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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:47:34 UTC
HMDB IDHMDB0015262
Secondary Accession Numbers
  • HMDB15262
Metabolite Identification
Common NamePrednicarbate
DescriptionPrednicarbate is a relatively new topical corticosteroid drug. It is similar in potency to hydrocortisone. It is used in the treatment of inflammatory skin diseases, such as atopic dermatitis. It has a favorable benefit-risk ratio, with an inflammatory action similar to that of a medium potency corticosteroid, but with a low potential to cause skin atrophy. The anti-inflammation action of corticosteroids is associated with the inhibition of the interleukin 1-alpha cytokine within keratinocytes. IL-1a is also found in fibroblasts, where it is responsible for proliferation, collagenase induction and IL-6 synthesis, which are related to skin thickness.
Structure
Data?1582753276
Synonyms
ValueSource
Prednicarbic acidGenerator
BatmenHMDB
HOE-777HMDB
PeitelHMDB
HOE 777HMDB
Prednisolone-17-ethylcarbonate-21-propionateHMDB
2-{14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl}-2-oxoethyl propanoic acidHMDB
DermatopMeSH
2-{14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadeca-3,6-dien-14-yl}-2-oxoethyl propanoic acidGenerator
Chemical FormulaC27H36O8
Average Molecular Weight488.5699
Monoisotopic Molecular Weight488.241018128
IUPAC Name2-{14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl}-2-oxoethyl propanoate
Traditional Nameprednicarbate
CAS Registry Number73771-04-7
SMILES
CCOC(=O)OC1(CCC2C3CCC4=CC(=O)C=CC4(C)C3C(O)CC12C)C(=O)COC(=O)CC
InChI Identifier
InChI=1S/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3
InChI KeyFNPXMHRZILFCKX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • Steroid ester
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 11-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-1,4-steroid
  • Alpha-acyloxy ketone
  • Carbonic acid diester
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Secondary alcohol
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0056 g/LNot Available
LogP2.9Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP3.08ALOGPS
logP3.83ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.82ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area116.2 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity127.8 m³·mol⁻¹ChemAxon
Polarizability51.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available215.0431661259
DarkChem[M-H]-PredictedNot Available206.04531661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Prednicarbate,1TMS,#13698.1902https://arxiv.org/abs/1905.12712
Prednicarbate,1TMS,#23733.4375https://arxiv.org/abs/1905.12712
Prednicarbate,1TBDMS,#13954.4216https://arxiv.org/abs/1905.12712
Prednicarbate,1TBDMS,#23972.2166https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-4592500000-c168de9f1beda4a468442017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0aba-7943180000-5892ea2d9f700823f8cb2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05g0-9000500000-27b7510bf5aef49df0c72017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9002100000-c9f47b9cb76563e258bd2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9002000000-b16c5a701fb6841bffa52017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05g1-2005900000-381abefd98e6b2ac50d42017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mn-6016900000-7b4c81e4b395fbcc42f02017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-4592000000-425000e1fff8e143c8492017-09-01View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01130 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01130 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID47402
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPrednicarbate
METLIN IDNot Available
PubChem Compound52421
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gupta AK, Chow M: A review of prednicarbate (Dermatop). Skin Therapy Lett. 2004 Dec-2005 Jan;9(10):5-6, 9. [PubMed:15657633 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.