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Identification
Name1,4-Butanediol
Accession NumberDB01955  (EXPT00771)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number110-63-4
WeightAverage: 90.121
Monoisotopic: 90.068079564
Chemical FormulaC4H10O2
InChI KeyWERYXYBDKMZEQL-UHFFFAOYSA-N
InChI
InChI=1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2
IUPAC Name
butane-1,4-diol
SMILES
OCCCCO
Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassPrimary alcohols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9068
CYP450 2D6 substrateNon-inhibitor0.9719
CYP450 2C19 substrateNon-inhibitor0.9475
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point20.1 °CPhysProp
boiling point235 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 Reference
  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
  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
  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
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase Q9UKM7 Details

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
  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

2. Phospholipase A2, membrane associated

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Phospholipase A2, membrane associated P14555 Details

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
  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
  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

3. Group IIE secretory phospholipase A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Group IIE secretory phospholipase A2 Q9NZK7 Details

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
  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
  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

4. Ribosomal small subunit pseudouridine synthase A

Kind: protein

Organism: Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)

Pharmacological action: unknown

Components

Name UniProt ID Details
Ribosomal small subunit pseudouridine synthase A P45124 Details

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
  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

5. Penicillin-insensitive murein endopeptidase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Penicillin-insensitive murein endopeptidase P0C0T5 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:16