6-[(1-carboxy-1,3,4-trihydroxy-5-oxopentan-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 134013
• Molecular Formular: C12H18O13
• Molecular Mass: 370.26352
• Monoisotopic Mass: 370.07474064
• SMILES: C(=O)C(C(C(C(C(=O)O)O)OC1C(C(C(C(O1)C(=O)O)O)O)O)O)O
• Canonical SMILES: O=CC(C(C(C(C(=O)O)O)OC1OC(C(=O)O)C(C(C1O)O)O)O)O
• InChI: InChI=1S/C12H18O13/c13-1-2(14)3(15)8(7(19)10(20)21)24-12-6(18)4(16)5(17)9(25-12)11(22)23/h1-9,12,14-19H,(H,20,21)(H,22,23)
• InChIKey: SYBQLSSECRIKMJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(1-carboxy-1,3,4-trihydroxy-5-oxopentan-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: 6-[(1-carboxy-1,3,4-trihydroxy-5-oxopentan-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: α-D-GalA-(1→4)-D-GalA; Digalacturonic acid

Database IDs

• CAS Number: 5894-59-7
• MDL Number: MFCD00079142
• PubChem SID: 24893853; 162228290
• PubChem CID: 3294434

CALCULATED PROPERTIES

• Acid pKa: 2.834702
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -9.314227
• LogD (pH = 7.4): -11.592745
• Log P: -4.698647
• Molar Refractivity: 69.4937 cm^3
• Polarizability: 29.165197 Å^3
• Polar Surface Area: 231.51 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥85% (HPLC)

DETAILS

Sigma Aldrich - D4288

Application
Digalacturonic acid (DGA), derived in vivo from pectin catabolism, is used for the cocrystallization of enzymes such as proteinase K. DGA is used as substrate to identify, differentiate and characterized exopolygalacturonase(s) and gluconase(s). DGA is used to study the transport of oligogalacturonides by systems such as the TogMNAB ABC transporter.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D4288.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.