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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:56 UTC

Update Date

2023-02-21 17:20:12 UTC

HMDB ID

HMDB0031256

Secondary Accession Numbers

HMDB31256

Metabolite Identification

Common Name

4-Hydroxy-2H-pyran-3-carboxaldehyde

Description

4-Hydroxy-2H-pyran-3-carboxaldehyde, also known as 3-formyl-4-hydroxy-2H-pyran, belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. Based on a literature review very few articles have been published on 4-Hydroxy-2H-pyran-3-carboxaldehyde.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Formyl-4-hydroxy-2H-pyran	HMDB

Chemical Formula

C₆H₆O₃

Average Molecular Weight

126.11

Monoisotopic Molecular Weight

126.031694058

IUPAC Name

4-hydroxy-2H-pyran-3-carbaldehyde

Traditional Name

4-hydroxy-2H-pyran-3-carbaldehyde

CAS Registry Number

26110-68-9

SMILES

OC1=C(COC=C1)C=O

InChI Identifier

InChI=1S/C6H6O3/c7-3-5-4-9-2-1-6(5)8/h1-3,8H,4H2

InChI Key

ZNUNRMPPGAAKKR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Not Available

Direct Parent

Pyrans

Alternative Parents

Substituents

Pyran
Vinylogous acid
Oxacycle
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031256)
Cytoplasm (HMDB: HMDB0031256)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031256)

Source

Endogenous

Endogenous (HMDB: HMDB0031256)

Plant

Plant (HMDB: HMDB0031256)

Exogenous

Food

Food (HMDB: HMDB0031256)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0031256)

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	77.9 g/L	ALOGPS
logP	-0.56	ALOGPS
logP	-0.61	ChemAxon
logS	-0.21	ALOGPS
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	33.18 m³·mol⁻¹	ChemAxon
Polarizability	11.4 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]+	126.036	31661259
DarkChem	[M-H]-	121.432	31661259
DeepCCS	[M+H]+	127.104	30932474
DeepCCS	[M-H]-	124.707	30932474
DeepCCS	[M-2H]-	161.163	30932474
DeepCCS	[M+Na]+	136.033	30932474
AllCCS	[M+H]+	126.2	32859911
AllCCS	[M+H-H2O]+	121.4	32859911
AllCCS	[M+NH4]+	130.7	32859911
AllCCS	[M+Na]+	132.0	32859911
AllCCS	[M-H]-	121.7	32859911
AllCCS	[M+Na-2H]-	123.8	32859911
AllCCS	[M+HCOO]-	126.0	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. Predicted by Afia on May 17, 2022.	2.75 minutes	32390414
Predicted by Siyang on May 30, 2022	9.4595 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.89 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	92.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1024.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	346.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	92.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	229.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	316.4 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	353.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	265.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	662.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	135.8 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	920.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	324.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	632.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	230.2 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	204.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-2H-pyran-3-carboxaldehyde	OC1=C(COC=C1)C=O	1938.7	Standard polar	33892256
4-Hydroxy-2H-pyran-3-carboxaldehyde	OC1=C(COC=C1)C=O	1041.4	Standard non polar	33892256
4-Hydroxy-2H-pyran-3-carboxaldehyde	OC1=C(COC=C1)C=O	1199.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-2H-pyran-3-carboxaldehyde,1TMS,isomer #1	C[Si](C)(C)OC1=C(C=O)COC=C1	1350.4	Semi standard non polar	33892256
4-Hydroxy-2H-pyran-3-carboxaldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C=O)COC=C1	1625.3	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 - 4-Hydroxy-2H-pyran-3-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-9100000000-be84f6288182462c270b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-6900000000-58d1a966f41b67bfec21	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 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 - 4-Hydroxy-2H-pyran-3-carboxaldehyde 10V, Positive-QTOF	splash10-004i-0900000000-f6bcab9d04261bda220d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 20V, Positive-QTOF	splash10-004i-6900000000-9b2e7e013ebd3e380a6c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 40V, Positive-QTOF	splash10-0a4i-9000000000-d6e69e3e16f978ebe8ec	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 10V, Negative-QTOF	splash10-004i-1900000000-96a642093bede997fb91	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 20V, Negative-QTOF	splash10-004i-4900000000-96d6f0ad1cbd627cbb0e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 40V, Negative-QTOF	splash10-052e-9000000000-e634dbd31ef9a01e6325	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 10V, Positive-QTOF	splash10-0a6r-9400000000-eab63026825a34ca0065	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 20V, Positive-QTOF	splash10-0a4i-9100000000-b25c8a792a4c76a4980d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 40V, Positive-QTOF	splash10-0a4i-9000000000-6b18443588211d124031	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 10V, Negative-QTOF	splash10-0002-9200000000-fe44de8d7c676afbd346	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 20V, Negative-QTOF	splash10-0007-9000000000-d73d3efb8df0a2603d65	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2H-pyran-3-carboxaldehyde 40V, Negative-QTOF	splash10-00kf-9000000000-6008162343ce1779d241	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

Cytoplasm
Extracellular

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

FDB003289

KNApSAcK ID

Not Available

Chemspider ID

30776894

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Hydroxy-2H-pyran-3-carboxaldehyde (HMDB0031256)

MOL for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

3D MOL for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

3D SDF for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

3D-SDF for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

PDB for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

3D PDB for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

SMILES for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

INCHI for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

Structure for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

3D Structure for HMDB0031256 (4-Hydroxy-2H-pyran-3-carboxaldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra