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MetaCyc Compound: L,L-di-myo-inositol 1,3'-phosphate

Synonyms: DIP, di-myo-inositol phosphate, bis(1L-myo-inositol) 1,3'-phosphate

Superclasses: an alcohola cyclic alcohola cyclitolan inositola modified inositolan inositol phosphate

Di-myo-inositol phosphate (DIP) is the most widespread organic solute in microorganisms adapted to hot environments. It was first identified in Pyrococcus woesei, in which it is the dominant counterion of K+, which ranges from 500 to 600 mM [Scholz92]. Since then it has been detected in many archaebacteria [Ciulla94, Goncalves03, Lamosa98, Lamosa06, Martins96, Martins97] and some thermophilic bacteria [Empadinhas07]. So far DIP has not been encountered in organisms with optimal growth temperatures below 60°C, and is believed to play a role in the thermoprotection of cellular components [Rodrigues07].

Chemical Formula: C12H22O14P

Molecular Weight: 421.27 Daltons

Monoisotopic Molecular Weight: 422.08254195769996 Daltons

L,L-di-<i>myo</i>-inositol 1,3'-phosphate compound structure

SMILES: C2(O)(C(O)C(O)C(OP([O-])(OC1(C(O)C(O)C(O)C(O)C(O)1))=O)C(O)C(O)2)

InChI: InChI=1S/C12H23O14P/c13-1-3(15)7(19)11(8(20)4(1)16)25-27(23,24)26-12-9(21)5(17)2(14)6(18)10(12)22/h1-22H,(H,23,24)/p-1/t1-,2-,3-,4+,5-,6+,7-,8-,9+,10+,11-,12-


Unification Links: PubChem:50986199

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -385.26736Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
a cyclic alcohol + a quinone → a cyclic ketone + a quinol

Reactions known to produce the compound:

di-myo-inositol phosphate biosynthesis :
bis(1L-myo-inositol) 3,1'-phosphate 1-phosphate + H2O → L,L-di-myo-inositol 1,3'-phosphate + phosphate

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphate acquisition :
a phosphate monoester + H2O → an alcohol + phosphate

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
a 6-phospho-β-D-galactoside + H2O → D-galactopyranose 6-phosphate + an alcohol
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol

In Reactions of unknown directionality:

Not in pathways:
an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
trans-cinnamoyl-β-D-glucoside + an alcohol = alkyl cinnamate + D-glucopyranose
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

Enzymes activated by L,L-di-myo-inositol 1,3'-phosphate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: phosphoenolpyruvate carboxylase [Izui83]

Created 29-Nov-2010 by Caspi R, SRI International


Ciulla94: Ciulla RA, Burggraf S, Stetter KO, Roberts MF (1994). "Occurrence and Role of Di-myo-Inositol-1,1'-Phosphate in Methanococcus igneus." Appl Environ Microbiol 60(10);3660-4. PMID: 16349412

Empadinhas07: Empadinhas N, Mendes V, Simoes C, Santos MS, Mingote A, Lamosa P, Santos H, Costa MS (2007). "Organic solutes in Rubrobacter xylanophilus: the first example of di-myo-inositol-phosphate in a thermophile." Extremophiles 11(5);667-73. PMID: 17510735

Goncalves03: Goncalves LG, Huber R, da Costa MS, Santos H (2003). "A variant of the hyperthermophile Archaeoglobus fulgidus adapted to grow at high salinity." FEMS Microbiol Lett 218(2);239-44. PMID: 12586398

Izui83: Izui K, Matsuda Y, Kameshita I, Katsuki H, Woods AE (1983). "Phosphoenolpyruvate carboxylase of Escherichia coli. Inhibition by various analogs and homologs of phosphoenolpyruvate." J Biochem (Tokyo) 1983;94(6);1789-95. PMID: 6368527

Lamosa06: Lamosa P, Goncalves LG, Rodrigues MV, Martins LO, Raven ND, Santos H (2006). "Occurrence of 1-glyceryl-1-myo-inosityl phosphate in hyperthermophiles." Appl Environ Microbiol 72(9);6169-73. PMID: 16957243

Lamosa98: Lamosa P, Martins LO, Da Costa MS , Santos H (1998). "Effects of temperature, salinity, and medium composition on compatible solute accumulation by thermococcus spp." Appl Environ Microbiol 64(10);3591-8. PMID: 9758772

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Martins96: Martins LO, Carreto LS, Da Costa MS, Santos H (1996). "New compatible solutes related to Di-myo-inositol-phosphate in members of the order Thermotogales." J Bacteriol 178(19);5644-51. PMID: 8824608

Martins97: Martins LO, Huber R, Huber H, Stetter KO, Da Costa MS, Santos H (1997). "Organic Solutes in Hyperthermophilic Archaea." Appl Environ Microbiol 63(3);896-902. PMID: 16535556

Rodrigues07: Rodrigues MV, Borges N, Henriques M, Lamosa P, Ventura R, Fernandes C, Empadinhas N, Maycock C, da Costa MS, Santos H (2007). "Bifunctional CTP:inositol-1-phosphate cytidylyltransferase/CDP-inositol:inositol-1-phosphate transferase, the key enzyme for di-myo-inositol-phosphate synthesis in several (hyper)thermophiles." J Bacteriol 189(15);5405-12. PMID: 17526717

Scholz92: Scholz S, Sonnenbichler J, Schafer W, Hensel R (1992). "Di-myo-inositol-1,1'-phosphate: a new inositol phosphate isolated from Pyrococcus woesei." FEBS Lett 306(2-3);239-42. PMID: 1633880

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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