PHENYLBUTANOIC ACID

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Search structure


Synonyms	Phenylbutanoic acid Phenylbutyrate
Status
Molecule Category	UNKNOWN
UNII	7WY7YBI87E
EPA CompTox	DTXSID2037631


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	OBKXEAXTFZPCHS-UHFFFAOYSA-N
Smiles	O=C(O)CCCc1ccccc1
InChI	InChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C10H12O2
Molecular Weight	164.2
AlogP	2.09
Hydrogen Bond Acceptor	1.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	4.0
Polar Surface Area	37.3
Molecular species	ACID
Aromatic Rings	1.0
Heavy Atoms	12.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of GSK3-beta at 2 mM relative to control	None	125.6 %
Inhibition of HDAC in human HeLa cells at 1.5 mM after 10 mins by fluorometric assay	Homo sapiens	40.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	62.24 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	71.09 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	7.47 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	8.43 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	14.97 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	13.63 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	2.48 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	6.54 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-6.41 %
Inhibition of human TAS2R39 expressed in HEK293 cells coexpressing G-protein at 10 mM assessed as reduction in epicatechin gallate-induced intracellular calcium release by Fluo-4-AM dye based fluorescence assay relative to control	Homo sapiens	40.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	20.4 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.11 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.11 %

Cross References

Resources	Reference
ChEBI	41500
ChEMBL	CHEMBL1469
DrugBank	DB06819
DrugCentral	24
FDA SRS	7WY7YBI87E
Human Metabolome Database	HMDB0000543
Guide to Pharmacology	8480
PDB	CLT
SureChEMBL	SCHEMBL1716
ZINC	ZINC000000056568

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).