1,4-Butanediol

Identification

Name
1,4-Butanediol
Accession Number
DB01955  (EXPT00771)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-406696
Categories
UNII
7XOO2LE6G3
CAS number
110-63-4
Weight
Average: 90.121
Monoisotopic: 90.068079564
Chemical Formula
C4H10O2
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEndoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidaseNot AvailableHuman
UPhospholipase A2, membrane associatedNot AvailableHuman
UGroup IIE secretory phospholipase A2Not AvailableHuman
URibosomal small subunit pseudouridine synthase ANot AvailableHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
UPenicillin-insensitive murein endopeptidaseNot AvailableEscherichia 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
  1. 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. [PubMed:12892832]
  2. 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. [PubMed:11150358]
  3. Poldrugo F, Snead OC 3rd: 1,4 Butanediol, gamma-hydroxybutyric acid and ethanol: relationships and interactions. Neuropharmacology. 1984 Jan;23(1):109-113. [PubMed:6717752]
External Links
PubChem Compound
8064
PubChem Substance
46506248
ChemSpider
13835209
ChEBI
41189
ChEMBL
CHEMBL171623
Therapeutic Targets Database
DAP000983
HET
BU1
Wikipedia
1,4-Butanediol
PDB Entries
1bk9 / 1m8r / 1m8s / 1tzp / 1vio / 1x9d / 2b9y / 2bab / 2hw8 / 2rh1
show 50 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)20.1 °CPhysProp
boiling point (°C)235 °CPhysProp
water solubility1E+006 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.83HANSCH,C ET AL. (1995)
pKa14.5 (at 25 °C)RIDDICK,JA ET AL. (1986)
Predicted Properties
PropertyValueSource
Water Solubility675.0 mg/mLALOGPS
logP-0.63ALOGPS
logP-0.63ChemAxon
logS0.87ALOGPS
pKa (Strongest Acidic)15.67ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.06 m3·mol-1ChemAxon
Polarizability10.16 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9406
Blood Brain Barrier+0.7789
Caco-2 permeable+0.5362
P-glycoprotein substrateNon-substrate0.7076
P-glycoprotein inhibitor INon-inhibitor0.9564
P-glycoprotein inhibitor IINon-inhibitor0.913
Renal organic cation transporterNon-inhibitor0.8661
CYP450 2C9 substrateNon-substrate0.8409
CYP450 2D6 substrateNon-substrate0.8664
CYP450 3A4 substrateNon-substrate0.7908
CYP450 1A2 substrateNon-inhibitor0.8355
CYP450 2C9 inhibitorNon-inhibitor0.9068
CYP450 2D6 inhibitorNon-inhibitor0.9719
CYP450 2C19 inhibitorNon-inhibitor0.9475
CYP450 3A4 inhibitorNon-inhibitor0.965
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9267
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6575
BiodegradationReady biodegradable0.7712
Rat acute toxicity1.7406 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8362
hERG inhibition (predictor II)Non-inhibitor0.9054
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-1c3e5028147c04eef039
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-e73d0286021e82006c29
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-798a32748fa78ba29b8e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Hydrocarbon derivative / Primary alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
glycol, butanediol (CHEBI:41189) / a glycol (CPD-13560)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Mannosyl-oligosaccharide 1,2-alpha-mannosidase activity
Specific 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)Glc...
Gene Name
MAN1B1
Uniprot ID
Q9UKM7
Uniprot Name
Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase
Molecular Weight
79579.18 Da
References
  1. 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]
  2. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phospholipid binding
Specific Function
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-ph...
Gene Name
PLA2G2A
Uniprot ID
P14555
Uniprot Name
Phospholipase A2, membrane associated
Molecular Weight
16082.525 Da
References
  1. 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]
  2. 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]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phospholipase a2 activity
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name
PLA2G2E
Uniprot ID
Q9NZK7
Uniprot Name
Group IIE secretory phospholipase A2
Molecular Weight
15988.525 Da
References
  1. 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]
  2. 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]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Unknown
General Function
Rna binding
Specific Function
Responsible for synthesis of pseudouridine from uracil-516 in 16S ribosomal RNA.
Gene Name
rsuA
Uniprot ID
P45124
Uniprot Name
Ribosomal small subunit pseudouridine synthase A
Molecular Weight
26212.405 Da
References
  1. 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]
  2. 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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Involved in the removal of murein from the sacculus. May also facilitate integration of nascent murein strands into the sacculus by cleaving the peptide bonds between neighboring strands in mature ...
Gene Name
mepA
Uniprot ID
P0C0T5
Uniprot Name
Penicillin-insensitive murein endopeptidase
Molecular Weight
30136.415 Da
References
  1. 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]
  2. 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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:51