Frangulanine (CHEM024225)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:34:19 UTC
Update Date2016-11-09 01:17:51 UTC
Accession NumberCHEM024225
Identification
Common NameFrangulanine
ClassSmall Molecule
DescriptionFrangulanine is found in fruits. Frangulanine is an alkaloid from the root bark of Ceanothus americanus (New Jersey tea), Hovenia dulcis (raisin tree) and Zizyphus jujuba var. inermi
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(Dimethylamino)-3-methyl-N-[3-(1-methylethyl)-7-(2-methylpropyl)-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-10,12,14,15-tetraen-4-yl]pentanamide, 9ciHMDB
Ceanothamine aHMDB
Daechuine S2HMDB
N-[(10Z)-5,8-Dihydroxy-7-(2-methylpropyl)-3-(propan-2-yl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(dimethylamino)-3-methylpentanimidateHMDB
FrangulanineMeSH
Chemical FormulaC28H44N4O4
Average Molecular Mass500.673 g/mol
Monoisotopic Mass500.336 g/mol
CAS Registry Number25350-22-5
IUPAC Name(Z)-N-[(5E,8E,10Z)-5,8-dihydroxy-7-(2-methylpropyl)-3-(propan-2-yl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(dimethylamino)-3-methylpentimidic acid
Traditional Name(Z)-N-[(5E,8E,10Z)-5,8-dihydroxy-3-isopropyl-7-(2-methylpropyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(dimethylamino)-3-methylpentimidic acid
SMILESCCC(C)C(N(C)C)C(\O)=N\C1C(OC2=CC=C(C=C2)\C=C/N=C(O)\C(CC(C)C)\N=C1\O)C(C)C
InChI IdentifierInChI=1S/C28H44N4O4/c1-9-19(6)24(32(7)8)28(35)31-23-25(18(4)5)36-21-12-10-20(11-13-21)14-15-29-26(33)22(16-17(2)3)30-27(23)34/h10-15,17-19,22-25H,9,16H2,1-8H3,(H,29,33)(H,30,34)(H,31,35)/b15-14-
InChI KeyULQXKOIGVXLOOC-PFONDFGASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Cyclic alpha peptide
  • Isoleucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Macrolactam
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Alkyl aryl ether
  • N-acyl-amine
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Amino acid or derivatives
  • Oxacycle
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.0072 g/LALOGPS
logP3.8ALOGPS
logP3.05ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area110.24 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity143.34 m³·mol⁻¹ChemAxon
Polarizability55.06 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0btc-9300200000-e79d2fd28e9e6648165bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0bt9-9300002000-28c04d045f8b060ee374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-114i-0509370000-2a4a9b8fe261b80a9618Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-4809000000-306ac7b273887873a3b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cka-9102000000-e2377b3e1a050d5e6494Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0101900000-d6357db6a82d431d3158Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-1305900000-ce612174b3f0176d0008Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-8409000000-425602382ba3185399e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-0009700000-d64303c8bc9b85499e05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0009200000-9213bf40c5dc768a4b60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2019000000-fc0ec1045717ff9c42b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000090000-714375b6bd04706159a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2303290000-96fac2404794e400d58eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-114j-5209000000-f64f73da7e736567f0beSpectrum
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 IDHMDB0030199
FooDB IDFDB002017
Phenol Explorer IDNot Available
KNApSAcK IDC00001998
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4476260
ChEBI IDNot Available
PubChem Compound ID5317388
Kegg Compound IDC10003
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.