[M+H]+208.632859911
AllCCS[M+H-H2O]+206.632859911
AllCCS[M+NH4]+210.432859911
AllCCS[M+Na]+210.932859911
AllCCS[M-H]-205.532859911
AllCCS[M+Na-2H]-207.532859911
AllCCS[M+HCOO]-210.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7-a,25-Dihydroxycholesterol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C2722.8Standard polar33892256
7-a,25-Dihydroxycholesterol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C3428.4Standard non polar33892256
7-a,25-Dihydroxycholesterol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C3489.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-a,25-Dihydroxycholesterol,1TMS,isomer #1C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3497.1Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,1TMS,isomer #2C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3402.0Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,1TMS,isomer #3C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3429.1Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,2TMS,isomer #1C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3513.8Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,2TMS,isomer #2C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3531.6Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,2TMS,isomer #3C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3306.3Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,3TMS,isomer #1C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3451.2Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,1TBDMS,isomer #1C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3751.4Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,1TBDMS,isomer #2C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3638.2Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,1TBDMS,isomer #3C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3660.1Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,2TBDMS,isomer #1C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3994.5Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,2TBDMS,isomer #2C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4018.4Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,2TBDMS,isomer #3C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3769.0Semi standard non polar33892256
7-a,25-Dihydroxycholesterol,3TBDMS,isomer #1C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4144.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-a,25-Dihydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-2149500000-545454a3fcc04ae6b5812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-a,25-Dihydroxycholesterol GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-2210139000-efdeb2df00f6b19d46542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-a,25-Dihydroxycholesterol 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 - 7-a,25-Dihydroxycholesterol 10V, Positive-QTOFsplash10-0f89-0009800000-7c696ae7b6e4c320a7992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 20V, Positive-QTOFsplash10-0f89-1009300000-73e3b4d1757a0cdd50d42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 40V, Positive-QTOFsplash10-00wc-1129000000-4f248849b872f93ee0292017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0005900000-232dc04b65e6de06ebab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 20V, Negative-QTOFsplash10-00kb-0009500000-11fef3b164b139cb37b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 40V, Negative-QTOFsplash10-0ul9-1009200000-b7f1840b17522a9af97e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 10V, Positive-QTOFsplash10-0zgi-0508900000-213057c1cb391a52a4a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 20V, Positive-QTOFsplash10-001i-5329200000-9c420237507a8ce71a792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 40V, Positive-QTOFsplash10-05di-5952000000-18ce46c15bdb91fa613a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0000900000-f2cb6399034352e924c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 20V, Negative-QTOFsplash10-014i-0001900000-e80cf3ceb31217f305312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 40V, Negative-QTOFsplash10-014i-0013900000-4960bc78b4ddc4f540b02021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023874
KNApSAcK IDNot Available
Chemspider ID10128492
KEGG Compound IDC15520
BioCyc IDNot Available
BiGG ID2430195
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6437063
PDB IDNot Available
ChEBI ID37623
Food Biomarker OntologyNot Available
VMH IDCE2954
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang J, Dricu A, Sjovall J: Studies on the relationships between 7 alpha-hydroxylation and the ability of 25- and 27-hydroxycholesterol to suppress the activity of HMG-CoA reductase. Biochim Biophys Acta. 1997 Feb 18;1344(3):241-9. [PubMed:9059514 ]

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 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
7-a,25-Dihydroxycholesterol + NAD → 7alpha,25-Dihydroxy-4-cholesten-3-one + NADH + Hydrogen Iondetails