Dimethylallyl diphosphate

Details

• Internal ID: 9338bf16-22d5-4f6b-8337-7383016724c8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Isoprenoid phosphates
• IUPAC Name: 3-methylbut-2-enyl phosphono hydrogen phosphate
• SMILES (Canonical): CC(=CCOP(=O)(O)OP(=O)(O)O)C
• SMILES (Isomeric): CC(=CCOP(=O)(O)OP(=O)(O)O)C
• InChI: InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)
• InChI Key: CBIDRCWHNCKSTO-UHFFFAOYSA-N
• Popularity: 576 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₁₂O₇P₂
• Molecular Weight: 246.09 g/mol
• Exact Mass: 246.00582671 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• Dimethylallyl diphosphate
• Dimethylallyl pyrophosphate
• Prenyl diphosphate
• 358-72-5
• 3,3-dimethylallyl pyrophosphate
• dimethylallyl-diphosphate
• dimethylallyl-PPi
• 2-Isopentenyl diphosphate
• CHEBI:16057
• 3-methylbut-2-enyl phosphono hydrogen phosphate
• delta2-Isopentenyl diphosphate
• dimethylallylpyrophosphate
• Monoprenyl diphosphate
• 3-Methyl-2-butenyl pyrophosphate
• 3-methylbut-2-en-1-yl trihydrogen diphosphate
• dimethylallyl-pyrophosphate
• 3-methylbut-2-enyl pyrophosphate
• Gamma gamma-dimethylallyl pyrophosphate&
• prenyl-diphosphate
• Diphosphoric acid, mono(3-methyl-2-butenyl) ester
• delta2-isopentenyl-diphosphate
• Prenol pyrophosphate
• starbld0005067
• Epitope ID:140428
• SCHEMBL153577
• CHEMBL343480
• DTXSID70189331
• 1x07
• BDBM50516699
• LMPR01010001
• 3-methyl-2-Buten-1-ol pyrophosphate
• AKOS040758082
• DB01785
• HY-130573
• CS-0109211
• C00235
• 2-Buten-1-ol, 3-methyl-, pyrophosphate (6CI)
• 3-methyl-2-Buten-1-ol trihydrogen pyrophosphate
• 3-methyl-but-2-enyl phosphono hydrogen phosphate
• Diphosphoric acid mono(3-methyl-2-butenyl) ester
• Q417398
• 2-Buten-1-ol, 3-methyl-, trihydrogen pyrophosphate
• gamma,gamma-Dimethyallyl pyrophosphate ammonium salt
• Diphosphoric acid, P-(3-methyl-2-buten-1-yl) ester
• Diphosphoric acid, mono(3-methyl-2-butenyl) ester (9CI)
• 3-methylbut-2-enyl pyrophosphate (dimethylallyl-diphosphate)
• 2-Buten-1-ol, 3-methyl-, trihydrogen pyrophosphate (7CI,8CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5812	58.12%
Caco-2	-	0.6600	66.00%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7583	75.83%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.9585	95.85%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8838	88.38%
BSEP inhibitior	-	0.9496	94.96%
P-glycoprotein inhibitior	-	0.9389	93.89%
P-glycoprotein substrate	-	0.9641	96.41%
CYP3A4 substrate	-	0.5704	57.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8240	82.40%
CYP3A4 inhibition	-	0.9481	94.81%
CYP2C9 inhibition	-	0.8098	80.98%
CYP2C19 inhibition	-	0.7910	79.10%
CYP2D6 inhibition	-	0.8769	87.69%
CYP1A2 inhibition	-	0.8712	87.12%
CYP2C8 inhibition	-	0.9695	96.95%
CYP inhibitory promiscuity	-	0.9149	91.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6000	60.00%
Carcinogenicity (trinary)	Non-required	0.5855	58.55%
Eye corrosion	-	0.6986	69.86%
Eye irritation	+	0.8324	83.24%
Skin irritation	-	0.5576	55.76%
Skin corrosion	-	0.5000	50.00%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7543	75.43%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7767	77.67%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	-	0.6889	68.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.8764	87.64%
Acute Oral Toxicity (c)	III	0.4953	49.53%
Estrogen receptor binding	-	0.6298	62.98%
Androgen receptor binding	-	0.7025	70.25%
Thyroid receptor binding	-	0.6192	61.92%
Glucocorticoid receptor binding	-	0.8525	85.25%
Aromatase binding	-	0.8331	83.31%
PPAR gamma	-	0.5540	55.40%
Honey bee toxicity	+	0.5659	56.59%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8155	81.55%
Fish aquatic toxicity	+	0.9565	95.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.95%	97.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.62%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	87.46%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.32%	96.95%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	84.13%	87.67%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	81.29%	94.01%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.09%	89.34%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 647
• LOTUS: LTS0152627
• wikiData: Q417398