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Record Information
Version1.0
Created at2021-06-22 17:29:02 UTC
Updated at2021-06-22 17:29:03 UTC
NP-MRD IDNP0043917
Secondary Accession NumbersNone
Natural Product Identification
Common NameLactone diacid 7-O-n-butyl ester
Description(2R)-2-(3-butoxy-3-oxopropyl)-4-hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylic acid belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Lactone diacid 7-O-n-butyl ester is found in Talaromyces rugulosus. It was first documented in 2017 (PMID: 29135916). Based on a literature review very few articles have been published on (2R)-2-(3-butoxy-3-oxopropyl)-4-hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylic acid.
Structure
Thumb
Synonyms
ValueSource
(2R)-2-(3-Butoxy-3-oxopropyl)-4-hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylateGenerator
Chemical FormulaC18H20O7
Average Mass348.3510 Da
Monoisotopic Mass348.12090 Da
IUPAC Name(2R)-2-(3-butoxy-3-oxopropyl)-4-hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylic acid
Traditional Name(2R)-2-(3-butoxy-3-oxopropyl)-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCCCOC(=O)CC[C@]1(OC(=O)C(O)=C1C1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C18H20O7/c1-2-3-11-24-13(19)9-10-18(17(22)23)14(15(20)16(21)25-18)12-7-5-4-6-8-12/h4-8,20H,2-3,9-11H2,1H3,(H,22,23)/t18-/m1/s1
InChI KeyUYFHDPQUHCRWMW-GOSISDBHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Talaromyces rugulosusLinigton's dataset
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Benzenoid
  • 2-furanone
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Dihydrofuran
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Enol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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
logP2.42ALOGPS
logP2.77ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity87.57 m³·mol⁻¹ChemAxon
Polarizability34.6 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID62816315
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound156583147
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kuppers L, Ebrahim W, El-Neketi M, Ozkaya FC, Mandi A, Kurtan T, Orfali RS, Muller WEG, Hartmann R, Lin W, Song W, Liu Z, Proksch P: Lactones from the Sponge-Derived Fungus Talaromyces rugulosus. Mar Drugs. 2017 Nov 14;15(11). pii: md15110359. doi: 10.3390/md15110359. [PubMed:29135916 ]