Basic Info

Common Name1,3-Butanediol(F05501)
2D Structure
Description

1,3-Butanediol is found in pepper (c. annuum). 1,3-Butanediol is a solvent for flavouring agents 1,3-Butanediol is an organic chemical, an alcohol. It is commonly used as a solvent for food flavouring agents and is a co-monomer used in certain polyurethane and polyester resins. It is one of four stable isomers of butanediol. In biology, 1,3-butanediol is used as a hypoglycaemic agent. 1,3-Butanediol belongs to the family of Secondary Alcohols. These are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

FRCD IDF05501
CAS Number107-88-0
PubChem CID7896
FormulaC4H10O2
IUPAC Name

butane-1,3-diol

InChI Key

PUPZLCDOIYMWBV-UHFFFAOYSA-N

InChI

InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3

Canonical SMILES

CC(CCO)O

Isomeric SMILES

CC(CCO)O

Wikipedia1,3-Butanediol
Synonyms
        
            Methyltrimethylene glycol
        
            1,3-BUTANEDIOL
        
            Butane-1,3-diol
        
            1,3-Butylene glycol
        
            107-88-0
        
            1,3-Dihydroxybutane
        
            1,3-Butandiol
        
            1-Methyl-1,3-propanediol
        
            beta-Butylene glycol
        
            1,3 Butylene glycol
        
Classifies
                

                  
                    Plant Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassAlcohols and polyols
Intermediate Tree NodesNot available
Direct ParentSecondary alcohols
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsSecondary alcohol - Hydrocarbon derivative - Primary alcohol - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as secondary alcohols. These are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Properties

Property NameProperty Value
Molecular Weight90.122
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Complexity28.7
Monoisotopic Mass90.068
Exact Mass90.068
XLogP-0.4
Formal Charge0
Heavy Atom Count6
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9037
Human Intestinal AbsorptionHIA+0.9908
Caco-2 PermeabilityCaco2+0.5724
P-glycoprotein SubstrateNon-substrate0.6708
P-glycoprotein InhibitorNon-inhibitor0.9123
Non-inhibitor0.8958
Renal Organic Cation TransporterNon-inhibitor0.8868
Distribution
Subcellular localizationLysosome0.4672
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8073
CYP450 2D6 SubstrateNon-substrate0.8439
CYP450 3A4 SubstrateNon-substrate0.7130
CYP450 1A2 InhibitorNon-inhibitor0.5422
CYP450 2C9 InhibitorNon-inhibitor0.9170
CYP450 2D6 InhibitorNon-inhibitor0.9044
CYP450 2C19 InhibitorNon-inhibitor0.8806
CYP450 3A4 InhibitorNon-inhibitor0.9135
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9078
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8909
Non-inhibitor0.9171
AMES ToxicityNon AMES toxic0.8505
CarcinogensNon-carcinogens0.6390
Fish ToxicityLow FHMT0.9513
Tetrahymena Pyriformis ToxicityLow TPT0.9971
Honey Bee ToxicityHigh HBT0.6874
BiodegradationReady biodegradable0.9733
Acute Oral ToxicityIV0.7380
Carcinogenicity (Three-class)Non-required0.7553

Model Value Unit
Absorption
Aqueous solubility0.7959LogS
Caco-2 Permeability1.0130LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity0.7164LD50, mol/kg
Fish Toxicity3.2619pLC50, mg/L
Tetrahymena Pyriformis Toxicity-2.1765pIGC50, ug/L

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]