MiMeDB: Showing metabocard for 1-C-(indol-3-yl)glycerol 3-phosphate (MMDBc0033092)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:34:23 UTC

Update Date

2022-08-31 22:26:00 UTC

Metabolite ID

MMDBc0033092

Metabolite Identification

Common Name

1-C-(indol-3-yl)glycerol 3-phosphate

Description

Structure

MOL SDF PDB SMILES InChI

ChEBI
  Mrv0541 02241222332D          

 19 20  0  0  0  0            999 V2000
   10.0942   -5.6031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5919   -4.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3091   -5.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3013   -4.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0975   -4.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5925   -5.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5948   -4.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8782   -4.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8930   -5.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9448   -2.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3573   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5948   -2.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1823   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5948   -4.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4198   -4.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1343   -3.8093    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.8487   -4.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1343   -2.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3478   -4.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5 11  1  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  5  2  2  0  0  0  0
  4  3  2  0  0  0  0
  6  3  1  0  0  0  0
  5  4  1  0  0  0  0
  7  4  1  0  0  0  0
  9  6  2  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 11 13  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033092

> <DATABASE_NAME>
MIME

> <SMILES>
OC(COP(O)(O)=O)C(O)C1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
NQEQTYPJSIEPHW-UHFFFAOYSA-N

> <FORMULA>
C11H14NO6P

> <MOLECULAR_WEIGHT>
287.2057

> <EXACT_MASS>
287.055873697

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.014286020577504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
-0.07957787366666655

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.512307194345704

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4864854788381807

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4498355399329936

> <JCHEM_POLAR_SURFACE_AREA>
123.01

> <JCHEM_REFRACTIVITY>
66.75829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.87e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
IGPS

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      18.843 -10.459   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      19.772  -9.248   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.377 -10.059   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.362  -8.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.849  -7.987   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.039 -10.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.044  -7.693   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.706  -8.406   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.734 -10.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      18.564  -5.213   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      19.334  -6.547   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      21.644  -5.213   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      20.874  -6.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.644  -7.881   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      23.184  -7.881   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0      24.517  -7.111   0.000  0.00  0.00           P+0
HETATM   17  O   UNK     0      25.851  -7.881   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      24.517  -5.571   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      24.916  -8.598   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    4    6                                                  
CONECT    4    3    5    7                                                  
CONECT    5   11    2    4                                                  
CONECT    6    3    9                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    6    8                                                       
CONECT   10   11                                                            
CONECT   11    5   10   13                                                  
CONECT   12   13                                                            
CONECT   13   11   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

Synonyms

Value	Source
(3-Indolyl)-glycerol phosphate	ChEBI
1-(indol-3-yl)Glycerol 3-phosphate	ChEBI
C1-(3-Indolyl)-glycerol 3-phosphate	ChEBI
IGPS	ChEBI
Indole-3-glycerophosphate	ChEBI
Indoleglycerol phosphate	ChEBI
(3-Indolyl)-glycerol phosphoric acid	Generator
1-(indol-3-yl)Glycerol 3-phosphoric acid	Generator
C1-(3-Indolyl)-glycerol 3-phosphoric acid	Generator
Indole-3-glycerophosphoric acid	Generator
Indoleglycerol phosphoric acid	Generator
1-C-(indol-3-yl)Glycerol 3-phosphoric acid	Generator

Molecular Formula

C₁₁H₁₄NO₆P

Average Mass

287.2057

Monoisotopic Mass

287.055873697

IUPAC Name

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

Traditional Name

IGPS

CAS Registry Number

Not Available

SMILES

OC(COP(O)(O)=O)C(O)C1=CNC2=C1C=CC=C2

InChI Identifier

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)

InChI Key

NQEQTYPJSIEPHW-UHFFFAOYSA-N

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

sn-glycerol 3-phosphates (CHEBI:18299 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	26.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-4900000000-b86813ef2800a8c9d2f8	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-1890000000-a7b462c4667e58366960	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ke-2920000000-b74ffd636745b49ea9c2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2900000000-0f66a4984ace6a3d5af8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-6390000000-7823b7805643711a888c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-74cc11198a19ba8b0ee0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-8f4e5a1ff60db4d426bb	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

799

PDB ID

Not Available

ChEBI ID

18299

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Zalkin H, Paluh JL, van Cleemput M, Moye WS, Yanofsky C: Nucleotide sequence of Saccharomyces cerevisiae genes TRP2 and TRP3 encoding bifunctional anthranilate synthase: indole-3-glycerol phosphate synthase. J Biol Chem. 1984 Mar 25;259(6):3985-92. [PubMed:6323449 ]
Herrgard MJ, Swainston N, Dobson P, Dunn WB, Arga KY, Arvas M, Bluthgen N, Borger S, Costenoble R, Heinemann M, Hucka M, Le Novere N, Li P, Liebermeister W, Mo ML, Oliveira AP, Petranovic D, Pettifer S, Simeonidis E, Smallbone K, Spasic I, Weichart D, Brent R, Broomhead DS, Westerhoff HV, Kirdar B, Penttila M, Klipp E, Palsson BO, Sauer U, Oliver SG, Mendes P, Nielsen J, Kell DB: A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology. Nat Biotechnol. 2008 Oct;26(10):1155-60. doi: 10.1038/nbt1492. [PubMed:18846089 ]

Showing metabocard for 1-C-(indol-3-yl)glycerol 3-phosphate (MMDBc0033092)

MOL for #<Metabolite:0x00007fed144ac4b0>

3D MOL for #<Metabolite:0x00007fed144ac4b0>

3D SDF for #<Metabolite:0x00007fed144ac4b0>

3D-SDF for #<Metabolite:0x00007fed144ac4b0>

PDB for #<Metabolite:0x00007fed144ac4b0>

3D PDB for #<Metabolite:0x00007fed144ac4b0>

SMILES for #<Metabolite:0x00007fed144ac4b0>

INCHI for #<Metabolite:0x00007fed144ac4b0>

Structure for #<Metabolite:0x00007fed144ac4b0>

3D Structure for #<Metabolite:0x00007fed144ac4b0>