1D-myo-inositol 1,4-bisphosphate (YMDB00852)

Identification

YMDB ID

YMDB00852

Name

1D-myo-inositol 1,4-bisphosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-myo-Inositol 1,4-bisphosphate, also known as inositol 1,4-bisphosphoric acid, belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety. D-myo-Inositol 1,4-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-myo-Inositol 1,4-bisphosphate exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1d-myo-inositol 1
1D-myo-Inositol 1,4-bisphosphate
1D-Myo-inositol 1,4-bisphosphic acid
4-bisphosphate
D-myo-inositol 1,4-bisphosphate
D-MYO-INOSITOL-1,4-BISPHOSPHATE
inositol 1
inositol 1,4-bisphosphate
myo-inositol 1
myo-inositol 1,4-bisphosphate
D-MYO-inositol-1,4-bisphosphoric acid
Inositol 1,4-bisphosphoric acid
Myo-inositol 1,4-bisphosphoric acid
D-Myo-inositol 1,4-bisphosphoric acid
1D-Myo-inositol 1,4-bisphosphoric acid

CAS number

47055-78-7

Weight

Average: 340.1157
Monoisotopic: 339.996048936

InChI Key

PELZSPZCXGTUMR-RTPHHQFDSA-N

InChI

InChI=1S/C6H14O12P2/c7-1-2(8)6(18-20(14,15)16)4(10)3(9)5(1)17-19(11,12)13/h1-10H,(H2,11,12,13)(H2,14,15,16)/t1-,2-,3-,4+,5+,6+/m1/s1

IUPAC Name

{[(1R,2R,3R,4R,5R,6S)-2,3,5,6-tetrahydroxy-4-(phosphonooxy)cyclohexyl]oxy}phosphonic acid

Traditional IUPAC Name

[(1R,2R,3R,4R,5R,6S)-2,3,5,6-tetrahydroxy-4-(phosphonooxy)cyclohexyl]oxyphosphonic acid

Chemical Formula

C₆H₁₄O₁₂P₂

SMILES

O[C@H]1[C@@H](O)[C@@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1OP(O)(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Inositol phosphates

Alternative Parents

Substituents

Inositol phosphate
Monoalkyl phosphate
Cyclohexanol
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Polyol
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

myo-inositol bisphosphate (CHEBI:17816 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	24.4 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	0.86	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	214.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.52 m³·mol⁻¹	ChemAxon
Polarizability	25.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Inositol Metabolism	PW002498
Inositol phosphate metabolism	PW002495

KEGG Pathways

Inositol phosphate metabolism

ec00562

SMPDB Reactions

Inositol 1,4,5-trisphosphate + water → 1D-myo-inositol 1,4-bisphosphate + phosphate

1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + water → 1D-myo-inositol 1,4-bisphosphate + phosphate

1D-myo-inositol 1,4-bisphosphate + water → D-Myo-inositol 4-phosphate + Phosphoric acid

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9321000000-9f623a36e7cbbf411892	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-03dj-9163026000-1848e4d3af73c15a6fe2	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-2039000000-30867310a54aeefc9f07	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-2029000000-09a80b30252576945f03	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-8920000000-da85c9dd4243595988cc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-4009000000-0bfc6eac93cb1d6f5150	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9012000000-52b4d66a2cc414f3c15f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-188d2aa04460c53bd120	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-409ec2d369e3f269fc61	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-9008000000-6a58e24bfb6d7b7533d3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-f53a8156649b945c2aee	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-0c0a6b1789da56429e47	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0029000000-7b521123b7ad2af2e51c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9100000000-1e618537818490a76e76	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Whisstock, J. C., Romero, S., Gurung, R., Nandurkar, H., Ooms, L. M., Bottomley, S. P., Mitchell, C. A. (2000). "The inositol polyphosphate 5-phosphatases and the apurinic/apyrimidinic base excision repair endonucleases share a common mechanism for catalysis." J Biol Chem 275:37055-37061.10962003
Morales-Johansson, H., Jenoe, P., Cooke, F. T., Hall, M. N. (2004). "Negative regulation of phosphatidylinositol 4,5-bisphosphate levels by the INP51-associated proteins TAX4 and IRS4." J Biol Chem 279:39604-39610.15265867

Synthesis Reference:

Auchus, Richard J.; Kaiser, Susan L.; Majerus, Philip W. Synthesis of inositol 1,2-(cyclic)-4,5-trisphosphate. Proceedings of the National Academy of Sciences of the United States of America (1987), 84(5), 1206-9.

External Links:

Resource	Link
CHEBI ID	17816
HMDB ID	HMDB00968
Pubchem Compound ID	805
Kegg ID	C01220
ChemSpider ID	17216032
FOODB ID	FDB022343
Wikipedia ID	Not Available
BioCyc ID	INOSITOL-1,4-BISPHOSPHATE

Enzymes

Protein Details

1. Inositol-1,4,5-trisphosphate 5-phosphatase 3

General function:: Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:: Controls the cellular levels and subcellular distribution of phosphatidylinositol 3-phosphate and phosphatidylinositol 4,5-bisphosphate. Plays an essential role in a TGN (trans Golgi network)-to-early endosome pathway. Involved in clathrin-mediated protein sorting at the TGN
Gene Name:: INP53
Uniprot ID:: Q12271
Molecular weight:: 124576.0

Reactions

1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H(2)O → 1-phosphatidyl-1D-myo-inositol 4-phosphate + phosphate.
D-myo-inositol 1,4,5-trisphosphate + H2O → D-myo-inositol 1,4-bisphosphate + phosphate
D-myo-inositol 1,3,4,5-tetrakisphosphate + H2O → D-myo-inositol 1,3,4-trisphosphate + phosphate

Protein Details

2. Inositol-1,4,5-trisphosphate 5-phosphatase 2

General function:: Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:: Controls the cellular levels and subcellular distribution of phosphatidylinositol 3-phosphate and phosphatidylinositol 4,5-bisphosphate. Specifically functions within the early endocytic pathway and actin organization
Gene Name:: INP52
Uniprot ID:: P50942
Molecular weight:: 133330.0

Reactions

1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H(2)O → 1-phosphatidyl-1D-myo-inositol 4-phosphate + phosphate.
D-myo-inositol 1,4,5-trisphosphate + H2O → D-myo-inositol 1,4-bisphosphate + phosphate
D-myo-inositol 1,3,4,5-tetrakisphosphate + H2O → D-myo-inositol 1,3,4-trisphosphate + phosphate

Protein Details

3. Inositol-1,4,5-trisphosphate 5-phosphatase 1

General function:: Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:: Controls the cellular levels and subcellular distribution of phosphatidylinositol 3-phosphate and phosphatidylinositol 4,5-bisphosphate. Plays an essential role in a TGN (trans Golgi network)-to-early endosome pathway. Involved in endocytosis and acts as a negative regulator of the Slm pathway which modulates polarized actin assembly and growth
Gene Name:: INP51
Uniprot ID:: P40559
Molecular weight:: 108429.0

Reactions

1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H(2)O → 1-phosphatidyl-1D-myo-inositol 4-phosphate + phosphate.

1D-myo-inositol 1,4-bisphosphate (YMDB00852)

Structure for #<Compound:0xb0255fe8>

Enzymes

Reactions

Reactions

Reactions