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Record Information
Version1.0
Created at2020-12-09 02:12:30 UTC
Updated at2021-07-15 16:50:11 UTC
NP-MRD IDNP0004797
Secondary Accession NumbersNone
Natural Product Identification
Common NameViridicatic acid
Provided ByNPAtlasNPAtlas Logo
Description2-(4-Hexanoyl-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)acetic acid belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Viridicatic acid is found in Penicillium and Penicillium aurantiogriseum. It was first documented in 1960 (PMID: 13800895). Based on a literature review very few articles have been published on 2-(4-hexanoyl-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)acetic acid (PMID: 25137015) (PMID: 23400446) (PMID: 11526019).
Structure
Data?1624571199
Synonyms
ValueSource
2-(4-Hexanoyl-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)acetateGenerator
ViridicatateGenerator
Chemical FormulaC12H16O6
Average Mass256.2540 Da
Monoisotopic Mass256.09469 Da
IUPAC Name2-[(2R)-4-hexanoyl-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl]acetic acid
Traditional Name[(2R)-4-hexanoyl-3-hydroxy-5-oxo-2H-furan-2-yl]acetic acid
CAS Registry NumberNot Available
SMILES
CCCCCC(=O)C1=C(O)C(CC(O)=O)OC1=O
InChI Identifier
InChI=1S/C12H16O6/c1-2-3-4-5-7(13)10-11(16)8(6-9(14)15)18-12(10)17/h8,16H,2-6H2,1H3,(H,14,15)
InChI KeyYZMZGKYVOIAWJS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
PenicilliumNPAtlas
Penicillium aurantiogriseumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous acid
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • 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
logP1.01ALOGPS
logP1.59ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.6ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity61.65 m³·mol⁻¹ChemAxon
Polarizability25.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA002248
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID64882632
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54715093
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. BIRKINSHAW JH, SAMANT MS: Studies in the biochemistry of micro-organisms. 107. Metabolites of Penicillium viridicatum Westling: viridicatic acid (ethylcarlosic acid). Biochem J. 1960 Feb;74:369-73. doi: 10.1042/bj0740369. [PubMed:13800895 ]
  2. Vida N, Pastyrikova T, Klepetarova B, Beier P: Synthesis of aliphatic sulfur pentafluorides by oxidation of SF(5)-containing anisole, phenols, and anilines. J Org Chem. 2014 Sep 19;79(18):8906-11. doi: 10.1021/jo501562z. Epub 2014 Aug 27. [PubMed:25137015 ]
  3. Schluter R, Lippmann R, Hammer E, Gesell Salazar M, Schauer F: Novel insights into the fungal oxidation of monoaromatic and biarylic environmental pollutants by characterization of two new ring cleavage enzymes. Appl Microbiol Biotechnol. 2013 Jun;97(11):5043-53. doi: 10.1007/s00253-013-4742-z. Epub 2013 Feb 12. [PubMed:23400446 ]
  4. Sietmann R, Hammer E, Specht M, Cerniglia CE, Schauer F: Novel ring cleavage products in the biotransformation of biphenyl by the yeast Trichosporon mucoides. Appl Environ Microbiol. 2001 Sep;67(9):4158-65. doi: 10.1128/AEM.67.9.4158-4165.2001. [PubMed:11526019 ]