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Identification
YMDB IDYMDB00179
Name(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionIndoleglycerol phosphate 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. Indoleglycerol phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Indoleglycerol phosphate exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • (1S,2R)-1-C-(Indol-3-yl)glycerol 3-phosphate
  • (3-Indolyl)-glycerol phosphate
  • 1-C-(Indol-3-yl)glycerol 3-phosphate
  • C1-(3-Indolyl)-glycerol 3-phosphate
  • Indole-3-glycerol phosphate
  • Indoleglycerol phosphate
  • (3-Indolyl)-glycerol phosphoric acid
  • 1-C-(indol-3-yl)Glycerol 3-phosphoric acid
  • C1-(3-Indolyl)-glycerol 3-phosphoric acid
  • Indole-3-glycerol phosphoric acid
  • (1S,2R)-1-C-(indol-3-yl)Glycerol 3-phosphoric acid
  • Indoleglycerol phosphoric acid
  • Indole-3-glycerophosphate
CAS numberNot Available
WeightAverage: 287.2057
Monoisotopic: 287.055873697
InChI KeyNQEQTYPJSIEPHW-MNOVXSKESA-N
InChIInChI=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)/t10-,11+/m1/s1
IUPAC Name[(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid
Traditional IUPAC Nameindole-3-glycerol phosphate
Chemical FormulaC11H14NO6P
SMILESO[C@H](COP(O)(O)=O)[C@@H](O)C1=CNC2=CC=CC=C12
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
  • Monoalkyl phosphate
  • 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
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.87 g/LALOGPS
logP-0.21ALOGPS
logP-0.08ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area123.01 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity66.76 m³·mol⁻¹ChemAxon
Polarizability25.41 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Tryptophan metabolismec00380 Map00380
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID51793
HMDB IDNot Available
Pubchem Compound ID444150
Kegg IDC03506
ChemSpider ID24785614
FOODB IDFDB030090
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
L-serine + 1-C-(indol-3-yl)glycerol 3- phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H(2)O
Gene Name:
TRP5
Uniprot ID:
P00931
Molecular weight:
76625.5
Reactions
L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate → L-tryptophan + glyceraldehyde 3-phosphate + H(2)O.