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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-24 09:50:04 UTC

Update Date

2023-05-30 20:55:53 UTC

HMDB ID

HMDB0004812

Secondary Accession Numbers

HMDB0000578
HMDB00578
HMDB04812

Metabolite Identification

Common Name

2,5-Furandicarboxylic acid

Description

2,5-Furandicarboxylic acid is a normal urinary metabolite in humans. (PMID:14708889 , 8087979 , 2338430 , 3711221 ). Dietary studies show that the furan derivatives or their precursors are of exogenous origin. They are originated from furan derivatives found in food prepared by strong heating. This may explain the absence of 2,5-furandicarboxylic acid in urine of breastfed children, and the absence of these acids in the urine of rats, pigs, cows, oxs, rabbits, and monkeys (PMID 4630229 ). 2,5-Furandicarboxylic acid is also a microbial metabolite, a product of the oxidation of hydroxymethylfurfural (HMF) by the enzyme furfural/HMF oxidoreductase which is found in the bacterium Cupriavidus basilensis. Cupriavidus basilensis is a gram-negative soil bacterium of the genus Cupriavidus and the family Burkholderiaceae. 2,5-Furandicarboxylic acid increases with the level of fructose consumed (PMID:20194784 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,5-Dicarboxyfuran	ChEBI
Dehydromucic acid	ChEBI
Furane-alpha,alpha'-dicarboxylic acid	ChEBI
Furan-2,5-dicarboxylate	Kegg
Dehydromucate	Generator
Furane-a,alpha'-dicarboxylate	Generator
Furane-a,alpha'-dicarboxylic acid	Generator
Furane-alpha,alpha'-dicarboxylate	Generator
Furane-α,alpha'-dicarboxylate	Generator
Furane-α,alpha'-dicarboxylic acid	Generator
Furan-2,5-dicarboxylic acid	Generator
2,5-Furandicarboxylate	Generator
(1,5-Dimethylhexyl)hydrazine	HMDB
Dehydroschleimsaeure	HMDB
Furan 2,5-dicarboxylate	HMDB
Furan 2,5-dicarboxylic acid	HMDB
Furan-2,5-dicarbonsaeure	HMDB
Furane-a,a'-dicarboxylate	HMDB
Furane-a,a'-dicarboxylic acid	HMDB
FDCA CPD	MeSH, HMDB
2,5-Furandicarboxylic acid	ChEBI

Chemical Formula

C₆H₄O₅

Average Molecular Weight

156.093

Monoisotopic Molecular Weight

156.005873238

IUPAC Name

furan-2,5-dicarboxylic acid

Traditional Name

2,5-furandicarboxylic acid

CAS Registry Number

3238-40-2

SMILES

OC(=O)C1=CC=C(O1)C(O)=O

InChI Identifier

InChI=1S/C6H4O5/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)

InChI Key

CHTHALBTIRVDBM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furoic acids. These are organic compounds containing a furoic acid moiety, with a structure characterized by a furan ring bearing a carboxylic acid group at the C2 or C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furans

Sub Class

Furoic acid and derivatives

Direct Parent

Furoic acids

Alternative Parents

Substituents

Furoic acid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:84212 )
furans (CHEBI:84212 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)

Source

Endogenous

Endogenous (HMDB: HMDB0004812)

Microbe

Microbe (HMDB: HMDB0004812)
Cupriavidus basilensis (HMDB: HMDB0004812)

Exogenous

Exogenous (HMDB: HMDB0004812)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	342 °C	Not Available
Boiling Point	419.20 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1 mg/mL at 18 °C	Not Available
LogP	-0.020 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.8 g/L	ALOGPS
logP	0.66	ALOGPS
logP	0.27	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	-4.6	ChemAxon
pKa (Strongest Basic)	11.11	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	32.84 m³·mol⁻¹	ChemAxon
Polarizability	13.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	132.838	31661259
DarkChem	[M-H]-	127.592	31661259
DeepCCS	[M+H]+	128.615	30932474
DeepCCS	[M-H]-	124.788	30932474
DeepCCS	[M-2H]-	162.098	30932474
DeepCCS	[M+Na]+	137.589	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.5	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	125.2	32859911
AllCCS	[M+Na-2H]-	126.4	32859911
AllCCS	[M+HCOO]-	127.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Furandicarboxylic acid	OC(=O)C1=CC=C(O1)C(O)=O	1995.9	Standard polar	33892256
2,5-Furandicarboxylic acid	OC(=O)C1=CC=C(O1)C(O)=O	1342.2	Standard non polar	33892256
2,5-Furandicarboxylic acid	OC(=O)C1=CC=C(O1)C(O)=O	1457.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,5-Furandicarboxylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(C(=O)O)O1	1584.6	Semi standard non polar	33892256
2,5-Furandicarboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(C(=O)O[Si](C)(C)C)O1	1654.9	Semi standard non polar	33892256
2,5-Furandicarboxylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(C(=O)O)O1	1852.5	Semi standard non polar	33892256
2,5-Furandicarboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)O1	2143.8	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 - 2,5-Furandicarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5i-6900000000-d288769ec5810d63b1b2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Furandicarboxylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0229-9480000000-8391a736007498218310	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Furandicarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Furandicarboxylic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0900000000-2edf2743af7ee90a29ae	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000l-9200000000-a9709e652d30a2063847	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00ku-9000000000-c9fcb98abb314bb78c67	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 10V, Positive-QTOF	splash10-0a4r-0900000000-c2840f2e7256d798d4fa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 20V, Positive-QTOF	splash10-052r-0900000000-c3d20c4a56763ab0900c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 40V, Positive-QTOF	splash10-000j-9100000000-0e380e427de8c76266bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 10V, Negative-QTOF	splash10-0udi-0900000000-ec73c307d1a6f5bd94d2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 20V, Negative-QTOF	splash10-0w29-2900000000-0b5e65af058aa2ef6db6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 40V, Negative-QTOF	splash10-00lr-9200000000-41c982464657e52513de	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 10V, Negative-QTOF	splash10-02t9-9500000000-ea0c20378ff74ce1345f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 20V, Negative-QTOF	splash10-014i-9100000000-4520e50e1c56f6782681	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 40V, Negative-QTOF	splash10-014i-9000000000-eb1155a9bb1577d1bb89	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 10V, Positive-QTOF	splash10-0a4r-1900000000-9fe216ad8db30c7901bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 20V, Positive-QTOF	splash10-0002-9600000000-bfeb15a5dbae92e0bbcd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 40V, Positive-QTOF	splash10-000i-9000000000-524d51557840cf7b7f3c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	2.7 (0.1-9.1) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	6.9 (3.7-10.1) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.5 (0.1-12.0) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.7 (0.1-8.7) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.9 (0.1-5.4) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.39 (0.64-3.43) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

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

FDB023423

KNApSAcK ID

Not Available

Chemspider ID

69178

KEGG Compound ID

C20450

BioCyc ID

CPD-14105

BiGG ID

Not Available

Wikipedia Link

2,5-Furandicarboxylic_acid

METLIN ID

7076

PubChem Compound

76720

PDB ID

Not Available

ChEBI ID

84212

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1435791

References

Synthesis Reference

Gonis, George; Amstutz, E. D. Preparation of furan-2,5-dicarboxylic acid. Journal of Organic Chemistry (1962), 27 2946-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Pettersen JE, Jellum E: The identification and metabolic origin of 2-furoylglycine and 2,5-furandicarboxylic acid in human urine. Clin Chim Acta. 1972 Oct;41:199-207. [PubMed:4630229 ]
Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed:2338430 ]
Koopman F, Wierckx N, de Winde JH, Ruijssenaars HJ: Identification and characterization of the furfural and 5-(hydroxymethyl)furfural degradation pathways of Cupriavidus basilensis HMF14. Proc Natl Acad Sci U S A. 2010 Mar 16;107(11):4919-24. doi: 10.1073/pnas.0913039107. Epub 2010 Mar 1. [PubMed:20194784 ]
Heindl A, Dietel P, Spiteller G: Distinction between urinary acids originating from nutrition and those produced in the human body. J Chromatogr. 1986 Apr 25;377:3-14. doi: 10.1016/s0378-4347(00)80756-2. [PubMed:3711221 ]

Showing metabocard for 2,5-Furandicarboxylic acid (HMDB0004812)

MOL for HMDB0004812 (2,5-Furandicarboxylic acid)

3D MOL for HMDB0004812 (2,5-Furandicarboxylic acid)

3D SDF for HMDB0004812 (2,5-Furandicarboxylic acid)

3D-SDF for HMDB0004812 (2,5-Furandicarboxylic acid)

PDB for HMDB0004812 (2,5-Furandicarboxylic acid)

3D PDB for HMDB0004812 (2,5-Furandicarboxylic acid)

SMILES for HMDB0004812 (2,5-Furandicarboxylic acid)

INCHI for HMDB0004812 (2,5-Furandicarboxylic acid)

Structure for HMDB0004812 (2,5-Furandicarboxylic acid)

3D Structure for HMDB0004812 (2,5-Furandicarboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra