P. aeruginosa Metabolome Database: ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine (PAMDB110607)

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

PAMDB110607

Identification

Name:

ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine

Description:

The organophosphate oxoanion of overall charge −4 being the major microspecies of undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine present at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

diphosphoundecaprenyl-[GlcNAc-MurNAc-pentapeptide]_n
lipid intermediate II
undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-ala-γ-D-glu-meso-2,6-diaminopimeloyl-D-ala-D-ala
lipid II

Chemical Formula:

C₉₅H₁₅₂N₈O₂₈P₂

Average Molecular Weight:

1916.2

Monoisotopic Molecular Weight:

1920.0582545201

InChI Key:

OXJNZXDFVLDLEI-MBCYCBSHSA-J

InChI:

InChI=1S/C95H156N8O28P2/c1-58(2)30-19-31-59(3)32-20-33-60(4)34-21-35-61(5)36-22-37-62(6)38-23-39-63(7)40-24-41-64(8)42-25-43-65(9)44-26-45-66(10)46-27-47-67(11)48-28-49-68(12)54-55-125-132(121,122)131-133(123,124)130-95-82(101-74(18)107)86(85(79(57-105)128-95)129-94-81(100-73(17)106)84(110)83(109)78(56-104)127-94)126-72(16)89(113)97-70(14)88(112)103-77(93(119)120)52-53-80(108)102-76(51-29-50-75(96)92(117)118)90(114)98-69(13)87(111)99-71(15)91(115)116/h30,32,34,36,38,40,42,44,46,48,54,69-72,75-79,81-86,94-95,104-105,109-110H,19-29,31,33,35,37,39,41,43,45,47,49-53,55-57,96H2,1-18H3,(H,97,113)(H,98,114)(H,99,111)(H,100,106)(H,101,107)(H,102,108)(H,103,112)(H,115,116)(H,117,118)(H,119,120)(H,121,122)(H,123,124)/p-4/b59-32+,60-34+,61-36-,62-38-,63-40-,64-42-,65-44-,66-46-,67-48-,68-54-/t69-,70+,71-,72-,75-,76+,77-,78-,79-,81-,82-,83-,84-,85-,86-,94+,95-/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)OC2(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(OC1(OC(CO)C(O)C(O)C(NC(=O)C)1))C(CO)O2))([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
Disaccharide phosphate
Glutamine or derivatives
N-acyl-alpha-hexosamine
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Disaccharide
Alanine or derivatives
O-glycosyl compound
Glycosyl compound
N-substituted-alpha-amino acid
Organic pyrophosphate
Isoprenoid phosphate
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Organic phosphoric acid derivative
Alkyl phosphate
Oxane
Phosphoric acid ester
Acetamide
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid salt
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Acetal
Ether
Dialkyl ether
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organic salt
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
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	1916.237 g/mol	PubChem
XLogP3-AA	11.3	PubChem
Hydrogen Bond Donor Count	12	PubChem
Hydrogen Bond Acceptor Count	28	PubChem
Rotatable Bond Count	61	PubChem
Exact Mass	1916.022 g/mol	PubChem
Monoisotopic Mass	1915.019 g/mol	PubChem
Topological Polar Surface Area	578 A^2	PubChem
Heavy Atom Count	133	PubChem
Formal Charge	-4	PubChem
Complexity	4190	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	17	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:

Peptidoglycan-with-DAP-pentapeptide + ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine → di-trans,octa-cis-undecaprenyl diphosphate + Peptidoglycan-with-DAP-pentapeptide

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
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	61388
IAF1260	46790
KEGG	C05898
PubChem	52940208

ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine (PAMDB110607)

Structure for ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine (PAMDB110607)