FR901463 (PAMDB100002)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB100002
Identification
Name: FR901463
Description:A cyclic hemiketal isolated from the fermentation broth of Pseudomonas sp.no.2663. It displays potent cytotoxic activity against human tumour cells.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (3Z)-5-[(6-{(2E,4E)-5-[(3R,4S,6S)-4-(chloromethyl)-3,4,6-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-5-oxopent-3-en-2-yl acetate
Chemical Formula: C27H42ClNO8
Average Molecular Weight: 544.077
Monoisotopic Molecular Weight: 543.26
InChI Key: RONUKPQOBQKEHX-FOUIGEGESA-N
InChI:
  • InChI=1S/C27H42ClNO8/c1-16(8-11-23-25(32)27(34,15-28)14-26(6,33)37-23)7-10-22-17(2)13-21(19(4)36-22)29-24(31)12-9-18(3)35-20(5)30/h7-9,11-12,17-19,21-23,25,32-34H,10,13-15H2,1-6H3,(H,29,31)/b11-8+,12-9-,16-7+/t17?,18?,19?,21?,22?,23?,25-,26+,27-/m1/s1
CAS number: Not Available
IUPAC Name:6-[(1E,3E)-5-(5-{[(2Z)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-dimethyltetrahydro-2H-pyran-2-yl)-3-methylpenta-1,3-dien-1-yl]-4-C-(chloromethyl)-1,3-dideoxy-a-D-erythro-hex-2-ulopyranose
Traditional IUPAC Name: Not Available
SMILES:CC1CC(NC(=O)\C=C/C(C)OC(C)=O)C(C)OC1C\C=C(C)\C=C\C1O[C@](C)(O)C[C@@](O)(CCl)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as n-acyl amines. These are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty amides
Direct Parent N-acyl amines
Alternative Parents
Substituents
  • Monosaccharide
  • N-acyl-amine
  • Oxane
  • Tertiary alcohol
  • 1,2-diol
  • Carboxamide group
  • Carboxylic acid ester
  • Chlorohydrin
  • Halohydrin
  • Hemiacetal
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Carbonyl group
  • Alkyl halide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Alkyl chloride
  • Organopnictogen compound
  • Organohalogen compound
  • Alcohol
  • Organochloride
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
  • monocarboxylic acid amide, organochlorine compound, acetate ester, cyclic hemiketal, pyrans (CHEBI:65914)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Mass544.0747ChemAxon
logP2.9042ChemAxon
H-bond acceptors9ChemAxon
H-bond donors4ChemAxon
Rotatable bonds11ChemAxon
PSA134.5500ChemAxon
RO5 violations1ChemAxon
RO3 violations5ChemAxon
Refractivity141.0671ChemAxon
Atoms79ChemAxon
Rings2ChemAxon
Heavy atoms37ChemAxon
Hydrogen atoms42ChemAxon
Heteroatoms10ChemAxon
N/O atoms9ChemAxon
Inorganic atoms0ChemAxon
Halogen atoms1ChemAxon
Chiral centers9ChemAxon
R/S chiral centers3ChemAxon
Unknown chiral centers0ChemAxon
Undefined chiral centers6ChemAxon
Stereo double bonds3ChemAxon
Cis/trans stereo double bonds0ChemAxon
Unknown stereo double bonds3ChemAxon
Undefined stereo double bonds 0ChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Nakajima, Hidenori, et al. "New antitumor substances, FR901463, FR901464 and FR901465. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities." The Journal of antibiotics 49.12 (1996): 1196-1203. Pubmed: 9031664
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links: Not Available