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Record Information
Version2.0
Created at2022-09-08 02:14:48 UTC
Updated at2022-09-08 02:14:49 UTC
NP-MRD IDNP0260167
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4r)-4-(2-carboxyethyl)-3h,5h,6h,7h-imidazo[4,5-c]pyridine-4,6-dicarboxylic acid
DescriptionMikimopine, also known as cucumopine, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). (4r)-4-(2-carboxyethyl)-3h,5h,6h,7h-imidazo[4,5-c]pyridine-4,6-dicarboxylic acid is found in Nicotiana tabacum. (4r)-4-(2-carboxyethyl)-3h,5h,6h,7h-imidazo[4,5-c]pyridine-4,6-dicarboxylic acid was first documented in 2004 (PMID: 15332121). Based on a literature review a small amount of articles have been published on Mikimopine (PMID: 25420106) (PMID: 25219519) (PMID: 25157257) (PMID: 22686249).
Structure
Thumb
Synonyms
ValueSource
Cucumopine, (4R-cis)-isomerMeSH
CucumopineMeSH
Chemical FormulaC11H13N3O6
Average Mass283.2400 Da
Monoisotopic Mass283.08044 Da
IUPAC Name(4R)-4-(2-carboxyethyl)-3H,4H,5H,6H,7H-imidazo[4,5-c]pyridine-4,6-dicarboxylic acid
Traditional Name(4R)-4-(2-carboxyethyl)-3H,5H,6H,7H-imidazo[4,5-c]pyridine-4,6-dicarboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC[C@]1(NC(CC2=C1NC=N2)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C11H13N3O6/c15-7(16)1-2-11(10(19)20)8-5(12-4-13-8)3-6(14-11)9(17)18/h4,6,14H,1-3H2,(H,12,13)(H,15,16)(H,17,18)(H,19,20)/t6?,11-/m1/s1
InChI KeyXGCZNSAJOHDWQS-MGAKOFKPSA-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
Nicotiana tabacumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Imidazopiperidine
  • Imidazopyridine
  • Tricarboxylic acid or derivatives
  • Aralkylamine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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-4.6ChemAxon
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)7.07ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area152.61 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.03 m³·mol⁻¹ChemAxon
Polarizability25.84 ųChemAxon
Number of Rings2ChemAxon
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 ID10143387
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11969982
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kovacova V, Zluvova J, Janousek B, Talianova M, Vyskot B: The evolutionary fate of the horizontally transferred agrobacterial mikimopine synthase gene in the genera Nicotiana and Linaria. PLoS One. 2014 Nov 24;9(11):e113872. doi: 10.1371/journal.pone.0113872. eCollection 2014. [PubMed:25420106 ]
  2. Chen K, Dorlhac de Borne F, Szegedi E, Otten L: Deep sequencing of the ancestral tobacco species Nicotiana tomentosiformis reveals multiple T-DNA inserts and a complex evolutionary history of natural transformation in the genus Nicotiana. Plant J. 2014 Nov;80(4):669-82. doi: 10.1111/tpj.12661. Epub 2014 Oct 14. [PubMed:25219519 ]
  3. Matveeva TV, Lutova LA: Horizontal gene transfer from Agrobacterium to plants. Front Plant Sci. 2014 Aug 11;5:326. doi: 10.3389/fpls.2014.00326. eCollection 2014. [PubMed:25157257 ]
  4. Kiyokawa K, Yamamoto S, Sato Y, Momota N, Tanaka K, Moriguchi K, Suzuki K: Yeast transformation mediated by Agrobacterium strains harboring an Ri plasmid: comparative study between GALLS of an Ri plasmid and virE of a Ti plasmid. Genes Cells. 2012 Jul;17(7):597-610. doi: 10.1111/j.1365-2443.2012.01612.x. Epub 2012 Jun 12. [PubMed:22686249 ]
  5. Moghaieb RE, Saneoka H, Fujita K: Shoot regeneration from GUS-transformed tomato (Lycopersicon esculentum) hairy root. Cell Mol Biol Lett. 2004;9(3):439-49. [PubMed:15332121 ]
  6. LOTUS database [Link]