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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:01:37 UTC
Update Date2020-02-26 21:37:41 UTC
HMDB IDHMDB0012492
Secondary Accession Numbers
  • HMDB12492
Metabolite Identification
Common Name1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate
DescriptionThe novel carbohydrate-derived b-carboline, 1-pentahydroxypentyl-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid, was identified in fruit- and vegetable-derived products such as juices, jams, and tomato sauces. This compound occurred as two diastereoisomers, a cis isomer (the major compound) and a trans isomer, ranging from undetectable amounts to 6.5 ug/g. Grape, tomato, pineapple, and tropical juices exhibited the highest amount of this alkaloid (up to 3.8 mg/L), whereas apple, banana, and peach juices showed very low or nondetectable levels. This tetrahydro-b-carboline was also found in jams (up to 0.45 ug/g), and a relative high amount was present in tomato concentrate (6.5 ug/g) and sauce (up to 1.8 ug/g). This b-carboline occurred in fruit-derived products as a glycoconjugate from a chemical condensation of d-glucose and l-tryptophan that is highly favored at low pH values and high temperature. Production, processing treatments, and storage of fruit juices and jams can then release this b-carboline. Fruit-derived products and other foods containing this compound might be an exogenous dietary source of this glucose-derived tetrahydro-b-carboline.(PMID: 12137498 ).
Structure
Data?1582753061
Synonyms
ValueSource
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-b-carboline-3-carboxylateGenerator
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acidGenerator
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acidGenerator
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylateGenerator
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acidGenerator
1,2,3,4-Tetrahydro-1-(1,2,3,4,5-pentahydroxypentyl)-b-carboline-3-carboxylic acidHMDB
1-C-(3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)pentitol, 9ciHMDB
1-(1,2,3,4,5-Pentahydroxypentyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylateGenerator
Chemical FormulaC17H22N2O7
Average Molecular Weight366.3658
Monoisotopic Molecular Weight366.142701068
IUPAC Name1-(1,2,3,4,5-pentahydroxypentyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
Traditional Name1-(1,2,3,4,5-pentahydroxypentyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
CAS Registry NumberNot Available
SMILES
OCC(O)C(O)C(O)C(O)C1NC(CC2=C1NC1=C2C=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C17H22N2O7/c20-6-11(21)14(22)16(24)15(23)13-12-8(5-10(19-13)17(25)26)7-3-1-2-4-9(7)18-12/h1-4,10-11,13-16,18-24H,5-6H2,(H,25,26)
InChI KeyLCHFAYIGHOVWSA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassHarmala alkaloids
Sub ClassNot Available
Direct ParentHarmala alkaloids
Alternative Parents
Substituents
  • Harman
  • Beta-carboline
  • Pyridoindole
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Monosaccharide
  • Benzenoid
  • 1,3-aminoalcohol
  • Heteroaromatic compound
  • Pyrrole
  • Secondary alcohol
  • Amino acid or derivatives
  • Amino acid
  • 1,2-aminoalcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility25.2 g/LALOGPS
logP-1.6ALOGPS
logP-4.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.04ChemAxon
pKa (Strongest Basic)6.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area166.27 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.22 m³·mol⁻¹ChemAxon
Polarizability37.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07bb-9086000000-f9817373dcbb48a00eadSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-066r-1092238000-8a73a9d7c71faf707742Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-2019000000-f66e1f938b58a2d0ba87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9453000000-e1c15a39669221325154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9820000000-4592a1a9ad5f5701322fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0q4u-7098000000-cf33a70ee23840fab676Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abl-8191000000-35b3333d76ce8a3c796cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9030000000-f91a3596176e7837fc7fSpectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB001280
KNApSAcK IDNot Available
Chemspider ID19993304
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21125948
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. Herraiz T, Galisteo J: Identification and occurrence of the novel alkaloid pentahydroxypentyl-tetrahydro-beta-carboline-3-carboxylic acid as a tryptophan glycoconjugate in fruit juices and jams. J Agric Food Chem. 2002 Jul 31;50(16):4690-5. [PubMed:12137498 ]