Showing Compound Geranylgeraniol (FDB001528)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:00 UTC

Update date

2019-11-26 02:56:34 UTC

Primary ID

FDB001528

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Geranylgeraniol

Description

Geranylgeraniol, also known as tetraprenol or (2e,6e,10e)-geranylgeraniol, is a member of the class of compounds known as acyclic diterpenoids. Acyclic diterpenoids are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, geranylgeraniol is considered to be an isoprenoid lipid molecule. Geranylgeraniol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Geranylgeraniol can be found in flaxseed, which makes geranylgeraniol a potential biomarker for the consumption of this food product. Geranylgeraniol is a diterpene alcohol which plays a role in several important biological processes. It is an intermediate in the biosynthesis of other diterpenes and of vitamins E and K. It also used in the post-translational modification known as geranylgeranylation. Geranylgeraniol is a pheromone for bumblebees and a variety of other insects .

CAS Number

24034-73-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E,6E,10E)-Geranylgeraniol	ChEBI
Geranylgeraniol, (e,e,e)-isomer	MeSH
Geranylgeraniol, (Z,Z,Z)-isomer	MeSH
Tetraprenol	MeSH
(2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol	PhytoBank
(E,E,E)-Geranylgeraniol	PhytoBank
(E,E,E)-Geranylgeranyl alcohol	PhytoBank
All-trans-Geranylgeraniol	PhytoBank
Geranylgeraniol	PhytoBank
Geranylgeranyl alcohol	PhytoBank
trans,trans,trans-Geranylgeraniol	PhytoBank
trans-Geranylgeraniol	PhytoBank
(e,e,e)-geranylgeraniol	biospider
2,6,10,14-hexadecatetraen-1-ol, 3,7,11,15-tetramethyl-	biospider
All-trans-geranylgeraniol	biospider
Gernaylgeraniol	biospider
Trans-geranylgeraniol	biospider
Trans,trans,trans-geranylgeraniol	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.0054 g/L	ALOGPS
logP	6.06	ALOGPS
logP	5.82	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	16.33	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	98.79 m³·mol⁻¹	ChemAxon
Polarizability	38.18 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H34O

IUPAC name

(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol

InChI Identifier

InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+

InChI Key

OJISWRZIEWCUBN-QIRCYJPOSA-N

Isomeric SMILES

[H]\C(CO)=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C

Average Molecular Weight

290.4834

Monoisotopic Molecular Weight

290.26096571

Classification

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
Long chain fatty alcohol
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

geranylgeraniol (CHEBI:46762 )
Acyclic diterpenoids (C09094 )
Linear diterpenes (C09094 )
Acyclic diterpenoids (LMPR0104010009 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
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	Not Available
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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-014i-9300000000-1ee3bddd85e9086b7517	2015-03-01	View Spectrum
Predicted GC-MS	Geranylgeraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0aor-6590000000-d53875d1d1717d638752	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006y-0290000000-406439b04dab8ae9f72a	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0603-4970000000-f76480cde6f70f69904f	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0lk9-9730000000-6885c45bb706a217604b	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-ae922ee5b3568def3a2b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0090000000-bd08abbb2b7066c4796a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-3590000000-59768ae8b64336ff3df0	2016-08-03	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C09094

Pubchem Compound ID

5281365

Pubchem Substance ID

Not Available

ChEBI ID

46762

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

GERANYL-GERANIOL

BIGG ID

Not Available

KNApSAcK ID

C00003428

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

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

Descriptor	ID	Definition	Reference
Anti adenomic	35610	An agent that inhibits adenoma growth, reducing tumor formation. It plays a biological role in regulating cell proliferation and differentiation. Therapeutically, it is used to prevent or treat adenoma-related disorders, with key medical applications in managing conditions such as colon polyps, pituitary adenomas, and other glandular tumors.	DUKE
Anti-cancer	35610	An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.	DUKE
Anti carcinomic	35610	An agent that inhibits the growth and proliferation of cancer cells, playing a crucial role in cancer prevention and treatment. Therapeutically, it is used to manage and treat various types of cancer, reducing tumor size and slowing disease progression, with key medical uses in oncology and chemotherapy.	DUKE
Anti leukemic	35610	An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.	DUKE
Anti proliferant		An agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.	DUKE
Apoptotic		An agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Protisticide		An agent that kills protozoans, used as a herbicide or in therapeutic applications to treat protozoan infections, with key medical uses including managing parasitic diseases and infections.	DUKE
Schistosomicide		An agent destructive to schistosomes, used to treat schistosomiasis, a disease caused by blood flukes transmitted by snails. Therapeutically, it eliminates the parasites, reducing inflammation and preventing long-term damage. Key medical uses include treating and preventing schistosomiasis in endemic regions, particularly in Africa, Brazil, and Asia.	DUKE