Butyric Acid - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (3)Enzymes (1)

Identification

Name

Butyric Acid

Accession Number

DB03568 (EXPT00774)

Type

Small Molecule

Groups

Experimental

Description

A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

1-propanecarboxylic acid

Butanoic acid

Butyrate

Butyricum acidum

Ethylacetic acid

N-butanoic acid

N-butyric acid

Propylformic acid

External IDs

FEMA NO. 2221 / NSC-8415

Product Ingredients

Not Available

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

Categories

UNII

40UIR9Q29H

CAS number

107-92-6

Weight

Average: 88.1051
Monoisotopic: 88.0524295

Chemical Formula

C₄H₈O₂

InChI Key

FERIUCNNQQJTOY-UHFFFAOYSA-N

InChI

InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)

IUPAC Name

butanoic acid

SMILES

CCCC(O)=O

Pharmacology

Indication

Not Available

Structured Indications

Not Available

Pharmacodynamics

Not Available

Mechanism of action

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
(S)-2-haloacid dehalogenase	Protein	unknown	Not Available	Pseudomonas sp. (strain YL)	Q53464	details
Cholinesterase	Protein	unknown	Not Available	Human	P06276	details
2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase	Protein	unknown	Not Available	Pseudomonas fluorescens	P96965	details

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Pathway	Category	SMPDB ID
Butyrate Metabolism	Metabolic	SMP00073
Fatty Acid Biosynthesis	Metabolic	SMP00456

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
2,5-Dimethoxy-4-ethylamphetamine	2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Butanoic Acid.	Experimental, Illicit
3,4-Methylenedioxyamphetamine	3,4-Methylenedioxyamphetamine may decrease the sedative activities of Butanoic Acid.	Experimental, Illicit
3,4-Methylenedioxymethamphetamine	3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Butanoic Acid.	Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine	4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Butanoic Acid.	Experimental, Illicit
Amphetamine	Amphetamine may decrease the sedative activities of Butanoic Acid.	Approved, Illicit
Benzphetamine	Benzphetamine may decrease the sedative activities of Butanoic Acid.	Approved, Illicit
Benzylpenicilloyl Polylysine	Butanoic Acid may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.	Approved
Betahistine	The therapeutic efficacy of Betahistine can be decreased when used in combination with Butanoic Acid.	Approved
Chlorphentermine	Chlorphentermine may decrease the sedative activities of Butanoic Acid.	Illicit, Withdrawn
Dextroamphetamine	Dextroamphetamine may decrease the sedative activities of Butanoic Acid.	Approved, Illicit
Diethylpropion	Diethylpropion may decrease the sedative activities of Butanoic Acid.	Approved, Illicit
Hyaluronidase	The therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Butanoic Acid.	Approved, Investigational
Hydroxyamphetamine	Hydroxyamphetamine hydrobromide may decrease the sedative activities of Butanoic Acid.	Approved
Lisdexamfetamine	Lisdexamfetamine may decrease the sedative activities of Butanoic Acid.	Approved, Investigational
Mephedrone	Mephedrone may decrease the sedative activities of Butanoic Acid.	Investigational
Mephentermine	Mephentermine may decrease the sedative activities of Butanoic Acid.	Approved
Methamphetamine	Methamphetamine may decrease the sedative activities of Butanoic Acid.	Approved, Illicit
MMDA	MMDA may decrease the sedative activities of Butanoic Acid.	Experimental, Illicit
Phentermine	Phentermine may decrease the sedative activities of Butanoic Acid.	Approved, Illicit
Pseudoephedrine	Pseudoephedrine may decrease the sedative activities of Butanoic Acid.	Approved
Ritobegron	Ritobegron may decrease the sedative activities of Butanoic Acid.	Investigational

Food Interactions

Not Available

References

Synthesis Reference

Haruhiko Kikuchi, "Process for preparing 4-(4-biphenylyl)-4-oxo-butanoic acid." U.S. Patent US4621154, issued November, 1977.

US4621154

General References

Not Available

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB00039
KEGG Compound	C00246
PubChem Compound	264
PubChem Substance	46505927
ChemSpider	259
BindingDB	26109
ChEBI	30772
ChEMBL	CHEMBL14227
IUPHAR	1059
Guide to Pharmacology	1059
HET	BUA
Wikipedia	Butyric_acid

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1P0I

FDA label

Not Available

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Unknown Status	Treatment	Ataxia Telangiectasia (AT)	1
Not Available	Completed	Basic Science	Visceral (Hyper)Sensitivity	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	-5.7 °C	PhysProp
boiling point (°C)	163.7 °C	PhysProp
water solubility	6E+004 mg/L (at 25 °C)	HEMPHILL,L & SWANSON,WS (1964)
logP	0.79	HANSCH,C ET AL. (1995)
logS	-0.19	ADME Research, USCD
pKa	4.82 (at 25 °C)	RIDDICK,JA ET AL. (1986)

Predicted Properties

Property	Value	Source
Water Solubility	239.0 mg/mL	ALOGPS
logP	0.78	ALOGPS
logP	0.92	ChemAxon
logS	0.43	ALOGPS
pKa (Strongest Acidic)	4.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	21.87 m³·mol^-1	ChemAxon
Polarizability	9.22 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9938
Blood Brain Barrier	+	0.9572
Caco-2 permeable	+	0.7456
P-glycoprotein substrate	Non-substrate	0.759
P-glycoprotein inhibitor I	Non-inhibitor	0.9554
P-glycoprotein inhibitor II	Non-inhibitor	0.9773
Renal organic cation transporter	Non-inhibitor	0.9544
CYP450 2C9 substrate	Non-substrate	0.8026
CYP450 2D6 substrate	Non-substrate	0.9177
CYP450 3A4 substrate	Non-substrate	0.7582
CYP450 1A2 substrate	Inhibitor	0.5106
CYP450 2C9 inhibitor	Non-inhibitor	0.9345
CYP450 2D6 inhibitor	Non-inhibitor	0.9519
CYP450 2C19 inhibitor	Non-inhibitor	0.9613
CYP450 3A4 inhibitor	Non-inhibitor	0.972
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9849
Ames test	Non AMES toxic	0.95
Carcinogenicity	Non-carcinogens	0.5611
Biodegradation	Ready biodegradable	0.9659
Rat acute toxicity	1.6755 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9484
hERG inhibition (predictor II)	Non-inhibitor	0.9677

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
GC-MS	GC-MS Spectrum - EI-B	splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1	View in MoNA
GC-MS	GC-MS Spectrum - EI-B	splash10-03dl-9000000000-032fc35b394786b5896a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-7f461db56bfd8568ec71	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000i-9000000000-66f857fa612f773837bc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000i-9000000000-e6689b2e6bf21570b934	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-03dl-9000000000-b2ffa7d67b2466dea94f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03dl-9000000000-7467bf19c64fd3f51105	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-9ae015043b014b3c93d9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-efbb0e35a19a1713240b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-9ae015043b014b3c93d9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-efbb0e35a19a1713240b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-acb5cf0017a9ee680dd8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-812e24462a71dccb0fec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f9d30338ca1ee9409964	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-9d749b6b6cf2f93a8f85	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ku-9000000000-ee742730266fb4997777	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-88fc445cddcb726e93d8	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-5338ff8a9c4e59150aba	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Lipids and lipid-like molecules

Sub Class

Fatty Acyls

Direct Parent

Straight chain fatty acids

Alternative Parents

Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds

Substituents

Straight chain fatty acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group / Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

straight-chain saturated fatty acid, short-chain fatty acid (CHEBI:30772 ) / Straight chain fatty acids, Saturated fatty acids (C00246 ) / Straight chain fatty acids (LMFA01010004 )

Targets

Details

1. (S)-2-haloacid dehalogenase

Kind: Protein
Organism: Pseudomonas sp. (strain YL)
Pharmacological action: unknown

General Function:: (s)-2-haloacid dehalogenase activity
Specific Function:: Catalyzes the hydrolytic dehalogenation of small (S)-2-haloalkanoic acids to yield the corresponding (R)-2-hydroxyalkanoic acids. Acts on acids of short chain lengths, C(2) to C(4), with inversion of configuration at C-2.
Gene Name:: Not Available
Uniprot ID:: Q53464
Uniprot Name:: (S)-2-haloacid dehalogenase
Molecular Weight:: 26176.335 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Details

2. Cholinesterase

Kind: Protein
Organism: Human
Pharmacological action: unknown

General Function:: Identical protein binding
Specific Function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Uniprot Name:: Cholinesterase
Molecular Weight:: 68417.575 Da

Details

3. 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase

Kind: Protein
Organism: Pseudomonas fluorescens
Pharmacological action: unknown

General Function:: Hydrolase activity
Specific Function:: Not Available
Gene Name:: cumD
Uniprot ID:: P96965
Uniprot Name:: 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase
Molecular Weight:: 31489.385 Da

Enzymes

Details

1. Cholinesterase

Kind: Protein
Organism: Human
Pharmacological action: unknown

General Function:: Identical protein binding
Specific Function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Uniprot Name:: Cholinesterase
Molecular Weight:: 68417.575 Da

Drug created on June 13, 2005 07:24 / Updated on September 01, 2017 11:06

Structure for DB03568 (Butyric Acid)

Targets

References

Enzymes