Antimycin A (CHEM004349)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:42:03 UTC
Update Date2016-11-09 01:09:20 UTC
Accession NumberCHEM004349
Identification
Common NameAntimycin A
ClassSmall Molecule
DescriptionA nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.
Contaminant Sources
  • Clean Air Act Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Antimycin a1ChEBI
Antimycin a1bChEBI
AntipiricullinChEBI
FintrolChEBI
VirosinChEBI
[(2R,3S,6S,7R,8R)-3-[(3-formamido-2-Hydroxybenzoyl)amino]-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoic acidGenerator
Antimycin aMeSH
Chemical FormulaC28H40N2O9
Average Molecular Mass548.633 g/mol
Monoisotopic Mass548.273 g/mol
CAS Registry Number1397-94-0
IUPAC NameN-[(3S,4R,7R,8R,9S)-7-hexyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzene-1-carboximidic acid
Traditional Nameantimycin A
SMILES[H][C@@]1(C)OC(=O)[C@@]([H])(N=C(O)C2=C(O)C(=CC=C2)N=CO)[C@@]([H])(C)OC(=O)[C@]([H])(CCCCCC)[C@@]1([H])OC(=O)CC(C)C
InChI IdentifierInChI=1S/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34)/t17-,18+,20-,23+,25+/m1/s1
InChI KeyUIFFUZWRFRDZJC-SBOOETFBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboximidic acid derivative
  • Carboximidic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP4.25ALOGPS
logP7.15ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)0.028ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area164.31 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity143.15 m³·mol⁻¹ChemAxon
Polarizability58.43 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015j-3011390000-9ccb16299ba56589df04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-9410330000-659f447fcd03095b19dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rj-5690000000-93afa9bd04a46f8c62d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0h0s-5290040000-49b5aea2537dfbc9590dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gea-4590220000-9bbe7fecc8584dee8acaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9610000000-adfa656d9e3bf0d68df7Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-5744
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAntimycin A
Chemspider IDNot Available
ChEBI ID2762
PubChem Compound ID14957
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16819166