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Record Information
Version2.0
Created at2022-09-06 17:23:55 UTC
Updated at2022-09-06 17:23:55 UTC
NP-MRD IDNP0235008
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-11,18-dihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioic acid
DescriptionFumonisin B3 belongs to the class of organic compounds known as fumonisins. These are diesters of propane-1,2,3-tricarboxylic acid (TCA) and similar long-chain aminopolyol backbones (for FB1: 2S-amino-12S,16R-dimethyl-3S,5R,10R,14S,15R-pentahydroxyeicosane). Structurally, fumonisins resemble the sphingoid bases sphinganine (SA) and sphingosine (SO) to which TCA groups have been added at the C-14 and C-15 positions. 2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-11,18-dihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioic acid is found in Fusarium verticillioides. Fumonisin B3 is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
Fumonisin-b3HMDB
2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-11,18-dihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioateGenerator
Fumonisin b3MeSH
Chemical FormulaC34H59NO14
Average Mass705.8306 Da
Monoisotopic Mass705.39356 Da
IUPAC Name2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-11,18-dihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioic acid
Traditional Name2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-11,18-dihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioic acid
CAS Registry NumberNot Available
SMILES
CCCCC(C)C(OC(=O)CC(CC(O)=O)C(O)=O)C(CC(C)CC(O)CCCCCCC(O)C(C)N)OC(=O)CC(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C34H59NO14/c1-5-6-11-21(3)32(49-31(43)19-24(34(46)47)17-29(40)41)27(48-30(42)18-23(33(44)45)16-28(38)39)15-20(2)14-25(36)12-9-7-8-10-13-26(37)22(4)35/h20-27,32,36-37H,5-19,35H2,1-4H3,(H,38,39)(H,40,41)(H,44,45)(H,46,47)
InChI KeyCPCRJSQNWHCGOP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fusarium verticillioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fumonisins. These are diesters of propane-1,2,3-tricarboxylic acid (TCA) and similar long-chain aminopolyol backbones (for FB1: 2S-amino-12S,16R-dimethyl-3S,5R,10R,14S,15R-pentahydroxyeicosane). Structurally, fumonisins resemble the sphingoid bases sphinganine (SA) and sphingosine (SO) to which TCA groups have been added at the C-14 and C-15 positions.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassFumonisins
Direct ParentFumonisins
Alternative Parents
Substituents
  • Fumonisin skeleton
  • Fumonisin-skeleton
  • Hexacarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP-0.38ALOGPS
logP0.79ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area268.28 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity174.08 m³·mol⁻¹ChemAxon
Polarizability75.27 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040967
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020822
KNApSAcK IDNot Available
Chemspider ID26515359
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15817722
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]