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(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate (M2MDB006319)

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
MOLSDFPDBSMILESInChI
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:
1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate + Hydrogen ion + 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate > Water + Carbon dioxide + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate
(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate > D-Glyceraldehyde 3-phosphate + Indole + D-Glyceraldehyde 3-phosphate
1-(2-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphate + Hydrogen ion > Carbon dioxide + Water + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate
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

Protein Details
1. Tryptophan biosynthesis protein trpCF
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.
Protein Details
2. Tryptophan synthase alpha chain
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.