1D-myo-inositol 4,5-bisphosphate (YMDB00764)

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Identification

YMDB ID

YMDB00764

Name

1D-myo-inositol 4,5-bisphosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

1-phosphatidyl-1D-myo-inositol-3,4-bisphosphate, also known as D-myo-inositol 4,5-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. 1-phosphatidyl-1D-myo-inositol-3,4-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-Phosphatidyl-1D-myo-inositol 4,5-bisphosphate
1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate
1D-Myo-inositol 1,4-bisphosphate
1D-Myo-inositol 1,4-bisphosphic acid
D-myo-inositol 1,4-bisphosphate
D-myo-Inositol 4,5-bisphosphate
D-MYO-INOSITOL-4,5-BISPHOSPHATE
inositol 1,4-bisphosphate
myo-inositol 1,4-bisphosphate
Phosphatidyl-myo-inositol 4,5-bisphosphate
Phosphatidylinositol-4,5-bisphosphate
D-Myo-inositol 4,5-bisphosphoric acid
D-MYO-inositol-4,5-bisphosphoric acid
1-Phosphatidyl-1D-myo-inositol-3,4-bisphosphoric acid
1D-Myo-inositol 4,5-bisphosphoric acid
Myo-inositol 4,5-diphosphate
Inositol 4,5-bisphosphate
Ins(4,5)P2
Inositol 4,5-biphosphate
Inositol-4,5-bisphosphate
Inositol 4,5-bisphosphate, (D)-isomer

CAS number

Not Available

Weight

Average: 340.1157
Monoisotopic: 339.996048936

InChI Key

MCKAJXMRULSUKI-UZAAGFTCSA-N

InChI

InChI=1S/C6H14O12P2/c7-1-2(8)4(10)6(18-20(14,15)16)5(3(1)9)17-19(11,12)13/h1-10H,(H2,11,12,13)(H2,14,15,16)/t1-,2+,3-,4-,5+,6+/m0/s1

IUPAC Name

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

Traditional IUPAC Name

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

Chemical Formula

C₆H₁₄O₁₂P₂

SMILES

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

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:18156 )

Physical Properties

State

Not Available

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	23.7 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-4	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	0.66	ChemAxon
pKa (Strongest Basic)	-3.6	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	25.04 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

cell envelope
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Inositol Metabolism	PW002498
Inositol phosphate metabolism	PW002495

KEGG Pathways

Inositol phosphate metabolism

ec00562

SMPDB Reactions

Not Available

KEGG Reactions

water + 1D-myo-inositol 4,5-bisphosphate ↔ phosphate + 1-phosphatidyl-1D-myo-inositol 4-phosphate + hydron

water + 1D-myo-inositol 4,5-bisphosphate → phosphate + 1-phosphatidyl-1D-myo-inositol 4-phosphate + hydron

Adenosine triphosphate + 1-phosphatidyl-1D-myo-inositol 4-phosphate + hydron ↔ ADP + 1D-myo-inositol 4,5-bisphosphate

water + 1D-myo-inositol 4,5-bisphosphate → DG(16:0/16:0/0:0) + Inositol 1,4,5-trisphosphate

Adenosine triphosphate + 1-phosphatidyl-1D-myo-inositol 4-phosphate → ADP + 1D-myo-inositol 4,5-bisphosphate

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	splash10-0002-9332000000-8240ef1e1d222135238a	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-01ot-9010135000-910c6826f5ad1ed949c7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-2029000000-1195e7ce60913971906d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-2029000000-c3e0fac36289e655819f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000w-8920000000-3aa518a31c4e7bc4857c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-4009000000-40bb88d61d505ce29206	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9012000000-a144b2a1549f5a9a9b8a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-39772b52beaff83371d8	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
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
Resnick, A. C., Snowman, A. M., Kang, B. N., Hurt, K. J., Snyder, S. H., Saiardi, A. (2005). "Inositol polyphosphate multikinase is a nuclear PI3-kinase with transcriptional regulatory activity." Proc Natl Acad Sci U S A 102:12783-12788.16123124

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18156
HMDB ID	HMDB0062191
Pubchem Compound ID	125004
Kegg ID	C04637
ChemSpider ID	24808071
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Inositol polyphosphate multikinase

General function:: Involved in inositol trisphosphate 3-kinase activity
Specific function:: Has kinase activity and phosphorylates inositol-1,4,5- trisphosphate (Ins(1,4,5)P3) and inositol-1,3,4,5- tetrakisphosphate (Ins(1,3,4,5)P4). Has low kinase activity towards InsP6. Originally it was proposed that the ARGRI and ARGRIII proteins are more likely to be involved in the control of ARGRII activity
Gene Name:: ARG82
Uniprot ID:: P07250
Molecular weight:: 40352.5

Reactions

ATP + 1D-myo-inositol 1,4,5-trisphosphate → ADP + 1D-myo-inositol 1,4,5,6-tetrakisphosphate.
ATP + 1D-myo-inositol 1,4,5,6-tetrakisphosphate → ADP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphate.

1D-myo-inositol 4,5-bisphosphate (YMDB00764)

Structure for #<Compound:0xb0e35f48>

Enzymes

Reactions