Milk Composition Database: Showing metabocard for Succinic acid (BMDB0000254)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:28 UTC

Update Date

2020-06-04 20:59:36 UTC

MCDB ID

BMDB0000254

Secondary Accession Numbers

BMDB00254

Metabolite Identification

Common Name

Succinic acid

Description

Succinic acid, also known as butanedionic acid or succinate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Succinic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Succinic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Succinic acid exists in all living species, ranging from bacteria to humans. Succinic acid is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1,2-Ethanedicarboxylic acid	ChEBI
Acide butanedioique	ChEBI
Acide succinique	ChEBI
Acidum succinicum	ChEBI
Amber acid	ChEBI
Asuccin	ChEBI
Bernsteinsaeure	ChEBI
Butandisaeure	ChEBI
Butanedionic acid	ChEBI
Dihydrofumaric acid	ChEBI
e363	ChEBI
Ethylenesuccinic acid	ChEBI
HOOC-CH2-CH2-COOH	ChEBI
Spirit OF amber	ChEBI
1,2-Ethanedicarboxylate	Generator
Butanedionate	Generator
Dihydrofumarate	Generator
Ethylenesuccinate	Generator
Succinate	Generator
1,2 Ethanedicarboxylic acid	MeSH
1,4 Butanedioic acid	MeSH
1,4-Butanedioic acid	MeSH
Ammonium succinate	MeSH
Butanedioic acid	MeSH
Potassium succinate	MeSH
Succinate, ammonium	MeSH
Succinate, potassium	MeSH
1,4-Butanedioate	HMDB
Katasuccin	HMDB
Wormwood acid	HMDB
2-Acetamido-2-deoxy-D-glucose	ChEBI, HMDB
D-GlcNAc	ChEBI, HMDB
N-Acetyl-D-glucosamine	ChEBI, HMDB
N-Acetylchitosamine	ChEBI, HMDB
N Acetyl D glucosamine	HMDB
2 Acetamido 2 deoxy D glucose	HMDB
2 Acetamido 2 deoxyglucose	HMDB
2-Acetamido-2-deoxyglucose	HMDB
Acetylglucosamine	HMDB

Chemical Formula

C₄H₆O₄

Average Molecular Weight

118.088

Monoisotopic Molecular Weight

118.02660868

IUPAC Name

butanedioic acid

Traditional Name

succinic acid

CAS Registry Number

110-15-6

SMILES

OC(=O)CCC(O)=O

InChI Identifier

InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

InChI Key

KDYFGRWQOYBRFD-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

Fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C4-dicarboxylic acid (CHEBI:15741 )
alpha,omega-dicarboxylic acid (CHEBI:15741 )
Dicarboxylic acids (LMFA01170043 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	185 - 188 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	83.2 mg/mL	Not Available
LogP	-0.59	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.53	ALOGPS
logP	-0.4	ChemAxon
logS	0.25	ALOGPS
pKa (Strongest Acidic)	3.55	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	3	ChemAxon
Refractivity	23.54 m³·mol⁻¹	ChemAxon
Polarizability	10.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-0920000000-f286e6204a4163b823ba	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-bf336910bb37d7f78140	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-9800000000-df5ff4e8457d2d4ef919	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00c1-3930000000-3cc18e719822b5af661a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-93b4807ae6275a3e59d7	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kos-9100000000-f1df0903a24c305e68ec	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0910000000-300c33b39fb991b5a73e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-f286e6204a4163b823ba	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-bf336910bb37d7f78140	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9800000000-df5ff4e8457d2d4ef919	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00c1-3930000000-3cc18e719822b5af661a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-f838d863ee7c2b111f02	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-9300000000-f0644daf4fbb11fcc2dc	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dj-9710000000-ff8325384b9eefd19106	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9300000000-f9dc864d93a09d3074f9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9300000000-76c151de384928b2256f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-01b9-7900000000-51d2341c097f04827944	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-004i-9000000000-93b4807ae6275a3e59d7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03dj-0971010000-37d214dc7a8fdc26116b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-249222ac742c1634cec9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-9000000000-6897d49472dba6a34a27	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0490000000-d138f8023125921b4b82	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-1900000000-4ffdabe5bde527b66982	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9100000000-c20baa818f5ff5f678c1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-7a49a18aa6fcb2540a12	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-9000000000-9955aeb0e5a9f88ae70e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00di-9000000000-7e1f195f111b4eafb4fa	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00xr-9400000000-e50afc90e20cd420ba9b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00xr-9600000000-43167f2549cbb5d5f7e8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-4ffdabe5bde527b66982	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9100000000-7a8bfa543dc087bea06d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-fdec6c7458176f3cbeb8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-9955aeb0e5a9f88ae70e	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-2900000000-9d959a53833b07094158	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0l6r-9600000000-c367e11e737714d41418	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-e65aa602a8293debec36	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-e1f840494c9003279869	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-7900000000-1089efd4a3469bcf14f1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0604-9000000000-0e0e60bb202ffb004894	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05di-9100000000-c629bea41d0d3d896425	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	16 - 106 uM	PMID: 20338431	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	PMID: 23438684	details
Detected but not Quantified	Not Applicable	PMID: 25108860	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	14 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	15 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	20 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	14 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	20 +/- 3.2 uM	PMID: 29642378	details
Detected and Quantified	23 +/- 4 uM	PMID: 29642378	details
Detected and Quantified	23 +/- 7 uM	PMID: 29642378	details

External Links

HMDB ID

HMDB0000254

DrugBank ID

DB00139

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Succinic_acid

METLIN ID

Not Available

PubChem Compound

1738118

PDB ID

Not Available

ChEBI ID

15741

References

Synthesis Reference

Berglund, Kris Arvid; Andersson, Christian; Rova, Ulrika. Process for the production of succinic acid. PCT Int. Appl. (2007), 30pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Succinic acid (BMDB0000254)

Structure for BMDB0000254 (Succinic acid)