Np mrd loader

Record Information
Version2.0
Created at2022-09-02 02:07:18 UTC
Updated at2022-09-02 02:07:18 UTC
NP-MRD IDNP0146680
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-1-(2-{[(2s)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid
DescriptionAla-Gly-Pro, also known as a-g-p or L-ala-gly-L-pro, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Ala-Gly-Pro 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. (2s)-1-(2-{[(2s)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid is found in Trypanosoma brucei. (2s)-1-(2-{[(2s)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid was first documented in 2020 (PMID: 33071314). Based on a literature review a small amount of articles have been published on Ala-Gly-Pro (PMID: 35662307) (PMID: 33825882) (PMID: 33822356) (PMID: 33496711).
Structure
Thumb
Synonyms
ValueSource
a-g-pChEBI
AGPChEBI
L-Ala-gly-L-proChEBI
Chemical FormulaC10H17N3O4
Average Mass243.2630 Da
Monoisotopic Mass243.12191 Da
IUPAC Name(2S)-1-(2-{[(2S)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid
Traditional Name(2S)-1-(2-{[(2S)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@H](N)C(O)=NCC(=O)N1CCC[C@H]1C(O)=O
InChI Identifier
InChI=1S/C10H17N3O4/c1-6(11)9(15)12-5-8(14)13-4-2-3-7(13)10(16)17/h6-7H,2-5,11H2,1H3,(H,12,15)(H,16,17)/t6-,7-/m0/s1
InChI KeyMQIGTEQXYCRLGK-BQBZGAKWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alanine or derivatives
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxylic acid salt
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic zwitterion
  • Primary aliphatic amine
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP-2.6ALOGPS
logP-3.7ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
pKa (Strongest Basic)9.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.81 m³·mol⁻¹ChemAxon
Polarizability24.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28477326
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound51389803
PDB IDNot Available
ChEBI ID73349
Good Scents IDNot Available
References
General References
  1. Sun L, Li M, Zhang S, Bao Z, Lin S: Mechanism of Ser-Ala-Gly-Pro-Ala-Phe treatment with a pulsed electric field to improve ethanol-induced gastric mucosa injury in mice. Food Funct. 2022 Jun 20;13(12):6716-6725. doi: 10.1039/d2fo00567k. [PubMed:35662307 ]
  2. Choudhury D, Biswas S: Structure-guided protein engineering of human cathepsin L for efficient collagenolytic activity. Protein Eng Des Sel. 2021 Feb 15;34:gzab005. doi: 10.1093/protein/gzab005. [PubMed:33825882 ]
  3. Xie Z, Wang X, Yu S, He M, Yu S, Xiao H, Song Y: Antioxidant and functional properties of cowhide collagen peptides. J Food Sci. 2021 May;86(5):1802-1818. doi: 10.1111/1750-3841.15666. Epub 2021 Apr 6. [PubMed:33822356 ]
  4. Shi J, Zhou X, Zhao Y, Tang X, Feng L, Wang B, Chen J: The three-spot seahorse-derived peptide PAGPRGPA attenuates ethanol-induced oxidative stress in LO2 cells through MAPKs, the Keap1/Nrf2 signalling pathway and amino acid metabolism. Food Funct. 2021 Mar 1;12(4):1672-1687. doi: 10.1039/d0fo02457k. [PubMed:33496711 ]
  5. Shi J, Su RQ, Zhang WT, Chen J: Purification and the secondary structure of a novel angiotensin I-converting enzyme (ACE) inhibitory peptide from the alcalase hydrolysate of seahorse protein. J Food Sci Technol. 2020 Nov;57(11):3927-3934. doi: 10.1007/s13197-020-04427-0. Epub 2020 Apr 15. [PubMed:33071314 ]
  6. LOTUS database [Link]