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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:58:25 UTC
Update Date2019-07-23 07:13:41 UTC
HMDB IDHMDB0060147
Secondary Accession Numbers
  • HMDB60147
Metabolite Identification
Common Name4,4-Dimethylcholesta-8(9),14-dien-3beta-ol
Descriptionrac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. rac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866021
Synonyms
ValueSource
rac-4-Hydroxy-4-O-(b-D-glucuronide)-all-trans-retinyl acetateGenerator
rac-4-Hydroxy-4-O-(b-D-glucuronide)-all-trans-retinyl acetic acidGenerator
rac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetic acidGenerator
rac-4-Hydroxy-4-O-(β-D-glucuronide)-all-trans-retinyl acetateGenerator
rac-4-Hydroxy-4-O-(β-D-glucuronide)-all-trans-retinyl acetic acidGenerator
4,4-Dimethylcholesta-8(9),14-dien-3b-olGenerator
4,4-Dimethylcholesta-8(9),14-dien-3β-olGenerator
Chemical FormulaC29H48O
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
IUPAC Name(2R,5R,7R,14S,15S)-2,6,6,15-tetramethyl-14-[(2S)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),11-dien-5-ol
Traditional Name(2R,5R,7R,14S,15S)-2,6,6,15-tetramethyl-14-[(2S)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),11-dien-5-ol
CAS Registry NumberNot Available
SMILES
CC(C)CCC[C@H](C)[C@@H]1CC=C2C3=C(CC[C@@]12C)[C@]1(C)CC[C@@H](O)C(C)(C)[C@@H]1CC3
InChI Identifier
InChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h13,19-20,22,25-26,30H,8-12,14-18H2,1-7H3/t20-,22-,25-,26+,28-,29-/m0/s1
InChI KeyOGQJUYXFIOFTMA-RNDGVDNBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentDiterpene glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Retinoid skeleton
  • Diterpenoid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Fatty alcohol ester
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00056 g/LALOGPS
logP7.6ALOGPS
logP7.41ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.07 m³·mol⁻¹ChemAxon
Polarizability52.97 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pk-1009000000-92b588074f7734ee2ec6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06di-3103900000-01bc2923151262e134cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0009500000-297ecf8f722d38ae479cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ya-3129100000-1decf3f66aa401d3199fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-4339000000-6479210c961a35aa68b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0001900000-322cae85ce921a9ef9e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-7e18591fb6a8fe32b4e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-1009000000-79dbea737a07aa6d7e54Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB034577
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769845
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  9. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..