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Identification
YMDB IDYMDB00017
Name2-(3-Carboxy-3-aminopropyl)-L-histidine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-(3-Carboxy-3-aminopropyl)-L-histidine is an unusual amino acid that results from the post-translational modification of histidine in certain proteins.
Structure
Thumb
Synonyms
  • 2-(3-amino-3-carboxypropyl)-L-histidine
  • 2-(3-Carboxy-3-aminopropyl)-L-histidine
  • 2-amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoate
  • 2-amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acid
CAS numberNot Available
WeightAverage: 256.2584
Monoisotopic: 256.11715502
InChI KeyCJCSNWWKPUXVRD-MLWJPKLSSA-N
InChIInChI=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
IUPAC Name2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid
Traditional IUPAC Name2-amino-4-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}butanoic acid
Chemical FormulaC10H16N4O4
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C1=C([H])N=C(N1[H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(=O)O[H]
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as histidine and derivatives. These 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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
2-(3-Carboxy-3-aminopropyl)-L-histidine + S-AdenosylmethionineS-Adenosylhomocysteine + hydron + 2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Mattheakis, L. C., Shen, W. H., Collier, R. J. (1992). "DPH5, a methyltransferase gene required for diphthamide biosynthesis in Saccharomyces cerevisiae." Mol Cell Biol 12:4026-4037.1508200
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17144
HMDB IDHMDB11655
Pubchem Compound ID440342
Kegg IDC04441
ChemSpider ID389308
FOODB IDFDB028346
Wikipedia IDNot Available
BioCyc ID2-3-CARBOXY-3-AMINOPROPYL-L-HISTIDINE

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Required for the methylation step in diphthamide biosynthesis
Gene Name:
DPH5
Uniprot ID:
P32469
Molecular weight:
33847.0
Reactions
3 S-adenosyl-L-methionine + 2-(3-carboxy-3-aminopropyl)-L-histidine → 3 S-adenosyl-L-homocysteine + 2-(3-carboxy-3-(trimethylammonio)propyl)-L-histidine.