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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-08 14:58:43 UTC

Update Date

2023-02-21 17:18:39 UTC

HMDB ID

HMDB0029171

Secondary Accession Numbers

HMDB29171

Metabolite Identification

Common Name

3-Hydroxyadipic acid 3,6-lactone

Description

3-Hydroxyadipic acid 3,6-lactone, also known as (5-oxotetrahydrofuran-2-yl)acetic acid or 2-furanacetic acid, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 3-Hydroxyadipic acid 3,6-lactone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyadipic acid 3,6-lactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxyadipic acid 3,6-lactone.

Structure

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

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0      -5.711   0.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.149  -0.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.068  -1.594   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.581  -1.993   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.742  -0.701   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -8.402  -2.364   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.254  -0.303   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0      -3.972  -2.035   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0      -2.856   1.185   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.945   2.274   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.368   0.786   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      -0.035   1.556   0.000  0.00  0.00           H+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4    7    8                                             
CONECT    6    3                                                            
CONECT    7    5    9                                                       
CONECT    8    5                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxyadipate 3,6-lactone	Generator
(5-Oxotetrahydrofuran-2-yl)acetic acid	HMDB
2-Furanacetic acid	HMDB
3-HA-3,6-la	HMDB
2-(5-Oxooxolan-2-yl)acetate	HMDB
3-Hydroxyadipic acid 3,6-lactone	MeSH

Chemical Formula

C₆H₈O₄

Average Molecular Weight

144.1253

Monoisotopic Molecular Weight

144.042258744

IUPAC Name

2-(5-oxooxolan-2-yl)acetic acid

Traditional Name

(5-oxooxolan-2-yl)acetic acid

CAS Registry Number

60551-20-4

SMILES

[H]OC(=O)CC1([H])CCC(=O)O1

InChI Identifier

InChI=1S/C6H8O4/c7-5(8)3-4-1-2-6(9)10-4/h4H,1-3H2,(H,7,8)

InChI Key

BWEICTHJUIJQPH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
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

Endogenous (HMDB: HMDB0029171)

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	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	235 g/L	ALOGPS
logP	0.11	ALOGPS
logP	-0.076	ChemAxon
logS	0.21	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	30.76 m³·mol⁻¹	ChemAxon
Polarizability	13.14 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]+	131.367	31661259
DarkChem	[M-H]-	125.302	31661259
DeepCCS	[M+H]+	131.616	30932474
DeepCCS	[M-H]-	129.071	30932474
DeepCCS	[M-2H]-	165.1	30932474
DeepCCS	[M+Na]+	140.055	30932474
AllCCS	[M+H]+	131.6	32859911
AllCCS	[M+H-H2O]+	127.2	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	136.9	32859911
AllCCS	[M-H]-	127.5	32859911
AllCCS	[M+Na-2H]-	129.2	32859911
AllCCS	[M+HCOO]-	131.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	2.62 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3692 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.17 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	77.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1227.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	316.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	99.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	199.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	82.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	273.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	325.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	688.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	236.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	898.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	619.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	223.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	289.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyadipic acid 3,6-lactone	[H]OC(=O)CC1([H])CCC(=O)O1	2179.8	Standard polar	33892256
3-Hydroxyadipic acid 3,6-lactone	[H]OC(=O)CC1([H])CCC(=O)O1	1179.3	Standard non polar	33892256
3-Hydroxyadipic acid 3,6-lactone	[H]OC(=O)CC1([H])CCC(=O)O1	1335.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyadipic acid 3,6-lactone,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1CCC(=O)O1	1433.0	Semi standard non polar	33892256
3-Hydroxyadipic acid 3,6-lactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1CCC(=O)O1	1681.9	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 - 3-Hydroxyadipic acid 3,6-lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9200000000-fc900a34eeb605905df9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone GC-MS (1 TMS) - 70eV, Positive	splash10-00bi-9500000000-bafa60ccc592602dfe8d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 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 - 3-Hydroxyadipic acid 3,6-lactone 10V, Positive-QTOF	splash10-004j-3900000000-588a741042f02175d2db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 20V, Positive-QTOF	splash10-00mt-9600000000-19caed7ae5ce662aba99	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 40V, Positive-QTOF	splash10-00ku-9000000000-3e8894774fa2437a1cea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 10V, Negative-QTOF	splash10-0007-5900000000-90d8d1023e15467f7639	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 20V, Negative-QTOF	splash10-0002-9500000000-080cf78e3e084c5114bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 40V, Negative-QTOF	splash10-0006-9000000000-ae72097e461eeccffbab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 10V, Positive-QTOF	splash10-0002-9300000000-e2e26bc548ea5e45deb4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 20V, Positive-QTOF	splash10-053m-9000000000-bdb61c552e244b22efc2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 40V, Positive-QTOF	splash10-052f-9000000000-b633d0c80af91209ccd1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 10V, Negative-QTOF	splash10-0005-9400000000-c8d72a43df3e70e601b8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 20V, Negative-QTOF	splash10-006t-9000000000-a9ae910b51717834c1b9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 40V, Negative-QTOF	splash10-052f-9000000000-0c20aafa91b0aa7ba3a9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB111656

KNApSAcK ID

Not Available

Chemspider ID

168429

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

194109

PDB ID

Not Available

ChEBI ID

173603

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

Tserng KY, Jin SJ, Hoppel CL, Kerr DS, Genuth SM: Urinary 3-hydroxyadipic acid 3,6-lactone: structural identification and effect of fasting in adults and children. Metabolism. 1989 Jul;38(7):655-61. [PubMed:2739576 ]

Showing metabocard for 3-Hydroxyadipic acid 3,6-lactone (HMDB0029171)

MOL for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

3D MOL for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

3D SDF for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

3D-SDF for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

PDB for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

3D PDB for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

SMILES for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

INCHI for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

Structure for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

3D Structure for HMDB0029171 (3-Hydroxyadipic acid 3,6-lactone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra