Livestock Metabolome Database: Showing metabocard for Adipic acid (LMDB00156)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:35 UTC

Update Date

2016-07-20 21:03:30 UTC

Lmdb

LMDB00156

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Adipic acid

Description

Adipic acid is an important inudstrial dicarboxylic acid with about 2.5 billion kilograms produced per year. It is used mainly in the production of nylon. It occurs relatively rarely in nature. It has a tart taste and is also used as an additive and gelling agent in jello or gelatins. It is also used in some calcium carbonate antacids to make them tart. Adipic acid has also been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. Adipic acid in the urine and in the blood is typically exogenous in origin and is a good biomarker of jello consumption. In fact, a condition known as adipic aciduria is actually an artifact of jello consumption (PMID: 1779643 ). However, certain disorders (such as diabetes and glutaric aciduria type I.) can lead to elevated levels of adipic acid snd other dicarboxcylic acids (such as suberic acid) in urine (PMID: 17520433 ; PMID: 6778884 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-Butanedicarboxylic acid	ChEBI
1,6-Hexanedioic acid	ChEBI
Adipinic acid	ChEBI
Adipinsaeure	ChEBI
e 355	ChEBI
e-355	ChEBI
e355	ChEBI
INS no. 355	ChEBI
Hexanedioate	Kegg
Hexan-1,6-dicarboxylate	Kegg
1,4-Butanedicarboxylate	Generator
1,6-Hexanedioate	Generator
Adipinate	Generator
Hexanedioic acid	Generator
Hexan-1,6-dicarboxylic acid	Generator
Adipate	Generator
Acifloctin	HMDB
Acinetten	HMDB
Adi-pure	HMDB
Adilactetten	HMDB
Kyselina adipova	HMDB
Molten adipate	HMDB
Molten adipic acid	HMDB
Adipic acid, calcium salt	HMDB
Adipic acid, disodium salt	HMDB
Sodium adipate	HMDB
Adipic acid, cu(+2) salt	HMDB
Adipic acid, cu(+2) salt (1:1)	HMDB
Adipic acid, diammonium salt	HMDB
Adipic acid, sodium salt	HMDB
Adipic acid, cu salt	HMDB
Adipic acid, potassium salt	HMDB
Ammonium adipate	HMDB
Magnesium adipate	HMDB
Adipic acid, MG salt (1:1)	HMDB
Adipic acid, monoammonium salt	HMDB
Adipic acid, nickel salt	HMDB
Diammonium adipate	HMDB
Adipic acid	KEGG

Chemical Formula

C₆H₁₀O₄

Average Molecular Weight

146.1412

Monoisotopic Molecular Weight

146.057908808

IUPAC Name

hexanedioic acid

Traditional Name

adipic acid

CAS Registry Number

124-04-9

SMILES

OC(=O)CCCCC(O)=O

InChI Identifier

InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)

InChI Key

WNLRTRBMVRJNCN-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,omega-dicarboxylic acid (CHEBI:30832 )
Dicarboxylic acids (LMFA01170048 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

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	0.13	ALOGPS
logP	0.49	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	32.74 m³·mol⁻¹	ChemAxon
Polarizability	14.24 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-03dj-0900000000-5378ec232b7bc8c84368	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-03di-2920000000-a4bb0f67851a49bcd19c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6u-9000000000-36d8bc2f7d1a77a7b466	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dm-0910000000-596aa8217b629d682b81	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03dj-0900000000-5378ec232b7bc8c84368	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03di-2920000000-a4bb0f67851a49bcd19c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03dj-0900000000-60ba84e1d479d88e3fac	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-9300000000-c0da1d9e52f67b1d7dbc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dr-9620000000-9525dd4ed0f987b19a68	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000x-3900000000-1c5a6a5287f8fd7736f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-001i-9100000000-3e9496a6da881edd91e0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0uea-9500000000-edb5529010e4b88414c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0a6u-9000000000-36d8bc2f7d1a77a7b466	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-a1852cfc66b4feae9b18	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0ue9-6900000000-90e783cc3522f0ce7880	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-9200000000-b5a64d560d8bc62d8d51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001i-9000000000-a96d5ee9551b944e4db8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001i-9000000000-2e61b7d2a4dbc9867123	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-a1852cfc66b4feae9b18	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0ue9-6900000000-90e783cc3522f0ce7880	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9200000000-b5a64d560d8bc62d8d51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-a96d5ee9551b944e4db8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-2e61b7d2a4dbc9867123	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-2900000000-983aa19fb3183a9bc5ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ue9-8900000000-a976da84fb798bd80a34	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0n33-9100000000-8ed018879ca3f86cd379	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9300000000-c6cf63d45cff0205c31a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9200000000-9d33c5f6441e75071938	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0900000000-ece39ae1f752cf2970f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fba-5900000000-682fc79230e6f03bacfb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-66b61bf2c65c15bb7fed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-ec5d2c95f1dac5349608	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-2900000000-27613c7de7a721350bb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-78804e4122c63b62ca5b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f6x-9200000000-988f76bb42297a8d9d3b	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000448

FooDB ID

FDB008309

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001178

BiGG ID

Not Available

BioCyc ID

ADIPATE

METLIN ID

115

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB02973

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Glick N, Fischer M: Adipic aciduria, a dietary artefact. J Inherit Metab Dis. 1991;14(5):849-50. [1779643 ]
Sonmez G, Mutlu H, Ozturk E, Sildiroglu HO, Keskin AT, Basekim CC, Kizilkaya E: Magnetic resonance imaging findings of adult-onset glutaric aciduria type I. Acta Radiol. 2007 Jun;48(5):557-9. [17520433 ]
Liebich HM, Pickert A, Stierle U, Woll J: Gas chromatography-mass spectrometry of saturated and unsaturated dicarboxylic acids in urine. J Chromatogr. 1980 Oct 31;199:181-9. [6778884 ]

Showing metabocard for Adipic acid (LMDB00156)

Structure for LMDB00156 (Adipic acid)