Indole-3-Glycerol Phosphate

Identification

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Name
Indole-3-Glycerol Phosphate
Accession Number
DB04143  (EXPT01850)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 287.2057
Monoisotopic: 287.055873697
Chemical Formula
C11H14NO6P
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
IUPAC Name
[(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid
SMILES
[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C1=CNC2=C1C=CC=C2

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTryptophan synthase alpha chainNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UTryptophan synthase beta chainNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C03506
PubChem Compound
444150
PubChem Substance
46504439
ChemSpider
392148
ChEBI
51793
HET
IGP
PDB Entries
1a53 / 1a5b / 1kfb / 1qoq / 2rh9 / 2rhg / 3t44

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.87 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity66.76 m3·mol-1ChemAxon
Polarizability25.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7361
Blood Brain Barrier+0.9404
Caco-2 permeable-0.6378
P-glycoprotein substrateNon-substrate0.6801
P-glycoprotein inhibitor INon-inhibitor0.9184
P-glycoprotein inhibitor IINon-inhibitor0.9912
Renal organic cation transporterNon-inhibitor0.9132
CYP450 2C9 substrateNon-substrate0.8349
CYP450 2D6 substrateNon-substrate0.7888
CYP450 3A4 substrateNon-substrate0.629
CYP450 1A2 substrateNon-inhibitor0.7448
CYP450 2C9 inhibitorNon-inhibitor0.8427
CYP450 2D6 inhibitorNon-inhibitor0.8961
CYP450 2C19 inhibitorNon-inhibitor0.8114
CYP450 3A4 inhibitorNon-inhibitor0.9575
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8602
Ames testNon AMES toxic0.6799
CarcinogenicityNon-carcinogens0.8898
BiodegradationNot ready biodegradable0.7256
Rat acute toxicity2.3004 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9349
hERG inhibition (predictor II)Non-inhibitor0.8204
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-1890000000-61a462086b1984fd95ce
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00r5-2920000000-9a1b057494b6f12812d3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-2900000000-0273b8f673c7daddc7ca
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002r-6390000000-f17b5507f97353c5dbf8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9300000000-935793bf974f83d59858
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-c0a8c6db2c733f0ed5e0

Taxonomy

Description
This compound belongs to the class of organic compounds known as 3-alkylindoles. These 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
Monoalkyl phosphates / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Secondary alcohols / 1,2-diols / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
3-alkylindole / Monoalkyl phosphate / Organic phosphoric acid derivative / Phosphoric acid ester / Substituted pyrrole / Alkyl phosphate / Benzenoid / Pyrrole / Heteroaromatic compound / Secondary alcohol
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
1-C-(indol-3-yl)glycerol 3-phosphate (CHEBI:51793)

Targets

Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Tryptophan synthase 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
P00929
Uniprot Name
Tryptophan synthase alpha chain
Molecular Weight
28670.485 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Tryptophan synthase activity
Specific Function
The beta subunit is responsible for the synthesis of L-tryptophan from indole and L-serine.
Gene Name
trpB
Uniprot ID
P0A2K1
Uniprot Name
Tryptophan synthase beta chain
Molecular Weight
42867.63 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 06:01