Cannabis Compound Database: Showing Compound Card for Geranylgeranyl-PP (CDB004969)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5) Show 10 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:55:41 UTC

Updated at

2020-12-07 19:11:23 UTC

CannabisDB ID

CDB004969

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Geranylgeranyl-PP

Description

Geranylgeranyl-PP, also known as GGDP or GGPP diphosphate, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, geranylgeranyl-PP is considered to be an isoprenoid lipid molecule. Geranylgeranyl-PP is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Geranylgeranyl-PP is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
all-trans-Geranylgeranyl diphosphate	ChEBI
all-trans-Geranylgeranyl pyrophosphate	ChEBI
Geranylgeranyl diphosphate	ChEBI
Geranylgeranyl pyrophosphate	ChEBI
GGDP	ChEBI
(2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphate	Kegg
all-trans-Geranylgeranyl diphosphoric acid	Generator
all-trans-Geranylgeranyl pyrophosphoric acid	Generator
Geranylgeranyl diphosphoric acid	Generator
Geranylgeranyl pyrophosphoric acid	Generator
(2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphoric acid	Generator
2-trans,6-trans,10-trans-Geranylgeranyl diphosphate	HMDB
3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl diphosphate	HMDB
all-trans-Geranyl-geranyl-PP	HMDB
Geranylgeranyl-diphosphate	HMDB
Geranylgeraniol diphosphate	HMDB
Geranylgeranyl pyrophosphate, (Z,e,e)-isomer	HMDB
Nerylneryl diphosphate	HMDB
GGPP Diphosphate	HMDB
Geranylgeranyl pyrophosphate, 14C-labeled, (e,e,e)-isomer	HMDB
GGPP CPD	HMDB

Chemical Formula

C₂₀H₃₆O₇P₂

Average Molecular Weight

450.44

Monoisotopic Molecular Weight

450.1936

IUPAC Name

{[hydroxy({[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]oxy})phosphoryl]oxy}phosphonic acid

Traditional Name

geranylgeranyl diphosphate

CAS Registry Number

6699-20-3

SMILES

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

InChI Identifier

InChI=1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+

InChI Key

OINNEUNVOZHBOX-QIRCYJPOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Organic pyrophosphate
Isoprenoid phosphate
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

geranylgeranyl diphosphate (CHEBI:48861 )
Acyclic diterpenoids (C00353 )
Linear diterpenes (C00353 )
Acyclic diterpenoids (LMPR0104010001 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Plant:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.57	ALOGPS
logP	5.28	ChemAxon
logS	-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	14	ChemAxon
Refractivity	120.53 m³·mol⁻¹	ChemAxon
Polarizability	47.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Geranylgeranyl-PP, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00p1-8966200000-998d239f267a150b43ed	Spectrum
Predicted GC-MS	Geranylgeranyl-PP, 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 11V, negative	splash10-0002-0000900000-e7c9a733fcef12117c3d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, negative	splash10-0002-1000900000-51a8d5ce498d65e79691	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, negative	splash10-004j-9000800000-4beea4fd2eb20ffa4ad9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 26V, negative	splash10-004i-9000000000-4db0a53ff36e5e4b9935	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 31V, negative	splash10-004i-9000000000-cf199ce4e78be9534fb7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 37V, negative	splash10-004i-9000000000-7867ab9db012f87e43c8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 44V, negative	splash10-004i-9000000000-be17e3662a7647d871aa	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 52V, negative	splash10-004i-9000000000-1f4ff46767d08f6c4824	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 60V, negative	splash10-004i-9000000000-d99bb72e9136380d8698	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 72V, negative	splash10-004i-9000000000-d99bb72e9136380d8698	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, negative	splash10-001i-0300900000-fecb2380f7e0ec863abc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, negative	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, negative	splash10-0a4i-0900000000-dc954ce23ecf1a263189	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, negative	splash10-0a4i-0900000000-8ab5606bd668c2535e4d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 31V, negative	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-1394600000-c6d91e9bfb5eeb46563e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-3592000000-c8aa1820057f6139aad8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xs-5690000000-5fa48d769648b6310c2d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0400900000-86700e111b6b2b0215c0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-7900100000-c5c0d2a89df8d138cebb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-0ec0eed3d4d479d9c002	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1214900000-f698165f4dfead7c9d55	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1189100000-6a265357a808fdf96bf8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05s1-3910000000-59003e6f3766239ee38a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000900000-582b037b919c4a7e747f	2021-09-23	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Geranylgeranyl pyrophosphate synthase	GGPS1	1q43	O95749	details
Geranylgeranyl transferase type-1 subunit beta	PGGT1B	5q22.3	P53609	details
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	FNTA	8p11	P49354	details
Geranylgeranyl transferase type-2 subunit alpha	RABGGTA	14q11.2	Q92696	details
Geranylgeranyl transferase type-2 subunit beta	RABGGTB	1p31	P53611	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Geranylgeranyl pyrophosphate synthase	GGPS1	1q43	O95749	details
Geranylgeranyl transferase type-1 subunit beta	PGGT1B	5q22.3	P53609	details
Geranylgeranyl transferase type-2 subunit alpha	RABGGTA	14q11.2	Q92696	details
Geranylgeranyl transferase type-2 subunit beta	RABGGTB	1p31	P53611	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	FNTA	8p11	P49354	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0004486

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

447277

PDB ID

GRG

ChEBI ID

48861

References

General References

Not Available

Enzymes

Enzyme Details

1. Geranylgeranyl pyrophosphate synthase

General function:: Involved in isoprenoid biosynthetic process
Specific function:: Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
Gene Name:: GGPS1
Uniprot ID:: O95749
Molecular weight:: 34870.625

Enzyme Details

2. Geranylgeranyl transferase type-1 subunit beta

General function:: Involved in CAAX-protein geranylgeranyltransferase acti
Specific function:: Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to a cysteine at the fourth position from the C-terminus of proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X. Acts on the Rac1, Rac2, Rap1A and Rap1B proteins. The beta subunit is responsible for peptide-binding.
Gene Name:: PGGT1B
Uniprot ID:: P53609
Molecular weight:: 42367.81

Enzyme Details

3. Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha

General function:: Involved in protein prenyltransferase activity
Specific function:: Catalyzes the transfer of a farnesyl or geranyl-geranyl moiety from farnesyl or geranyl-geranyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X. The alpha subunit is thought to participate in a stable complex with the substrate. The beta subunit binds the peptide substrate. Through RAC1 prenylation and activation may positively regulate neuromuscular junction development downstream of MUSK (By similarity).
Gene Name:: FNTA
Uniprot ID:: P49354
Molecular weight:: 44408.32

Enzyme Details

4. Geranylgeranyl transferase type-2 subunit alpha

General function:: Not Available
Specific function:: Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to both cysteines in Rab proteins with an -XXCC, -XCXC and -CCXX C-terminal, such as RAB1A, RAB3A and RAB5A respectively.
Gene Name:: RABGGTA
Uniprot ID:: Q92696
Molecular weight:: 65071.06

Enzyme Details

5. Geranylgeranyl transferase type-2 subunit beta

General function:: Not Available
Specific function:: Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to both cysteines in Rab proteins with an -XXCC, -XCXC and -CCXX C-terminal, such as RAB1A, RAB3A and RAB5A respectively.
Gene Name:: RABGGTB
Uniprot ID:: P53611
Molecular weight:: 36924.04

Showing Compound Card for Geranylgeranyl-PP (CDB004969)

Structure for CDB004969 (Geranylgeranyl-PP)

Enzymes