ChemFOnt: Showing chemical card for Tryptophan 2-C-mannoside (CFc000220559)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:44 UTC

Chemfont ID

CFc000220559

Molecule Identification

Common Name

Tryptophan 2-C-mannoside

Definition

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is an L-tryptophan derivative and a C-glycosyl compound in which the hydrogen at position 2 on the indole portion has been replaced by an alpha-mannosyl residue.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 (PMID: 29234020 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R)-1,5-Anhydro-1-{3-[(2S)-2-amino-2-carboxyethyl]-1H-indol-2-yl}-D-mannitol	ChEBI
2'-alpha-D-Mannosyl-L-tryptophan	ChEBI
2'-alpha-D-Mannosyltryptophan	ChEBI
2'-alpha-Mannosyltryptophan	ChEBI
2'-Tryptophan C-mannoside	ChEBI
C(2)-alpha-D-Mannopyranosyl-L-tryptophan	ChEBI
2'-a-D-Mannosyl-L-tryptophan	Generator
2'-Α-D-mannosyl-L-tryptophan	Generator
2'-a-D-Mannosyltryptophan	Generator
2'-Α-D-mannosyltryptophan	Generator
2'-a-Mannosyltryptophan	Generator
2'-Α-mannosyltryptophan	Generator
C(2)-a-D-Mannopyranosyl-L-tryptophan	Generator
C(2)-Α-D-mannopyranosyl-L-tryptophan	Generator
2'-a-Mannosyl-L-tryptophan	HMDB
2'-Α-mannosyl-L-tryptophan	HMDB
2-(alpha-D-Mannopyranosyl)-L-tryptophan	HMDB
2-(Α-D-mannopyranosyl)-L-tryptophan	HMDB
2-alpha-D-Mannopyranosyl-L-tryptophan	HMDB
2-Α-D-mannopyranosyl-L-tryptophan	HMDB
C2-alpha-D-Mannopyranosyltryptophan	HMDB
C2-Α-D-mannopyranosyltryptophan	HMDB
2-(alpha-Mannopyranosyl)-L-tryptophan	HMDB
2-(Α-mannopyranosyl)-L-tryptophan	HMDB
2-alpha-D-Mannopyranosyltryptophan	HMDB
2-alpha-D-Mannosyl-L-tryptophan	HMDB
2-alpha-D-Mannosyltryptophan	HMDB
2-Α-D-mannopyranosyltryptophan	HMDB
2-Α-D-mannosyl-L-tryptophan	HMDB
2-Α-D-mannosyltryptophan	HMDB
C-Glycosyltryptophan	HMDB
C-Man-TRP	HMDB
C-Mannosyl tryptophan	HMDB
C-Mannosyltryptophan	HMDB
L-Tryptophan 2-C-alpha-D-mannopyranoside	HMDB
L-Tryptophan 2-C-mannopyranoside	HMDB
L-Tryptophan 2-C-α-D-mannopyranoside	HMDB
alpha-C-Man-TRP	HMDB
Α-C-man-TRP	HMDB
2-(Mannopyranosyl)-tryptophan	MeSH
2(MP)-L-T	MeSH
Tryptophan 2-C-mannoside	HMDB

Chemical Formula

C₁₇H₂₂N₂O₇

Average Molecular Weight

366.37

Monoisotopic Molecular Weight

366.142701056

IUPAC Name

(2S)-2-amino-3-{2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoic acid

Traditional Name

(2S)-2-amino-3-{2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoic acid

CAS Registry Number

180509-18-6

SMILES

N[C@@H](CC1=C(NC2=CC=CC=C12)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)C(O)=O

InChI Identifier

InChI=1S/C17H22N2O7/c18-9(17(24)25)5-8-7-3-1-2-4-10(7)19-12(8)16-15(23)14(22)13(21)11(6-20)26-16/h1-4,9,11,13-16,19-23H,5-6,18H2,(H,24,25)/t9-,11+,13+,14-,15-,16+/m0/s1

InChI Key

CPXSBHKDEPPWIX-RAYCSJGISA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Hexose monosaccharide
C-glycosyl compound
Glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
3-alkylindole
Indole
Aralkylamine
Benzenoid
Substituted pyrrole
Monosaccharide
Oxane
Heteroaromatic compound
Pyrrole
Secondary alcohol
Amino acid
Amino acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Amine
Organic oxygen compound
Organic nitrogen compound
Alcohol
Primary amine
Primary alcohol
Primary aliphatic amine
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 29234020)

Organ

Placenta (HMDB: HMDB0240296)

Excreta

Biofluid or Excreta

Urine (PMID: 29234020)

Source

Exogenous

Exogenous (HMDB: HMDB0240296)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.66 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.9	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	169.26 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.2 m³·mol⁻¹	ChemAxon
Polarizability	36.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240296

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9157171

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10981970

PDB ID

Not Available

ChEBI ID

19232

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Tryptophan 2-C-mannoside (CFc000220559)

MOL for CFc000220559 (Tryptophan 2-C-mannoside)

3D MOL for CFc000220559 (Tryptophan 2-C-mannoside)

3D SDF for CFc000220559 (Tryptophan 2-C-mannoside)

3D-SDF for CFc000220559 (Tryptophan 2-C-mannoside)

PDB for CFc000220559 (Tryptophan 2-C-mannoside)

3D PDB for CFc000220559 (Tryptophan 2-C-mannoside)

SMILES for CFc000220559 (Tryptophan 2-C-mannoside)

INCHI for CFc000220559 (Tryptophan 2-C-mannoside)

Structure for CFc000220559 (Tryptophan 2-C-mannoside)

3D Structure for CFc000220559 (Tryptophan 2-C-mannoside)