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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-12 21:20:02 UTC

Update Date

2023-02-21 17:16:41 UTC

HMDB ID

HMDB0003453

Secondary Accession Numbers

HMDB03453

Metabolite Identification

Common Name

3-Hydroxypropanal

Description

3-Hydroxypropanal is a broad-spectrum antimicrobial substance termed reuterin produced by Lactobacillus reuteri. L. reuteri resides in the gastrointestinal tract of healthy humans and animals, and is believed to. function as a symbiont in the enteric ecosystem. Synthesis of such an antimicrobial substance by an enteric resident raises a number of interesting questions and possibilities as to the role these residents may play in the health of the host. (PMID 3245697 ). In vivo, glycerol is converted in one enzymatic step into 3-Hydroxypropanal. The 3-Hydroxypropanal -producing Lactobacillus reuteri is used as a probiotic in the health care of humans and animals. 3-Hydroxypropanal forms, together with Hydroxypropanal-hydrate and Hydroxypropanal-dimer, a dynamic, multi-component system (Hydroxypropanal system) used in food preservation, as a precursor for many modern chemicals such as acrolein, acrylic acid, and 1,3-propanediol (1,3-PDO), and for polymer production. 3-Hydroxypropanal can be obtained both through traditional chemistry and bacterial fermentation. To date, 3-HPA has been produced from petrochemical resources as an intermediate in 1,3-PDO production. The biotechnological production of 3-Hydroxypropanal from renewable resources is desirable both for use of 3-Hydroxypropanal in foods and for the production of bulk chemicals. The main challenge will be the efficient production and recovery of pure 3-Hydroxypropanal. (PMID 14669058 ).

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-Hydroxypropionaldehyde	HMDB, MeSH
3-oxo-1-Propanol	HMDB
b-Hydroxypropanal	HMDB
b-Hydroxypropionaldehyde	HMDB
beta-Hydroxypropanal	HMDB
beta-Hydroxypropionaldehyde	HMDB, MeSH
Hydracrolein	HMDB
Reuterin	HMDB, MeSH
3-HPA	MeSH, HMDB

Chemical Formula

C₃H₆O₂

Average Molecular Weight

74.0785

Monoisotopic Molecular Weight

74.036779436

IUPAC Name

3-hydroxypropanal

Traditional Name

β-hydroxypropionaldehyde

CAS Registry Number

2134-29-4

SMILES

OCCC=O

InChI Identifier

InChI=1S/C3H6O2/c4-2-1-3-5/h2,5H,1,3H2

InChI Key

AKXKFZDCRYJKTF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydrogen aldehydes

Alternative Parents

Substituents

Alpha-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-CH2-containing aldehyde (CHEBI:17871 )
propanals (CHEBI:17871 )
a small molecule (HYDROXYPROPANAL )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0003453)

Source

Endogenous

Endogenous (HMDB: HMDB0003453)

Microbe

Microbe (HMDB: HMDB0003453)

Exogenous

Exogenous (HMDB: HMDB0003453)

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	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	645 g/L	ALOGPS
logP	-0.74	ALOGPS
logP	-0.96	ChemAxon
logS	0.94	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	18.12 m³·mol⁻¹	ChemAxon
Polarizability	7.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	112.165	31661259
DarkChem	[M-H]-	105.323	31661259
DeepCCS	[M+H]+	120.117	30932474
DeepCCS	[M-H]-	118.233	30932474
DeepCCS	[M-2H]-	153.584	30932474
DeepCCS	[M+Na]+	127.702	30932474
AllCCS	[M+H]+	122.6	32859911
AllCCS	[M+H-H2O]+	118.1	32859911
AllCCS	[M+NH4]+	126.8	32859911
AllCCS	[M+Na]+	128.0	32859911
AllCCS	[M-H]-	131.2	32859911
AllCCS	[M+Na-2H]-	136.7	32859911
AllCCS	[M+HCOO]-	142.8	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.	1.42 minutes	32390414
Predicted by Siyang on May 30, 2022	8.1441 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.74 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	203.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	648.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	324.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	94.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	230.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	244.3 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	271.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	322.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	551.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	52.4 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	705.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	240.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	598.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	294.0 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	254.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxypropanal	OCCC=O	1544.2	Standard polar	33892256
3-Hydroxypropanal	OCCC=O	648.4	Standard non polar	33892256
3-Hydroxypropanal	OCCC=O	732.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxypropanal,1TMS,isomer #1	C[Si](C)(C)OCCC=O	944.9	Semi standard non polar	33892256
3-Hydroxypropanal,1TMS,isomer #2	C[Si](C)(C)OC=CCO	983.1	Semi standard non polar	33892256
3-Hydroxypropanal,2TMS,isomer #1	C[Si](C)(C)OC=CCO[Si](C)(C)C	1105.5	Semi standard non polar	33892256
3-Hydroxypropanal,2TMS,isomer #1	C[Si](C)(C)OC=CCO[Si](C)(C)C	1046.5	Standard non polar	33892256
3-Hydroxypropanal,2TMS,isomer #1	C[Si](C)(C)OC=CCO[Si](C)(C)C	1076.4	Standard polar	33892256
3-Hydroxypropanal,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC=O	1165.5	Semi standard non polar	33892256
3-Hydroxypropanal,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CCO	1194.7	Semi standard non polar	33892256
3-Hydroxypropanal,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCO[Si](C)(C)C(C)(C)C	1511.0	Semi standard non polar	33892256
3-Hydroxypropanal,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCO[Si](C)(C)C(C)(C)C	1504.4	Standard non polar	33892256
3-Hydroxypropanal,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCO[Si](C)(C)C(C)(C)C	1391.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxypropanal GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-6f0de04be07974a052bd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxypropanal GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9300000000-044493864a3d344227bf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxypropanal 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-Hydroxypropanal 10V, Positive-QTOF	splash10-056r-9000000000-b527dd76b295599a6707	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 20V, Positive-QTOF	splash10-0a4i-9000000000-5d755fc67c397e2dd621	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 40V, Positive-QTOF	splash10-0a70-9000000000-54f403409b830f57b589	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 10V, Negative-QTOF	splash10-00di-9000000000-c121e90d5362a1780d7c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 20V, Negative-QTOF	splash10-00dl-9000000000-2dc320e96b74616f40eb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 40V, Negative-QTOF	splash10-0006-9000000000-0021ce0ee9221943ac40	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 10V, Positive-QTOF	splash10-0a4i-9000000000-46f5a128789cb1a670a2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 20V, Positive-QTOF	splash10-0a4i-9000000000-f9cf01f57aa08ed9654e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 40V, Positive-QTOF	splash10-052r-9000000000-ed02d307841f6070f7ea	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 10V, Negative-QTOF	splash10-00di-9000000000-93afe7a35357d19abf66	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 20V, Negative-QTOF	splash10-0a4i-9000000000-c17ad0c9c3a8a7d2783c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxypropanal 40V, Negative-QTOF	splash10-052f-9000000000-68a03885b61bc7330d49	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

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 (predicted from logP)

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

FDB023176

KNApSAcK ID

Not Available

Chemspider ID

67601

KEGG Compound ID

C00969

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Reuterin

METLIN ID

6935

PubChem Compound

75049

PDB ID

Not Available

ChEBI ID

17871

Food Biomarker Ontology

Not Available

VMH ID

3HPPNL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Lu, Shunfeng; Wang, Shiliang; Peng, Bin; Qin, Yanhuang; Zhou, Zhiquan; Wu, Xiuxiang. Process for preparation of 3-hydroxypropanal and 1,3-propanediol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 10 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Olivares M, Diaz-Ropero MP, Martin R, Rodriguez JM, Xaus J: Antimicrobial potential of four Lactobacillus strains isolated from breast milk. J Appl Microbiol. 2006 Jul;101(1):72-9. [PubMed:16834593 ]
Talarico TL, Casas IA, Chung TC, Dobrogosz WJ: Production and isolation of reuterin, a growth inhibitor produced by Lactobacillus reuteri. Antimicrob Agents Chemother. 1988 Dec;32(12):1854-8. [PubMed:3245697 ]
Vollenweider S, Lacroix C: 3-hydroxypropionaldehyde: applications and perspectives of biotechnological production. Appl Microbiol Biotechnol. 2004 Mar;64(1):16-27. Epub 2003 Dec 11. [PubMed:14669058 ]

Showing metabocard for 3-Hydroxypropanal (HMDB0003453)

MOL for HMDB0003453 (3-Hydroxypropanal)

3D MOL for HMDB0003453 (3-Hydroxypropanal)

3D SDF for HMDB0003453 (3-Hydroxypropanal)

3D-SDF for HMDB0003453 (3-Hydroxypropanal)

PDB for HMDB0003453 (3-Hydroxypropanal)

3D PDB for HMDB0003453 (3-Hydroxypropanal)

SMILES for HMDB0003453 (3-Hydroxypropanal)

INCHI for HMDB0003453 (3-Hydroxypropanal)

Structure for HMDB0003453 (3-Hydroxypropanal)

3D Structure for HMDB0003453 (3-Hydroxypropanal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra