P. aeruginosa Metabolome Database: undecaprenyl-diphospho-<i>N</i>-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl- D-alanyl-D-alanine (PAMDB110606)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110606

Identification

Name:

undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl- D-alanyl-D-alanine

Description:

The ion of overall charge −3 formed from undecaprenyldiphospho-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-L-lysyl-D-alanyl-D-alanine at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

mur2Ac(oyl-L-Ala-γ-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
lipid I

Chemical Formula:

C₈₆H₁₄₀N₇O₂₁P₂

Average Molecular Weight:

1670

Monoisotopic Molecular Weight:

1672.9890527429

InChI Key:

SULOOAFLXMQJSF-OGDYFQGPSA-K

InChI:

InChI=1S/C86H143N7O21P2/c1-57(2)30-20-31-58(3)32-21-33-59(4)34-22-35-60(5)36-23-37-61(6)38-24-39-62(7)40-25-41-63(8)42-26-43-64(9)44-27-45-65(10)46-28-47-66(11)48-29-49-67(12)53-55-110-115(106,107)114-116(108,109)113-86-77(91-72(17)95)79(78(97)75(56-94)112-86)111-71(16)82(100)88-69(14)81(99)93-74(85(104)105)51-52-76(96)92-73(50-18-19-54-87)83(101)89-68(13)80(98)90-70(15)84(102)103/h30,32,34,36,38,40,42,44,46,48,53,68-71,73-75,77-79,86,94,97H,18-29,31,33,35,37,39,41,43,45,47,49-52,54-56,87H2,1-17H3,(H,88,100)(H,89,101)(H,90,98)(H,91,95)(H,92,96)(H,93,99)(H,102,103)(H,104,105)(H,106,107)(H,108,109)/p-3/b58-32+,59-34+,60-36-,61-38-,62-40-,63-42-,64-44-,65-46-,66-48-,67-53-/t68-,69+,70-,71-,73+,74-,75-,77-,78-,79-,86-/m1/s1

CAS number:

Not Available

IUPAC Name:

N-[(4R)-4-({N-[(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-({[({[(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}phosphinato)oxy]phosphinato}oxy)tetrahydro-2H-pyran-4-yl]oxy}propanoyl]-L-alanyl}amino)-4-carboxylatobutanoyl]-6-azaniumyl-L-norleucyl-N-[(1R)-1-carboxylatoethyl]-D-alaninamide

Traditional IUPAC Name:

Not Available

SMILES:

CC(C)=CCCC(C)=CCCC(C)=CCCC(=CCCC(=CCCC(=CCCC(C)=CCCC(=CCCC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)OC1(OC(CO)C(O)C(OC(C)C(=O)NC(C)C(=O)NC(CCC(NC(CCCC[N+])C(=O)NC(C)C(NC(C(=O)[O-])C)=O)=O)C([O-])=O)C(NC(C)=O)1))([O-])=O)C)C)C)C)C)C)C

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
Polyprenyl phospho carbohydrate
Bactoprenol diphosphate
Alpha-oligopeptide
Polyprenyl monophosphate
Polyprenyl phosphate skeleton
Alpha peptide
Glutamine or derivatives
N-acyl-alpha-hexosamine
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Hexose monosaccharide
Alanine or derivatives
Monosaccharide phosphate
N-substituted-alpha-amino acid
Organic pyrophosphate
Alpha-amino acid or derivatives
Isoprenoid phosphate
Dicarboxylic acid or derivatives
Fatty amide
Monosaccharide
N-acyl-amine
Fatty acyl
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Acetamide
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid salt
Carboxamide group
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organic salt
Alcohol
Primary alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	1670.042 g/mol	PubChem
XLogP3-AA	13.2	PubChem
Hydrogen Bond Donor Count	9	PubChem
Hydrogen Bond Acceptor Count	21	PubChem
Rotatable Bond Count	57	PubChem
Exact Mass	1668.958 g/mol	PubChem
Monoisotopic Mass	1668.958 g/mol	PubChem
Topological Polar Surface Area	449 A^2	PubChem
Heavy Atom Count	116	PubChem
Formal Charge	-3	PubChem
Complexity	3560	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	11	PubChem
Undefined Atom Stereocenter Count	0	PubChem
Defined Bond Stereocenter Count	10	PubChem
Undefined Bond Stereocenter Count	0	PubChem
Covalently-Bonded Unit Count	1	PubChem

Biological Properties

Cellular Locations:

Not Available

Reactions:

UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + di-trans,octa-cis-undecaprenyl phosphate → undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl- D-alanyl-D-alanine + UMP
undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl- D-alanyl-D-alanine + UDP-N-acetyl-α-D-glucosamine → Hydrogen ion + undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + UDP

Pathways:

Spectra

Spectra:

Not Available

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
ChEBI	60032
KEGG	C05888
PubChem	46173369

undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl- D-alanyl-D-alanine (PAMDB110606)

Structure for undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl- D-alanyl-D-alanine (PAMDB110606)