ECMDB: Octaprenyl diphosphate (ECMDB01094) (M2MDB000251)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (738)

Record Information

Version

2.0

Creation Date

2012-05-31 13:45:03 -0600

Update Date

2015-06-03 15:53:43 -0600

Secondary Accession Numbers

ECMDB01094

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

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

Weight:

Average: 722.9112
Monoisotopic: 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

Description

belongs to the class of organic compounds known as tetraterpenoids. These are terpenoid molecules containing 10 consecutively linked isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Tetraterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

all-trans-polyprenyl diphosphate (CHEBI:16275 )
octaprenyl diphosphate (CHEBI:16275 )
C40 isoprenoids (tetraterpenes) (C04146 )
Polyterpenoids (C04146 )
C40 isoprenoids (tetraterpenes) (LMPR01070226 )

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 g/L	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:

SMPDB Pathways:

Menaquinol biosythesis	PW001897
Secondary Metabolites: Ubiquinol biosynthesis	PW000981
Secondary Metabolites: Ubiquinol biosynthesis 2	PW002036
Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesis	PW000958

KEGG Pathways:

Terpenoid backbone biosynthesis ec00900
Ubiquinone and other terpenoid-quinone biosynthesis ec00130

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ar4-9586675700-c09c2172d7687ee2bec8	View in MoNA
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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000900-0e05243384d31408f117	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-2400012900-2af9ecf51e941f2cf27e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9400000000-12bf027442e46427ee3b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1100045900-3d26e24195e3426533cb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7n-0001189000-532965cd65681f27a370	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02dj-0529441000-76d7ae0a97092fd5d7a8	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

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

Enzymes

Protein Details

1. 1,4-dihydroxy-2-naphthoate octaprenyltransferase

General function:: Involved in transferase activity
Specific function:: Conversion of 1,4-dihydroxy-2-naphthoate (DHNA) to dimethylmenaquinone (DMK). Attaches octaprenylpyrophosphate, a membrane-bound 40-carbon side chain to DHNA. The conversion of DHNA to DMK proceeds in three stages:the removal of the carboxyl group of DHNA as CO(2), the attachment of the isoprenoid side chain, and a quinol-to-quinone oxidation, which is thought to be spontaneous
Gene Name:: menA
Uniprot ID:: P32166
Molecular weight:: 33594

Reactions

An all-trans-polyprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = a demethylmenaquinol + diphosphate + CO(2).

Protein Details

2. 4-hydroxybenzoate octaprenyltransferase

General function:: Involved in prenyltransferase activity
Specific function:: Synthesis of 3-octaprenyl-4-hydroxybenzoate
Gene Name:: ubiA
Uniprot ID:: P0AGK1
Molecular weight:: 32511

Reactions

4-hydroxybenzoate + farnesylfarnesylgeraniol = 3-octaprenyl-4-hydroxybenzoate.

Protein Details

3. Octaprenyl-diphosphate synthase

General function:: Involved in isoprenoid biosynthetic process
Specific function:: Supplies octaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone and menaquinone
Gene Name:: ispB
Uniprot ID:: P0AD57
Molecular weight:: 35217

Reactions

(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-octaprenyl diphosphate.

Octaprenyl diphosphate (ECMDB01094) (M2MDB000251)

Structure for #<Compound:0xa33a2124>

Enzymes

Reactions

Reactions

Reactions