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Record Information
Version2.0
Created at2024-09-11 18:56:15 UTC
Updated at2024-09-11 18:56:16 UTC
NP-MRD IDNP0338958
Secondary Accession NumbersNone
Natural Product Identification
Common Name11-Epi-PGF2a
Description11-Epi-PGF2a belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. 11-Epi-PGF2a is an extremely weak basic (essentially neutral) compound (based on its pKa). 11-Epi-PGF2a can be biosynthesized from prostaglandin D2 through its interaction with the enzyme aldo-keto reductase family 1 member C3. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. 11-Epi-PGF2alpha is converted from (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate via the enzyme prostaglandin-F synthase (EC1.1.1.188). In humans, 11-epi-PGF2a is involved in mefenamic acid action pathway. Prostaglandins are eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. The PGs and TXs are collectively identified as prostanoids. 11-Epi-PGF2alpha is an intermediate in Arachidonic acid metabolism.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H34O5
Average Mass354.4810 Da
Monoisotopic Mass354.24062 Da
IUPAC Name7-[(2R,3S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name7-[(2R,3S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
CAS Registry NumberNot Available
SMILES
[H]C(=C[C@]1([H])C(CC=CCCCC(O)=O)C(O)C[C@]1([H])O)[C@@]([H])(O)CCCCC
InChI Identifier
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16?,17+,18?,19-/m0/s1
InChI KeyPXGPLTODNUVGFL-UVSIREBESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP3.11ALOGPS
logP2.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.47 m³·mol⁻¹ChemAxon
Polarizability41.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027915
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available