P. aeruginosa Metabolome Database: GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol (PAMDB003414)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB003414

Identification

Name:

GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

Description:

GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol is an intermediate in peptidoglycan synthesis. It is a substrate for peptidoglycan glycosyltransferase (EC 2.4.1.129) which catalyzes the chemical reaction [GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n- diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)- diphosphoundecaprenol <=> [GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n+1- diphosphoundecaprenol + undecaprenyl diphosphate.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2R)-2-(2S)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-5-(2S,3R,4R,5S,6R)-3-acetamido-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yloxy-2-hydroxy-hydroxy-(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaenoxyphosphoryloxyphosphoryloxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-5-(2S)-6-amino-1-(2R)-1-(1R)-1-carboxyethylamino-1-oxopropan-2-ylamino-1-oxohexan-2-ylamino-5-oxopentanoate
(2R)-2-(2S)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-5-(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yloxy-2-hydroxy-hydroxy-(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaenoxyphosphoryloxyphosphoryloxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-5-(2S)-6-amino-1-(2R)-1-(1R)-1-carboxyethylamino-1-oxopropan-2-ylamino-1-oxohexan-2-ylamino-5-oxopentanoic acid
(2R,5R,8S,13R,16S,19R)-19-{(2R,3R,4R,5S,6R)-3-acetamido-5-{(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy}-2-({hydroxy(hydroxy{(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yloxy}phosphoryl)oxyphosphoryl}oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-8-(4-aminobutyl)-13-carboxy-2,5,16-trimethyl-4,7,10,15,18-pentaoxo-3,6,9,14,17-pentaazaicosan-1-Oate (N
(2R,5R,8S,13R,16S,19R)-19-{(2R,3R,4R,5S,6R)-3-Acetamido-5-{(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy}-2-({hydroxy(hydroxy{(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yloxy}phosphoryl)oxyphosphoryl}oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-8-(4-aminobutyl)-13-carboxy-2,5,16-trimethyl-4,7,10,15,18-pentaoxo-3,6,9,14,17-pentaazaicosan-1-oic acid (n
GlcNAc-(1->4)-mur2ac(oyl-L-ala-g-D-glu-L-lys-D-ala-D-ala)-diphosphoundecaprenol
GlcNAc-(1->4)-mur2ac(oyl-L-ala-γ-D-glu-L-lys-D-ala-D-ala)-diphosphoundecaprenol
Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-g-D-glutamyl-L-lysyl-D-alanyl-D-alanine
Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine
Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine
undecaprenyldiphospho-N-Acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-g-glutamyl-L-lysyl-D-alanyl-D-alanine
Undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-gamma-glutamyl-L-lysyl-D-alanyl-D-alanine
undecaprenyldiphospho-N-Acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-γ-glutamyl-L-lysyl-D-alanyl-D-alanine

Chemical Formula:

C₉₄H₁₅₆N₈O₂₆P₂

Average Molecular Weight:

1876.23

Monoisotopic Molecular Weight:

1875.060600228

InChI Key:

ULXTYUPMJXVUHQ-OVTFQNCVSA-N

InChI:

InChI=1S/C94H156N8O26P2/c1-59(2)31-21-32-60(3)33-22-34-61(4)35-23-36-62(5)37-24-38-63(6)39-25-40-64(7)41-26-42-65(8)43-27-44-66(9)45-28-46-67(10)47-29-48-68(11)49-30-50-69(12)54-56-122-129(118,119)128-130(120,121)127-94-82(100-75(18)106)86(85(79(58-104)125-94)126-93-81(99-74(17)105)84(109)83(108)78(57-103)124-93)123-73(16)89(112)96-71(14)88(111)102-77(92(116)117)52-53-80(107)101-76(51-19-20-55-95)90(113)97-70(13)87(110)98-72(15)91(114)115/h31,33,35,37,39,41,43,45,47,49,54,70-73,76-79,81-86,93-94,103-104,108-109H,19-30,32,34,36,38,40,42,44,46,48,50-53,55-58,95H2,1-18H3,(H,96,112)(H,97,113)(H,98,110)(H,99,105)(H,100,106)(H,101,107)(H,102,111)(H,114,115)(H,116,117)(H,118,119)(H,120,121)/b60-33+,61-35+,62-37-,63-39-,64-41-,65-43-,66-45-,67-47-,68-49-,69-54-/t70-,71+,72-,73-,76+,77-,78-,79-,81-,82-,83-,84-,85-,86-,93+,94-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2R)-4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-2-[(2S)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-{[hydroxy({[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-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})phosphoryl]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanoic acid

Traditional IUPAC Name:

lipid II

SMILES:

NCCCC[C@H](NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@@H]1NC(C)=O)C(O)=O)C(=O)N[C@H](C)C(=O)N[C@H](C)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Polyprenyl phospho carbohydrates

Alternative Parents

Substituents

Polyterpenoid
Bactoprenol diphosphate
Polyprenyl phospho carbohydrate
Alpha peptide
N-acyl-alpha-hexosamine
Disaccharide phosphate
N-acyl-aliphatic-alpha amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Glucosamine
Amino sugar
O-glycosyl compound
Glycosyl compound
Disaccharide
Organic pyrophosphate
Isoprenoid phosphate
Alpha-amino acid or derivatives
Monoalkyl phosphate
Amino saccharide
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Organic phosphate
Dicarboxylic acid or derivatives
Saccharide
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Acetal
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

undecaprenyldiphospho-N-acetylmuramoyl peptide (CHEBI:27692 )
Bactoprenol diphosphates (C05893 )

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.0031 mg/mL	ALOGPS
logP	3.23	ALOGPS
logP	8.79	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	1.71	ChemAxon
pKa (Strongest Basic)	10.19	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	524.45 Å²	ChemAxon
Rotatable Bond Count	63	ChemAxon
Refractivity	503.83 m³·mol^-1	ChemAxon
Polarizability	202.75 Å³	ChemAxon
Number of Rings	2	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:

Membrane

Reactions:

(GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol > (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + Undecaprenyl diphosphate
Uridine diphosphate-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol > Uridine 5'-diphosphate + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

Pathways:

Not Available

Spectra

Spectra:

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	27692
HMDB ID	Not Available
Pubchem Compound ID	46173749
Kegg ID	C05893
ChemSpider ID	26333143
Wikipedia ID	Not Available
BioCyc ID	Not Available

GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol (PAMDB003414)

Structure for GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol (PAMDB003414)