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Record Information
Version2.0
Created at2021-06-20 19:15:26 UTC
Updated at2021-06-30 00:07:20 UTC
NP-MRD IDNP0035954
Secondary Accession NumbersNone
Natural Product Identification
Common Name5'-epichaetoviridin A
Provided ByJEOL DatabaseJEOL Logo
Description5'-Epichaetoviridin A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 5'-Epichaetoviridin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 5'-epichaetoviridin A is found in Chaetomium cochliodes, Chaetomium cochliodes CTh05, Chaetomium elatum no. 89-1-3-1 and Chaetomium globosum. 5'-epichaetoviridin A was first documented in 2011 (PMID: 21548578). Based on a literature review very few articles have been published on 5'-epichaetoviridin A.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H25ClO6
Average Mass432.9000 Da
Monoisotopic Mass432.13397 Da
IUPAC Name(6aS)-5-chloro-9-[(2S,3S)-3-hydroxy-2-methylbutanoyl]-6a-methyl-3-[(1E,3S)-3-methylpent-1-en-1-yl]-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione
Traditional Name(6aS)-5-chloro-9-[(2S,3S)-3-hydroxy-2-methylbutanoyl]-6a-methyl-3-[(1E,3S)-3-methylpent-1-en-1-yl]furo[2,3-h]isochromene-6,8-dione
CAS Registry NumberNot Available
SMILES
[H]O[C@@]([H])(C([H])([H])[H])[C@@]([H])(C(=O)C1=C2C3=C([H])OC(\C([H])=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])=C([H])C3=C(Cl)C(=O)[C@]2(OC1=O)C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C23H25ClO6/c1-6-11(2)7-8-14-9-15-16(10-29-14)18-17(20(26)12(3)13(4)25)22(28)30-23(18,5)21(27)19(15)24/h7-13,25H,6H2,1-5H3/b8-7+/t11-,12-,13-,23-/m0/s1
InChI KeyHWSQVPGTQUYLEQ-XURDPWNDSA-N
Experimental Spectra
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Chaetomium cochliodesLOTUS Database
Chaetomium cochliodes CTh05Fungi
Chaetomium elatum no. 89-1-3-1Fungi
Chaetomium globosumJEOL database
    • Borges, W. S., et al, J. Nat. Prod. 74, 1182 (2011)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Alpha-acyloxy ketone
  • Beta-hydroxy ketone
  • 2-furanone
  • Pyran
  • Alpha-haloketone
  • Alpha-chloroketone
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Chloroalkene
  • Haloalkene
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Vinyl chloride
  • Vinyl halide
  • Alcohol
  • Organohalogen compound
  • Organochloride
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
logP3.7ALOGPS
logP3.41ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)15.05ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.9 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity116.71 m³·mol⁻¹ChemAxon
Polarizability45.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00052734
Chemspider ID26631688
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID67615
Good Scents IDNot Available
References
General References
  1. Borges WS, Mancilla G, Guimaraes DO, Duran-Patron R, Collado IG, Pupo MT: Azaphilones from the endophyte Chaetomium globosum. J Nat Prod. 2011 May 27;74(5):1182-7. doi: 10.1021/np200110f. Epub 2011 May 6. [PubMed:21548578 ]
  2. Borges, W. S., et al. (2011). Borges, W. S., et al, J. Nat. Prod. 74, 1182 (2011). J. Nat. Prod..