P. aeruginosa Metabolome Database: Octaprenyl diphosphate (PAMDB000251)

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

PAMDB000251

Identification

Name:

Octaprenyl diphosphate

Description:

Octaprenyl diphosphate belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)Octaprenyl diphosphate is invovled in Terpenoid backbone biosynthesis, Ubiquinone and other terpenoid-quinone biosynthesis, and Biosynthesis of secondary metabolites. (KEGG)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

All-trans-octaprenyl diphosphate
all-trans-Octaprenyl diphosphoric acid
Farnesylfarnesylgeraniol
Octaprenyl diphosphate
Octaprenyl diphosphoric acid
Octaprenyl pyrophosphate
Octaprenyl pyrophosphoric acid
Octaprenyl-PP
OPP
OPrPP

Chemical Formula:

C₄₀H₆₈O₇P₂

Average Molecular Weight:

722.9112

Monoisotopic Molecular Weight:

722.444027554

InChI Key:

IKKLDISSULFFQO-DJMILUHSSA-N

InChI:

InChI=1S/C40H68O7P2/c1-33(2)17-10-18-34(3)19-11-20-35(4)21-12-22-36(5)23-13-24-37(6)25-14-26-38(7)27-15-28-39(8)29-16-30-40(9)31-32-46-49(44,45)47-48(41,42)43/h17,19,21,23,25,27,29,31H,10-16,18,20,22,24,26,28,30,32H2,1-9H3,(H,44,45)(H2,41,42,43)/b34-19+,35-21+,36-23+,37-25+,38-27+,39-29+,40-31+

CAS number:

Not Available

IUPAC Name:

{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid

Traditional IUPAC Name:

octaprenyl pyrophosphate

SMILES:

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

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

Bactoprenol diphosphate
Organic pyrophosphate
Isoprenoid phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C40 isoprenoids (tetraterpenes) (C04146 )
Polyterpenoids (C04146 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	5.072	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.00037 mg/mL	ALOGPS
logP	7.6	ALOGPS
logP	11.92	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	215.74 m³·mol^-1	ChemAxon
Polarizability	86.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Membrane

Reactions:

Pathways:

Terpenoid backbone biosynthesis pae00900
Ubiquinone and other terpenoid-quinone biosynthesis pae00130

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0595-0201096600-12d9480675cd5f367894	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-3212193000-99403f42aaf79fd7add2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ke-2335391000-ecd9b80ad726186992c4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0400000900-88615cb1e1738fc988da	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9400000000-62cd480f8009a6a20390	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fdd80c5aec3a18d6c4d0	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Okada K, Suzuki K, Kamiya Y, Zhu X, Fujisaki S, Nishimura Y, Nishino T, Nakagawa T, Kawamukai M, Matsuda H: Polyprenyl diphosphate synthase essentially defines the length of the side chain of ubiquinone. Biochim Biophys Acta. 1996 Aug 16;1302(3):217-23. Pubmed: 8765142
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16275
HMDB ID	HMDB01094
Pubchem Compound ID	5280651
Kegg ID	C04146
ChemSpider ID	4444251
Wikipedia ID	Not Available
BioCyc ID	CPD-9454
EcoCyc ID	CPD-9454
Ligand Expo	OTP

Octaprenyl diphosphate (PAMDB000251)

Structure for Octaprenyl diphosphate (PAMDB000251)