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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:09:08 UTC
Update Date2021-09-14 15:40:09 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
4-oxo-all-trans-Retinoic acidChEBI
4-oxo-AtRAChEBI
4-oxo-all-trans-RetinoateGenerator
4-oxo-RetinoateGenerator
4-Keto-retinoateHMDB
4-Keto-retinoic acidHMDB
4-KetoretinoateHMDB
4-Ketoretinoic acidHMDB
4-OxoretinoateHMDB
4-Oxoretinoic acidHMDB
4-OxotretinoinHMDB
all-trans-4-OxoretinoateHMDB
all-trans-4-Oxoretinoic acidHMDB
Ro 11-4824HMDB
Ro 12-4824HMDB
4-oxo-13-cis-Retinoic acidHMDB
4-oxo-IsotretinoinHMDB
4-oxo-trans-Retinoic acidHMDB
4-Oxoretinoic acid, (13-cis)-isomerHMDB
3beta,7alpha,25-Trihydroxycholest-5-eneChEBI
5-Cholesten-3beta,7alpha,25-triolChEBI
Cholest-5-ene-3beta,7alpha,25-triolChEBI
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
7-alpha,25-DihydroxycholesterolHMDB
7alpha,25-DihydroxycholesterolHMDB, KEGG
Cholest-5-ene-3-b,7-a,25-triolHMDB
Cholest-5-ene-3-beta,7-alpha,25-triolHMDB
7a,25-DihydroxycholesterolGenerator
7Α,25-dihydroxycholesterolGenerator
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 retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoic acid
  • Diterpenoid
  • Retinoid skeleton
  • Medium-chain fatty acid
  • Cyclohexenone
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0051 g/LALOGPS
logP10(4.54) g/LALOGPS
logP10(4.49) g/LChemAxon
logS10(-4.9) g/LALOGPS
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 Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.92731661259
DarkChem[M-H]-193.66731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-a,25-Dihydroxycholesterol,1TMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,1TMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,1TMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,2TMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,2TMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,2TMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,3TMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,1TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,1TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,1TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,2TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,2TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,2TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
7-a,25-Dihydroxycholesterol,3TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
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 IDFDB023877
KNApSAcK IDNot Available
Chemspider ID4941652
KEGG Compound IDC16678
BioCyc IDNot Available
BiGG ID2430195
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6437063
PDB IDNot Available
ChEBI ID80656
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