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Record Information
Version1.0
Created at2022-09-08 17:46:12 UTC
Updated at2022-09-08 17:46:13 UTC
NP-MRD IDNP0271467
Secondary Accession NumbersNone
Natural Product Identification
Common Name[4,5-dihydroxy-2,3-bis(hydroxymethyl)cyclopent-2-en-1-yl]acetic acid
Description2-[4,5-Dihydroxy-2,3-bis(hydroxymethyl)cyclopent-2-en-1-yl]acetic acid belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. 2-[4,5-Dihydroxy-2,3-bis(hydroxymethyl)cyclopent-2-en-1-yl]acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
2-[4,5-Dihydroxy-2,3-bis(hydroxymethyl)cyclopent-2-en-1-yl]acetateGenerator
Chemical FormulaC9H14O6
Average Mass218.2050 Da
Monoisotopic Mass218.07904 Da
IUPAC Name2-[4,5-dihydroxy-2,3-bis(hydroxymethyl)cyclopent-2-en-1-yl]acetic acid
Traditional Name[4,5-dihydroxy-2,3-bis(hydroxymethyl)cyclopent-2-en-1-yl]acetic acid
CAS Registry NumberNot Available
SMILES
OCC1=C(CO)C(CC(O)=O)C(O)C1O
InChI Identifier
InChI=1S/C9H14O6/c10-2-5-4(1-7(12)13)8(14)9(15)6(5)3-11/h4,8-11,14-15H,1-3H2,(H,12,13)
InChI KeyCONHPIXHDVSPCH-UHFFFAOYSA-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 iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentIridoids and derivatives
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • 11-noriridane monoterpenoid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • 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
logP-2.1ALOGPS
logP-3ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)4.11ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.85 m³·mol⁻¹ChemAxon
Polarizability20.58 ųChemAxon
Number of Rings1ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85321010
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]