Farnesyl pyrophosphate

Details

• Internal ID: 67be68e0-d13f-4e3e-8245-dfecb6f0ee3f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: phosphono [(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] hydrogen phosphate
• InChI: InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
• InChI Key: VWFJDQUYCIWHTN-YFVJMOTDSA-N
• Popularity: 906 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₈O₇P₂
• Molecular Weight: 382.33 g/mol
• Exact Mass: 382.13102722 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 4.63
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 11

Synonyms

• farnesyl pyrophosphate
• (2E,6E)-Farnesyl diphosphate
• Farnesylpyrophosphate
• all-trans-Farnesyl pyrophosphate
• (all-E)-Farnesyl diphosphate
• (E,E)-Farnesyl pyrophosphate
• trans,trans-Farnesyl diphosphate
• (2E,6E)-Farnesyl pyrophosphate
• 13058-04-3
• 372-97-4
• trans-Farnesyl pyrophosphate
• 2-trans,6-trans-farnesyl diphosphate
• 2-trans,6-trans-Farnesyl pyrophosphate
• farnesyl-PP
• (E,E)-Farnesyl diphosphate
• (2E,6E)-farnesol diphosphate
• trans-trans-farnesyl diphosphate
• CHEBI:17407
• trans,trans-Farnesyl pyrophosphate
• Sq 32709
• CHEMBL69330
• (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate
• phosphono [(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] hydrogen phosphate
• 79W6B01D07
• FPP
• Diphosphoric acid, P-(3,7,11-trimethyl-2,6,10-dodecatrien-1-yl) ester
• 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, trihydrogen pyrophosphate, (E,E)-
• Diphosphoric acid, mono(3,7,11-trimethyl-2,6,10-dodecatrienyl) ester, (E,E)-
• Farnesol pyrophosphate
• Diphosphoric acid,P-(3,7,11-trimethyl-2,6,10-dodecatrienyl) ester
• Farnesyldiphosphat
• UNII-79W6B01D07
• Farnesyl trihydrogen pyrophosphate
• Diphosphoric acid, mono((2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl) ester
• Diphosphoric acid, mono[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl] ester
• Epitope ID:153909
• phosphono 3,7,11-trimethyldodeca-2,6,10-trienyl hydrogen phosphate
• GTPL3050
• trans-trans-Farnesyl pyrophosphate
• VWFJDQUYCIWHTN-YFVJMOTDSA-N
• DTXSID701020624
• BDBM50366477
• Diphosphoric acid, mono(3,7,11-trimethyl-2,6,10-dodecatrienyl) ester
• DB07780
• LMPR0103010002
• trans,trans-Farnesyl diphosphate (FPP)
• HY-113037
• CS-0059409
• C00448
• Q2699676
• BRD-A57226833-001-01-1
• 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, trihydrogen pyrophosphate
• Diphosphoric acid, P-(3,7,11-trimethyl-2,6,10-dodecatrienyl) ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6338	63.38%
Caco-2	-	0.5788	57.88%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6895	68.95%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.9424	94.24%
OATP1B3 inhibitior	+	0.9365	93.65%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6522	65.22%
P-glycoprotein inhibitior	-	0.7584	75.84%
P-glycoprotein substrate	-	0.9320	93.20%
CYP3A4 substrate	+	0.5212	52.12%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.7971	79.71%
CYP3A4 inhibition	-	0.8565	85.65%
CYP2C9 inhibition	-	0.7835	78.35%
CYP2C19 inhibition	-	0.7799	77.99%
CYP2D6 inhibition	-	0.8795	87.95%
CYP1A2 inhibition	-	0.8244	82.44%
CYP2C8 inhibition	-	0.9255	92.55%
CYP inhibitory promiscuity	-	0.8918	89.18%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6500	65.00%
Carcinogenicity (trinary)	Non-required	0.6334	63.34%
Eye corrosion	-	0.6278	62.78%
Eye irritation	-	0.8584	85.84%
Skin irritation	-	0.6659	66.59%
Skin corrosion	-	0.6078	60.78%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3675	36.75%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.7155	71.55%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.6778	67.78%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.8325	83.25%
Acute Oral Toxicity (c)	III	0.6206	62.06%
Estrogen receptor binding	+	0.6960	69.60%
Androgen receptor binding	-	0.5739	57.39%
Thyroid receptor binding	+	0.7133	71.33%
Glucocorticoid receptor binding	+	0.6691	66.91%
Aromatase binding	+	0.6466	64.66%
PPAR gamma	+	0.8023	80.23%
Honey bee toxicity	-	0.4684	46.84%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9938	99.38%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2094108	P49354	Protein farnesyltransferase	2 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.85%	92.08%
CHEMBL3401	O75469	Pregnane X receptor	90.53%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.96%	96.09%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	88.56%	97.29%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.21%	83.57%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.69%	99.17%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.64%	93.10%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.38%	96.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.41%	89.34%
CHEMBL2581	P07339	Cathepsin D	81.24%	98.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 445713
• LOTUS: LTS0094975
• wikiData: Q2699676