1,4-Butanediol
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Identification
- Generic Name
- 1,4-Butanediol
- DrugBank Accession Number
- DB01955
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 90.121
Monoisotopic: 90.068079564 - Chemical Formula
- C4H10O2
- Synonyms
- Not Available
- External IDs
- NSC-406696
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism APhospholipase A2, membrane associated inhibitorHumans UEndoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase Not Available Humans UGroup IIE secretory phospholipase A2 Not Available Humans URibosomal small subunit pseudouridine synthase A Not Available Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) UPenicillin-insensitive murein endopeptidase Not Available Escherichia coli (strain K12) - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as primary alcohols. These are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Alcohols and polyols
- Direct Parent
- Primary alcohols
- Alternative Parents
- Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Hydrocarbon derivative / Primary alcohol
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- glycol, butanediol (CHEBI:41189) / a glycol (CPD-13560)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 7XOO2LE6G3
- CAS number
- 110-63-4
- InChI Key
- WERYXYBDKMZEQL-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2
- IUPAC Name
- butane-1,4-diol
- SMILES
- OCCCCO
References
- Synthesis Reference
William E. Smith, "Production of tetrahydrofuran from 1,4-butanediol using tungsten on alumina catalysts." U.S. Patent US4136099, issued September, 1941.
US4136099- General References
- Satta R, Dimitrijevic N, Manev H: Drosophila metabolize 1,4-butanediol into gamma-hydroxybutyric acid in vivo. Eur J Pharmacol. 2003 Jul 25;473(2-3):149-52. [Article]
- Zvosec DL, Smith SW, McCutcheon JR, Spillane J, Hall BJ, Peacock EA: Adverse events, including death, associated with the use of 1,4-butanediol. N Engl J Med. 2001 Jan 11;344(2):87-94. [Article]
- Poldrugo F, Snead OC 3rd: 1,4 Butanediol, gamma-hydroxybutyric acid and ethanol: relationships and interactions. Neuropharmacology. 1984 Jan;23(1):109-113. [Article]
- External Links
- PubChem Compound
- 8064
- PubChem Substance
- 46506248
- ChemSpider
- 13835209
- ChEBI
- 41189
- ChEMBL
- CHEMBL171623
- ZINC
- ZINC000001599375
- Therapeutic Targets Database
- DAP000983
- PDBe Ligand
- BU1
- Wikipedia
- 1,4-Butanediol
- PDB Entries
- 1bk9 / 1m8r / 1m8s / 1tzp / 1vio / 1x9d / 2b9y / 2bab / 2hw8 / 2rh1 … show 74 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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) 20.1 °C PhysProp boiling point (°C) 235 °C PhysProp water solubility 1E+006 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -0.83 HANSCH,C ET AL. (1995) pKa 14.5 (at 25 °C) RIDDICK,JA ET AL. (1986) - Predicted Properties
Property Value Source Water Solubility 675.0 mg/mL ALOGPS logP -0.63 ALOGPS logP -0.63 Chemaxon logS 0.87 ALOGPS pKa (Strongest Acidic) 15.67 Chemaxon pKa (Strongest Basic) -2.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 24.06 m3·mol-1 Chemaxon Polarizability 10.16 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9406 Blood Brain Barrier + 0.7789 Caco-2 permeable + 0.5362 P-glycoprotein substrate Non-substrate 0.7076 P-glycoprotein inhibitor I Non-inhibitor 0.9564 P-glycoprotein inhibitor II Non-inhibitor 0.913 Renal organic cation transporter Non-inhibitor 0.8661 CYP450 2C9 substrate Non-substrate 0.8409 CYP450 2D6 substrate Non-substrate 0.8664 CYP450 3A4 substrate Non-substrate 0.7908 CYP450 1A2 substrate Non-inhibitor 0.8355 CYP450 2C9 inhibitor Non-inhibitor 0.9068 CYP450 2D6 inhibitor Non-inhibitor 0.9719 CYP450 2C19 inhibitor Non-inhibitor 0.9475 CYP450 3A4 inhibitor Non-inhibitor 0.965 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9267 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.6575 Biodegradation Ready biodegradable 0.7712 Rat acute toxicity 1.7406 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8362 hERG inhibition (predictor II) Non-inhibitor 0.9054
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 110.233385 predictedDarkChem Lite v0.1.0 [M-H]- 112.375985 predictedDarkChem Lite v0.1.0 [M-H]- 122.14549 predictedDeepCCS 1.0 (2019) [M+H]+ 111.922185 predictedDarkChem Lite v0.1.0 [M+H]+ 113.139785 predictedDarkChem Lite v0.1.0 [M+H]+ 124.076065 predictedDeepCCS 1.0 (2019) [M+Na]+ 110.629285 predictedDarkChem Lite v0.1.0 [M+Na]+ 112.169385 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.35194 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsPhospholipase A2, membrane associated
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Secretory calcium-dependent phospholipase A2 that primarily targets extracellular phospholipids with implications in host antimicrobial defense, inflammatory response and tissue regeneration (PubMed:10455175, PubMed:10681567, PubMed:2925633). Hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity) with preference for phosphatidylethanolamines and phosphatidylglycerols over phosphatidylcholines (PubMed:10455175, PubMed:10681567). Contributes to lipid remodeling of cellular membranes and generation of lipid mediators involved in pathogen clearance. Displays bactericidal activity against Gram-positive bacteria by directly hydrolyzing phospholipids of the bacterial membrane (PubMed:10358193, PubMed:11694541). Upon sterile inflammation, targets membrane phospholipids of extracellular mitochondria released from activated platelets, generating free unsaturated fatty acids such as arachidonate that is used by neighboring leukocytes to synthesize inflammatory eicosanoids such as leukotrienes. Simultaneously, by compromising mitochondrial membrane integrity, promotes the release in circulation of potent damage-associated molecular pattern molecules that activate the innate immune response (PubMed:25082876). Plays a stem cell regulator role in the intestinal crypt. Within intracellular compartment mediates Paneth cell differentiation and its stem cell supporting functions by inhibiting Wnt signaling pathway in intestinal stem cell (ICS). Secreted in the intestinal lumen upon inflammation, acts in an autocrine way and promotes prostaglandin E2 synthesis that stimulates Wnt signaling pathway in ICS cells and tissue regeneration (By similarity). May play a role in the biosynthesis of N-acyl ethanolamines that regulate energy metabolism and inflammation. Hydrolyzes N-acyl phosphatidylethanolamines to N-acyl lysophosphatidylethanolamines, which are further cleaved by a lysophospholipase D to release N-acyl ethanolamines (PubMed:14998370). Independent of its catalytic activity, acts as a ligand for integrins (PubMed:18635536, PubMed:25398877). Binds to and activates integrins ITGAV:ITGB3, ITGA4:ITGB1 and ITGA5:ITGB1 (PubMed:18635536, PubMed:25398877). Binds to a site (site 2) which is distinct from the classical ligand-binding site (site 1) and induces integrin conformational changes and enhanced ligand binding to site 1 (PubMed:25398877). Induces cell proliferation in an integrin-dependent manner (PubMed:18635536)
- Specific Function
- calcium ion binding
- Gene Name
- PLA2G2A
- Uniprot ID
- P14555
- Uniprot Name
- Phospholipase A2, membrane associated
- Molecular Weight
- 16082.525 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. [Article]
- 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. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Involved in glycoprotein quality control targeting of misfolded glycoproteins for degradation. It primarily trims a single alpha-1,2-linked mannose residue from Man(9)GlcNAc(2) to produce Man(8)GlcNAc(2), but at high enzyme concentrations, as found in the ER quality control compartment (ERQC), it further trims the carbohydrates to Man(5-6)GlcNAc(2)
- Specific Function
- calcium ion binding
- Gene Name
- MAN1B1
- Uniprot ID
- Q9UKM7
- Uniprot Name
- Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase
- Molecular Weight
- 79579.18 Da
References
3. DetailsGroup IIE secretory phospholipase A2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Secretory calcium-dependent phospholipase A2 that primarily targets extracellular phospholipids (PubMed:10681567, PubMed:11922621, PubMed:28883454). Hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity), releasing various unsaturated fatty acids including oleoate, linoleoate, arachidonate, docosahexaenoate and lysophosphatidylethanolamines in preference to lysophosphatidylcholines (PubMed:10681567, PubMed:28883454). In response to high-fat diet, hydrolyzes minor lipoprotein phospholipids including phosphatidylserines, phosphatidylinositols and phosphatidylglycerols, altering lipoprotein composition and fat storage in adipose tissue and liver (By similarity). May act in an autocrine and paracrine manner (PubMed:11922621). Contributes to lipid remodeling of cellular membranes and generation of lipid mediators involved in pathogen clearance. Cleaves sn-2 fatty acyl chains of phosphatidylglycerols and phosphatidylethanolamines, which are major components of membrane phospholipids in bacteria (PubMed:11922621). Acts as a hair follicle phospholipase A2. Selectively releases lysophosphatidylethanolamines (LPE) and various unsaturated fatty acids in skin to regulate hair follicle homeostasis (By similarity). May regulate the inflammatory response by releasing arachidonate, a precursor of prostaglandins and leukotrienes (PubMed:11922621). Upon allergen exposure, may participate in allergic inflammatory response by enhancing leukotriene C4 synthesis and degranulation in mast cells (By similarity)
- Specific Function
- calcium ion binding
- Gene Name
- PLA2G2E
- Uniprot ID
- Q9NZK7
- Uniprot Name
- Group IIE secretory phospholipase A2
- Molecular Weight
- 15988.525 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. [Article]
- 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. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
- Pharmacological action
- Unknown
- General Function
- Responsible for synthesis of pseudouridine from uracil-516 in 16S ribosomal RNA.
- Specific Function
- 16S rRNA pseudouridine(516) synthase activity
- Gene Name
- rsuA
- Uniprot ID
- P45124
- Uniprot Name
- Ribosomal small subunit pseudouridine synthase A
- Molecular Weight
- 26212.405 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Murein endopeptidase that cleaves the D-alanyl-meso-2,6-diamino-pimelyl amide bond that connects peptidoglycan strands. Likely plays a role in the removal of murein from the sacculus and could also play a role in the integration of nascent murein strands into the sacculus.
- Specific Function
- endopeptidase activity
- Gene Name
- mepA
- Uniprot ID
- P0C0T5
- Uniprot Name
- Penicillin-insensitive murein endopeptidase
- Molecular Weight
- 30136.415 Da
References
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22