GERANYLGERANIOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H34O
Molecular Weight	290.4834
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO

InChI

InChIKey=OJISWRZIEWCUBN-QIRCYJPOSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C20H34O
Molecular Weight	290.4834
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	3
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
osteoclast development 6 Target ID: GO:0036035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14715241	Inhibitor 8504

PubMed

Title	Date	PubMed
Dysfunction of vascular smooth muscle and vascular remodeling by simvastatin.	2014-04	24449418
Roles of rat and human aldo-keto reductases in metabolism of farnesol and geranylgeraniol.	2011-05-30	21187079
Mevalonate pathway intermediates downregulate zoledronic acid-induced isopentenyl pyrophosphate and ATP analog formation in human breast cancer cells.	2010-03-01	19819230
Cyr61 downmodulation potentiates the anticancer effects of zoledronic acid in androgen-independent prostate cancer cells.	2009-11-01	19530242
Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro.	2007-10	17924309
Simvastatin potentiates tumor necrosis factor alpha-mediated apoptosis of human vascular endothelial cells via the inhibition of the geranylgeranylation of RhoA.	2006-09-05	16740276
Zoledronic acid treatment impairs protein geranyl-geranylation for biological effects in prostatic cells.	2006-03-15	16539721
Zoledronic acid up-regulates bone sialoprotein expression in osteoblastic cells through Rho GTPase inhibition.	2004-12-15	15324309
Rosiglitazone upregulates caveolin-1 expression in THP-1 cells through a PPAR-dependent mechanism.	2004-11	15314095
Lysine beta311 of protein geranylgeranyltransferase type I partially replaces magnesium.	2004-07-16	15131129
Lovastatin induces apoptosis of anaplastic thyroid cancer cells via inhibition of protein geranylgeranylation and de novo protein synthesis.	2003-09	12933658
Simvastatin suppresses tissue factor expression and increases fibrinolytic activity in tumor necrosis factor-alpha-activated human peritoneal mesothelial cells.	2003-06	12753293
Simvastatin increases fibrinolytic activity in human peritoneal mesothelial cells independent of cholesterol lowering.	2002-11	12371961
Fibrate and statin synergistically increase the transcriptional activities of PPARalpha/RXRalpha and decrease the transactivation of NFkappaB.	2002-01-11	11779144
Lovastatin induces apoptosis by inhibiting mitotic and post-mitotic events in cultured mesangial cells.	1997-10-30	9398081
Geranylgeraniol potentiates lovastatin inhibition of oncogenic H-Ras processing and signaling while preventing cytotoxicity.	1997-01-23	9018116

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:56:45 GMT 2025` Edited by `admin` on `Mon Mar 31 18:56:45 GMT 2025`
Record UNII	AIA02AJA3A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRAPRENOL

Preferred Name

English

GERANYLGERANIOL

Systematic Name

English

(2E,6E,10E)-3,7,11,15-TETRAMETHYLHEXADECA-2,6,10,14-TETRAEN-1-OL

Systematic Name

English

Code System Code Type Description

CAS

7614-21-3