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Nicotianamine (FDB004236)

Record Information
Version1.0
Creation date2010-04-08 22:06:09 UTC
Update date2019-11-26 02:59:54 UTC
Primary IDFDB004236
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNicotianamine
DescriptionNicotianamine is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Nicotianamine is soluble (in water) and a moderately acidic compound (based on its pKa). Nicotianamine can be found in a number of food items such as common beet, oat, sweet cherry, and italian sweet red pepper, which makes nicotianamine a potential biomarker for the consumption of these food products. Nicotianamine is a metal-chelating molecule ubiquitous in higher plants. Biochemically, it is synthesized by the enzyme nicotianamine synthase, which uses three molecules of S-adenosylmethionine .
CAS Number34441-14-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.2 g/LALOGPS
logP-3.1ALOGPS
logP-9.3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.05ChemAxon
pKa (Strongest Basic)10.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.19 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity70.78 m³·mol⁻¹ChemAxon
Polarizability29.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H21N3O6
IUPAC name(2S)-1-[(3S)-3-{[(3S)-3-amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid
InChI IdentifierInChI=1S/C12H21N3O6/c13-7(10(16)17)1-4-14-8(11(18)19)2-5-15-6-3-9(15)12(20)21/h7-9,14H,1-6,13H2,(H,16,17)(H,18,19)(H,20,21)/t7-,8-,9-/m0/s1
InChI KeyKRGPXXHMOXVMMM-CIUDSAMLSA-N
Isomeric SMILESN[C@@H](CCN[C@@H](CCN1CC[C@H]1C(O)=O)C(O)=O)C(O)=O
Average Molecular Weight303.3116
Monoisotopic Molecular Weight303.143035419
Classification
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Azetidinecarboxylic acid
  • Fatty acyl
  • Azetidine
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSNicotianamine, 4 TMS, GC-MS Spectrumsplash10-000i-1951000000-8d5613fbdf3654bc2125Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0191000000-515d89288f4f60ece5192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-2490000000-2c02458352c72287fe472016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-6930000000-ce55b78c9ce426cdb8312016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-3094000000-cee38fc4593e1b490b4f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0r00-4291000000-8575a159791b0750d6122016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9820000000-b671a7f5ad24cf059ed72016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC05324
Pubchem Compound ID9882882
Pubchem Substance IDNot Available
ChEBI ID17721
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNICOTIANAMINE
BIGG IDNot Available
KNApSAcK IDC00016287
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).