Livestock Metabolome Database: Showing metabocard for Sebacic acid (LMDB00246)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:35 UTC

Update Date

2016-07-20 21:03:46 UTC

Lmdb

LMDB00246

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Sebacic acid

Description

Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD) or glutaric aciduria type II (GAII) are a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. Sebacic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition. Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Sebacic Acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. It is used in the synthesis of polyamide and alkyd resins. It is also used as an intermediate for aromatics, antiseptics and painting materials. (PMID: 10556649 , 1738216 , 8442769 , 12706375 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,10-Decanedioic acid	ChEBI
1,8-Dicarboxyoctane	ChEBI
Decanedioic acid	ChEBI
Sebacinsaeure	ChEBI
1,10-Decanedioate	Generator
Decanedioate	Generator
Sebacate	Generator
1,8-Octanedicarboxylate	HMDB
1,8-Octanedicarboxylic acid	HMDB
4,7-Dioxosebacic acid	HMDB
4-Oxodecanedioate	HMDB
4-Oxodecanedioic acid	HMDB
Acide sebacique	HMDB
Decanedicarboxylic acid	HMDB
Dicarboxylic acid C10	HMDB
Ipomic acid	HMDB
N-Decanedioate	HMDB
N-Decanedioic acid	HMDB
Sebacic acids	HMDB
Sebacinsaure	HMDB
Seracic acid	HMDB
Sebacic acid, aluminum salt	HMDB
Sebacic acid, monocadmium salt	HMDB
Sebacic acid, sodium salt	HMDB

Chemical Formula

C₁₀H₁₈O₄

Average Molecular Weight

202.2475

Monoisotopic Molecular Weight

202.120509064

IUPAC Name

decanedioic acid

Traditional Name

sebacic acid

CAS Registry Number

111-20-6

SMILES

OC(=O)CCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)

InChI Key

CXMXRPHRNRROMY-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:41865 )
Dicarboxylic acids (C08277 )
Dicarboxylic acids (LMFA01170006 )

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	1.93	ALOGPS
logP	2.27	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.72	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	9	ChemAxon
Refractivity	51.14 m³·mol⁻¹	ChemAxon
Polarizability	22.61 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) (2 TMS)	splash10-00mk-2910000000-944d83241331f8be19a6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00mk-1910000000-2e3fc1189a96874a25c9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00fr-9400000000-d288a779699c505fde08	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00pj-3910000000-87feed2c593dbff7fae8	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-2910000000-944d83241331f8be19a6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-1910000000-2e3fc1189a96874a25c9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00fr-9400000000-d288a779699c505fde08	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00pj-3910000000-87feed2c593dbff7fae8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9600000000-0d93a938bd873800d5e0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9750000000-c51f62deffa53727f438	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)	splash10-0udi-0290000000-cd204cf662cb75a52f8c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0540-5910000000-d9df3022a95972158b37	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0ue9-9660000000-49a78126c0d15f6e3eb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0090000000-841b953970b4cd52f8be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0uei-0950000000-001fe11fe26a2d644897	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-0900000000-83a69e4c3ab60df51781	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-08i9-7900000000-951787b9bed084d77a6b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-057i-9000000000-83b9d67dcdf5f385ab57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0f80-0950000000-7fec916790f882e8630a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-841b953970b4cd52f8be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0uei-0950000000-001fe11fe26a2d644897	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-83a69e4c3ab60df51781	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-08i9-7900000000-951787b9bed084d77a6b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-057i-9000000000-83b9d67dcdf5f385ab57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0019-0900000000-e9711749ce4f183c8c63	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f80-0950000000-e264d8b786405e562fd4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-007d-8900000000-fb7880caeb9e996f8bba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0uei-0960000000-b0edb62684a8bf743208	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0f80-0930000000-e6d1038fa517b1259227	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0970000000-b21ac000bbddcd19753b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k9l-2910000000-aad49769e8652ff2ea40	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06rw-9200000000-bab98f63e58992b52316	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0290000000-f600fa6f22d1c40d97d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-2790000000-3f24f2c725d420658a66	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-1aa6408615ab7e415691	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0532-9200000000-34e843efdffcce316afd	Spectrum
1D NMR	1H 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

Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details

External Links

DrugBank ID

DB07645

HMDB ID

HMDB0000792

FooDB ID

FDB022247

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001202

BiGG ID

Not Available

BioCyc ID

CPD-3623

METLIN ID

4240

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Capristo E, Mingrone G, De Gaetano A, Addolorato G, Greco AV, Gasbarrini G: A new HPLC method for the direct analysis of triglycerides of dicarboxylic acids in biological samples. Clin Chim Acta. 1999 Nov;289(1-2):11-21. [10556649 ]
Mingrone G, Tacchino RM, Castagneto M, Finotti E, Greco AV: Use of even-numbered carbon atom dicarboxylic salts in parenteral nutrition as fuel substrate. JPEN J Parenter Enteral Nutr. 1992 Jan-Feb;16(1):32-8. [1738216 ]
Bertuzzi A, Finotti E, Mingrone G, Greco AV: Sebacic acid binding to human plasma albumin. Biochem Pharmacol. 1993 Feb 9;45(3):697-702. [8442769 ]
Curcoy A, Olsen RK, Ribes A, Trenchs V, Vilaseca MA, Campistol J, Osorio JH, Andresen BS, Gregersen N: Late-onset form of beta-electron transfer flavoprotein deficiency. Mol Genet Metab. 2003 Apr;78(4):247-9. [12706375 ]

Showing metabocard for Sebacic acid (LMDB00246)

Structure for LMDB00246 (Sebacic acid)