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Showing Compound 2-(3-Carboxy-3-aminopropyl)-L-histidine (FDB028346)

Record Information
Version1.0
Creation date2011-09-21 01:38:19 UTC
Update date2015-07-21 06:59:23 UTC
Primary IDFDB028346
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-(3-Carboxy-3-aminopropyl)-L-histidine
Description2-(3-Carboxy-3-aminopropyl)-L-histidine is an unusual amino acid that results from the post-translational modification of histidine in certain proteins. In particular, it is a post-translational derivative of histidine that exists in protein synthesis elongation factor 2 (EF2) at the site of diphtheria toxin-catalyzed ADP-ribosylation of elongation factor 2. It is a precursor for diphthamide. This compound is a substrate for the enzyme diphthine synthase (EC 2.1.1.98). This enzyme catalyzes the chemical reaction: S-adenosyl-L-methionine + 2-(3-carboxy-3-aminopropyl)-L-histidine = S-adenosyl-L-homocysteine + 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-(3-Carboxy-3-aminopropyl)-L-histidineChEBI
2-(3-amino-3-Carboxypropyl)-L-histidineHMDB
2-amino-4-[[4-(2-amino-2-Carboxy-ethyl)-1H-imidazol-2-yl]] butanoateHMDB
2-amino-4-[[4-(2-amino-2-Carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acidHMDB
2-(3-amino-3-carboxypropyl)-L-histidinehmdb
2-amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoatehmdb
2-amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility8.71 g/LALOGPS
logP-4.1ALOGPS
logP-6.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.63ChemAxon
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.32 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity61.14 m³·mol⁻¹ChemAxon
Polarizability25.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16N4O4
IUPAC name2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid
InChI IdentifierInChI=1S/C10H16N4O4/c11-6(9(15)16)1-2-8-13-4-5(14-8)3-7(12)10(17)18/h4,6-7H,1-3,11-12H2,(H,13,14)(H,15,16)(H,17,18)/t6?,7-/m0/s1
InChI KeyCJCSNWWKPUXVRD-MLWJPKLSSA-N
Isomeric SMILESNC(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O
Average Molecular Weight256.2584
Monoisotopic Molecular Weight256.11715502
Classification
Description Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-(3-Carboxy-3-aminopropyl)-L-histidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02mu-5940000000-c3310ff9a24aa7c862e6Spectrum
Predicted GC-MS2-(3-Carboxy-3-aminopropyl)-L-histidine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-3592000000-a21b1849129fc09978d0Spectrum
Predicted GC-MS2-(3-Carboxy-3-aminopropyl)-L-histidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0490000000-b169c82b73ecee75fb2e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-0930000000-88b257572c5443b2894a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-1900000000-34de02163a51cec0b9202016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-6fb3de3d4334b0f51e462016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1790000000-4f147519032e147413162016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-7910000000-b899dda5046bb04ed5ec2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0190000000-c2328930b95b5240880d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052u-1950000000-d39ef30f4993bac546fc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bc-2900000000-34f57b5e9afde72e67e12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-6b70ce39004c223ed4472021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vo-0590000000-de801a6acbb75116fe8e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00y0-1900000000-c344db411f89e38f99b32021-09-22View Spectrum
NMRNot Available
ChemSpider ID389308
ChEMBL IDNot Available
KEGG Compound IDC04441
Pubchem Compound ID440342
Pubchem Substance IDNot Available
ChEBI ID17144
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11655
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference