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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-12 03:18:55 UTC
Update Date2018-05-20 09:58:19 UTC
HMDB IDHMDB0041623
Secondary Accession Numbers
  • HMDB41623
Metabolite Identification
Common NameN6-Carbamoyl-L-threonyladenosine
DescriptionN6-Carbamoyl-L-threonyladenosine is a member of the class of compounds known as purine nucleosides. Purine nucleosides are compounds composed of a purine base attached to a ribosyl or deoxyribosyl moiety. N6-Carbamoyl-L-threonyladenosine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Within the cell, N6-carbamoyl-L-threonyladenosine is primarily located in the cytoplasm. It can also be found in the extracellular space. N6-Carbamoyl-L-threonyladenosine is a minor constituent found in human and bovine milk (PMID: 7702711 ).
Structure
Thumb
Synonyms
ValueSource
N6-CarbamoylthreonyladenosineCAS
Chemical FormulaC15H21N7O7
Average Molecular Weight411.375
Monoisotopic Molecular Weight411.150246044
IUPAC Name(2S,3R)-2-(carbamoylamino)-N-{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}-3-hydroxybutanamide
Traditional Name(2S,3R)-2-(carbamoylamino)-N-{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl}-3-hydroxybutanamide
CAS Registry Number89019-62-5
SMILES
C[C@@H](O)[C@H](NC(N)=O)C(=O)NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1
InChI Identifier
InChI=1S/C15H21N7O7/c1-5(24)7(20-15(16)28)13(27)21-11-8-12(18-3-17-11)22(4-19-8)14-10(26)9(25)6(2-23)29-14/h3-7,9-10,14,23-26H,2H2,1H3,(H3,16,20,28)(H,17,18,21,27)/t5-,6-,7+,9-,10-,14-/m1/s1
InChI KeyGYCVHQYQICRFAX-CKTDUXNWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • N-carbamoyl-alpha-amino acid or derivatives
  • Alpha-amino acid amide
  • Glycosyl compound
  • N-glycosyl compound
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • N-arylamide
  • Fatty amide
  • Fatty acyl
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Azole
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • Urea
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carbonic acid derivative
  • Carboxamide group
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

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
Water Solubility5.34 g/LALOGPS
logP-2ALOGPS
logP-3.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)10.63ChemAxon
pKa (Strongest Basic)0.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area217.97 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.29 m³·mol⁻¹ChemAxon
Polarizability38.92 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Breast Milk
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified0.40 +/- 0.23 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021785
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92021849
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Schlimme E, Schneehagen K: Ribonucleosides in human milk. Concentration profiles of these minor constituents as a function of the nursing time. Z Naturforsch C. 1995 Jan-Feb;50(1-2):105-13. [PubMed:7702711 ]