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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:24 UTC
Update Date2019-07-23 06:05:52 UTC
HMDB IDHMDB0030199
Secondary Accession Numbers
  • HMDB30199
Metabolite Identification
Common NameFrangulanine
DescriptionFrangulanine, also known as ceanothamine a or daechuine S2, 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. Frangulanine is a very strong basic compound (based on its pKa). Outside of the human body, Frangulanine has been detected, but not quantified in, fruits and tea. This could make frangulanine a potential biomarker for the consumption of these foods.
Structure
Data?1563861952
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-methylpentanimidateGenerator
FrangulanineMeSH
Chemical FormulaC28H44N4O4
Average Molecular Weight500.6734
Monoisotopic Molecular Weight500.336255916
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
CAS Registry Number25350-22-5
SMILES
CCC(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 Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point276 - 279 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002017
KNApSAcK IDC00001998
Chemspider ID4476260
KEGG Compound IDC10003
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5317388
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .