(R)-(-)-Ibuprofen

Details

• Internal ID: 3d0b7c7c-ddd5-4ee1-95f1-1d6d93bf126b
• Taxonomy: Phenylpropanoids and polyketides > Phenylpropanoic acids
• IUPAC Name: (2R)-2-[4-(2-methylpropyl)phenyl]propanoic acid
• SMILES (Canonical): CC(C)CC1=CC=C(C=C1)C(C)C(=O)O
• SMILES (Isomeric): C[C@H](C1=CC=C(C=C1)CC(C)C)C(=O)O
• InChI: InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m1/s1
• InChI Key: HEFNNWSXXWATRW-SNVBAGLBSA-N
• Popularity: 382 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28 g/mol
• Exact Mass: 206.130679813 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 51146-57-7
• (R)-Ibuprofen
• (-)-Ibuprofen
• levibuprofen
• l-Ibuprofen
• (R)-2-(4-Isobutylphenyl)propanoic acid
• r-ibuprofen
• (2R)-2-[4-(2-methylpropyl)phenyl]propanoic acid
• (2R)-2-(4-isobutylphenyl)propanoic acid
• (-)-Ibuprophen
• Ibuprofen, (-)-
• CHEMBL427526
• UNII-99W8H60N62
• CHEBI:47835
• (r,s)-ibuprofen
• R-(-)-p-Isobutylhydratropic acid
• alphaR-Sethyl-4-(2-methylpropyl)benzeneacetic acid
• (R)-alpha-methyl-4-(2-methylpropyl)benzeneacetic acid
• 99W8H60N62
• Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (R)-
• (alphaR)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid
• (R,S)-2-(4-(2-methylpropyl)phenyl)propanoic acid
• IZP
• (r)(-) ibuprofen
• (r)(-)-ibuprofen
• (R)-IBUPROPHEN
• IBUPROFEN, (R)-
• SCHEMBL29057
• HEFNNWSXXWATRW-SNVBAGLBSA-N
• EX-A1358
• BDBM50169044
• HY-78131B
• MFCD00069290
• s5899
• AKOS027320481
• CS-1394
• AC-32024
• DS-11337
• EN300-6505221
• Q27120818
• (-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid
• (-)-.ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETIC ACID
• benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (alphaR)-
• (.ALPHA.R)-.ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETIC ACID
• BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (R)-
• Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (alphaR)- (9CI)
• BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (.ALPHA.R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.9143	91.43%
Subcellular localzation	Mitochondria	0.6974	69.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9403	94.03%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8666	86.66%
P-glycoprotein inhibitior	-	0.9785	97.85%
P-glycoprotein substrate	-	0.9430	94.30%
CYP3A4 substrate	-	0.7932	79.32%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.9655	96.55%
CYP2C9 inhibition	-	0.9305	93.05%
CYP2C19 inhibition	-	0.9881	98.81%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9936	99.36%
CYP inhibitory promiscuity	-	0.9691	96.91%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5398	53.98%
Carcinogenicity (trinary)	Non-required	0.7313	73.13%
Eye corrosion	-	0.7115	71.15%
Eye irritation	-	0.5205	52.05%
Skin irritation	+	0.7733	77.33%
Skin corrosion	+	0.5953	59.53%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6106	61.06%
Micronuclear	-	0.9441	94.41%
Hepatotoxicity	+	0.8625	86.25%
skin sensitisation	+	0.7552	75.52%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8208	82.08%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8242	82.42%
Acute Oral Toxicity (c)	III	0.8084	80.84%
Estrogen receptor binding	-	0.9133	91.33%
Androgen receptor binding	-	0.5951	59.51%
Thyroid receptor binding	-	0.6868	68.68%
Glucocorticoid receptor binding	-	0.9187	91.87%
Aromatase binding	-	0.7391	73.91%
PPAR gamma	+	0.5483	54.83%
Honey bee toxicity	-	0.9639	96.39%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.9100	91.00%
Fish aquatic toxicity	+	0.9534	95.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	2.8 nM	Potency	via Super-PRED
CHEMBL221	P23219	Cyclooxygenase-1	212 nM; 98.65 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL230	P35354	Cyclooxygenase-2	730 nM	IC50	via Super-PRED
CHEMBL2157	P10145	Interleukin-8	50 nM; 50 nM	IC50; IC50	via Super-PRED; PMID: 19560921
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	223.9 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	5.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.08%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	93.48%	83.82%
CHEMBL3492	P49721	Proteasome Macropain subunit	90.88%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.62%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	86.42%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.89%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.06%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.21%	95.56%
CHEMBL4208	P20618	Proteasome component C5	81.93%	90.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.71%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.26%	90.71%

Plants that contains it

• Artemisia argyi
• Artemisia montana
• Artemisia princeps

Cross-Links

• PubChem: 114864
• NPASS: NPC86670
• ChEMBL: CHEMBL427526