General Information of MET (ID: META00759)
Name Tryptophan 2-C-mannoside
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2-alpha-D-Mannopyranosyltryptophan; 2-alpha-D-Mannosyl-L-tryptophan; C-Glycosyltryptophan; C-Man-Trp; C-Mannosyl tryptophan; C-Mannosyltryptophan; L-Tryptophan 2-C-alpha-D-mannopyranoside; Tryptophan 2-C-mannoside
Source Aromatic heteropolycyclic compounds
Structure Type   Indolyl carboxylic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Indoles and derivatives
Indolyl carboxylic acids and derivatives
PubChem CID
10981970
HMDB ID
HMDB0240296
Formula
C17H22N2O7
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
19232
ChemSpider ID
9157171
Physicochemical Properties Molecular Weight 366.4 Topological Polar Surface Area 169
XlogP -3.7 Complexity 508
Heavy Atom Count 26 Rotatable Bond Count 5
Hydrogen Bond Donor Count 7 Hydrogen Bond Acceptor Count 8
Function
Tryptophan 2-C-mannoside, also known as 2-alpha-D-mannopyranosyl-L-tryptophan or C-mannosyltryptophan, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. It is an L-tryptophan derivative and a C-glycosyl compound in which the hydrogen at position 2 on the indole portion has been replaced by an alpha-mannosyl residue. Tryptophan 2-C-mannoside is a very strong basic compound (based on its pKa). Tryptophan 2-C-mannoside has been identified in blood and urine and is a marker of kidney function.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Tryptophan 2-C-mannoside concentration: increase (FC = 1.71 - 3.82)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of tryptophan 2-c-mannoside levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.

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