carnosine   Click here for help

GtoPdb Ligand ID: 4559

Synonyms: β-alanyl-L-histidine | L-carnosine
PDB Ligand
Compound class: Metabolite

carnosine is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 121.1
Molecular weight 226.11
XLogP -3.79
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES NCCC(=O)NC(C(=O)O)Cc1nc[nH]c1
Isomeric SMILES NCCC(=O)N[C@H](C(=O)O)Cc1nc[nH]c1
InChI InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1
InChI Key CQOVPNPJLQNMDC-ZETCQYMHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Bhardwaj RK, Herrera-Ruiz D, Eltoukhy N, Saad M, Knipp GT. (2006)
The functional evaluation of human peptide/histidine transporter 1 (hPHT1) in transiently transfected COS-7 cells.
Eur J Pharm Sci, 27 (5): 533-42. [PMID:16289537]
2. Oppermann H, Heinrich M, Birkemeyer C, Meixensberger J, Gaunitz F. (2019)
The proton-coupled oligopeptide transporters PEPT2, PHT1 and PHT2 mediate the uptake of carnosine in glioblastoma cells.
Amino Acids, 51 (7): 999-1008. [PMID:31073693]
3. Sakata K, Yamashita T, Maeda M, Moriyama Y, Shimada S, Tohyama M. (2001)
Cloning of a lymphatic peptide/histidine transporter.
Biochem J, 356 (Pt 1): 53-60. [PMID:11336635]
4. Yamashita T, Shimada S, Guo W, Sato K, Kohmura E, Hayakawa T, Takagi T, Tohyama M. (1997)
Cloning and functional expression of a brain peptide/histidine transporter.
J Biol Chem, 272 (15): 10205-11. [PMID:9092568]
5. Yee SW, Buitrago D, Stecula A, Ngo HX, Chien HC, Zou L, Koleske ML, Giacomini KM. (2020)
Deorphaning a solute carrier 22 family member, SLC22A15, through functional genomic studies.
FASEB J, 34 (12): 15734-15752. [PMID:33124720]