P. aeruginosa Metabolome Database: undecaprenyldiphospho-<i>N</i>-acetylmuramoyl-L-alanyl-γ-D-glutamyl-<I>meso</I>-2,6-diaminopimeloyl-D-alanyl-D-alanine (PAMDB110605)

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

PAMDB110605

Identification

Name:

undecaprenyldiphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine

Description:

The organophosphate oxoanion of overall charge −4 formed from undecaprenyldiphospho-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate-D-alanyl-D-alanine-diphosphoundecaprenol
a peptidoglycan with cleaved N-acetyl-glucosamine
lipid intermediate I
undecaprenyl-pyrophosphoryl-MurNAc-pentapeptide

Chemical Formula:

C₈₇H₁₃₉N₇O₂₃P₂

Average Molecular Weight:

1713

Monoisotopic Molecular Weight:

1716.9788819871

InChI Key:

PNWZQTONLRRPST-KLDRQJOASA-J

InChI:

InChI=1S/C87H143N7O23P2/c1-56(2)29-18-30-57(3)31-19-32-58(4)33-20-34-59(5)35-21-36-60(6)37-22-38-61(7)39-23-40-62(8)41-24-42-63(9)43-25-44-64(10)45-26-46-65(11)47-27-48-66(12)53-54-113-118(109,110)117-119(111,112)116-87-77(92-71(17)96)79(78(98)75(55-95)115-87)114-70(16)82(101)89-68(14)81(100)94-74(86(107)108)51-52-76(97)93-73(50-28-49-72(88)85(105)106)83(102)90-67(13)80(99)91-69(15)84(103)104/h29,31,33,35,37,39,41,43,45,47,53,67-70,72-75,77-79,87,95,98H,18-28,30,32,34,36,38,40,42,44,46,48-52,54-55,88H2,1-17H3,(H,89,101)(H,90,102)(H,91,99)(H,92,96)(H,93,97)(H,94,100)(H,103,104)(H,105,106)(H,107,108)(H,109,110)(H,111,112)/p-4/b57-31+,58-33+,59-35-,60-37-,61-39-,62-41-,63-43-,64-45-,65-47-,66-53-/t67-,68+,69-,70-,72-,73+,74-,75-,77-,78-,79-,87-/m1/s1

CAS number:

Not Available

IUPAC Name:

Not Available

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(C(NC(=O)C)C(OC(C)C(=O)NC(C)C(=O)NC(C(=O)[O-])CCC(=O)NC(CCCC([N+])C(=O)[O-])C(NC(C)C(=O)NC(C)C([O-])=O)=O)C(O)C(CO)O1))([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
N-acyl-alpha-hexosamine
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Hexose monosaccharide
Alanine or derivatives
Organic pyrophosphate
Monosaccharide phosphate
N-substituted-alpha-amino acid
Isoprenoid phosphate
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
N-acyl-amine
Phosphoric acid ester
Fatty amide
Oxane
Alkyl phosphate
Fatty acyl
Organic phosphoric acid derivative
Monosaccharide
Acetamide
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid salt
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Organic oxide
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic salt
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	1713.043 g/mol	PubChem
XLogP3-AA	13.5	PubChem
Hydrogen Bond Donor Count	9	PubChem
Hydrogen Bond Acceptor Count	23	PubChem
Rotatable Bond Count	57	PubChem
Exact Mass	1711.94 g/mol	PubChem
Monoisotopic Mass	1711.94 g/mol	PubChem
Topological Polar Surface Area	490 A^2	PubChem
Heavy Atom Count	119	PubChem
Formal Charge	-4	PubChem
Complexity	3700	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	10	PubChem
Undefined Atom Stereocenter Count	2	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:

Pathways:

KDO₂-lipid A and peptidoglycan biosynthesisKDO-PEP-LIPASYN-PWY
peptidoglycan biosynthesis I (meso-diaminopimelate containing)PEPTIDOGLYCANSYN-PWY
peptidoglycan and lipid A precursor biosynthesisPEP-LIPA-SYN-PWY

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	61387
IAF1260	46787
KEGG	C05897
PubChem	25245499
PubChem	52940090

undecaprenyldiphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine (PAMDB110605)

Structure for undecaprenyldiphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine (PAMDB110605)