Showing Compound Geranyl diphosphate (FDB001463)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:58 UTC

Update date

2020-09-17 15:41:14 UTC

Primary ID

FDB001463

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Geranyl diphosphate

Description

Geranyl-PP, also known as neryl diphosphate, belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit. Thus, geranyl-PP is considered to be an isoprenoid lipid molecule. Geranyl-PP is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

CAS Number

763-10-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Geranyl pyrophosphate	ChEBI
Polyisopentenylpyrophosphate	Kegg
Polyisopentenyldiphosphate	Kegg
trans-Polyisopentenyldiphosphate	Kegg
Polyprenyl diphosphate	Kegg
Geranyl pyrophosphoric acid	Generator
Polyisopentenylpyrophosphoric acid	Generator
Polyisopentenyldiphosphoric acid	Generator
trans-Polyisopentenyldiphosphoric acid	Generator
Polyprenyl diphosphoric acid	Generator
(2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate	HMDB
Geranyl diphosphate	HMDB
Geranyl-diphosphate	HMDB
Geranyl-pyrophosphate	HMDB
Monoterpenyl diphosphate	HMDB
Neryl diphosphate	HMDB
trans-Geranyl pyrophosphate	HMDB
P-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]diphosphoric acid	HMDB
trans-geranyl-PP	HMDB
(2e)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diate	HMDB
(2E)-3,7-dimethylocta-2,6-dien-1-yl trihydrogen diphosphate	biospider
(e,e,e)-geranylgeranyl diphosphate	biospider
All-trans-geranylgeranyl diphosphate	biospider
All-trans-geranylgeranyl pyrophosphate	biospider
GERANYL diATE	ChEBI
GERANYL diic acid	Generator
Geranyl pyroate	ChEBI
Geranyl pyroic acid	Generator
Geranyl pyrophosphate (6CI)	biospider
Geranyl pyrophosphate ammonium salt	biospider
Geranyl pyrophosphic acid	biospider
Geranyl-diate	HMDB
Geranyl-PP	biospider
Geranyl-pyroate	HMDB
Geranylgeraniol diphosphate	biospider
Geranylgeraniol pyrophosphate	biospider
Geranylgeranyl diphosphate	biospider
Geranylgeranyl pyrophosphate	biospider
GGDP	biospider
GPP	biospider
GRG	biospider
Monoterpenyl diate	HMDB
Neryl diate	HMDB
Neryl pyrophosphate	biospider
Polyprenylpyrophosphate	biospider
Pyrophosphoric acid, (E)-3,7-dimethyl-2,6-octadienyl ester	biospider
Trans geranyl PP	biospider
Trans geranyl pyrophosphate	biospider
trans-3,7-Dimethyl-2,6-octadienyl pyrophosphate	biospider
trans-Geranyl pyroate	HMDB
Trans-geranyl pyrophosphate	biospider
Trans-geranyl-PP	biospider
Trans-geranylgeranyl pyrophosphate	biospider
Trans-polyisopentenyldiphosphate	biospider
Trans,trans,trans-geranylgeranyl diphosphate	biospider
Trans,trans,trans-geranylgeranyl pyrophosphate	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.9 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.96	ChemAxon
logS	-2.5	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	8	ChemAxon
Refractivity	72.93 m³·mol⁻¹	ChemAxon
Polarizability	28.52 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H20O7P2

IUPAC name

[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

InChI Identifier

InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+

InChI Key

GVVPGTZRZFNKDS-JXMROGBWSA-N

Isomeric SMILES

CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O

Average Molecular Weight

314.2091

Monoisotopic Molecular Weight

314.068426018

Classification

Description

Belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Isoprenoid phosphates

Direct Parent

Isoprenoid phosphates

Alternative Parents

Substituents

Organic pyrophosphate
Monoterpenoid
Isoprenoid phosphate
Acyclic monoterpenoid
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

polyprenol diphosphate (CHEBI:17211 )
Acyclic monoterpenoids (C00341 )
Linear monoterpenes (C00341 )
Acyclic monoterpenoids (LMPR0102010001 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Blood

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	-3
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Geranyl diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004j-9640000000-9ce32c835bdcfa97fa15	Spectrum
Predicted GC-MS	Geranyl diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Geranyl diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0002-0090000000-b5ca864b0ba8818ad627	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-0002-0090000000-c7f7c5c529a56d532304	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, negative	splash10-0002-3390000000-010bee66d1e4bd685e95	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-004i-9440000000-13e525f66230aae586a2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, negative	splash10-004i-9200000000-a9da8f03edb73eec50bf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, negative	splash10-004i-9100000000-fe3060700600ee72f8dd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 23V, negative	splash10-004i-9000000000-15de26c097afd86b7007	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 27V, negative	splash10-004i-9000000000-bcc45bf0bf3bbb46af13	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, negative	splash10-004i-9000000000-b8b56dc9ea06c2ce52b5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-0a4i-0900000000-f2685d197409ed952f02	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-0a4i-0900000000-60b9e910670cbc6ebe0c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-0bt9-0390000000-6532032bbb594aa54d9c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-03di-0009000000-3bcab8c3688c96a4cec5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-03di-2009000000-42fa98db20ae4d6f687e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-01t9-9005000000-44618200345aed481b48	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, negative	splash10-004i-9000000000-befed7a961a777eb5f66	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, negative	splash10-004i-9000000000-8afaaf750b51acbd1a01	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, negative	splash10-004i-9000000000-b5b3b346fecad6ae473d	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-1953000000-e5ee3340554c9ecac23e	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-5910000000-82bcd2195a53b847981c	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gc0-9400000000-f87d391f1b3c01743515	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0509000000-43083a162145718cd977	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9500000000-053b6323e620a16328a8	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4faed4c921d605619caf	2015-09-15	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB02552

HMDB ID

HMDB01285

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

34712

KNApSAcK ID

C00000846

HET ID

GPP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Geranyl pyrophosphate

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Geranylgeranyl pyrophosphate synthase	GGPS1	O95749
Farnesyl pyrophosphate synthase	FDPS	P14324
4-hydroxybenzoate polyprenyltransferase, mitochondrial	COQ2	Q96H96