ECMDB: Indoleglycerol phosphate (ECMDB20160) (M2MDB001007)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (1269)

Record Information

Version

2.0

Creation Date

2012-05-31 14:30:39 -0600

Update Date

2015-06-03 17:19:26 -0600

Secondary Accession Numbers

ECMDB20160

Identification

Name:

Indoleglycerol phosphate

Description

Indoleglycerol 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. Indoleglycerol phosphate is involved in tryptophan biosynthesis. The latter is the competent substrate of indoleglycerol 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

(1S,2R)-1-C-(Indol-3-yl)glycerol 3-phosphate
(1S,2R)-1-C-(indol-3-yl)Glycerol 3-phosphoric acid
(3-Indolyl)-glycerol phosphate
(3-Indolyl)-glycerol phosphoric acid
1-(Indol-3-yl)glycerol-3-P
1-(Indol-3-yl)glycerol-3-phosphate
1-(indol-3-yl)Glycerol-3-phosphoric acid
1-C-(Indol-3-yl)glycerol 3-phosphate
1-C-(indol-3-yl)Glycerol 3-phosphoric acid
C1-(3-Indolyl)-glycerol 3-phosphate
C1-(3-Indolyl)-glycerol 3-phosphoric acid
C¹-(3-Indolyl)-glycerol 3-phosphate
IG-P
IGP
Indole-3-glycerol phosphate
Indole-3-glycerol phosphoric acid
Indole-3-glycerol-P
Indole-3-glycerol-phosphate
Indole-3-glycerol-phosphoric acid
Indoleglycerol phosphate
Indoleglycerol phosphoric acid

Chemical Formula:

C₁₁H₁₄NO₆P

Weight:

Average: 287.2057
Monoisotopic: 287.055873697

InChI Key:

NQEQTYPJSIEPHW-MNOVXSKESA-N

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)/t10-,11+/m1/s1

CAS number:

4220-97-7

IUPAC Name:

[(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid

Traditional IUPAC Name:

indole-3-glycerol phosphate

SMILES:

[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-C-(indol-3-yl)glycerol 3-phosphate (CHEBI:51793 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	3.87 g/L	ALOGPS
logP	-0.21	ALOGPS
logP	-0.08	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	123.01 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.76 m³·mol⁻¹	ChemAxon
Polarizability	25.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Glycine, serine and threonine metabolism ec00260
Metabolic pathways eco01100
Phenylalanine, tyrosine and tryptophan biosynthesis ec00400

EcoCyc Pathways:

tryptophan biosynthesis TRPSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-4900000000-b86813ef2800a8c9d2f8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-6390000000-f17b5507f97353c5dbf8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-935793bf974f83d59858	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-c0a8c6db2c733f0ed5e0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2190000000-3b43102cb004791c424b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-e5ea87f5b0fb91d7b6d8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-82df9ca2bde740a861b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-1890000000-61a462086b1984fd95ce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00r5-2920000000-9a1b057494b6f12812d3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-2900000000-0273b8f673c7daddc7ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0076-0960000000-319b59ecadb65b48b371	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-8de19e23796875d3b9fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-2900000000-5d4265af530fb3dd738f	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Hommel, U., Eberhard, M., Kirschner, K. (1995). "Phosphoribosyl anthranilate isomerase catalyzes a reversible amadori reaction." Biochemistry 34:5429-5439. Pubmed: 7727401
Jeong, M. S., Jang, S. B. (2005). "Crystallization and X-ray crystallographic studies of wild-type and mutant tryptophan synthase alpha-subunits from Escherichia coli." Mol Cells 19:219-222. Pubmed: 15879705
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18299
HMDB ID	HMDB0303952
Pubchem Compound ID	444150
Kegg ID	C03506
ChemSpider ID	392148
Wikipedia ID	Not Available
BioCyc ID	INDOLE-3-GLYCEROL-P
EcoCyc ID	INDOLE-3-GLYCEROL-P
Ligand Expo	IGP

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.

Protein Details

3. Tryptophan synthase beta chain

General function:: Involved in catalytic activity
Specific function:: The beta subunit is responsible for the synthesis of L- tryptophan from indole and L-serine
Gene Name:: trpB
Uniprot ID:: P0A879
Molecular weight:: 42983

Reactions

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H(2)O.

Indoleglycerol phosphate (ECMDB20160) (M2MDB001007)

Structure for #<Compound:0xab0bf030>

Enzymes

Reactions

Reactions

Reactions