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Record Information
Version2.0
Created at2022-09-06 22:42:39 UTC
Updated at2022-09-06 22:42:39 UTC
NP-MRD IDNP0239178
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,5'-dimethyl (5s,5's)-5,5'-dihydroxy-4,4'-dimethoxy-1,1'-dimethyl-2,2'-dioxo-[3,3'-bipyrrole]-5,5'-dicarboxylate
Description5,5'-Dimethyl (5S,5'S)-5,5'-dihydroxy-4,4'-dimethoxy-1,1'-dimethyl-2,2'-dioxo-1H,1'H,2H,2'H,5H,5'H-[3,3'-bipyrrole]-5,5'-dicarboxylate belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. 5,5'-dimethyl (5s,5's)-5,5'-dihydroxy-4,4'-dimethoxy-1,1'-dimethyl-2,2'-dioxo-[3,3'-bipyrrole]-5,5'-dicarboxylate is found in Mercurialis leiocarpa. Based on a literature review very few articles have been published on 5,5'-dimethyl (5S,5'S)-5,5'-dihydroxy-4,4'-dimethoxy-1,1'-dimethyl-2,2'-dioxo-1H,1'H,2H,2'H,5H,5'H-[3,3'-bipyrrole]-5,5'-dicarboxylate.
Structure
Thumb
Synonyms
ValueSource
5,5'-Dimethyl (5S,5's)-5,5'-dihydroxy-4,4'-dimethoxy-1,1'-dimethyl-2,2'-dioxo-1H,1'H,2H,2'H,5H,5'H-[3,3'-bipyrrole]-5,5'-dicarboxylic acidGenerator
Chemical FormulaC16H20N2O10
Average Mass400.3400 Da
Monoisotopic Mass400.11179 Da
IUPAC Name5,5'-dimethyl (5S,5'S)-5,5'-dihydroxy-4,4'-dimethoxy-1,1'-dimethyl-2,2'-dioxo-1H,1'H,2H,2'H,5H,5'H-[3,3'-bipyrrole]-5,5'-dicarboxylate
Traditional Name5,5'-dimethyl (5S,5'S)-5,5'-dihydroxy-4,4'-dimethoxy-1,1'-dimethyl-2,2'-dioxo-[3,3'-bipyrrole]-5,5'-dicarboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)[C@]1(O)N(C)C(=O)C(=C1OC)C1=C(OC)[C@@](O)(N(C)C1=O)C(=O)OC
InChI Identifier
InChI=1S/C16H20N2O10/c1-17-11(19)7(9(25-3)15(17,23)13(21)27-5)8-10(26-4)16(24,14(22)28-6)18(2)12(8)20/h23-24H,1-6H3/t15-,16-/m0/s1
InChI KeyVWULKWWBQVWDNQ-HOTGVXAUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Mercurialis leiocarpaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Pyrroline carboxylic acid
  • Pyrroline carboxylic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Pyrroline
  • Tertiary carboxylic acid amide
  • Vinylogous ester
  • Methyl ester
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Alkanolamine
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP-2.5ChemAxon
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-0.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area152.14 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity91.47 m³·mol⁻¹ChemAxon
Polarizability37.57 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9318943
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11143831
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]