Record Information
Version2.0
Creation Date2015-09-08 17:50:03 -0600
Update Date2015-09-14 16:46:09 -0600
Secondary Accession Numbers
  • ECMDB24202
Identification
Name:(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate
Description(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate is a member of the chemical class known as Indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate is involved in tryptophan biosynthesis. The latter is the competent substrate of (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate synthase, which catalyzes the subsequent step of tryptophan biosynthesis. (PMID 7727401) alphaTS by itself catalyzes the cleavage of indole-3-glycerol phosphate to glyceraldehyde-3-phosphate and indole, which is converted to tryptophan in tryptophan biosynthesis. (PMID 15879705)
Structure
Thumb
Synonyms:
  • (1S,2R)-1-C-(indol-3-yl)Glycerol 3-phosphoric acid
Chemical Formula:C11H12NO6P
Weight:Average: 285.193
Monoisotopic: 285.041321268
InChI Key:NQEQTYPJSIEPHW-UHFFFAOYSA-L
InChI:InChI=1S/C11H14NO6P/c13-10(6-18-19(15,16)17)11(14)8-5-12-9-4-2-1-3-7(8)9/h1-5,10-14H,6H2,(H2,15,16,17)/p-2
CAS number:Not Available
IUPAC Name:1-(1H-indol-3-yl)-3-(phosphonatooxy)propane-1,2-diol
Traditional IUPAC Name:1-(1H-indol-3-yl)-3-(phosphonatooxy)propane-1,2-diol
SMILES:OC(COP([O-])([O-])=O)C(O)C1=CNC2=C1C=CC=C2
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Substituted pyrrole
  • Alkyl phosphate
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility20.5 g/LALOGPS
logP0.12ALOGPS
logP-0.08ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.51 m³·mol⁻¹ChemAxon
Polarizability25.52 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Tryptophan metabolismPW000815 ThumbThumb?image type=greyscaleThumb?image type=simple
tryptophan metabolism IIPW001916 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-d6edd9533591edccc5feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-0190000000-33fd31bb35f5c119d546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qa-6910000000-1c2758a367c37aff8144View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-29f156f93694c4e1ed43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2190000000-dc2560f39d55366ecadbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003s-9100000000-03955eeb8f28e1b25ab3View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID60820
HMDB IDNot Available
Pubchem Compound ID25246146
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes two sequential steps of tryptophan biosynthetic pathway. The first reaction is catalyzed by the isomerase, coded by the trpF domain; the second reaction is catalyzed by the synthase, coded by the trpC domain
Gene Name:
trpC
Uniprot ID:
P00909
Molecular weight:
49361
Reactions
N-(5-phospho-beta-D-ribosyl)anthranilate = 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate.
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-C-(3-indolyl)-glycerol 3-phosphate + CO(2) + H(2)O.
General function:
Involved in catalytic activity
Specific function:
The alpha subunit is responsible for the aldol cleavage of indoleglycerol phosphate to indole and glyceraldehyde 3- phosphate
Gene Name:
trpA
Uniprot ID:
P0A877
Molecular weight:
28724
Reactions
L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H(2)O.