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Record Information
Version2.0
Created at2020-12-09 03:25:44 UTC
Updated at2021-07-15 16:54:42 UTC
NP-MRD IDNP0006403
Secondary Accession NumbersNone
Natural Product Identification
Common NameGEODIN
Provided ByNPAtlasNPAtlas Logo
Description GEODIN is found in Aspergillus terreus and Aspergillus terreus IMI16043 . GEODIN was first documented in 1936 (PMID: 16746160). Based on a literature review very few articles have been published on methyl 5,7-dichloro-4-hydroxy-6'-methoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-2'-carboxylate.
Structure
Data?1624574697
Synonyms
ValueSource
Methyl 5,7-dichloro-4-hydroxy-6'-methoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-2'-carboxylic acidGenerator
EstinMeSH
Chemical FormulaC17H12Cl2O7
Average Mass399.1800 Da
Monoisotopic Mass397.99601 Da
IUPAC Namemethyl (2S)-5,7-dichloro-4-hydroxy-2'-methoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate
Traditional Namemethyl (2S)-5,7-dichloro-4-hydroxy-2'-methoxy-6-methyl-3,4'-dioxospiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)C1=CC(=O)C=C(OC)C11OC2=C(C1=O)C(O)=C(Cl)C(C)=C2Cl
InChI Identifier
InChI=1S/C17H12Cl2O7/c1-6-11(18)13(21)10-14(12(6)19)26-17(15(10)22)8(16(23)25-3)4-7(20)5-9(17)24-2/h4-5,21H,1-3H3
InChI KeyLUBKKVGXMXTXOZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus terreusNPAtlas
Aspergillus terreus IMI16043Fungi
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Coumaran
  • Benzofuran
  • Aryl alkyl ketone
  • Aryl ketone
  • 4-halophenol
  • 2-halophenol
  • Alkyl aryl ether
  • Phenol
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Vinylogous ester
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Carboxylic acid ester
  • Cyclic ketone
  • Ketone
  • Ether
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP3.41ALOGPS
logP3.55ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)6.69ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.13 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity93.98 m³·mol⁻¹ChemAxon
Polarizability36.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA017530
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID187606
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound216465
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Raistrick H, Smith G: Studies in the biochemistry of micro-organisms: The metabolic products of Aspergillus terreus Thom. Part II. Two new chlorine-containing mould metabolic products, geodin and erdin. Biochem J. 1936 Aug;30(8):1315-22. doi: 10.1042/bj0301315. [PubMed:16746160 ]