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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:22:48 UTC

Update Date

2021-09-26 22:51:48 UTC

HMDB ID

HMDB0244202

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,4-Butanediol diacrylate

Description

4-(prop-2-enoyloxy)butyl prop-2-enoate belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Based on a literature review very few articles have been published on 4-(prop-2-enoyloxy)butyl prop-2-enoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,4-butanediol diacrylate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,4-Butanediol diacrylate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0      -9.597   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.073   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.264   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.739   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.929   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.595   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.263   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.262   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.930   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.406   4.771   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.930   2.461   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.406   6.311   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.596   4.771   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.072   4.001   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    9                                                       
CONECT    4    2   10                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   13                                                       
CONECT    8    6   14                                                       
CONECT    9    3   11   13                                                  
CONECT   10    4   12   14                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13    7    9                                                       
CONECT   14    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0244202
HETATM    1  C1  UNL     1      -3.005  -1.842   1.297  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.785  -1.117   0.520  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.337   0.144  -0.007  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.105   0.834  -0.759  1.00  0.00           O  
HETATM    5  O2  UNL     1      -2.091   0.685   0.249  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.682   1.920  -0.280  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.316   2.339   0.102  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.823   1.466  -0.326  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.720   0.119   0.223  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.742  -0.782  -0.071  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.046  -0.555   0.288  1.00  0.00           C  
HETATM   12  O4  UNL     1       3.250   0.519   0.898  1.00  0.00           O  
HETATM   13  C9  UNL     1       4.130  -1.505  -0.022  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.858  -2.625  -0.669  1.00  0.00           C  
HETATM   15  H1  UNL     1      -1.999  -1.523   1.572  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.318  -2.790   1.704  1.00  0.00           H  
HETATM   17  H3  UNL     1      -4.756  -1.480   0.286  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.436   2.671   0.102  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.817   1.929  -1.406  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.304   2.494   1.230  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.165   3.412  -0.253  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.750   2.022  -0.064  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.805   1.383  -1.458  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.208  -0.367  -0.210  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.567   0.147   1.314  1.00  0.00           H  
HETATM   26  H12 UNL     1       5.147  -1.295   0.275  1.00  0.00           H  
HETATM   27  H13 UNL     1       4.631  -3.318  -0.898  1.00  0.00           H  
HETATM   28  H14 UNL     1       2.853  -2.885  -0.990  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3   17
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   26
CONECT   14   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(Prop-2-enoyloxy)butyl prop-2-enoic acid	Generator
Butanediol diacrylate	MeSH
1,4-Butanediol diacrylic acid	Generator

Chemical Formula

C₁₀H₁₄O₄

Average Molecular Weight

198.218

Monoisotopic Molecular Weight

198.089208931

IUPAC Name

4-(prop-2-enoyloxy)butyl prop-2-enoate

Traditional Name

butanediol diacrylate

CAS Registry Number

Not Available

SMILES

C=CC(=O)OCCCCOC(=O)C=C

InChI Identifier

InChI=1S/C10H14O4/c1-3-9(11)13-7-5-6-8-14-10(12)4-2/h3-4H,1-2,5-8H2

InChI Key

JHWGFJBTMHEZME-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Acrylic acid ester
Dicarboxylic acid or derivatives
Acrylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	1.57	ALOGPS
logP	2.23	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	51.66 m³·mol⁻¹	ChemAxon
Polarizability	21.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	145.916	30932474
DeepCCS	[M-H]-	142.362	30932474
DeepCCS	[M-2H]-	179.773	30932474
DeepCCS	[M+Na]+	155.311	30932474
AllCCS	[M+H]+	147.0	32859911
AllCCS	[M+H-H2O]+	143.4	32859911
AllCCS	[M+NH4]+	150.3	32859911
AllCCS	[M+Na]+	151.3	32859911
AllCCS	[M-H]-	146.4	32859911
AllCCS	[M+Na-2H]-	147.6	32859911
AllCCS	[M+HCOO]-	149.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,4-Butanediol diacrylate	C=CC(=O)OCCCCOC(=O)C=C	1927.7	Standard polar	33892256
1,4-Butanediol diacrylate	C=CC(=O)OCCCCOC(=O)C=C	1393.6	Standard non polar	33892256
1,4-Butanediol diacrylate	C=CC(=O)OCCCCOC(=O)C=C	1460.6	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 - 1,4-Butanediol diacrylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100000000-dfa10a7038bb6582694d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4-Butanediol diacrylate 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 - 1,4-Butanediol diacrylate 10V, Positive-QTOF	splash10-0002-3900000000-4b7b1351ad620d0caebc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 20V, Positive-QTOF	splash10-0a4i-9400000000-2c4df9683eb0ab9ee688	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 40V, Positive-QTOF	splash10-0a4i-9100000000-38f6ceada83d75b5371d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 10V, Negative-QTOF	splash10-0f6t-6900000000-5afe2bda9b88ed767a51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 20V, Negative-QTOF	splash10-0fk9-9200000000-7203330d2308dd1d1de6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 40V, Negative-QTOF	splash10-0uk9-9000000000-f7aff4a47dc0968cc886	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 10V, Negative-QTOF	splash10-0077-9700000000-ff983d0fb6d569e0c044	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 20V, Negative-QTOF	splash10-00di-9000000000-0f4ee86788d2a13f4cc6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 40V, Negative-QTOF	splash10-00di-9000000000-cdade2721b4496ab66b6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 10V, Positive-QTOF	splash10-0a4i-9300000000-31d643dfc2417f31964e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 20V, Positive-QTOF	splash10-0a4i-9100000000-7084d7c212b299d8efeb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediol diacrylate 40V, Positive-QTOF	splash10-0a4i-9000000000-c37e823ea9fde3962f12	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

63781

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70613

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 1,4-Butanediol diacrylate (HMDB0244202)

MOL for HMDB0244202 (1,4-Butanediol diacrylate)

3D MOL for HMDB0244202 (1,4-Butanediol diacrylate)

3D SDF for HMDB0244202 (1,4-Butanediol diacrylate)

3D-SDF for HMDB0244202 (1,4-Butanediol diacrylate)

PDB for HMDB0244202 (1,4-Butanediol diacrylate)

3D PDB for HMDB0244202 (1,4-Butanediol diacrylate)

SMILES for HMDB0244202 (1,4-Butanediol diacrylate)

INCHI for HMDB0244202 (1,4-Butanediol diacrylate)

Structure for HMDB0244202 (1,4-Butanediol diacrylate)

3D Structure for HMDB0244202 (1,4-Butanediol diacrylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra