2.0
2012-05-31 14:38:34 -0600
2015-06-03 17:19:45 -0600
ECMDB20310
M2MDB001145
Di-trans,poly-cis-undecaprenyl phosphate
Di-trans,poly-cis-undecaprenyl phosphate is an undecaprenyl phosphate having two (E)- and eight (Z)-double bonds. It is invovled in Peptidoglycan biosynthesis. (KEGG). Escherichia coli and other Gram-negative bacteria utilize the methylerythritol phosphate pathway to synthesize isopentenyl diphosphate and dimethylallyl diphosphate which are the precursors of (2E,6E)-farnesyl diphosphate. The latter compound is a precursor of di-trans,poly-cis-undecaprenyl phosphate, which leads to the biosynthesis of cell wall polymers. Initially (2E,6E)-farnesyl diphosphate is formed by the joining of geranyl diphosphate and isopentenyl diphosphate in a reaction catalyzed by geranyl diphosphate synthase / farnesyl diphosphate synthase encoded by gene ispA. Subsequently multiple units of isopentenyl diphosphate are polymerized to form di-trans,octa-cis-undecaprenyl diphosphate in a series of sequential condensation reactions catalyzed by undecaprenyl diphosphate synthase encoded by gene ispU.
<i>ditrans,octacis</i>-undecaprenyl phosphate
<i>ditrans,polycis</i>-undecaprenyl phosphate
Di-trans,poly-cis-undecaprenyl phosphoric acid
Ditrans,octacis-undecaprenyl phosphate
Ditrans,octacis-undecaprenyl phosphoric acid
Ditrans,polycis-undecaprenyl phosphate
Ditrans,polycis-undecaprenyl phosphoric acid
C55H89O4P
845.2665
844.649847848
{dioxo[(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxy]-λ⁵-phosphanuidyl}oxidanyl
{dioxo[(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxy]-λ⁵-phosphanuidyl}oxidanyl
CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO[P-]([O])(=O)=O
InChI=1S/C55H89O4P/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-59-60(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3/q-1
DCZTULDWWVSYKM-UHFFFAOYSA-N
Inner membrane
Membrane
Outer membrane
logp
9.49
ALOGPS
logs
-6.56
ALOGPS
solubility
2.36e-04 g/l
ALOGPS
logp
15.14
ChemAxon
iupac
{dioxo[(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxy]-λ⁵-phosphanuidyl}oxidanyl
ChemAxon
average_mass
845.2665
ChemAxon
mono_mass
844.649847848
ChemAxon
smiles
CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO[P-]([O])(=O)=O
ChemAxon
formula
C55H89O4P
ChemAxon
inchi
InChI=1S/C55H89O4P/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-59-60(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3/q-1
ChemAxon
inchikey
DCZTULDWWVSYKM-UHFFFAOYSA-N
ChemAxon
polar_surface_area
43.37
ChemAxon
refractivity
274.04
ChemAxon
polarizability
108.06
ChemAxon
rotatable_bond_count
33
ChemAxon
acceptor_count
3
ChemAxon
donor_count
0
ChemAxon
physiological_charge
-1
ChemAxon
formal_charge
-1
ChemAxon
Amino sugar and nucleotide sugar metabolism
ec00520
Peptidoglycan biosynthesis
ec00550
Cationic antimicrobial peptide (CAMP) resistance
eco01503
Metabolic pathways
eco01100
polymyxin resistance
PWY0-1338
enterobacterial common antigen biosynthesis
ECASYN-PWY
peptidoglycan biosynthesis I (<I>meso</I>-diaminopimelate containing)
PEPTIDOGLYCANSYN-PWY
Specdb::NmrOneD
302685
Specdb::NmrOneD
302686
Specdb::NmrOneD
302687
Specdb::NmrOneD
302688
Specdb::NmrOneD
302689
Specdb::NmrOneD
302690
Specdb::NmrOneD
302691
Specdb::NmrOneD
302692
Specdb::NmrOneD
302693
Specdb::NmrOneD
302694
Specdb::NmrOneD
302695
Specdb::NmrOneD
302696
Specdb::NmrOneD
302697
Specdb::NmrOneD
302698
Specdb::NmrOneD
302699
Specdb::NmrOneD
302700
Specdb::NmrOneD
302701
Specdb::NmrOneD
302702
Specdb::NmrOneD
302703
Specdb::NmrOneD
302704
25202932
C17556
CPD-9646
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.
21097882
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.
22080510
Phospho-N-acetylmuramoyl-pentapeptide-transferase
P0A6W3
MRAY_ECOLI
mraY
http://ecmdb.ca/proteins/P0A6W3.xml
Phosphatidylglycerophosphatase B
P0A924
PGPB_ECOLI
pgpB
http://ecmdb.ca/proteins/P0A924.xml
Undecaprenyl-phosphate alpha-N-acetylglucosaminyl 1-phosphate transferase
P0AC78
WECA_ECOLI
wecA
http://ecmdb.ca/proteins/P0AC78.xml
Undecaprenyl-diphosphatase
P60932
UPPP_ECOLI
uppP
http://ecmdb.ca/proteins/P60932.xml
Putative undecaprenyl-diphosphatase ybjG
P75806
YBJG_ECOLI
ybjG
http://ecmdb.ca/proteins/P75806.xml
Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase
P77757
ARNC_ECOLI
arnC
http://ecmdb.ca/proteins/P77757.xml
Undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase
P76473
ARNT_ECOLI
arnT
http://ecmdb.ca/proteins/P76473.xml
Inner membrane protein yeiU
P76445
YEIU_ECOLI
yeiU
http://ecmdb.ca/proteins/P76445.xml
di-trans,poly-cis-Undecaprenyl diphosphate + Water + Undecaprenyl diphosphate <> Di-trans,poly-cis-undecaprenyl phosphate + Phosphate
R05627
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate + UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) <> Uridine 5'-monophosphate + MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
R05629
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine
R05630
Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + Di-trans,poly-cis-undecaprenyl phosphate <> Undecaprenyl phosphate alpha-L-Ara4FN + Uridine 5'-diphosphate + 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate
R07661
Uridine diphosphate-N-acetylglucosamine + Di-trans,poly-cis-undecaprenyl phosphate <> N-Acetyl-D-glucosaminyldiphosphoundecaprenol + Uridine 5'-monophosphate + N-Acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol
R08856
Undecaprenyl phosphate alpha-L-Ara4N + 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> Lipid IIA + Di-trans,poly-cis-undecaprenyl phosphate
R09773
Undecaprenyl phosphate alpha-L-Ara4N + Di[3-deoxy-D-manno-octulosonyl]-lipid IV(A) <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid IVA + Di-trans,poly-cis-undecaprenyl phosphate
R09774
Hydrogen ion + Lipid A-core + Undecaprenyl diphosphate lipid A-core 1-diphosphate + Di-trans,poly-cis-undecaprenyl phosphate
RXN0-5383
Di-trans,poly-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + Uridine 5'-monophosphate
GLCNACPTRANS-RXN
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate > N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol + Uridine 5'-monophosphate
PHOSNACMURPENTATRANS-RXN
KDO2-Lipid A + 4-amino-4-deoxy-α-L-arabinopyranosyl <i>ditrans,octacis</i>-undecaprenyl phosphate > L-Ara4N-modified KDO2-Lipid A + Di-trans,poly-cis-undecaprenyl phosphate
RXN0-2001
Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + Di-trans,poly-cis-undecaprenyl phosphate > 4-deoxy-4-formamido-α-L-arabinopyranosyl <i>ditrans,octacis</i>-undecaprenyl phosphate + Uridine 5'-diphosphate
RXN0-3521
Undecaprenyl diphosphate + Water > Hydrogen ion + Di-trans,poly-cis-undecaprenyl phosphate + Phosphate
UNDECAPRENYL-DIPHOSPHATASE-RXN
undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + Di-trans,poly-cis-undecaprenyl phosphate + Lipid IIA
R09781
UDP-Glucose + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + alpha-D-Glucopyranosyl-diphospho-ditrans,octacis-undecaprenol
R09641
di-trans,octa-cis-undecaprenyl diphosphate + Water + Undecaprenyl diphosphate <> Di-trans,poly-cis-undecaprenyl phosphate + Phosphate
undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + Di-trans,poly-cis-undecaprenyl phosphate + Lipid IIA