ChemFOnt: Showing chemical card for alpha-Amino adipic acid (CFc000334404)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:15:29 UTC

Chemfont ID

CFc000334404

Molecule Identification

Common Name

alpha-Amino adipic acid

Definition

Aminoadipic acid, also known as A-aminoadipate or dl-2-aminohexanedioic acid, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Thus, aminoadipic acid is considered to be a fatty acid lipid molecule. Aminoadipic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Aminoadipic acid can be found in common sage and spearmint, which makes aminoadipic acid a potential biomarker for the consumption of these food products. Aminoadipic acid can be found primarily in blood, feces, saliva, and urine, as well as in human prostate tissue. In humans, aminoadipic acid is involved in a couple of metabolic pathways, which include lysine degradation and pyridoxine dependency with seizures. Aminoadipic acid is also involved in several metabolic disorders, some of which include glutaric aciduria type I, saccharopinuria/hyperlysinemia II, 2-aminoadipic 2-oxoadipic aciduria, and hyperlysinemia I, familial. Moreover, aminoadipic acid is found to be associated with alpha-aminoadipic aciduria, schizophrenia, and 2-Ketoadipic acidemia. Aminoadipic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Chronically high levels of aminoadipic acid are associated with at least 2 inborn errors of metabolism including: : 2-aminoadipic and 2-oxoadipic aciduria (T3DB).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+/-)-2-aminoadipic acid	ChEBI
Aad	ChEBI
alpha-Aminoadipic acid	ChEBI
DL-2-Aminoadipic acid	ChEBI
DL-2-Aminohexanedioic acid	ChEBI
DL-alpha-Aminoadipic acid	ChEBI
(+/-)-2-aminoadipate	Generator
a-Aminoadipate	Generator
a-Aminoadipic acid	Generator
alpha-Aminoadipate	Generator
Α-aminoadipate	Generator
Α-aminoadipic acid	Generator
DL-2-Aminoadipate	Generator
DL-2-Aminohexanedioate	Generator
DL-a-Aminoadipate	Generator
DL-a-Aminoadipic acid	Generator
DL-alpha-Aminoadipate	Generator
DL-Α-aminoadipate	Generator
DL-Α-aminoadipic acid	Generator
Aminoadipate	Generator
2 Aminoadipic acid	MeSH
2 Aminohexanedioic acid	MeSH
2-Aminoadipic acid	MeSH
Acid, 2 aminoadipic	MeSH
Acid, 2-aminoadipic	MeSH
Acid, 2-aminohexanedioic	MeSH
Acid, alpha-aminoadipic	MeSH
Aminoadipic acid, 2	MeSH
alpha Aminoadipic acid	MeSH
2-Aminoadipate	HMDB
alpha-amino-Adipic acid	HMDB
L-2-Aminoadipate	HMDB
L-2-Aminoadipic acid	HMDB
L-2-Aminohexanedioate	HMDB
L-2-Aminohexanedioic acid	HMDB
L-alpha-Aminoadipate	HMDB
L-alpha-Aminoadipic acid	HMDB
2-Aminohexanedioic acid	MeSH, HMDB

Chemical Formula

C₆H₁₁NO₄

Average Molecular Weight

161.1558

Monoisotopic Molecular Weight

161.068807845

IUPAC Name

2-aminohexanedioic acid

Traditional Name

aminoadipic acid

CAS Registry Number

542-32-5

SMILES

NC(CCCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)

InChI Key

OYIFNHCXNCRBQI-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
Medium-chain fatty acid
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

amino dicarboxylic acid (CHEBI:37024 )
non-proteinogenic alpha-amino acid (CHEBI:37024 )
Dicarboxylic acids (LMFA01170098 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0000510)

Food

Pulse

Pea

Common pea (FooDB: FOOD00141)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	32.7 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-2.8	ChemAxon
logS	-0.69	ALOGPS
pKa (Strongest Acidic)	2.01	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	35.89 m³·mol⁻¹	ChemAxon
Polarizability	15.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon