Isopentenyl pyrophosphate

Details

• Internal ID: 1b8493bc-e7f2-49cc-9e16-08992a15ea87
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Isoprenoid phosphates
• IUPAC Name: 3-methylbut-3-enyl phosphono hydrogen phosphate
• SMILES (Canonical): CC(=C)CCOP(=O)(O)OP(=O)(O)O
• SMILES (Isomeric): CC(=C)CCOP(=O)(O)OP(=O)(O)O
• InChI: InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)
• InChI Key: NUHSROFQTUXZQQ-UHFFFAOYSA-N
• Popularity: 1,040 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: -0.90
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• isopentenyl diphosphate
• 358-71-4
• 3-Methyl-3-butenyl pyrophosphate
• Isopentenyl-diphosphate
• IPPP
• Mono(3-methyl-3-butenyl) diphosphate
• 3-methylbut-3-enyl phosphono hydrogen phosphate
• 3-methylbut-3-en-1-yl trihydrogen diphosphate
• delta3-Isopentenyl diphosphate
• isopentenyl-pp
• Diphosphoric acid mono(3-methyl-3-butenyl) ester
• delta-3-Isopentenyl pyrophosphat
• CHEBI:16584
• delta3-methyl-3-butenyl diphosphate
• LSC8849M7B
• delta-3-Isopentenyl pyrophosphate
• 3-METHYLBUT-3-ENYL TRIHYDROGEN DIPHOSPHATE
• IPP
• ISOPENTENYL PYROPHOSPHATE AMMONIUM 200
• Diphosphoric acid, P-(3-methyl-3-buten-1-yl) ester
• delta(3)-isopentenyl-PP
• delta3-isopentenyl pyrophosphate
• isopentenylpyrophosphate
• Epitope ID:194668
• UNII-LSC8849M7B
• [14C]isopentenyl diphosphate
• SCHEMBL125521
• [14C]IPP
• CHEMBL356362
• GTPL3048
• BDBM25257
• DTXSID80861893
• NUHSROFQTUXZQQ-UHFFFAOYSA-N
• LMPR01010008
• DB04714
• Isopentenyl Pyrophosphate Ammonium Salt
• 3-Buten-1-ol, 3-methyl-, pyrophosphate
• C00129
• Diphosphoric acid, mono(3-methyl-3-butenyl) ester
• Q417403
• DIPHOSPHORIC ACID,P-(3-METHYL-3-BUTEN-1-YL) ESTER
• ({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7729	77.29%
Caco-2	-	0.7300	73.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7002	70.02%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9467	94.67%
OATP1B3 inhibitior	+	0.9438	94.38%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8907	89.07%
BSEP inhibitior	-	0.9809	98.09%
P-glycoprotein inhibitior	-	0.9470	94.70%
P-glycoprotein substrate	-	0.9457	94.57%
CYP3A4 substrate	-	0.5243	52.43%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.7971	79.71%
CYP3A4 inhibition	-	0.8896	88.96%
CYP2C9 inhibition	-	0.8070	80.70%
CYP2C19 inhibition	-	0.7755	77.55%
CYP2D6 inhibition	-	0.8539	85.39%
CYP1A2 inhibition	-	0.8083	80.83%
CYP2C8 inhibition	-	0.9325	93.25%
CYP inhibitory promiscuity	-	0.8961	89.61%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6900	69.00%
Carcinogenicity (trinary)	Non-required	0.5571	55.71%
Eye corrosion	-	0.5563	55.63%
Eye irritation	-	0.7356	73.56%
Skin irritation	-	0.7022	70.22%
Skin corrosion	-	0.5135	51.35%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6801	68.01%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.7869	78.69%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	-	0.8444	84.44%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.7610	76.10%
Acute Oral Toxicity (c)	III	0.6420	64.20%
Estrogen receptor binding	-	0.7468	74.68%
Androgen receptor binding	-	0.7286	72.86%
Thyroid receptor binding	-	0.5430	54.30%
Glucocorticoid receptor binding	-	0.8997	89.97%
Aromatase binding	-	0.8631	86.31%
PPAR gamma	-	0.6469	64.69%
Honey bee toxicity	+	0.6265	62.65%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9582	95.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	95.33%	83.82%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	93.71%	94.01%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.38%	96.09%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.37%	97.29%
CHEMBL2581	P07339	Cathepsin D	87.91%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	84.53%	94.73%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.78%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.54%	99.17%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	80.49%	80.33%

Plants that contains it

• Citrus japonica

Cross-Links

• PubChem: 1195
• LOTUS: LTS0270004
• wikiData: Q417403