ChemFOnt: Showing chemical card for N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid (CFc000234550)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 02:05:31 UTC

Chemfont ID

CFc000234550

Molecule Identification

Common Name

N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid

Definition

nicotianamine 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). nicotianamine is a very strong basic compound (based on its pKa). Biochemically, it is synthesized by the enzyme nicotianamine synthase, which uses three molecules of S-adenosylmethionine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid	ChEBI
N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylate	Generator
Nicotianamine	MeSH

Chemical Formula

C₁₂H₂₁N₃O₆

Average Molecular Weight

303.315

Monoisotopic Molecular Weight

303.143035408

IUPAC Name

1-{3-[(3-amino-3-carboxypropyl)amino]-3-carboxypropyl}azetidine-2-carboxylic acid

Traditional Name

nicotianamine

CAS Registry Number

34441-14-0

SMILES

NC(CCNC(CCN1CCC1C(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=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)

InChI Key

KRGPXXHMOXVMMM-UHFFFAOYSA-N

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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Tricarboxylic acid or derivatives
Amino fatty acid
Azetidinecarboxylic acid
Fatty acyl
Azetidine
Amino acid
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Primary amine
Amine
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

mugineic acids (CHEBI:25520 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	14.2 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-9.3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.05	ChemAxon
pKa (Strongest Basic)	10.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.19 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	70.78 m³·mol⁻¹	ChemAxon
Polarizability	30.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nicotianamine

METLIN ID

Not Available

PubChem Compound

3450503

PDB ID

Not Available

ChEBI ID

25520

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid (CFc000234550)

MOL for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)

3D MOL for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)

3D SDF for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)

3D-SDF for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)

PDB for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)

3D PDB for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)

SMILES for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)

INCHI for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)

Structure for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)

3D Structure for CFc000234550 (N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid)