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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:24 UTC
Update Date2019-01-11 19:39:46 UTC
HMDB IDHMDB0030199
Secondary Accession Numbers
  • HMDB30199
Metabolite Identification
Common NameFrangulanine
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
Structure
Data?1547235586
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
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
DescriptionThis compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • N-substituted-alpha-amino acid
  • Alkyl aryl ether
  • Benzenoid
  • Cyclic carboximidic acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Ether
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0btc-9300200000-e79d2fd28e9e6648165bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0bt9-9300002000-28c04d045f8b060ee374JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-114i-0509370000-2a4a9b8fe261b80a9618JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-4809000000-306ac7b273887873a3b5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cka-9102000000-e2377b3e1a050d5e6494JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0101900000-d6357db6a82d431d3158JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-1305900000-ce612174b3f0176d0008JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-8409000000-425602382ba3185399e4JSpectraViewer | MoNA
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
FoodDB 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
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.. .