Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:42 UTC
NP-MRD IDNP0001037
Secondary Accession NumbersNone
Natural Product 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 medium-chain acyl-CoA dehydrogenase deficiency (MCAD). Suberic acid is also found to be associated with carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency, which are also inborn errors of metabolism.
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
1,6-HexanedicarboxylateGenerator
1,8-OctanedioateGenerator
HexamethylenedicarboxylateGenerator
Octane-1,8-dioateGenerator
OctanedioateGenerator
SuberateGenerator
Suberic acid, manganese (+2) (1:1) saltHMDB
Suberic acid, disodium saltHMDB
Suberic acid, cadmium (1:1) saltHMDB
Suberic acid, monosodium saltHMDB
Suberic acid, dipotassium saltHMDB
Suberic acidMeSH
Chemical FormulaC8H14O4
Average Mass174.1944 Da
Monoisotopic Mass174.08921 Da
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 KeyTYFQFVWCELRYAO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Arabidopsis thalianaLOTUS Database
Arbutus unedoLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Bufo gargarizansAnimalia
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Hibiscus syriacusKNApSAcK Database
Isatis tinctoriaLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Populus tremulaLOTUS Database
Rhodiola sacraLOTUS Database
Ricinus communisKNApSAcK Database
Solanum lycopersicumLOTUS Database
Stellaria dichotomaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trichosanthes kirilowiiLOTUS Database
Trichosanthes tricuspidataLOTUS Database
Trypanosoma bruceiLOTUS Database
Vincetoxicum atratumLOTUS Database
Species Where Detected
Species NameSourceReference
Bufo bufo gargarizansKNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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.
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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144 °CNot Available
Boiling Point345.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility11.9 mg/mLNot Available
LogP0.687 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility5.8 g/LALOGPS
logP1ALOGPS
logP1.38ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.15ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity41.94 m³·mol⁻¹ChemAxon
Polarizability18.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000893
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003340
KNApSAcK IDC00001204
Chemspider ID10025
KEGG Compound IDC08278
BioCyc IDCPD0-1264
BiGG IDNot Available
Wikipedia LinkSuberic_acid
METLIN ID4243
PubChem Compound10457
PDB IDNot Available
ChEBI ID9300
Good Scents IDrw1284661
References
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. doi: 10.1038/nature07762. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:11248463 ]