P. aeruginosa Metabolome Database: UDP-<i>N</i>-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-<I>meso</I>-2,6-diaminopimeloyl-D-alanyl-D-alanine (PAMDB110521)

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

PAMDB110521

Identification

Name:

UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine

Description:

Tetranion of UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine having anionic diphosphate and carboxy groups and a cationic amino group.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

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

Chemical Formula:

C₄₁H₆₁N₉O₂₈P₂

Average Molecular Weight:

1189.9

Monoisotopic Molecular Weight:

1194.3492506042

InChI Key:

IMWOXEZVYQDRDF-MCZXNMLPSA-J

InChI:

InChI=1S/C41H65N9O28P2/c1-15(32(58)45-17(3)37(62)63)44-35(61)21(8-6-7-20(42)38(64)65)47-25(53)10-9-22(39(66)67)48-33(59)16(2)43-34(60)18(4)74-31-27(46-19(5)52)40(76-23(13-51)29(31)56)77-80(71,72)78-79(69,70)73-14-24-28(55)30(57)36(75-24)50-12-11-26(54)49-41(50)68/h11-12,15-18,20-24,27-31,36,40,51,55-57H,6-10,13-14,42H2,1-5H3,(H,43,60)(H,44,61)(H,45,58)(H,46,52)(H,47,53)(H,48,59)(H,62,63)(H,64,65)(H,66,67)(H,69,70)(H,71,72)(H,49,54,68)/p-4/t15-,16+,17-,18-,20-,21+,22-,23-,24-,27-,28-,29-,30-,31-,36-,40-/m1/s1

CAS number:

Not Available

IUPAC Name:

Not Available

Traditional IUPAC Name:

Not Available

SMILES:

CC(C(=O)NC(C)C([O-])=O)NC(=O)C(CCCC([N+])C(=O)[O-])NC(=O)CCC(C(=O)[O-])NC(=O)C(C)NC(=O)C(C)OC1(C(O)C(CO)OC(C(NC(=O)C)1)OP([O-])(OP([O-])(OCC2(C(O)C(O)C(O2)N3(C=CC(=O)NC(=O)3)))=O)=O)

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pentose-5-phosphate
Pentose phosphate
N-acyl-alpha-hexosamine
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-glycosyl compound
Glycosyl compound
Alanine or derivatives
Monosaccharide phosphate
Organic pyrophosphate
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Tricarboxylic acid or derivatives
Pyrimidone
Fatty amide
Hydropyrimidine
Monosaccharide
N-acyl-amine
Organic phosphoric acid derivative
Fatty acyl
Oxane
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Vinylogous amide
Tetrahydrofuran
Acetamide
Heteroaromatic compound
Carboxamide group
Urea
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Carboxylic acid salt
Organoheterocyclic compound
Azacycle
Oxacycle
Dialkyl ether
Carboxylic acid
Ether
Organooxygen compound
Organonitrogen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Primary alcohol
Organic salt
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	1189.922 g/mol	PubChem
XLogP3-AA	-9	PubChem
Hydrogen Bond Donor Count	12	PubChem
Hydrogen Bond Acceptor Count	28	PubChem
Rotatable Bond Count	28	PubChem
Exact Mass	1189.31 g/mol	PubChem
Monoisotopic Mass	1189.31 g/mol	PubChem
Topological Polar Surface Area	589 A^2	PubChem
Heavy Atom Count	80	PubChem
Formal Charge	-4	PubChem
Complexity	2410	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	16	PubChem
Undefined Atom Stereocenter Count	0	PubChem
Defined Bond Stereocenter Count	0	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-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + trans,octacis-decaprenyl phosphate → decaprenyl-diphospho-N-acetylmuramoyl-pentapeptide + UMP
UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Water → UDP-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimeloyl-D-alanine + D-Alanine

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
UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-DAP-containing)PWY-6387
peptidoglycan biosynthesis III (mycobacteria)PWY-6385

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	61386
IAF1260	44801
KEGG	C04882
PubChem	25244658

UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine (PAMDB110521)

Structure for UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine (PAMDB110521)