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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:22:25 UTC

Update Date

2023-02-21 17:30:01 UTC

HMDB ID

HMDB0060461

Secondary Accession Numbers

HMDB60461

Metabolite Identification

Common Name

cis-Acetylacrylate

Description

cis-Acetylacrylate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. cis-Acetylacrylate is an extremely weak basic (essentially neutral) compound (based on its pKa). cis-Acetylacrylate exists in all living organisms, ranging from bacteria to humans. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(Z)-Acetylacrylic acid	ChEBI
cis-4-Oxopent-2-enoic acid	ChEBI
(Z)-Acetylacrylate	Generator
cis-4-Oxopent-2-enoate	Generator
cis-Acetylacrylic acid	Generator
cis-Acetylacrylate	Generator

Chemical Formula

C₅H₆O₃

Average Molecular Weight

114.0993

Monoisotopic Molecular Weight

114.031694058

IUPAC Name

(2Z)-4-oxopent-2-enoic acid

Traditional Name

cis-acetylacrylic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/[H])C(O)=O)C(C)=O

InChI Identifier

InChI=1S/C5H6O3/c1-4(6)2-3-5(7)8/h2-3H,1H3,(H,7,8)/b3-2-

InChI Key

XGTKSWVCNVUVHG-IHWYPQMZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Fatty acyl
Unsaturated fatty acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

4-oxo monocarboxylic acid (CHEBI:28993 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060461)

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	38.5 g/L	ALOGPS
logP	0.31	ALOGPS
logP	0.29	ChemAxon
logS	-0.47	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	28.16 m³·mol⁻¹	ChemAxon
Polarizability	10.5 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	126.218	30932474
DeepCCS	[M-H]-	123.773	30932474
DeepCCS	[M-2H]-	159.578	30932474
DeepCCS	[M+Na]+	134.246	30932474
AllCCS	[M+H]+	126.1	32859911
AllCCS	[M+H-H2O]+	121.8	32859911
AllCCS	[M+NH4]+	130.2	32859911
AllCCS	[M+Na]+	131.4	32859911
AllCCS	[M-H]-	123.0	32859911
AllCCS	[M+Na-2H]-	126.2	32859911
AllCCS	[M+HCOO]-	129.7	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.	2.11 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1674 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.87 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1127.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	370.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	100.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	243.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	68.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	314.9 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	399.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	185.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	723.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	228.5 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	1022.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	258.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	622.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.3 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	163.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-Acetylacrylate	[H]\C(=C(/[H])C(O)=O)C(C)=O	1760.6	Standard polar	33892256
cis-Acetylacrylate	[H]\C(=C(/[H])C(O)=O)C(C)=O	931.8	Standard non polar	33892256
cis-Acetylacrylate	[H]\C(=C(/[H])C(O)=O)C(C)=O	994.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-Acetylacrylate,1TMS,isomer #1	CC(=O)/C=C\C(=O)O[Si](C)(C)C	1155.9	Semi standard non polar	33892256
cis-Acetylacrylate,1TMS,isomer #2	C=C(/C=C\C(=O)O)O[Si](C)(C)C	1276.5	Semi standard non polar	33892256
cis-Acetylacrylate,2TMS,isomer #1	C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1309.7	Semi standard non polar	33892256
cis-Acetylacrylate,2TMS,isomer #1	C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1277.2	Standard non polar	33892256
cis-Acetylacrylate,2TMS,isomer #1	C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1347.5	Standard polar	33892256
cis-Acetylacrylate,1TBDMS,isomer #1	CC(=O)/C=C\C(=O)O[Si](C)(C)C(C)(C)C	1410.5	Semi standard non polar	33892256
cis-Acetylacrylate,1TBDMS,isomer #2	C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C	1527.9	Semi standard non polar	33892256
cis-Acetylacrylate,2TBDMS,isomer #1	C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1767.8	Semi standard non polar	33892256
cis-Acetylacrylate,2TBDMS,isomer #1	C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1749.1	Standard non polar	33892256
cis-Acetylacrylate,2TBDMS,isomer #1	C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1661.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cis-Acetylacrylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9000000000-2061ae1a8861f42f1c73	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-Acetylacrylate GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9400000000-f73d0beec9860c695eec	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-Acetylacrylate 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 - cis-Acetylacrylate 10V, Positive-QTOF	splash10-0002-9100000000-853b506b94b09ffadf54	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 20V, Positive-QTOF	splash10-0ftb-9000000000-12b21331ddede63beb81	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 40V, Positive-QTOF	splash10-0ufr-9000000000-e9848e2a1399185ca489	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 10V, Negative-QTOF	splash10-03di-6900000000-f4fc97ecbaa587d81b1b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 20V, Negative-QTOF	splash10-03xs-9300000000-f9afeb3b5ff5e9af4bb8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 40V, Negative-QTOF	splash10-0fr2-9000000000-c0b2fd76e44f097e767b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 10V, Positive-QTOF	splash10-014m-9000000000-1c4c26eebab1a2f95b1c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 20V, Positive-QTOF	splash10-0fr6-9000000000-aa47fe3b96e724c2df4b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 40V, Positive-QTOF	splash10-0006-9000000000-06ea02079a8a17b618db	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 10V, Negative-QTOF	splash10-014i-9300000000-1628c355975cd34af232	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 20V, Negative-QTOF	splash10-014i-9000000000-818e5c336756d6610c5b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Acetylacrylate 40V, Negative-QTOF	splash10-0gb9-9000000000-8840275d4a41857285d2	2021-10-12	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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C07091

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281015

PDB ID

Not Available

ChEBI ID

28993

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Carboxymethylenebutenolidase homolog

General function:: Involved in hydrolase activity
Specific function:: Cysteine hydrolase. Can convert the prodrug olmesartan medoxomil into its pharmacologically active metabolite olmerstatan, an angiotensin receptor blocker, in liver and intestine. May also activate beta-lactam antibiotics faropenem medoxomil and lenampicillin.
Gene Name:: CMBL
Uniprot ID:: Q96DG6
Molecular weight:: Not Available

Reactions

Protoanemonin + Water → cis-Acetylacrylate	details

Showing metabocard for cis-Acetylacrylate (HMDB0060461)

MOL for HMDB0060461 (cis-Acetylacrylate)

3D MOL for HMDB0060461 (cis-Acetylacrylate)

3D SDF for HMDB0060461 (cis-Acetylacrylate)

3D-SDF for HMDB0060461 (cis-Acetylacrylate)

PDB for HMDB0060461 (cis-Acetylacrylate)

3D PDB for HMDB0060461 (cis-Acetylacrylate)

SMILES for HMDB0060461 (cis-Acetylacrylate)

INCHI for HMDB0060461 (cis-Acetylacrylate)

Structure for HMDB0060461 (cis-Acetylacrylate)

3D Structure for HMDB0060461 (cis-Acetylacrylate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions