Cannabis Compound Database: Showing Compound Card for Aminoadipic acid (CDB005134)

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Record Information

Version

1.0

Created at

2020-04-17 19:12:45 UTC

Updated at

2022-12-13 23:36:24 UTC

CannabisDB ID

CDB005134

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Aminoadipic acid

Description

Aminoadipic acid, also known as a-aminoadipate or Aad, 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). Aminoadipic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Aminoadipic acid exists in all eukaryotes, ranging from yeast to humans. Within humans, aminoadipic acid participates in a number of enzymatic reactions. In particular, aminoadipic acid can be biosynthesized from allysine; which is mediated by the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In addition, aminoadipic acid and oxoglutaric acid can be converted into oxoadipic acid and L-glutamic acid; which is catalyzed by the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In humans, aminoadipic acid is involved in the metabolic disorder called 2-aminoadipic 2-oxoadipic aciduria. Outside of the human body, Aminoadipic acid is found, on average, in the highest concentration within a few different foods, such as wheats, milk (cow), and ryes and in a lower concentration in dills, garden onions, and white cabbages. Aminoadipic acid has also been detected, but not quantified in, several different foods, such as barley, cow milks, cow milks, cow milks, and cow milks. This could make aminoadipic acid a potential biomarker for the consumption of these foods. Aminoadipic acid is a potentially toxic compound. Aminoadipic acid, with regard to humans, has been found to be associated with several diseases such as alpha-aminoadipic and alpha-ketoadipic aciduria, colorectal cancer, metastatic melanoma, and eosinophilic esophagitis; aminoadipic acid has also been linked to the inborn metabolic disorder 2-ketoadipic acidemia. An alpha-amino acid that is adipic acid bearing a single amino substituent at position 2. Aminoadipic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

161.16

Monoisotopic Molecular Weight

161.0688

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 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Aminoadipic acid, non-derivatized, GC-MS Spectrum	splash10-02di-0950000000-ec4fd991a53a8b6bc6ae	Spectrum
GC-MS	Aminoadipic acid, non-derivatized, GC-MS Spectrum	splash10-02di-0950000000-ec4fd991a53a8b6bc6ae	Spectrum
Predicted GC-MS	Aminoadipic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00r6-9300000000-9ef33042820e032c1af3	Spectrum
Predicted GC-MS	Aminoadipic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00ri-9620000000-052fe671da5a64787657	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03xv-2900000000-58b4f0b3e06cbb7abb90	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4j-9000000000-cc9c0c03f7c3890b531c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-7b74167f01c922da9ef7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-9400000000-71832a0d1e49341749a7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 20V, negative	splash10-014l-2900000000-08df6df87d0bea6dce31	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0006-0900000000-99e7d8729f7099c6e9ea	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-03di-0900000000-f542aa2756da9aa3ecb6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-03di-0900000000-3133117467ce925161cb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-03di-0900000000-9e5f27d91fd799c059d6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-03xu-0900000000-b801b3a34049e54a2915	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-014i-1900000000-2ef33d8640c4e5788618	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-014i-1900000000-281e4277990becc84832	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-014i-2900000000-a56c711aeb57c767fed8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0006-0900000000-862ae5fa10820c14bdf1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-006t-9400000000-e007d0e2c3cec7f1a02c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0002-9000000000-4755db14192225e1eebf	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kg-2900000000-3e45ac769d3b229221a3	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ba-9600000000-c51318834cc371625d46	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fu-9000000000-edbc970f12ea186bcf06	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-0f7002659f604cc69395	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-4900000000-bf42ddc971a2a05516a2	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9100000000-1979c27463bab7d33d58	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-7913a597d0c94eebe02d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dj-9100000000-523aa25ee55f888299e1	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-0dcf3a7ca5d4e20885ee	2021-10-21	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.103 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.0522 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.0933 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.0301 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.111 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0377 mg/g dry wt	David S. Wishart,...	details