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Identification
YMDB IDYMDB00709
Name1-C-(indol-3-yl)glycerol 3-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1-C-(indol-3-yl)glycerol 3-phosphate, also known as IGPS or (3-indolyl)-glycerol phosphoric acid, 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. 1-C-(indol-3-yl)glycerol 3-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-C-(indol-3-yl)glycerol 3-phosphate may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • (1S,2R)-1-C-(Indol-3-yl)glycerol 3-phosphate
  • (3-Indolyl)-glycerol phosphate
  • 1-(Indol-3-yl)glycerol 3-phosphate
  • C1-(3-Indolyl)-glycerol 3-phosphate
  • IGPS
  • Indole-3-glycerol phosphate
  • Indole-3-glycerophosphate
  • Indoleglycerol phosphate
  • (3-Indolyl)-glycerol phosphoric acid
  • 1-(indol-3-yl)Glycerol 3-phosphoric acid
  • C1-(3-Indolyl)-glycerol 3-phosphoric acid
  • Indole-3-glycerophosphoric acid
  • Indoleglycerol phosphoric acid
  • 1-C-(indol-3-yl)Glycerol 3-phosphoric acid
CAS numberNot Available
WeightAverage: 287.2057
Monoisotopic: 287.055873697
InChI KeyNQEQTYPJSIEPHW-UHFFFAOYSA-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)
IUPAC Name[2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid
Traditional IUPAC NameIGPS
Chemical FormulaC11H14NO6P
SMILESOC(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
  • 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
Polarizability26.01 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 Reactions
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate + hydron1-C-(indol-3-yl)glycerol 3-phosphate + Carbon dioxide + water
L-Serine + 1-C-(indol-3-yl)glycerol 3-phosphateD-Glyceraldehyde 3-phosphate + water + L-Tryptophan
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Zalkin, H., Paluh, J. L., van Cleemput, M., Moye, W. S., Yanofsky, C. (1984). "Nucleotide sequence of Saccharomyces cerevisiae genes TRP2 and TRP3 encoding bifunctional anthranilate synthase: indole-3-glycerol phosphate synthase." J Biol Chem 259:3985-3992.6323449
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18299
HMDB IDNot Available
Pubchem Compound ID444150
Kegg IDC03506
ChemSpider ID777
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
TRP3
Uniprot ID:
P00937
Molecular weight:
53488.89844
Reactions
Chorismate + L-glutamine → anthranilate + pyruvate + L-glutamate.
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:
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.