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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-26 19:03:03 UTC

Update Date

2022-03-07 03:17:36 UTC

HMDB ID

HMDB0059767

Secondary Accession Numbers

HMDB59767

Metabolite Identification

Common Name

Tetrahydro-2,5-furan-diacetic acid

Description

Tetrahydro-2,5-furan-diacetic acid belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Tetrahydro-2,5-furan-diacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02261312032D          

 13 13  0  0  0  0            999 V2000
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
  5 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059767

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1CCC(CC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C8H12O5/c9-7(10)3-5-1-2-6(13-5)4-8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12)

> <INCHI_KEY>
CVYAVSIMBYOCGA-UHFFFAOYSA-N

> <FORMULA>
C8H12O5

> <MOLECULAR_WEIGHT>
188.1779

> <EXACT_MASS>
188.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
17.86987564813657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[5-(carboxymethyl)oxolan-2-yl]acetic acid

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
0.07987313100000004

> <ALOGPS_LOGS>
-0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.4778847027456505

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7442997278590804

> <JCHEM_PKA_STRONGEST_BASIC>
-4.173748480527701

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
41.46190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(carboxymethyl)oxolan-2-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-FEB-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-FEB-13         0                                  
HETATM    1  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.727   3.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.147  -1.375   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.052  -2.621   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.773   0.032   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8    5                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Tetrahydro-2,5-furan-diacetate	Generator
2-[5-(Carboxymethyl)oxolan-2-yl]acetate	Generator

Chemical Formula

C₈H₁₂O₅

Average Molecular Weight

188.1779

Monoisotopic Molecular Weight

188.068473494

IUPAC Name

2-[5-(carboxymethyl)oxolan-2-yl]acetic acid

Traditional Name

[5-(carboxymethyl)oxolan-2-yl]acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC1CCC(CC(O)=O)O1

InChI Identifier

InChI=1S/C8H12O5/c9-7(10)3-5-1-2-6(13-5)4-8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12)

InChI Key

CVYAVSIMBYOCGA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Tetrahydrofuran
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 2338430)

Source

Exogenous

Exogenous (HMDB: HMDB0059767)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	43.4 g/L	ALOGPS
logP	0.94	ALOGPS
logP	0.08	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.46 m³·mol⁻¹	ChemAxon
Polarizability	17.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.898	31661259
DarkChem	[M-H]-	137.058	31661259
DeepCCS	[M+H]+	140.949	30932474
DeepCCS	[M-H]-	137.444	30932474
DeepCCS	[M-2H]-	174.729	30932474
DeepCCS	[M+Na]+	150.104	30932474
AllCCS	[M+H]+	142.2	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	145.9	32859911
AllCCS	[M+Na]+	147.0	32859911
AllCCS	[M-H]-	139.8	32859911
AllCCS	[M+Na-2H]-	140.6	32859911
AllCCS	[M+HCOO]-	141.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydro-2,5-furan-diacetic acid	OC(=O)CC1CCC(CC(O)=O)O1	2870.0	Standard polar	33892256
Tetrahydro-2,5-furan-diacetic acid	OC(=O)CC1CCC(CC(O)=O)O1	1453.9	Standard non polar	33892256
Tetrahydro-2,5-furan-diacetic acid	OC(=O)CC1CCC(CC(O)=O)O1	1648.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydro-2,5-furan-diacetic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1CCC(CC(=O)O)O1	1682.8	Semi standard non polar	33892256
Tetrahydro-2,5-furan-diacetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1CCC(CC(=O)O[Si](C)(C)C)O1	1746.4	Semi standard non polar	33892256
Tetrahydro-2,5-furan-diacetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1CCC(CC(=O)O)O1	1942.0	Semi standard non polar	33892256
Tetrahydro-2,5-furan-diacetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1CCC(CC(=O)O[Si](C)(C)C(C)(C)C)O1	2213.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydro-2,5-furan-diacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9400000000-848fd387006c83791337	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydro-2,5-furan-diacetic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0g70-9251000000-e8fe87f2776e0efa0042	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydro-2,5-furan-diacetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 10V, Positive-QTOF	splash10-00dr-0900000000-d5191127ef6a23bbace6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 20V, Positive-QTOF	splash10-00g0-2900000000-2efec8c0612592e751fb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 40V, Positive-QTOF	splash10-0ar3-9000000000-eb9821fea1e001521461	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 10V, Negative-QTOF	splash10-000i-0900000000-e37001711a4c6df71381	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 20V, Negative-QTOF	splash10-05p6-3900000000-392b616a4085a7dd4a92	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 40V, Negative-QTOF	splash10-0a4i-9200000000-ff025308db8201e00a6f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 10V, Positive-QTOF	splash10-003j-6900000000-64f8370a590ed407c192	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 20V, Positive-QTOF	splash10-0044-9500000000-ae030e44bf3ebb8f4f1e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 40V, Positive-QTOF	splash10-0537-9100000000-544bfbba4c1a698bf8f1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 10V, Negative-QTOF	splash10-000i-1900000000-e1fb35f3c32b9a2a7ac0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 20V, Negative-QTOF	splash10-0a5d-9400000000-88e052bdb4a3c5925843	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2,5-furan-diacetic acid 40V, Negative-QTOF	splash10-0a5c-9000000000-2cec2597855f923a4366	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	2338430	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13220191

PDB ID

Not Available

ChEBI ID

89885

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Tetrahydro-2,5-furan-diacetic acid (HMDB0059767)

MOL for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

3D MOL for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

3D SDF for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

3D-SDF for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

PDB for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

3D PDB for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

SMILES for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

INCHI for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

Structure for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

3D Structure for HMDB0059767 (Tetrahydro-2,5-furan-diacetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra