P. aeruginosa Metabolome Database: <i>di-trans,octa-cis</i>-undecaprenyl diphosphate (PAMDB110809)

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

PAMDB110809

Identification

Name:

di-trans,octa-cis-undecaprenyl diphosphate

Description:

The trianion of di-trans,poly-cis-undecaprenyl diphosphate.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

di-trans-poly-cis-undecaprenyl diphosphate
undecaprenyl-PP (ambiguous)
bactoprenyl pyrophosphate
undecaprenyl pyrophosphate (ambiguous)
UPP (ambiguous)
di-trans,octa-cis-undecaprenyl diphosphate

Chemical Formula:

C₅₅H₈₉O₇P₂

Average Molecular Weight:

924.25

Monoisotopic Molecular Weight:

926.6318283279

InChI Key:

NTXGVHCCXVHYCL-NTDVEAECSA-K

InChI:

InChI=1S/C55H92O7P2/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-61-64(59,60)62-63(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H,59,60)(H2,56,57,58)/p-3/b46-25+,47-27+,48-29-,49-31-,50-33-,51-35-,52-37-,53-39-,54-41-,55-43-

CAS number:

Not Available

IUPAC Name:

{[(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 phosphonato]oxy}phosphonate

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-])=O)([O-])=O)C)C)C)C)C)C)C

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Bactoprenol diphosphates

Alternative Parents

Substituents

Polyterpenoid
Bactoprenol diphosphate
Polyprenyl diphosphate
Polyprenyl monophosphate
Organic pyrophosphate
Isoprenoid phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a di-\u003ci\u003etrans\u003c/i\u003e, poly-\u003ci\u003ecis\u003c/i\u003e-polyisoprenyl diphosphate (UNDECAPRENYL-DIPHOSPHATE)

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	924.258 g/mol	PubChem
XLogP3-AA	17.2	PubChem
Hydrogen Bond Donor Count	0	PubChem
Hydrogen Bond Acceptor Count	7	PubChem
Rotatable Bond Count	34	PubChem
Exact Mass	923.608 g/mol	PubChem
Monoisotopic Mass	923.608 g/mol	PubChem
Topological Polar Surface Area	122 A^2	PubChem
Heavy Atom Count	64	PubChem
Formal Charge	-3	PubChem
Complexity	1780	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	0	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:

di-trans,octa-cis-undecaprenyl diphosphate + Water → Hydrogen ion + di-trans,octa-cis-undecaprenyl phosphate + phosphate
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
a peptidoglycan dimer (E. faeciums) + Water → Hydrogen ion + a peptidoglycan with D,D cross-link (E. faecium) + D-Alanine + di-trans,octa-cis-undecaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate → di-trans,octa-cis-undecaprenyl diphosphate + diphosphate
a peptidoglycan dimer (S. aureus) + Water → Hydrogen ion + a peptidoglycan with D,D cross-link (S. aureus) + D-Alanine + di-trans,octa-cis-undecaprenyl diphosphate

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
di-trans,poly-cis-undecaprenyl phosphate biosynthesisPWY-5785

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	58405
IAF1260	42055
KEGG	C04574
PubChem	25245563

di-trans,octa-cis-undecaprenyl diphosphate (PAMDB110809)

Structure for di-trans,octa-cis-undecaprenyl diphosphate (PAMDB110809)