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Showing NP-Card for Tetrahydrofuran (NP0001090)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:24 UTC
NP-MRD IDNP0001090
Secondary Accession NumbersNone
Natural Product Identification
Common NameTetrahydrofuran
DescriptionTetrahydrofuran (THF) is a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity and a smell similar to diethyl ether. At low concentrations it has a faint, fruity aroma. It is one of the most polar ethers. THF is naturally present in coffee aroma, floured chickpeas, and cooked chicken. It is used in the manufacture of polymers as well as agricultural, pharmaceutical, and commodity chemicals. Because of its widespread use (industrially) and its presence in many foods, THF is a contaminant of exposure and can appear in human biofluids. THF oxidizes readily, which can lead to instability and result in cytotoxicity. In chemical synthesis applications, THF is often used for hydroborations used to synthesize primary alcohols. THF is frequently used as a solvent for Grignard reagents because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent (an organometallic chemical reaction involving alkyl- or aryl-magnesium halides). THF is often used in polymer science. For example, it can be used to dissolve rubber prior to determining its molecular mass using gel permeation chromatography. THF tends to form peroxides on storage in air. (PMID: 16999122 , 12742700 , 14619948 ). THF can be degraded by certain strains of Rhodococcus bacteria (PMID: 19230656 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001090 (Tetrahydrofuran)


  Mrv1652305271900302D          

  5  5  0  0  0  0            999 V2000
    9.2080  -11.1626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6205   -9.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7954   -9.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8754  -10.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5405  -10.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
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3D MOL for NP0001090 (Tetrahydrofuran)

HMDB0000246
     RDKit          3D
Tetrahydrofuran
 13 13  0  0  0  0  0  0  0  0999 V2000
   -0.9146   -0.5908   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -0.8969   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    0.4204    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3464    1.3296   -0.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014    0.9094    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -0.7754   -1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4869   -1.1459    0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8409   -1.6482    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.1689   -1.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3389    0.6352    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2142    0.4339   -0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6886    1.4414   -0.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    1.0563    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  5 12  1  0
  5 13  1  0
M  END
Download

3D SDF for NP0001090 (Tetrahydrofuran)


  Mrv1652305271900302D          

  5  5  0  0  0  0            999 V2000
    9.2080  -11.1626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6205   -9.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7954   -9.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8754  -10.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5405  -10.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1CCOC1

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2

> <INCHI_KEY>
WYURNTSHIVDZCO-UHFFFAOYSA-N

> <FORMULA>
C4H8O

> <MOLECULAR_WEIGHT>
72.1057

> <EXACT_MASS>
72.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.143121394001305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
oxolane

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.5303469016666666

> <ALOGPS_LOGS>
-0.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.122667250833544

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
20.5535

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.97e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrahydrofuran

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0001090 (Tetrahydrofuran)

HMDB0000246
     RDKit          3D
Tetrahydrofuran
 13 13  0  0  0  0  0  0  0  0999 V2000
   -0.9146   -0.5908   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -0.8969   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    0.4204    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3464    1.3296   -0.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014    0.9094    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -0.7754   -1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4869   -1.1459    0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8409   -1.6482    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.1689   -1.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3389    0.6352    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2142    0.4339   -0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6886    1.4414   -0.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    1.0563    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  5 12  1  0
  5 13  1  0
M  END
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PDB for NP0001090 (Tetrahydrofuran)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      17.188 -20.837   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      17.958 -18.467   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.418 -18.467   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.434 -19.932   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.942 -19.932   0.000  0.00  0.00           C+0
CONECT    1    4    5                                                       
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    1    2                                                       
CONECT    5    1    3                                                       
MASTER        0    0    0    0    0    0    0    0    5    0   10    0
END
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3D PDB for NP0001090 (Tetrahydrofuran)

COMPND    HMDB0000246
HETATM    1  C1  UNL     1      -0.915  -0.591  -0.175  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.567  -0.897  -0.132  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.217   0.420   0.176  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.346   1.330  -0.404  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.901   0.909   0.074  1.00  0.00           C  
HETATM    6  H1  UNL     1      -1.369  -0.775  -1.159  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.487  -1.146   0.571  1.00  0.00           H  
HETATM    8  H3  UNL     1       0.841  -1.648   0.606  1.00  0.00           H  
HETATM    9  H4  UNL     1       0.855  -1.169  -1.179  1.00  0.00           H  
HETATM   10  H5  UNL     1       1.339   0.635   1.238  1.00  0.00           H  
HETATM   11  H6  UNL     1       2.214   0.434  -0.299  1.00  0.00           H  
HETATM   12  H7  UNL     1      -1.689   1.441  -0.472  1.00  0.00           H  
HETATM   13  H8  UNL     1      -1.018   1.056   1.155  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    8    9
CONECT    3    4   10   11
CONECT    4    5
CONECT    5   12   13
END
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SMILES for NP0001090 (Tetrahydrofuran)

C1CCOC1
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INCHI for NP0001090 (Tetrahydrofuran)

InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
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View in JSmol
Synonyms
ValueSource
1,4-EpoxybutaneChEBI
Butane alpha,delta-oxideChEBI
Butylene oxideChEBI
FuranidineChEBI
Tetramethylene oxideChEBI
THFChEBI
Butane a,delta-oxideGenerator
Butane α,δ-oxideGenerator
Butane a,δ-oxideHMDB
1,4-Epoxy-butaneHMDB
Butane a,D-oxideHMDB
CyclotetramethyleneHMDB
Cyclotetramethylene oxideHMDB
Diethylene oxideHMDB
HydrofuranHMDB
OxacyclopentaneHMDB
OxolaneHMDB
PolytetrahydrofuranHMDB
TetrahydrofuraanHMDB
TetrahydrofuraneHMDB
TetrahydrofuranneHMDB
TetraidrofuranoHMDB
TetrahydrofuranChEBI
Chemical FormulaC4H8O
Average Mass72.1057 Da
Monoisotopic Mass72.05751 Da
IUPAC Nameoxolane
Traditional Nametetrahydrofuran
CAS Registry Number109-99-9
SMILES
C1CCOC1
InChI Identifier
InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
InChI KeyWYURNTSHIVDZCO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea fragrantissimaKNApSAcK Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea var. botrytisFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydrofurans
Sub ClassNot Available
Direct ParentTetrahydrofurans
Alternative Parents
Substituents
  • Tetrahydrofuran
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-108.3 °CNot Available
Boiling Point65.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP0.46Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility69.7 g/LALOGPS
logP0.35ALOGPS
logP0.53ChemAxon
logS-0.01ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.55 m³·mol⁻¹ChemAxon
Polarizability8.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000246
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021917
KNApSAcK IDC00010358
Chemspider ID7737
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTHF
METLIN IDNot Available
PubChem Compound8028
PDB IDNot Available
ChEBI ID26911
Good Scents IDrw1287631
References
General References
  1. Dietzen DJ, Wilhite TR, Kenagy DN, Milliner DS, Smith CH, Landt M: Extraction of glyceric and glycolic acids from urine with tetrahydrofuran: utility in detection of primary hyperoxaluria. Clin Chem. 1997 Aug;43(8 Pt 1):1315-20. [PubMed:9267307 ]
  2. Sadler BM, Chittick GE, Polk RE, Slain D, Kerkering TM, Studenberg SD, Lou Y, Moore KH, Woolley JL, Stein DS: Metabolic disposition and pharmacokinetics of [14C]-amprenavir, a human immunodeficiency virus type 1 (HIV-1) protease inhibitor, administered as a single oral dose to healthy male subjects. J Clin Pharmacol. 2001 Apr;41(4):386-96. [PubMed:11304895 ]
  3. Ilett KF, Ethell BT, Maggs JL, Davis TM, Batty KT, Burchell B, Binh TQ, Thu le TA, Hung NC, Pirmohamed M, Park BK, Edwards G: Glucuronidation of dihydroartemisinin in vivo and by human liver microsomes and expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2002 Sep;30(9):1005-12. [PubMed:12167566 ]
  4. Zhao B, Tham SY, Lu J, Lai MH, Lee LK, Moochhala SM: Simultaneous determination of vitamins C, E and beta-carotene in human plasma by high-performance liquid chromatography with photodiode-array detection. J Pharm Pharm Sci. 2004 Jun 30;7(2):200-4. [PubMed:15367376 ]
  5. Unni LK, Becker RE: Determination of heptylphysostigmine in plasma by high-performance liquid chromatography with electrochemical detection. J Chromatogr. 1992 Jan 17;573(2):275-81. [PubMed:1601960 ]
  6. Clayton PT, Leonard JV, Lawson AM, Setchell KD, Andersson S, Egestad B, Sjovall J: Familial giant cell hepatitis associated with synthesis of 3 beta, 7 alpha-dihydroxy-and 3 beta,7 alpha, 12 alpha-trihydroxy-5-cholenoic acids. J Clin Invest. 1987 Apr;79(4):1031-8. [PubMed:3470305 ]
  7. Breithaupt H, Wilfling M: Determination of mexiletine in biological fluids by high-performance liquid chromatography. J Chromatogr. 1982 Jun 11;230(1):97-105. [PubMed:7107772 ]
  8. Imbenotte M, Azaroual N, Cartigny B, Vermeersch G, Lhermitte M: Identification and quantitation of xenobiotics by 1H NMR spectroscopy in poisoning cases. Forensic Sci Int. 2003 Apr 23;133(1-2):132-5. [PubMed:12742700 ]
  9. Mahendra S, Alvarez-Cohen L: Kinetics of 1,4-dioxane biodegradation by monooxygenase-expressing bacteria. Environ Sci Technol. 2006 Sep 1;40(17):5435-42. [PubMed:16999122 ]
  10. Authors unspecified: International Conference on Harmonisation; final recommendations on the revision of the permitted daily exposures for two solvents, n-methylpyrrolidone and tetrahydrofuran, according to the maintenance procedures for the guidance Q3C Impurities: Residual Solvents; Availability. Notice. Fed Regist. 2003 Nov 13;68(219):64352-3. [PubMed:14619948 ]
  11. Yao Y, Lv Z, Min H, Lv Z, Jiao H: Isolation, identification and characterization of a novel Rhodococcus sp. strain in biodegradation of tetrahydrofuran and its medium optimization using sequential statistics-based experimental designs. Bioresour Technol. 2009 Jun;100(11):2762-9. doi: 10.1016/j.biortech.2009.01.006. Epub 2009 Feb 18. [PubMed:19230656 ]