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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2019-03-07 00:03:56 UTC
Update Date2020-02-26 19:17:42 UTC
HMDB IDHMDB0240296
Secondary Accession NumbersNone
Metabolite Identification
Common NameTryptophan 2-C-mannoside
DescriptionTryptophan 2-C-mannoside, also known as 2-alpha-D-mannopyranosyl-L-tryptophan or C-mannosyltryptophan, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. It is an L-tryptophan derivative and a C-glycosyl compound in which the hydrogen at position 2 on the indole portion has been replaced by an alpha-mannosyl residue. Tryptophan 2-C-mannoside is a very strong basic compound (based on its pKa). Tryptophan 2-C-mannoside has been identified in blood and urine and is a marker of kidney function (PMID: 29234020 ).
Structure
Data?1572384480
Synonyms
ValueSource
(1R)-1,5-Anhydro-1-{3-[(2S)-2-amino-2-carboxyethyl]-1H-indol-2-yl}-D-mannitolChEBI
2'-alpha-D-Mannosyl-L-tryptophanChEBI
2'-alpha-D-MannosyltryptophanChEBI
2'-alpha-MannosyltryptophanChEBI
2'-Tryptophan C-mannosideChEBI
C(2)-alpha-D-Mannopyranosyl-L-tryptophanChEBI
2'-a-D-Mannosyl-L-tryptophanGenerator
2'-Α-D-mannosyl-L-tryptophanGenerator
2'-a-D-MannosyltryptophanGenerator
2'-Α-D-mannosyltryptophanGenerator
2'-a-MannosyltryptophanGenerator
2'-Α-mannosyltryptophanGenerator
C(2)-a-D-Mannopyranosyl-L-tryptophanGenerator
C(2)-Α-D-mannopyranosyl-L-tryptophanGenerator
2'-a-Mannosyl-L-tryptophanGenerator
2'-Α-mannosyl-L-tryptophanGenerator
2-(alpha-D-Mannopyranosyl)-L-tryptophanHMDB
2-(Α-D-mannopyranosyl)-L-tryptophanHMDB
2-alpha-D-Mannopyranosyl-L-tryptophanHMDB
2-Α-D-mannopyranosyl-L-tryptophanHMDB
C2-alpha-D-MannopyranosyltryptophanHMDB
C2-Α-D-mannopyranosyltryptophanHMDB
2-(alpha-Mannopyranosyl)-L-tryptophanHMDB
2-(α-Mannopyranosyl)-L-tryptophanHMDB
2-alpha-D-MannopyranosyltryptophanHMDB
2-alpha-D-Mannosyl-L-tryptophanHMDB
2-alpha-D-MannosyltryptophanHMDB
2-α-D-MannopyranosyltryptophanHMDB
2-α-D-Mannosyl-L-tryptophanHMDB
2-α-D-MannosyltryptophanHMDB
C-GlycosyltryptophanHMDB
C-Man-TrpHMDB
C-Mannosyl tryptophanHMDB
C-MannosyltryptophanHMDB
L-Tryptophan 2-C-alpha-D-mannopyranosideHMDB
L-Tryptophan 2-C-mannopyranosideHMDB
L-Tryptophan 2-C-α-D-mannopyranosideHMDB
Tryptophan 2-C-mannosideHMDB
alpha-C-Man-TrpHMDB
α-C-Man-TrpHMDB
Chemical FormulaC17H22N2O7
Average Molecular Weight366.37
Monoisotopic Molecular Weight366.142701056
IUPAC Name(2S)-2-amino-3-{2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoic acid
Traditional Name(2S)-2-amino-3-{2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoic acid
CAS Registry Number180509-18-6
SMILES
N[C@@H](CC1=C(NC2=CC=CC=C12)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)C(O)=O
InChI Identifier
InChI=1S/C17H22N2O7/c18-9(17(24)25)5-8-7-3-1-2-4-10(7)19-12(8)16-15(23)14(22)13(21)11(6-20)26-16/h1-4,9,11,13-16,19-23H,5-6,18H2,(H,24,25)/t9-,11+,13+,14-,15-,16+/m0/s1
InChI KeyCPXSBHKDEPPWIX-RAYCSJGISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • Hexose monosaccharide
  • C-glycosyl compound
  • Glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Monosaccharide
  • Oxane
  • Heteroaromatic compound
  • Pyrrole
  • Secondary alcohol
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxide
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Primary amine
  • Primary alcohol
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

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-2ALOGPS
logP-3.9ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area169.26 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.2 m³·mol⁻¹ChemAxon
Polarizability36.57 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 10V, Positivesplash10-014i-0049000000-429d66198fdcf1cabf9fSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.26 +/- 0.05 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.39 +/- 0.80 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.72 +/- 0.28 uMAdult (>18 years old)Both
Chronic kidney disease
details
UrineDetected and Quantified4.30 +/- 1.05 umol/mmol creatinineAdult (>18 years old)Both
Chronic kidney disease
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9157171
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10981970
PDB IDNot Available
ChEBI ID19232
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sekula P, Dettmer K, Vogl FC, Gronwald W, Ellmann L, Mohney RP, Eckardt KU, Suhre K, Kastenmuller G, Oefner PJ, Kottgen A: From Discovery to Translation: Characterization of C-Mannosyltryptophan and Pseudouridine as Markers of Kidney Function. Sci Rep. 2017 Dec 12;7(1):17400. doi: 10.1038/s41598-017-17107-5. [PubMed:29234020 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]