Gambieric acid A (CHEM003089)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:24:19 UTC
Update Date2026-05-21 00:20:20 UTC
Accession NumberCHEM003089
Identification
Common NameGambieric acid A
ClassSmall Molecule
DescriptionGambieric acid A is an antifungal compound isolated from the marine dinoflagellate Gambierdiscus toxicus that produces ciguatoxin precursors and maitotoxin. The skeletal structure of gambieric acids (GAs) consists of a nonacrylic polyether core involuving six-, seven-, and nine- membered cyclic ethers, arranged with an isolated tetrahydrofuran ring (A-ring). GAs share the structural characteristics common to those of polycyclic ether neurotoxins, which are produced by G. toxicus, for example, ciguatoxin, maitotoxin, and gambierol (1).
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ether
  • Marine Toxin
  • Natural Compound
  • Organic Compound
  • PFAS
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-Gambierate aGenerator
Gambierate aGenerator
(3S)-3-[(2S,3R,5S)-5-[(2R)-3-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-17,34-Dihydroxy-11-[(4R)-5-hydroxy-2,4-dimethylpent-2-en-1-yl]-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]tritetracont-22-en-35-yl]-2-hydroxypropyl]-3-methyloxolan-2-yl]butanoateGenerator
(3S)-3-[(2S,3R,5S)-5-[(2R)-3-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-17,34-Dihydroxy-11-[(4R)-5-hydroxy-2,4-dimethylpent-2-en-1-yl]-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0,.0,.0,.0,.0,.0,.0,]tritetracont-22-en-35-yl]-2-hydroxypropyl]-3-methyloxolan-2-yl]butanoateGenerator
Chemical FormulaC59H92O16
Average Molecular Mass1057.352 g/mol
Monoisotopic Mass1056.639 g/mol
CAS Registry NumberNot Available
IUPAC NameNot Available
Traditional Name(3S)-3-[(2S,3R,5S)-5-[(2R)-3-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-17,34-dihydroxy-11-[(4R)-5-hydroxy-2,4-dimethylpent-2-en-1-yl]-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]tritetracont-22-en-35-yl]-2-hydroxypropyl]-3-methyloxolan-2-yl]butanoic acid
SMILES[H]C(=C(C)C[C@]1([H])O[C@]2(C)C[C@]3([H])O[C@]4([H])C[C@]5([H])O[C@]6([H])CC[C@]7([H])O[C@]8([H])C[C@]9([H])O[C@]([H])(C[C@]([H])(O)C[C@]%10([H])C[C@@]([H])(C)[C@]([H])(O%10)[C@@]([H])(C)CC(O)=O)[C@@]([H])(O)CC[C@@]9([H])O[C@@]8(C)C[C@@]7(C)O[C@@]6([H])C\C([H])=C([H])/[C@@]([H])(C)[C@@]5([H])O[C@@]4(C)[C@]([H])(O)[C@@]3([H])O[C@@]2([H])CC1=C)[C@@]([H])(C)CO
InChI IdentifierInChI=1S/C59H92O16/c1-30(18-31(2)28-60)19-42-33(4)21-48-56(7,74-42)27-46-54(71-48)55(65)59(10)50(69-46)26-45-53(75-59)32(3)12-11-13-40-39(67-45)16-17-47-57(8,72-40)29-58(9)49(70-47)25-44-41(73-58)15-14-38(62)43(68-44)24-36(61)23-37-20-34(5)52(66-37)35(6)22-51(63)64/h11-12,18,31-32,34-50,52-55,60-62,65H,4,13-17,19-29H2,1-3,5-10H3,(H,63,64)/b12-11-,30-18+/t31-,32-,34-,35+,36-,37+,38+,39-,40+,41-,42+,43-,44+,45+,46+,47+,48+,49-,50-,52+,53-,54+,55-,56-,57-,58+,59-/m1/s1
InChI KeyMSZMCMVREIGRAG-FKAXGPHESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • Fatty alcohol
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Oxepane
  • Monosaccharide
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Metabolic PathwaysNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP3.52ALOGPS
logP4.4ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.55ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area210.52 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity277.62 m³·mol⁻¹ChemAxon
Polarizability121.22 ųChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-9100000001-e734ab6a0eaaa7239240Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-4510001019-95f1e86c31f81ebce40fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9011008232-cb810c6a5af0531810a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06vi-9171205601-59d8e6d980b2c9fe3f8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03g0-4539120150-3ef862bd3af3ada96ae3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0imi-1296220000-0e4c358d4fdf5c5c4549Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesGambieric acid A is an antifungal compound isolated from the marine dinoflagellate Gambierdiscus toxicus that produces ciguatoxin precursors and maitotoxin. The skeletal structure of gambieric acids (GAs) consists of a nonacrylic polyether core involuving six-, seven-, and nine- membered cyclic ethers, arranged with an isolated tetrahydrofuran ring (A-ring). GAs share the structural characteristics common to those of polycyclic ether neurotoxins, which are produced by G. toxicus, for example, ciguatoxin, maitotoxin, and gambierol (1).
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 IDC00016806
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID80777
PubChem Compound ID46173842
Kegg Compound IDC16885
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available