CAS 24034-73-9|CAS 7614-21-3|tetraprenol|3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol|GERANYLGERANIOL|Tetraprenol|all trans-3,7,11-15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol|(2E,6E,10E)-3...

General Information

Structure

Molecular Formula

C₂₀H₃₄O

Molecular Mass

290.48336

Exact Mass

290.26096571

Charge

InChI

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

InChIKey

OJISWRZIEWCUBN-UHFFFAOYSA-N

Canonic Smiles

OCC=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C

Isomeric Smiles

CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/C)/C)C

Calculated Properties

JChem

LogD (pH = 7.4)

5.82

LogD (pH = 5.5)

5.82

Log P

5.82

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

16.33

Polar Surface Area

20.23

Polarizability

38.73

Molar Refractivity

98.79

LOG S

-6.51

Data Source

Names and Identifiers

IUPAC Traditional name

tetraprenol geranylgeraniol geranylgeraniols

IUPAC name

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

Synonyms

GERANYLGERANIOLTetraprenolall trans-3,7,11-15-Tetramethyl-2,6,10,14-hexadecatetraen-1-olGeranylgeranioltrans-GeranylgeraniolAll-trans-Geranylgeraniol(E,E,E)- 3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-oltrans,trans,trans-Geranylgeraniol(2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol(E,E,E)-Geranylgeraniolgeranylgeraniol

Names and Identifiers

Registration numbers

CAS Number

Chemspider ID

PubChem CID

Wikipedia Title

PubChem SID

1620938862489512026744239

Beilstein Number

19137791797446

MDL Number

MFCD00129083

UniProt Database

P9WMS5Q7X3G5P33326Q9M3W5P95619Q9NPH2P9WMS4P26172Q9Z5D6P26170Q55087O75223

Patent number

US2002187532WO2007104790

CHEBI ID

CHEBI:24229

LINCS Database

LSM-5994

PubMed Citation Links

23983115240063062330419524762323

MetaboLights Database

MTBLS2878MTBLS3487MTBLS1115

Reaxys Registry

1797446

Registration numbers

Properties

Product Information

Certificate of Analysis

Download link

Purity

≥85% (GC)

Safety Information

Download link

0°C

-86°C Freezer

H315-H319-H335

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Geranylgeraniol

Sigma Aldrich

G3278

Biochem/physiol Actions
As the pyrophosphate, the metabolic precursor of all diterpenes. Screening in vitro shows this to be a potent and selective agent against Mycobacterium tuberculosis.1

MP Biomedicals

02198770

Clear, colorless liquid.
Useful for studying mammalian cell protein isoprenylation.
May affect regulation of cell cycle progress.

TRC

G367500

Geranylgeraniol, a precursor to Geranylgeranylpyrophosphate (G367600), is an intermediate in the mevalonate pathway. Geranylgeraniol has been shown to prevent bone re-adsorption, inhibition of osteoclast formation, and kinase activation in vitro.

ChEBI

CHEBI:24229

A diterpenoid that is hexadeca-2,6,10,14-tetraene substituted by methyl groups at positions 3, 7, 11 and 15 and a hydroxy group at position 1.

Molecule Details

References

PubChem Literature

From Data Sources

• Crick, et al. Biochemical and Biophysical Research Commun. , 237 : 483.

• Montero, M.T., et al.: J. Immunol., 173, 4936 (1998)

• Campia, I., et al.: Br. J. Pharmacol., 158, 1777 (1998)

• Aiuchi, T., et al.: J. Biochem., 124, 300 (1998)

• Fisher, J.E., et al.: Proc. Natl. Acad. Sci. U.S.A. 96, 133 (1998)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

tetraprenol geranylgeraniol geranylgeraniols

IUPAC name

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

Synonyms

Registration numbers

CAS Number

Chemspider ID

PubChem CID

Wikipedia Title

PubChem SID

1620938862489512026744239

Beilstein Number

19137791797446

MDL Number

MFCD00129083

UniProt Database

P9WMS5Q7X3G5P33326Q9M3W5P95619Q9NPH2P9WMS4P26172Q9Z5D6P26170Q55087O75223

Patent number

US2002187532WO2007104790

CHEBI ID

CHEBI:24229

LINCS Database

LSM-5994

PubMed Citation Links

23983115240063062330419524762323

MetaboLights Database

MTBLS2878MTBLS3487MTBLS1115

Reaxys Registry

Molecule Details

G3278

Biochem/physiol Actions
As the pyrophosphate, the metabolic precursor of all diterpenes. Screening in vitro shows this to be a potent and selective agent against Mycobacterium tuberculosis.1

MP Biomedicals

02198770

Clear, colorless liquid.
Useful for studying mammalian cell protein isoprenylation.
May affect regulation of cell cycle progress.

TRC

G367500

ChEBI

CHEBI:24229

A diterpenoid that is hexadeca-2,6,10,14-tetraene substituted by methyl groups at positions 3, 7, 11 and 15 and a hydroxy group at position 1.

References

PubChem Literature

From Data Sources

• Crick, et al. Biochemical and Biophysical Research Commun. , 237 : 483.