Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:07 UTC
Update Date2021-09-14 15:41:37 UTC
HMDB IDHMDB0028689
Secondary Accession Numbers
  • HMDB28689
Metabolite Identification
Common NameAlanylhistidine
DescriptionAlanylhistidine, also known as AH or L-ala-L-his, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Alanylhistidine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make alanylhistidine a potential biomarker for the consumption of these foods. Alanylhistidine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Alanylhistidine.
Structure
Data?1582753326
Synonyms
ValueSource
AHChEBI
Alanyl-histidineChEBI
L-Ala-L-hisChEBI
N-L-Alanyl-L-histidineChEBI
Alanylhistidine, (D-his-L-ala)-isomerHMDB
a-H DipeptideHMDB
AH dipeptideHMDB
Ala-hisHMDB
Alanine histidine dipeptideHMDB
Alanine-histidine dipeptideHMDB
L-Alanyl-L-histidineHMDB
N-AlanylhistidineHMDB
AlanylhistidineChEBI
Chemical FormulaC9H14N4O3
Average Molecular Weight226.236
Monoisotopic Molecular Weight226.106590327
IUPAC Name(2S)-2-[(2S)-2-aminopropanamido]-3-(1H-imidazol-4-yl)propanoic acid
Traditional Name(2S)-2-[(2S)-2-aminopropanamido]-3-(1H-imidazol-4-yl)propanoic acid
CAS Registry Number3253-17-6
SMILES
C[C@H](N)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O
InChI Identifier
InChI=1S/C9H14N4O3/c1-5(10)8(14)13-7(9(15)16)2-6-3-11-4-12-6/h3-5,7H,2,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/t5-,7-/m0/s1
InChI KeyXZWXFWBHYRFLEF-FSPLSTOPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Histidine or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alanine or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.92Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.1 g/LALOGPS
logP-2.8ALOGPS
logP-3.9ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.36ChemAxon
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.1 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.79 m³·mol⁻¹ChemAxon
Polarizability21.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+152.53530932474
DeepCCS[M-H]-150.1430932474
DeepCCS[M-2H]-183.10130932474
DeepCCS[M+Na]+158.5630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AlanylhistidineC[C@H](N)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O3179.8Standard polar33892256
AlanylhistidineC[C@H](N)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O2004.0Standard non polar33892256
AlanylhistidineC[C@H](N)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O2357.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Alanylhistidine,1TMS,isomer #1C[C@H](N)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C2236.1Semi standard non polar33892256
Alanylhistidine,1TMS,isomer #2C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O2293.7Semi standard non polar33892256
Alanylhistidine,1TMS,isomer #3C[C@H](N)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C2184.4Semi standard non polar33892256
Alanylhistidine,1TMS,isomer #4C[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O2350.1Semi standard non polar33892256
Alanylhistidine,2TMS,isomer #1C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C2309.6Semi standard non polar33892256
Alanylhistidine,2TMS,isomer #1C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C2232.3Standard non polar33892256
Alanylhistidine,2TMS,isomer #1C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C3299.8Standard polar33892256
Alanylhistidine,2TMS,isomer #2C[C@H](N)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2197.9Semi standard non polar33892256
Alanylhistidine,2TMS,isomer #2C[C@H](N)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2213.8Standard non polar33892256
Alanylhistidine,2TMS,isomer #2C[C@H](N)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3528.1Standard polar33892256
Alanylhistidine,2TMS,isomer #3C[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C2364.2Semi standard non polar33892256
Alanylhistidine,2TMS,isomer #3C[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C2159.0Standard non polar33892256
Alanylhistidine,2TMS,isomer #3C[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C3771.6Standard polar33892256
Alanylhistidine,2TMS,isomer #4C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2407.3Semi standard non polar33892256
Alanylhistidine,2TMS,isomer #4C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2428.1Standard non polar33892256
Alanylhistidine,2TMS,isomer #4C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C3472.4Standard polar33892256
Alanylhistidine,2TMS,isomer #5C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C2246.4Semi standard non polar33892256
Alanylhistidine,2TMS,isomer #5C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C2318.8Standard non polar33892256
Alanylhistidine,2TMS,isomer #5C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C3258.9Standard polar33892256
Alanylhistidine,2TMS,isomer #6C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O2408.4Semi standard non polar33892256
Alanylhistidine,2TMS,isomer #6C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O2287.7Standard non polar33892256
Alanylhistidine,2TMS,isomer #6C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O3424.0Standard polar33892256
Alanylhistidine,2TMS,isomer #7C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C2321.9Semi standard non polar33892256
Alanylhistidine,2TMS,isomer #7C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C2280.5Standard non polar33892256
Alanylhistidine,2TMS,isomer #7C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C3543.3Standard polar33892256
Alanylhistidine,3TMS,isomer #1C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2382.5Semi standard non polar33892256
Alanylhistidine,3TMS,isomer #1C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2366.1Standard non polar33892256
Alanylhistidine,3TMS,isomer #1C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3048.4Standard polar33892256
Alanylhistidine,3TMS,isomer #2C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2255.7Semi standard non polar33892256
Alanylhistidine,3TMS,isomer #2C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2290.0Standard non polar33892256
Alanylhistidine,3TMS,isomer #2C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2916.7Standard polar33892256
Alanylhistidine,3TMS,isomer #3C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C2428.4Semi standard non polar33892256
Alanylhistidine,3TMS,isomer #3C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C2252.3Standard non polar33892256
Alanylhistidine,3TMS,isomer #3C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C3073.7Standard polar33892256
Alanylhistidine,3TMS,isomer #4C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2334.8Semi standard non polar33892256
Alanylhistidine,3TMS,isomer #4C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2292.6Standard non polar33892256
Alanylhistidine,3TMS,isomer #4C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3312.0Standard polar33892256
Alanylhistidine,3TMS,isomer #5C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2350.9Semi standard non polar33892256
Alanylhistidine,3TMS,isomer #5C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2441.1Standard non polar33892256
Alanylhistidine,3TMS,isomer #5C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3038.7Standard polar33892256
Alanylhistidine,3TMS,isomer #6C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2559.5Semi standard non polar33892256
Alanylhistidine,3TMS,isomer #6C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2420.0Standard non polar33892256
Alanylhistidine,3TMS,isomer #6C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C3194.5Standard polar33892256
Alanylhistidine,3TMS,isomer #7C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C2375.6Semi standard non polar33892256
Alanylhistidine,3TMS,isomer #7C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C2356.7Standard non polar33892256
Alanylhistidine,3TMS,isomer #7C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C3045.3Standard polar33892256
Alanylhistidine,4TMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2397.9Semi standard non polar33892256
Alanylhistidine,4TMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2427.3Standard non polar33892256
Alanylhistidine,4TMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2677.2Standard polar33892256
Alanylhistidine,4TMS,isomer #2C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2540.3Semi standard non polar33892256
Alanylhistidine,4TMS,isomer #2C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2413.3Standard non polar33892256
Alanylhistidine,4TMS,isomer #2C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2902.3Standard polar33892256
Alanylhistidine,4TMS,isomer #3C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2393.0Semi standard non polar33892256
Alanylhistidine,4TMS,isomer #3C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2356.1Standard non polar33892256
Alanylhistidine,4TMS,isomer #3C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2792.8Standard polar33892256
Alanylhistidine,4TMS,isomer #4C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2485.9Semi standard non polar33892256
Alanylhistidine,4TMS,isomer #4C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2500.9Standard non polar33892256
Alanylhistidine,4TMS,isomer #4C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2905.3Standard polar33892256
Alanylhistidine,5TMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2538.5Semi standard non polar33892256
Alanylhistidine,5TMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2504.4Standard non polar33892256
Alanylhistidine,5TMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2681.2Standard polar33892256
Alanylhistidine,1TBDMS,isomer #1C[C@H](N)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C2471.8Semi standard non polar33892256
Alanylhistidine,1TBDMS,isomer #2C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O2521.5Semi standard non polar33892256
Alanylhistidine,1TBDMS,isomer #3C[C@H](N)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2436.2Semi standard non polar33892256
Alanylhistidine,1TBDMS,isomer #4C[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O2628.0Semi standard non polar33892256
Alanylhistidine,2TBDMS,isomer #1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C2757.9Semi standard non polar33892256
Alanylhistidine,2TBDMS,isomer #1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C2660.0Standard non polar33892256
Alanylhistidine,2TBDMS,isomer #1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C3312.6Standard polar33892256
Alanylhistidine,2TBDMS,isomer #2C[C@H](N)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2671.8Semi standard non polar33892256
Alanylhistidine,2TBDMS,isomer #2C[C@H](N)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2628.2Standard non polar33892256
Alanylhistidine,2TBDMS,isomer #2C[C@H](N)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3522.7Standard polar33892256
Alanylhistidine,2TBDMS,isomer #3C[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C2853.6Semi standard non polar33892256
Alanylhistidine,2TBDMS,isomer #3C[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C2550.8Standard non polar33892256
Alanylhistidine,2TBDMS,isomer #3C[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C3717.4Standard polar33892256
Alanylhistidine,2TBDMS,isomer #4C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2859.1Semi standard non polar33892256
Alanylhistidine,2TBDMS,isomer #4C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2810.6Standard non polar33892256
Alanylhistidine,2TBDMS,isomer #4C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3412.0Standard polar33892256
Alanylhistidine,2TBDMS,isomer #5C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2718.4Semi standard non polar33892256
Alanylhistidine,2TBDMS,isomer #5C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2719.6Standard non polar33892256
Alanylhistidine,2TBDMS,isomer #5C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C(C)(C)C3283.1Standard polar33892256
Alanylhistidine,2TBDMS,isomer #6C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O2903.7Semi standard non polar33892256
Alanylhistidine,2TBDMS,isomer #6C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O2663.7Standard non polar33892256
Alanylhistidine,2TBDMS,isomer #6C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O3401.6Standard polar33892256
Alanylhistidine,2TBDMS,isomer #7C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2809.7Semi standard non polar33892256
Alanylhistidine,2TBDMS,isomer #7C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2641.9Standard non polar33892256
Alanylhistidine,2TBDMS,isomer #7C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C3520.7Standard polar33892256
Alanylhistidine,3TBDMS,isomer #1C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3101.4Semi standard non polar33892256
Alanylhistidine,3TBDMS,isomer #1C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2937.9Standard non polar33892256
Alanylhistidine,3TBDMS,isomer #1C[C@@H](C(=O)N[C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3157.5Standard polar33892256
Alanylhistidine,3TBDMS,isomer #2C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2952.1Semi standard non polar33892256
Alanylhistidine,3TBDMS,isomer #2C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2867.6Standard non polar33892256
Alanylhistidine,3TBDMS,isomer #2C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3094.4Standard polar33892256
Alanylhistidine,3TBDMS,isomer #3C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C3091.0Semi standard non polar33892256
Alanylhistidine,3TBDMS,isomer #3C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C2850.7Standard non polar33892256
Alanylhistidine,3TBDMS,isomer #3C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C3191.1Standard polar33892256
Alanylhistidine,3TBDMS,isomer #4C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2999.9Semi standard non polar33892256
Alanylhistidine,3TBDMS,isomer #4C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2853.4Standard non polar33892256
Alanylhistidine,3TBDMS,isomer #4C[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3385.6Standard polar33892256
Alanylhistidine,3TBDMS,isomer #5C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3021.8Semi standard non polar33892256
Alanylhistidine,3TBDMS,isomer #5C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2994.6Standard non polar33892256
Alanylhistidine,3TBDMS,isomer #5C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3160.6Standard polar33892256
Alanylhistidine,3TBDMS,isomer #6C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3235.3Semi standard non polar33892256
Alanylhistidine,3TBDMS,isomer #6C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2956.4Standard non polar33892256
Alanylhistidine,3TBDMS,isomer #6C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3272.8Standard polar33892256
Alanylhistidine,3TBDMS,isomer #7C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C3074.9Semi standard non polar33892256
Alanylhistidine,3TBDMS,isomer #7C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2914.9Standard non polar33892256
Alanylhistidine,3TBDMS,isomer #7C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C3194.1Standard polar33892256
Alanylhistidine,4TBDMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3257.2Semi standard non polar33892256
Alanylhistidine,4TBDMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3135.6Standard non polar33892256
Alanylhistidine,4TBDMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=C[NH]C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2987.5Standard polar33892256
Alanylhistidine,4TBDMS,isomer #2C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3414.0Semi standard non polar33892256
Alanylhistidine,4TBDMS,isomer #2C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3139.1Standard non polar33892256
Alanylhistidine,4TBDMS,isomer #2C[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3139.7Standard polar33892256
Alanylhistidine,4TBDMS,isomer #3C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3258.7Semi standard non polar33892256
Alanylhistidine,4TBDMS,isomer #3C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3091.6Standard non polar33892256
Alanylhistidine,4TBDMS,isomer #3C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3097.1Standard polar33892256
Alanylhistidine,4TBDMS,isomer #4C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3376.5Semi standard non polar33892256
Alanylhistidine,4TBDMS,isomer #4C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3186.3Standard non polar33892256
Alanylhistidine,4TBDMS,isomer #4C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3141.5Standard polar33892256
Alanylhistidine,5TBDMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3575.3Semi standard non polar33892256
Alanylhistidine,5TBDMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3370.0Standard non polar33892256
Alanylhistidine,5TBDMS,isomer #1C[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3057.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alanylhistidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 10V, Positive-QTOFsplash10-056r-4390000000-79952bcbc9ced3c0a2082019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 20V, Positive-QTOFsplash10-0006-9300000000-f5b750e7134970fc2f962019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 40V, Positive-QTOFsplash10-052f-9400000000-3fa802e757722275f65c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 10V, Negative-QTOFsplash10-004i-0290000000-6c4a74535fd60f51ba5b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 20V, Negative-QTOFsplash10-0fa9-4930000000-a6b871c53bf3c10802582019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 40V, Negative-QTOFsplash10-00el-9400000000-96ee6aa9db8324b285da2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 10V, Positive-QTOFsplash10-004i-0290000000-87d68e5230e1353b5f722021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 20V, Positive-QTOFsplash10-03dr-1900000000-4b04aca6987c205034922021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 40V, Positive-QTOFsplash10-01po-9400000000-86a177a2fb8bb71bb59d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 10V, Negative-QTOFsplash10-004i-0190000000-4c3687ed3b16bcde3e562021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 20V, Negative-QTOFsplash10-00a6-9310000000-973141e5fb8a4618fa752021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylhistidine 40V, Negative-QTOFsplash10-066u-9400000000-5fe2bb76010ea05627d02021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal 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
FooDB IDFDB111748
KNApSAcK IDNot Available
Chemspider ID8013175
KEGG Compound IDNot Available
BioCyc IDCPD-13401
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9837455
PDB IDNot Available
ChEBI ID73771
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kuroda M, Harada T: Increase of gamma-glutamyl-beta-alanyl-histidine isopeptide in the macromolecular fraction of model chicken extract during heating and distribution in commercial chicken extracts. Poult Sci. 2002 Apr;81(4):590-4. [PubMed:11989761 ]
  2. Mastrolorenzo A, Scozzafava A, Supuran CT: 4-toluenesulfonylureido derivatives of amines, amino acids and dipeptides: a novel class of potential antitumor agents. Eur J Pharm Sci. 2000 Oct;11(4):325-32. [PubMed:11033076 ]
  3. Gorzsas A, Andersson I, Pettersson L: Speciation in aqueous vanadate-ligand and peroxovanadate-ligand systems. J Inorg Biochem. 2009 Apr;103(4):517-26. doi: 10.1016/j.jinorgbio.2008.12.006. Epub 2008 Dec 24. [PubMed:19162328 ]
  4. Brotman DN, Flancbaum L, Kang YH, Merrill GF, Fisher H: Positive inotropic effect of carcinine in the isolated perfused guinea pig heart. Crit Care Med. 1990 Mar;18(3):317-21. [PubMed:2302959 ]
  5. Shimizu M: Detection of the peptidyltransferase activity of a dipeptide, alanylhistidine, in the absence of ribosomes. J Biochem. 1996 May;119(5):832-4. [PubMed:8797080 ]
  6. Zhu X, Gallogly MM, Mieyal JJ, Anderson VE, Sayre LM: Covalent cross-linking of glutathione and carnosine to proteins by 4-oxo-2-nonenal. Chem Res Toxicol. 2009 Jun;22(6):1050-9. doi: 10.1021/tx9000144. [PubMed:19480392 ]
  7. Reeve VE, Bosnic M, Rozinova E: Carnosine (beta-alanylhistidine) protects from the suppression of contact hypersensitivity by ultraviolet B (280-320 nm) radiation or by cis urocanic acid. Immunology. 1993 Jan;78(1):99-104. [PubMed:8436408 ]
  8. Fitzpatrick JC, Fisher H, Flancbaum L: Effect of histamine antagonists on myocardial carcinine metabolism during compound 48/80-induced shock. J Surg Res. 1990 Oct;49(4):293-7. [PubMed:2214737 ]
  9. Tanaka Y, Kamei K, Otoguro K, Omura S: Heme-dependent radical generation: possible involvement in antimalarial action of non-peroxide microbial metabolites, nanaomycin A and radicicol. J Antibiot (Tokyo). 1999 Oct;52(10):880-8. [PubMed:10604757 ]
  10. Baslow MH: A novel key-lock mechanism for inactivating amino acid neurotransmitters during transit across extracellular space. Amino Acids. 2010 Jan;38(1):51-5. doi: 10.1007/s00726-009-0232-0. Epub 2009 Jan 17. [PubMed:19151913 ]
  11. Brasun J, Matera-Witkiewicz A, Oldziej S, Pratesi A, Ginanneschi M, Messori L: Impact of ring size on the copper(II) coordination abilities of cyclic tetrapeptides. J Inorg Biochem. 2009 May;103(5):813-7. doi: 10.1016/j.jinorgbio.2009.02.003. Epub 2009 Feb 23. [PubMed:19329186 ]
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