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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:20 UTC

Update Date

2023-02-21 17:21:58 UTC

HMDB ID

HMDB0032352

Secondary Accession Numbers

HMDB32352

Metabolite Identification

Common Name

3-Isopropenylpentanedioic acid

Description

3-Isopropenylpentanedioic acid, also known as 3-(prop-1-en-2-yl)pentanedioate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Based on a literature review a significant number of articles have been published on 3-Isopropenylpentanedioic acid.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    6    7                                                       
CONECT    4    6    8                                                       
CONECT    5    1    2    6                                                  
CONECT    6    3    4    5                                                  
CONECT    7    3    9   10                                                  
CONECT    8    4   11   12                                                  
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Isopropenylpentanedioate	Generator
3-(Prop-1-en-2-yl)pentanedioate	HMDB

Chemical Formula

C₈H₁₂O₄

Average Molecular Weight

172.1785

Monoisotopic Molecular Weight

172.073558872

IUPAC Name

3-(prop-1-en-2-yl)pentanedioic acid

Traditional Name

3-(prop-1-en-2-yl)pentanedioic acid

CAS Registry Number

6839-75-4

SMILES

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

InChI Identifier

InChI=1S/C8H12O4/c1-5(2)6(3-7(9)10)4-8(11)12/h6H,1,3-4H2,2H3,(H,9,10)(H,11,12)

InChI Key

PULOWZXUQOLRBK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0032352)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032352)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032352)

Source

Endogenous

Endogenous (HMDB: HMDB0032352)

Animal

Animal (HMDB: HMDB0032352)

Exogenous

Food

Food (HMDB: HMDB0032352)

Exogenous (HMDB: HMDB0032352)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032352)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032352)

Lipid metabolism pathway (HMDB: HMDB0032352)

Cellular process

Cell signaling (HMDB: HMDB0032352)

Biochemical process

Lipid transport (HMDB: HMDB0032352)

Role

Biological role

Energy source (HMDB: HMDB0032352)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032352)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	110.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	297.00 to 299.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	18680 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.683 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	18.9 g/L	ALOGPS
logP	0.77	ALOGPS
logP	0.72	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	41.61 m³·mol⁻¹	ChemAxon
Polarizability	16.85 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
DarkChem	[M+H]+	140.634	31661259
DarkChem	[M-H]-	133.974	31661259
DeepCCS	[M+H]+	132.928	30932474
DeepCCS	[M-H]-	129.098	30932474
DeepCCS	[M-2H]-	166.368	30932474
DeepCCS	[M+Na]+	141.908	30932474
AllCCS	[M+H]+	139.7	32859911
AllCCS	[M+H-H2O]+	135.9	32859911
AllCCS	[M+NH4]+	143.3	32859911
AllCCS	[M+Na]+	144.3	32859911
AllCCS	[M-H]-	135.4	32859911
AllCCS	[M+Na-2H]-	137.0	32859911
AllCCS	[M+HCOO]-	138.9	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.	3.27 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7737 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.37 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	135.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1217.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	283.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	95.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	58.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	272.4 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	346.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	658.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	283.1 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	975.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	457.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	238.1 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	259.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Isopropenylpentanedioic acid	CC(=C)C(CC(O)=O)CC(O)=O	2411.5	Standard polar	33892256
3-Isopropenylpentanedioic acid	CC(=C)C(CC(O)=O)CC(O)=O	1203.4	Standard non polar	33892256
3-Isopropenylpentanedioic acid	CC(=C)C(CC(O)=O)CC(O)=O	1473.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Isopropenylpentanedioic acid,1TMS,isomer #1	C=C(C)C(CC(=O)O)CC(=O)O[Si](C)(C)C	1451.3	Semi standard non polar	33892256
3-Isopropenylpentanedioic acid,2TMS,isomer #1	C=C(C)C(CC(=O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	1511.3	Semi standard non polar	33892256
3-Isopropenylpentanedioic acid,1TBDMS,isomer #1	C=C(C)C(CC(=O)O)CC(=O)O[Si](C)(C)C(C)(C)C	1688.9	Semi standard non polar	33892256
3-Isopropenylpentanedioic acid,2TBDMS,isomer #1	C=C(C)C(CC(=O)O[Si](C)(C)C(C)(C)C)CC(=O)O[Si](C)(C)C(C)(C)C	1965.2	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-Isopropenylpentanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-021e9c1fe5a9600b3035	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Isopropenylpentanedioic acid GC-MS (2 TMS) - 70eV, Positive	splash10-007c-9210000000-6218a9e78fa1583126c4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Isopropenylpentanedioic acid 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-Isopropenylpentanedioic acid 10V, Positive-QTOF	splash10-05fr-0900000000-e1a7648f7bd8c8c2b331	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 20V, Positive-QTOF	splash10-056r-2900000000-7164be95760ff90db70c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 40V, Positive-QTOF	splash10-014i-9300000000-c323e6d1541179932ffa	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 10V, Negative-QTOF	splash10-00di-0900000000-e18526971334b45ecc56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 20V, Negative-QTOF	splash10-00fr-2900000000-5083b402aeb2aa277d74	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 40V, Negative-QTOF	splash10-0aor-9700000000-a1d42a96ca692b2f3e0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 10V, Positive-QTOF	splash10-0159-9400000000-f4cc8e907832d4b7b357	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 20V, Positive-QTOF	splash10-0159-9100000000-91b914165162d3bed9de	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 40V, Positive-QTOF	splash10-014l-9000000000-7e2e81a5753ea28421c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 10V, Negative-QTOF	splash10-00gi-4900000000-ecbbdb9ec2185484ed0a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 20V, Negative-QTOF	splash10-0a6r-7900000000-168c875fe54d462e2263	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 40V, Negative-QTOF	splash10-052f-9000000000-ac504438a38b60492045	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Cytoplasm
Extracellular
Membrane

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

FDB009649

KNApSAcK ID

C00057499

Chemspider ID

21105929

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71586903

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1593981

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3-Isopropenylpentanedioic acid (HMDB0032352)

MOL for HMDB0032352 (3-Isopropenylpentanedioic acid)

3D MOL for HMDB0032352 (3-Isopropenylpentanedioic acid)

3D SDF for HMDB0032352 (3-Isopropenylpentanedioic acid)

3D-SDF for HMDB0032352 (3-Isopropenylpentanedioic acid)

PDB for HMDB0032352 (3-Isopropenylpentanedioic acid)

3D PDB for HMDB0032352 (3-Isopropenylpentanedioic acid)

SMILES for HMDB0032352 (3-Isopropenylpentanedioic acid)

INCHI for HMDB0032352 (3-Isopropenylpentanedioic acid)

Structure for HMDB0032352 (3-Isopropenylpentanedioic acid)

3D Structure for HMDB0032352 (3-Isopropenylpentanedioic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra