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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:29 UTC
HMDB IDHMDB00893
Secondary Accession Numbers
  • HMDB00837
Metabolite Identification
Common NameSuberic acid
DescriptionSuberic acid, also octanedioic acid, is a dicarboxylic acid, with formula C6H12(COOH)2. It is present in the urine of patients with Fatty Acid Oxidation Disorders (PMID 10404733 ). A metabolic breakdown product derived from oleic acid. Elevated levels of this unstaruated dicarboxylic acid are found in individuals with dicarboxylic acid and medium-chain acyl-CoA dehydrogenase deficiency (MCAD).
Structure
Thumb
Synonyms
ValueSource
1,6-DicarboxyhexaneChEBI
1,6-Hexanedicarboxylic acidChEBI
1,8-Octanedioic acidChEBI
Cork acidChEBI
Hexamethylenedicarboxylic acidChEBI
KorksaeureChEBI
Octane-1,8-dioic acidChEBI
Octanedioic acidChEBI
OktandisaeureChEBI
SuberinsaeureChEBI
SuberateGenerator
1,6-HexanedicarboxylateGenerator
1,8-OctanedioateGenerator
HexamethylenedicarboxylateGenerator
Octane-1,8-dioateGenerator
OctanedioateGenerator
Chemical FormulaC8H14O4
Average Molecular Weight174.1944
Monoisotopic Molecular Weight174.089208936
IUPAC Nameoctanedioic acid
Traditional Namesuberic acid
CAS Registry Number505-48-6
SMILES
OC(=O)CCCCCCC(O)=O
InChI Identifier
InChI=1S/C8H14O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1-6H2,(H,9,10)(H,11,12)
InChI KeyInChIKey=TYFQFVWCELRYAO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.9 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.8 mg/mLALOGPS
logP1ALOGPS
logP1.38ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.15ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity41.94 m3·mol-1ChemAxon
Polarizability18.41 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00kk-1910000000-952e95dc54b5db1c622bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00kr-4910000000-5746b8e489013c10f927View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-0900000000-06eceea912f97922f307View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-053r-9400000000-89400a660cc11e2dbf37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-053r-9200000000-fd72cf0bb8c1688e773eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-066u-9000000000-53eb5eaccee7a26c26c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-844f655c35c880c5f7ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-0900000000-a817a3858303459fad6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03e9-5900000000-5cd959b0437224a4617fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-053r-9200000000-36bb7dd756513f3371f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-003r-9000000000-060ff759568c0e7409a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0pb9-0900000000-d3f20c39439fdb1997c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-052b-9800000000-3c750dfd59f5f942ad1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0pc0-9600000000-ac31ff4a1eb241fe7a55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a5i-9100000000-f235866b0941a9c8e495View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9300000000-1abec6742a0a70596a3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0900000000-0ce1109135b91db83e1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-4900000000-497b35b2ed425bc2c1e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067l-9100000000-bb0a668a71757557492dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-a2ea6904052f6faa706bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-1900000000-0632d4666e090256224dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-da94304d9610cbd18197View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.6 (0.0-10.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.7 +/- 1.7 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified23.307 +/- 19.00176 uMNot SpecifiedNot Specified
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified6.158 +/- 5.683 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified1.325 +/- 0.885 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified4.34 +/- 5.99 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified2.00 +/- 1.3 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified16.85 +/- 2.73 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified9.0 (4.0-20.0) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified10.317 +/- 3.66 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.5 (0.0-2.9) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified6.6 +/- 5.5 umol/mmol creatinineAdolescent (13-18 years old)FemaleNormal details
UrineDetected and Quantified<13 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0-0.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified7.0 (3.4-14.0) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified6.7 (6.3-10.6) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified1.7 (0.9-4.9) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.8 (0.6-7.0) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.6 (0.5-6.9) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.6 (0.9-2.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.2 (0.5-1.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified3.281 +/- 2.82 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified7.288 +/- 10.275 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified34.00 +/- 7.00 umol/mmol creatinineChildren (1-13 years old)BothMalnutrition (type kwashiorkor and marasmus) details
UrineDetected and Quantified14.956 +/- 18.528 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified9.5 +/- 3.9 umol/mmol creatinineAdolescent (13-18 years old)FemaleAnorexia nervosa details
UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdult (>18 years old)BothGlutaric aciduria II details
UrineDetected and Quantified100.00 (0.00-200.00) umol/mmol creatinineChildren (1-13 years old)BothGlutaric Aciduria II details
UrineDetected and Quantified11.00 (0.00-22.00) umol/mmol creatinineChildren (1-13 years old)BothLong-Chain Acyl CoA Dehydrogenase deficiency (LCAD) details
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  1. Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [10197568 ]
Glutaric acidemia type 2
  1. MetaGene [Link]
Long chain acyl-CoA dehydrogenase deficiency (LCAD)
  1. MetaGene [Link]
Glutaric aciduria II
  1. MetaGene [Link]
Associated OMIM IDs
  • 606788 (Anorexia nervosa)
  • 231680 (Glutaric aciduria II)
  • 231680 (Glutaric acidemia type 2)
  • 201460 (Long chain acyl-CoA dehydrogenase deficiency (LCAD))
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003340
KNApSAcK IDC00001204
Chemspider ID10025
KEGG Compound IDC08278
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSuberic acid
NuGOwiki LinkHMDB00893
Metagene LinkHMDB00893
METLIN ID4243
PubChem Compound10457
PDB IDOCE
ChEBI ID9300
References
Synthesis ReferenceAyorinde, Folahan O.; Osman, Gamal; Shepard, Robert L.; Powers, Fiona T. Synthesis of azelaic acid and suberic acid from Vernonia galamensis oil. JAOCS, J. Am. Oil Chem. Soc. (1988), 65(11), 1774-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  2. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [2026685 ]
  3. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  4. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [8412012 ]
  5. Jakobs C, Sweetman L, Wadman SK, Duran M, Saudubray JM, Nyhan WL: Prenatal diagnosis of glutaric aciduria type II by direct chemical analysis of dicarboxylic acids in amniotic fluid. Eur J Pediatr. 1984 Jan;141(3):153-7. [6698061 ]
  6. Hagen T, Korson MS, Sakamoto M, Evans JE: A GC/MS/MS screening method for multiple organic acidemias from urine specimens. Clin Chim Acta. 1999 May;283(1-2):77-88. [10404733 ]
  7. Hayakawa S: Microbial transformation of bile acids. A unified scheme for bile acid degradation, and hydroxylation of bile acids. Z Allg Mikrobiol. 1982;22(5):309-26. [7123999 ]
  8. Truscott RJ, Hick L, Pullin C, Halpern B, Wilcken B, Griffiths H, Silink M, Kilham H, Grunseit F: Dicarboxylic aciduria: the response to fasting. Clin Chim Acta. 1979 May 16;94(1):31-9. [455718 ]
  9. Yoshioka K, Shimojo N, Nakanishi T, Naka K, Okuda K: Measurements of urinary adipic acid and suberic acid using high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1994 May 13;655(2):189-93. [8081464 ]
  10. Liang Y, Liu L, Wei H, Luo XP, Wang MT: [Late-onset riboflavin-responsive multiple acyl-CoA dehydrogenase deficiency (glutaric aciduria type II)] Zhonghua Er Ke Za Zhi. 2003 Dec;41(12):916-20. [14723814 ]
  11. Manjula BN, Roy RP, Smith PK, Acharya AS: Bissulfosuccinimidyl esters of aliphatic dicarboxylic acids: a new class of 'affinity directed' beta beta crosslinkers of HbA. Artif Cells Blood Substit Immobil Biotechnol. 1994;22(3):747-52. [7994397 ]
  12. Ishiguro Y, Kajita M, Aoshima T, Watanabe K, Kimura M, Yamaguchi S: The first case of 4-hydroxybutyric aciduria in Japan. Brain Dev. 2001 Mar;23(2):128-30. [11248463 ]