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Showing Compound 7alpha,25-Dihydroxycholesterol (FDB023874)

Record Information
Version1.0
Creation date2011-09-21 00:36:09 UTC
Update date2015-07-21 06:57:55 UTC
Primary IDFDB023874
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7alpha,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) [HMDB]
CAS Number64907-22-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
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
3β,7α,25-trihydroxycholest-5-eneGenerator
7-a,25-Dihydroxycholesterolhmdb
7α,25-dihydroxycholesterolGenerator
Predicted 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
Chemical FormulaC27H46O3
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS7alpha,25-Dihydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zfr-2149500000-545454a3fcc04ae6b581Spectrum
Predicted GC-MS7alpha,25-Dihydroxycholesterol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xr-2210139000-efdeb2df00f6b19d4654Spectrum
Predicted GC-MS7alpha,25-Dihydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0009800000-7c696ae7b6e4c320a7992017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1009300000-73e3b4d1757a0cdd50d42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00wc-1129000000-4f248849b872f93ee0292017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0005900000-232dc04b65e6de06ebab2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0009500000-11fef3b164b139cb37b12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ul9-1009200000-b7f1840b17522a9af97e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgi-0508900000-213057c1cb391a52a4a42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-5329200000-9c420237507a8ce71a792021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05di-5952000000-18ce46c15bdb91fa613a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-f2cb6399034352e924c82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0001900000-e80cf3ceb31217f305312021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0013900000-4960bc78b4ddc4f540b02021-09-22View Spectrum
NMRNot Available
ChemSpider ID10128492
ChEMBL IDNot Available
KEGG Compound IDC15520
Pubchem Compound ID11954197
Pubchem Substance IDNot Available
ChEBI ID37623
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06280
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2197800
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference