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Record Information
Version1.0
Creation Date2016-09-30 23:21:10 UTC
Update Date2020-04-22 15:17:10 UTC
BMDB IDBMDB0006280
Secondary Accession Numbers
  • BMDB06280
Metabolite Identification
Common Name7-a,25-Dihydroxycholesterol
Description4-oxo-Retinoic acid, also known as 4-oxo-retinoate or 4-oxo-atra, 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. 4-oxo-Retinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-2149500000-545454a3fcc04ae6b581View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-2210139000-efdeb2df00f6b19d4654View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0009800000-7c696ae7b6e4c320a799View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1009300000-73e3b4d1757a0cdd50d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00wc-1129000000-4f248849b872f93ee029View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0005900000-232dc04b65e6de06ebabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0009500000-11fef3b164b139cb37b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ul9-1009200000-b7f1840b17522a9af97eView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006285
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available