2-Phenylbutyric acid

Details

• Internal ID: 4ae261e7-df7f-43f6-947a-43951ac7ffc9
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylpropanes
• IUPAC Name: 2-phenylbutanoic acid
• SMILES (Canonical): CCC(C1=CC=CC=C1)C(=O)O
• SMILES (Isomeric): CCC(C1=CC=CC=C1)C(=O)O
• InChI: InChI=1S/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12)
• InChI Key: OFJWFSNDPCAWDK-UHFFFAOYSA-N
• Popularity: 352 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20 g/mol
• Exact Mass: 164.083729621 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.26
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 2-Phenylbutanoic acid
• 90-27-7
• alpha-Ethylphenylacetic acid
• Butyric acid, 2-phenyl-
• Benzeneacetic acid, .alpha.-ethyl-
• alpha-Phenylbutyric acid
• Benzeneacetic acid, alpha-ethyl-
• (+/-)-2-Phenylbutyric acid
• NSC 1860
• 2-phenyl-butyric acid
• a-Ethylphenylacetic acid
• MFCD00002667
• .alpha.-Phenylbutyric acid
• (RS)-2-Phenylbutanoic acid
• alpha-Ethyl-alpha-toluic acid
• (2RS)-2-Phenylbutanoic Acid
• CHEBI:86545
• NSC1860
• S7S079H2C2
• NSC-1860
• .alpha.-Toluic acid, .alpha.-ethyl-
• alpha-Phenyl butyric acid
• 2-Phenylbutanoicacid
• 2-Phenylburyric acid
• alpha-Toluic acid, alpha-ethyl-
• EINECS 201-982-5
• BRN 0509876
• 2-Ethyl-2-phenylacetic Acid
• UNII-S7S079H2C2
• a-Phenylbutyrate
• AI3-11228
• (2RS)-2-Phenylbutanoic Acid; Primidone Imp. E (EP); Primidone Impurity E
• 2-Phenylbutyrate
• 2-phenylbutanoate
• a-Ethyl-a-toluate
• a-Ethylphenylacetate
• alpha-Phenylbutyrate
• phenyl butanoic acid
• a-Ethylbenzeneacetate
• Primidone Impurity E
• a-Ethyl-a-toluic acid
• alpha-Ethylphenylacetate
• Spectrum_001673
• alpha-Ethylbenzeneacetate
• SpecPlus_000897
• a-Ethylbenzeneacetic acid
• (RS)-2-Phenylbutanoate
• alpha-Ethyl-alpha-toluate
• Spectrum2_000510
• Spectrum3_001664
• Spectrum4_000626
• Spectrum5_001396
• (+)2-phenylbutyric acid
• bmse000617
• A-PHENYLBUTYRIC ACID
• Cambridge id 5132265
• SCHEMBL1715
• WLN: QVY2&R
• .alpha.-Phenyl butyric acid
• alpha-Ethylbenzeneacetic acid
• 2-Phenylbutyric acid, 98%
• BSPBio_003447
• KBioGR_001212
• KBioSS_002153
• 2-09-00-00356 (Beilstein Handbook Reference)
• DivK1c_006993
• .alpha.-Ethylphenylacetic acid
• SPBio_000439
• .alpha.-Phenyl-n-butyric acid
• (4-CARBOXYPHENYL)ACETONE
• CHEMBL1616045
• KBio1_001937
• KBio2_002153
• KBio2_004721
• KBio2_007289
• KBio3_002667
• DTXSID90861682
• (.+/-.)-2-Phenylbutyric acid
• (.+/-.)-2-Phenylbutanoic acid
• AMY40956
• s6086
• AKOS000120324
• AKOS016040111
• (+/-)-2-PHENYLBUTANOIC ACID
• BS-3887
• CS-W017910
• HY-W017194
• SB44765
• AC-10409
• PD065554
• SY036812
• PRIMIDONE IMPURITY E [EP IMPURITY]
• FT-0605052
• FT-0605258
• FT-0613342
• P0164
• EN300-20606
• E78161
• A843486
• J-520787
• W-100334
• Q27159231
• F2191-0104
• Z104479150
• (+/-)-2-Phenylbutyric acid, Vetec(TM) reagent grade, 98%
• ?-Ethylphenylacetic acid; (+/-)-2-Phenylbutyric acid; (RS)-2-Phenylbutanoic acid; 2-Ethyl-2-phenylacetic Acid
• InChI=1/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8567	85.67%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6615	66.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9332	93.32%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8865	88.65%
P-glycoprotein inhibitior	-	0.9941	99.41%
P-glycoprotein substrate	-	0.9814	98.14%
CYP3A4 substrate	-	0.8087	80.87%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.9754	97.54%
CYP2C9 inhibition	-	0.8921	89.21%
CYP2C19 inhibition	-	0.9697	96.97%
CYP2D6 inhibition	-	0.9509	95.09%
CYP1A2 inhibition	-	0.8511	85.11%
CYP2C8 inhibition	-	0.9832	98.32%
CYP inhibitory promiscuity	-	0.9689	96.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5104	51.04%
Carcinogenicity (trinary)	Non-required	0.6816	68.16%
Eye corrosion	-	0.5727	57.27%
Eye irritation	+	0.9243	92.43%
Skin irritation	+	0.9276	92.76%
Skin corrosion	+	0.9004	90.04%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7713	77.13%
Micronuclear	-	0.9041	90.41%
Hepatotoxicity	+	0.6843	68.43%
skin sensitisation	+	0.7896	78.96%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.7922	79.22%
Acute Oral Toxicity (c)	III	0.9068	90.68%
Estrogen receptor binding	-	0.9483	94.83%
Androgen receptor binding	-	0.8733	87.33%
Thyroid receptor binding	-	0.8814	88.14%
Glucocorticoid receptor binding	-	0.9394	93.94%
Aromatase binding	-	0.9292	92.92%
PPAR gamma	-	0.6914	69.14%
Honey bee toxicity	-	0.9819	98.19%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8882	88.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.87%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.40%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.71%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.18%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.08%	94.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.97%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.01%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.37%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.85%	99.17%

Plants that contains it

• Artemisia judaica
• Artemisia sericea
• Glycyrrhiza glabra
• Opuntia ficus-indica
• Zea mays

Cross-Links

• PubChem: 7012
• LOTUS: LTS0194202
• wikiData: Q27159231