MiMeDB: Showing metabocard for Iduronic acid (MMDBc0000218)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:40:10 UTC

Update Date

2024-04-30 19:31:32 UTC

Metabolite ID

MMDBc0000218

Metabolite Identification

Common Name

Iduronic acid

Description

Iduronic acid is a constituent of glycosaminoglycans heparin and heparan sulfate in varying proportions providing considerable diversity in sequence and biological function. The glycosaminoglycans (GAGs) are linear polysaccharides with alternating uronic acids (Iduronic acid and Glucuronic acid) and hexosamine residues, in which a limited set of monosaccharide units gives rise to a number of complex sequences by variable substitution with O-sulfate, N-sulfate, and N-acetyl groups. GAGs usually exist as the O-linked side-chains of proteoglycans, displaying a set of physiological functions which is remarkably wide and as yet incompletely explored. They may act as structural components of connective tissue and the extracellular matrix, or as specific ligands in the relationship between the cell surface and its surroundings. Heparan sulfate exists on the surface of most or all mammalian cells and can display a remarkable range of different sequence motifs; its range of interactions and possible functions reflect its structural complexity. The main repeat unit of heparin structurally resembles the protein binding sequences in heparan sulfate, but contains a higher percentage of sulfated residues. Utilized therapeutically as an anticoagulant and readily available in good quantities heparin serves as a useful model for heparan sulfate. Theoretical and experimental studies indicate that L-Iduronic acid residues of glycosaminoglycans are in equilibrium of different conformations, the relative proportion of conformers being a function of sulfation pattern and sequence. This unique conformational flexibility may provide an explanation for the stronger binding and associated higher biological activities of Iduronic acid-containing glycosaminoglycans (such as heparin, heparan sulfate and dermatan sulfate) as compared with other GAGs having similar charge density but with the more rigid glucuronic acid as the major uronic acid residue. Dermatan sulfates and heparins, which contain L-Iduronic acid in their backbone, show higher low-density lipoprotein (LDL)-affinity than chondroitin sulfates, which contain only D-glucuronic acid. Though confirming a non-specific, predominantly electrostatic interaction between GAGs and LDL, these results indicate modulation of LDL affinity by the polysaccharide backbone. Naturally oversulfated dermatan sulfate (SO3H/COOH ca. 1.2), mainly oversulfated at C-2 of Iduronic acid residues, show comparatively higher anticoagulant activity. (PMID: 3076283 , 8466951 , 8542607 , 11087707 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      34.538 -22.171   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.871 -18.320   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      33.204 -18.320   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      37.205 -22.171   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.536 -19.860   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      31.870 -22.171   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      38.539 -18.320   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      34.538 -20.631   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.871 -19.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.204 -19.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      37.205 -20.631   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.870 -20.631   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.539 -19.860   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   12                                                            
CONECT    7   13                                                            
CONECT    8    1    9   10                                                  
CONECT    9    2    8   11                                                  
CONECT   10    3    8   12                                                  
CONECT   11    4    9   13                                                  
CONECT   12    5    6   10                                                  
CONECT   13    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
Iduronate	Generator
L-Iduronate	HMDB
L-Iduronic acid	HMDB
Acid, iduronic	HMDB
(2S,3R,4R,5S)-2,3,4,5-Tetrahydroxy-6-oxohexanoate	HMDB
Iduronic acid	MeSH

Molecular Formula

C₆H₁₀O₇

Average Mass

194.1394

Monoisotopic Mass

194.042652674

IUPAC Name

(2S,3R,4R,5S)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid

Traditional Name

iduronic acid

CAS Registry Number

3402-98-0

SMILES

O[C@H](C=O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O

InChI Identifier

InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4-,5+/m1/s1

InChI Key

IAJILQKETJEXLJ-LECHCGJUSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9700000000-cdaf9f94e02e4e7ba7d2	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-009i-4212940000-02a8091c226f3a41d70e	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056s-2900000000-86606b8382ffe403bc8e	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9500000000-af67bc97552641417bee	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-205a7cff1e298283a080	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05p9-9700000000-ee070fab487c9f3e49b7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9400000000-284825e422ba9585f17b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-64d4f9d758e2a4eeba68	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-9300000000-77aa1619935fe785e397	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-9000000000-da4be7e32a829503c021	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9000000000-c1c9308cd925f43d015f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01y5-7900000000-df218a4e340a0ff668c1	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03kl-9100000000-d22d4d2644d77203331d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fu-9000000000-93301767b758d212114f	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for Iduronic acid (MMDBc0000218)

MOL for #<Metabolite:0x00007fd5cc374f70>

3D MOL for #<Metabolite:0x00007fd5cc374f70>

3D SDF for #<Metabolite:0x00007fd5cc374f70>

3D-SDF for #<Metabolite:0x00007fd5cc374f70>

PDB for #<Metabolite:0x00007fd5cc374f70>

3D PDB for #<Metabolite:0x00007fd5cc374f70>

SMILES for #<Metabolite:0x00007fd5cc374f70>

INCHI for #<Metabolite:0x00007fd5cc374f70>

Structure for #<Metabolite:0x00007fd5cc374f70>

3D Structure for #<Metabolite:0x00007fd5cc374f70>