Geranyl diphosphate

Details

• Internal ID: 143f6763-e239-4e11-81d9-ae146430f800
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Isoprenoid phosphates
• IUPAC Name: [(2E)-3,7-dimethylocta-2,6-dienyl] phosphono hydrogen phosphate
• SMILES (Canonical): CC(=CCCC(=CCOP(=O)(O)OP(=O)(O)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)C
• InChI: InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+
• InChI Key: GVVPGTZRZFNKDS-JXMROGBWSA-N
• Popularity: 135 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₂₀O₇P₂
• Molecular Weight: 314.21 g/mol
• Exact Mass: 314.06842697 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• geranyl pyrophosphate
• 763-10-0
• geranyl-PP
• trans-Geranyl pyrophosphate
• trans-geranyl-PP
• CHEBI:17211
• geranyl-diphosphate
• [(2E)-3,7-dimethylocta-2,6-dienyl] phosphono hydrogen phosphate
• 7X7DBM66JG
• GERANYL PYROPHOSPHATE AMMONIUM 200
• GERANYL PYROPHOSPHATE AMMONIUM*200 UG/VI AL
• GPP
• (2E)-3,7-dimethylocta-2,6-dien-1-yl trihydrogen diphosphate
• geranyl-pyrophosphate
• Pyrophosphoric acid, (E)-3,7-dimethyl-2,6-octadienyl ester
• diphosphoric acid, mono[(2E)-3,7-dimethyl-2,6-octadienyl] ester
• Diphosphoric acid, P-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-
• Diphosphoric acid, mono(3,7-dimethyl-2,6-octadienyl) ester, (E)-
• Monoterpenyl diphosphate
• geranylpyrophosphoric acid
• Epitope ID:153910
• Geranyl diphosphate (GPP)
• UNII-7X7DBM66JG
• trans-3,7-Dimethyl-2,6-octadienyl pyrophosphate
• Geranyl pyrophosphate (6CI)
• CHEMBL41342
• SCHEMBL109367
• SCHEMBL109368
• GTPL3051
• CHEBI:55337
• DTXSID801315430
• DB02552
• LMPR0102010001
• HY-114295
• CS-0081958
• C00341
• C05847
• Q418125
• Diphosphoric acid, P-(3,7-dimethyl-2,6-octadien-1-yl) ester
• P-(3,7-Dimethyl-2,6-octadien-1-yl) trihydrogen (diphosphate)
• 2,6-Octadien-1-ol, 3,7-dimethyl-, trihydrogen pyrophosphate, (E)-
• 2,6-Octadien-1-ol, 3,7-dimethyl-, trihydrogen pyrophosphate, (E)- (8CI)
• Diphosphoric acid, mono[(2E)-3,7-dimethyl-2,6-octadienyl] ester (9CI)
• Geranyl pyrophosphate ammonium salt, 1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3)), >=95% (TLC)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6338	63.38%
Caco-2	-	0.5892	58.92%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6895	68.95%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9404	94.04%
OATP1B3 inhibitior	+	0.9365	93.65%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8837	88.37%
P-glycoprotein inhibitior	-	0.9007	90.07%
P-glycoprotein substrate	-	0.9389	93.89%
CYP3A4 substrate	-	0.5000	50.00%
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	-	0.9324	93.24%
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	-	0.8477	84.77%
Skin irritation	-	0.6659	66.59%
Skin corrosion	-	0.6078	60.78%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5836	58.36%
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	+	0.8285	82.85%
Acute Oral Toxicity (c)	III	0.6206	62.06%
Estrogen receptor binding	+	0.5637	56.37%
Androgen receptor binding	-	0.6044	60.44%
Thyroid receptor binding	-	0.5248	52.48%
Glucocorticoid receptor binding	-	0.6634	66.34%
Aromatase binding	-	0.5059	50.59%
PPAR gamma	+	0.7598	75.98%
Honey bee toxicity	-	0.5000	50.00%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5855	58.55%
Fish aquatic toxicity	+	0.9938	99.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	90.47%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.85%	96.09%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	88.54%	97.29%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.04%	92.08%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.42%	83.57%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.41%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.15%	96.95%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.09%	93.10%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.03%	89.34%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	81.22%	94.01%
CHEMBL2581	P07339	Cathepsin D	80.28%	98.95%

Plants that contains it

• Citrus japonica
• Lithospermum erythrorhizon
• Perilla frutescens

Cross-Links

• PubChem: 445995
• LOTUS: LTS0051684
• wikiData: Q418125