MiMeDB: Showing metabocard for cis-Aconitic acid (MMDBc0000021)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:27:29 UTC

Update Date

2022-08-30 23:03:51 UTC

Metabolite ID

MMDBc0000021

Metabolite Identification

Common Name

cis-Aconitic acid

Description

cis-Aconitic acid is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. The enzyme aconitase (aconitate hydratase; EC 4.2.1.3) catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid cycle.

Structure

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

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: cis-Aconitic acid.mol                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.001  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.667   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.001  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    7    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3    9   10                                                  
CONECT    5    3    6                                                       
CONECT    6    5   11   12                                                  
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    4                                                            
CONECT   10    4                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Synonyms

Value	Source
(Z)-1-Propene-1,2,3-tricarboxylic acid	ChEBI
cis-1-Propene-1,2,3-tricarboxylic acid	ChEBI
(Z)-1-Propene-1,2,3-tricarboxylate	Generator
cis-1-Propene-1,2,3-tricarboxylate	Generator
cis-Aconitate	Generator
(1Z)-1-Propene-1,2,3-tricarboxylate	HMDB
(1Z)-1-Propene-1,2,3-tricarboxylic acid	HMDB
(Z)-Aconitate	HMDB
(Z)-Aconitic acid	HMDB
1-cis-2,3-Propenetricarboxylate	HMDB
1-cis-2,3-Propenetricarboxylic acid	HMDB
1-Propene-1,2,3-tricarboxylate	HMDB
1-Propene-1,2,3-tricarboxylic acid	HMDB
cis-Aconate	HMDB
cis-Aconic acid	HMDB
cis-Oxaloacetate	HMDB
cis-Oxaloacetic acid	HMDB
Acid, citridic	HMDB
Acid, citridinic	HMDB
Aconitic acid	HMDB
Acontic acid	HMDB
Adonic acid	HMDB
Achilleic acid	HMDB
Acid, acontic	HMDB
Acid, equisetic	HMDB
Citridinic acid	HMDB
Acid, achilleic	HMDB
Aconitate	HMDB
Citridic acid	HMDB
Pyrocitric acid	HMDB
Acid, aconitic	HMDB
Acid, adonic	HMDB
Acid, carboxyglutaconic	HMDB
Acid, pyrocitric	HMDB
Carboxyglutaconic acid	HMDB
Equisetic acid	HMDB

Molecular Formula

C₆H₆O₆

Average Mass

174.1082

Monoisotopic Mass

174.016437924

IUPAC Name

(1Z)-prop-1-ene-1,2,3-tricarboxylic acid

Traditional Name

cis-aconitic acid

CAS Registry Number

585-84-2

SMILES

OC(=O)C\C(=C\C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1-

InChI Key

GTZCVFVGUGFEME-IWQZZHSRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic 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

aconitic acid (CHEBI:32805 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.72 g/L	ALOGPS
logP	-0.41	ALOGPS
logP	-0.52	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.11	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.23 m³·mol⁻¹	ChemAxon
Polarizability	14.16 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

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) (3 TMS)	splash10-0002-1940000000-24c70788b42e3006de46	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)	splash10-0002-0940000000-3ab0a8161f2ec8f04452	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00dj-9630000000-1dc322333cb48ef39588	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-004i-3591000000-a58ec1ba633b098e0867	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1940000000-24c70788b42e3006de46	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0940000000-3ab0a8161f2ec8f04452	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-9630000000-1dc322333cb48ef39588	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-3591000000-a58ec1ba633b098e0867	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06w9-4900000000-38239492ad0e66d6533b	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00di-9167000000-07ccdac5775cc3e75c95	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 (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 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_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9300000000-1f04239a9a7133f89d08	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000f-9000000000-49f5c2a7959cfbbbe09f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000f-9100000000-d4857c30b96cf4786dbe	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0911000000-3197b86ab2053b968bf9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-9000000000-74977ead259f739d154b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-9f4cc240b2470f2bbb93	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-5034c256b831c6173452	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0912000000-a603cd799b70c1089ddd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-9000000000-ce8dbec6a7b0d83b372c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-927f79de2cf5ffcb2c52	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-003r-0194000000-75d834c69fbfd0a2f7be	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00fr-0900000000-aad30bb884e0e9a5f01c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9200000000-e90e540bcd0659005472	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-0edcc061c37b1fbb9fa1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000l-9000000000-1e762d38e4e5cabfcb6b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-000f-9000000000-5602736cc28db9eb9085	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9400000000-c8ec5b3e604b870eab95	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00fr-0900000000-aad30bb884e0e9a5f01c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9200000000-e90e540bcd0659005472	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-8e26562af9ae45eb3303	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02di-1900000000-7fec32a5e34c3b55d683	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01w0-9600000000-ee172c3013370ab0da31	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-1900000000-18635ce5a20ce1b78139	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-2900000000-58bb75a2a1b28dbffd73	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rf-9300000000-19df730d01f07fcf6573	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Prostate
Saliva
Sweat
Urine

Tissue Locations

Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192363	Aconitate hydratase, mitochondrial	Enzyme	Q99798	Homo sapiens
MMDBp0192364	Cytoplasmic aconitate hydratase	Unknown	P21399	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002509	Citric acid	Water	Aconitase 1, soluble	Citrate Hydro-Lyase	VMH	15263083 16511074
MMDBr0002550	Isocitric acid	Water	Aconitase 1, soluble	Isocitrate Hydro-Lyase	VMH	15263083 16511074
MMDBr0003726	Citric acid	Citric acid	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172
MMDBr0003727	cis-Aconitic acid	cis-Aconitic acid	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172
MMDBr0003732	Oxoglutaric acid	Oxoglutaric acid	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172 16919238 17173541 18406340 8132483
MMDBr0003733	cis-Aconitic acid	cis-Aconitic acid	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172 16919238 17173541 18406340 8132483
MMDBr0003734	cis-Aconitic acid	cis-Aconitic acid	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172 16919238 17173541 18406340 8132483
MMDBr0003735	cis-Aconitic acid	cis-Aconitic acid	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172 16919238 17173541 18406340 8132483
MMDBr0003743	Oxoglutaric acid	Oxoglutaric acid	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172
MMDBr0003744	Hydrogen Ion	Hydrogen Ion	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172
MMDBr0003745	Hydrogen Ion	Hydrogen Ion	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172
MMDBr0003746	Hydrogen Ion	Hydrogen Ion	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172
MMDBr0003748	cis-Aconitic acid	cis-Aconitic acid	Solute carrier family 25 (mitochondrial carrier; citrate transporter), member 1	Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2	VMH	14598172
MMDBr0005713	cis-Aconitic acid	cis-Aconitic acid	Not Available	Transport of Cis-Aconitate, Extracellular	VMH	30371894
MMDBr0012873	Citric acid	cis-Aconitic acid	Citrate/2-methylcitrate dehydratase	Hydration/dehydration of C-O bond	RHEA	34755880
MMDBr0013406	cis-Aconitic acid	Carbon dioxide	Cis-aconitate decarboxylase	Decarboxylation	RHEA	34755880
MMDBr0013634	trans-Aconitic acid	cis-Aconitic acid	Aconitate isomerase	Isomerization	RHEA	34755880
MMDBr0014175	cis-Aconitic acid	D-threo-Isocitric acid	Methanogen homoaconitase large subunit	Hydrolysis	RHEA	34755880
MMDBr0018086	Citric acid	cis-Aconitic acid	Aconitate hydratase A	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0018087	cis-Aconitic acid	D-threo-Isocitric acid	Aconitate hydratase A	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0018429	Citric acid	cis-Aconitic acid	Homoaconitase, mitochondrial	Hydrolysis	PathBank	31602464
MMDBr0018430	cis-Aconitic acid	Isocitric acid	Homoaconitase, mitochondrial	Hydrolysis	PathBank	31602464
MMDBr0019150	cis-Aconitic acid	Isocitric acid	Aconitate hydratase A	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0019151	cis-Aconitic acid	Citric acid	Aconitate hydratase A	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0019391	Citric acid	cis-Aconitic acid	Not Available		PathBank	31602464
MMDBr0019392	cis-Aconitic acid	D-threo-Isocitric acid	Not Available		PathBank	31602464
MMDBr0019586	Citric acid	cis-Aconitic acid	Aconitate hydratase, mitochondrial	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0019587	cis-Aconitic acid	D-threo-Isocitric acid	Aconitate hydratase, mitochondrial	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0023294	cis-Aconitic acid	D-threo-Isocitric acid	Aconitate hydratase A	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0023295	cis-Aconitic acid	D-threo-Isocitric acid	Aconitate hydratase B	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0023296	Citric acid	cis-Aconitic acid	Aconitate hydratase A	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0023297	Citric acid	cis-Aconitic acid	Aconitate hydratase B	Hydration/dehydration of C-O bond	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease	Increased	Association	Human Saliva	HMDB	23857558
Frontotemporal dementia	Increased	Association	Human Saliva	HMDB	23857558
Lung cancer	Slight Decrease	Association	Human Urine	HMDB	18953024
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	4	Human ; Human feces	Microbial culture
Bacteria	Firmicutes	3	Human stool; Human feces	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown
Archaea/Archaea	Euryarchaeota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Leaves	Helianthus annuus	FooDB	31437929
Plant	Plant	Beta vulgaris var. rubra	FooDB	31437929
Plant	Plant	Solanum tuberosum	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Saliva	Detected and Quantified	2.80	2.11			uM	Adult (>18 years old)	Male	Alzheimer's disease	HMDB	23857558
Human Urine	Detected and Quantified			6.494	293.514	umol/mmol creatinine	Infant (0-1 year old)	Both	Amish lethal microcephaly	HMDB	12376931
Human Saliva	Detected and Quantified	2.17	0.53			uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	HMDB	23857558
Human Saliva	Detected and Quantified	2.72	0.53			uM	Adult (>18 years old)	Both	Lewy body disease	HMDB	23857558
Human Urine	Detected and Quantified	32.0		0.0	70.0	umol/mmol creatinine	Adult (>18 years old)	Both	Lung cancer	HMDB	18953024
Human Cerebrospinal fluid (csf)	Detected and Quantified	2				uM	Children (1-13 years old)	Both	Normal	HMDB	8412012
Human Sweat	Detected and Quantified	< 10				uM	Adult (60 years old)	Male	Normal	HMDB	22194922
Human Sweat	Detected and Quantified	< 10				uM	Adult (40 years old)	Male	Normal	HMDB	22194922
Human Breast milk	Detected and Quantified	10.1	3.1			uM	Adult (>18 years old)	Female	Normal	HMDB	24027187
Human Urine	Detected and Quantified	10.3		5.2	16.3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	13		2.7	44	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected and Quantified			2.0	23.6	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Cerebrospinal fluid (csf)	Detected and Quantified	20.0		13.0	27.0	uM	Adult (>18 years old)	Both	Normal	HMDB	9693263
Human Urine	Detected and Quantified	20.9		3.8	95.3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	29.8		14.7	93.1	umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	8087979
Human Saliva	Detected and Quantified	3.17	1.17			uM	Adult (>18 years old)	Female	Normal	HMDB	23857558
Human Urine	Detected and Quantified	37.9		17.3	63.3	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified			48	103	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified	54.5		32.4	76.6	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	14708889
Human Urine	Detected and Quantified			58	85	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	67.9		14.3	100.7	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified			7	30.6	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified	73.8		64.0	130.3	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified			8	26.0	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			8	40.7	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			9.740	38.962	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	12376931
Human Urine	Detected and Quantified	38.74	40.952			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	33.685	14.03			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	<102.12				umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified	35.95				umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Human Saliva	Detected and Quantified	0.172	0.179			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.176	0.107			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.358	0.198			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.363	0.169			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22024767
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	28157703
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000072

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Citric acid cycle

METLIN ID

5130

PubChem Compound

643757

PDB ID

Not Available

ChEBI ID

32805

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Swart PJ, Kuipers EM, Smit C, Van Der Strate BW, Harmsen MC, Meijer DK: Lactoferrin. Antiviral activity of lactoferrin. Adv Exp Med Biol. 1998;443:205-13. [PubMed:9781360 ]
Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6. doi: 10.1203/00006450-197601000-00012. [PubMed:813176 ]
Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. doi: 10.1515/CCLM.2003.248. [PubMed:14708889 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. doi: 10.1159/000022031. [PubMed:9693263 ]
Swart PJ, Kuipers ME, Smit C, Pauwels R, deBethune MP, de Clercq E, Meijer DK, Huisman JG: Antiviral effects of milk proteins: acylation results in polyanionic compounds with potent activity against human immunodeficiency virus types 1 and 2 in vitro. AIDS Res Hum Retroviruses. 1996 Jun 10;12(9):769-75. doi: 10.1089/aid.1996.12.769. [PubMed:8738428 ]
Matsuishi T, Urabe F, Percy AK, Komori H, Yamashita Y, Schultz RS, Ohtani Y, Kuriya N, Kato H: Abnormal carbohydrate metabolism in cerebrospinal fluid in Rett syndrome. J Child Neurol. 1994 Jan;9(1):26-30. doi: 10.1177/088307389400900105. [PubMed:8151077 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

Showing metabocard for cis-Aconitic acid (MMDBc0000021)

MOL for #<Metabolite:0x00007f25f04e83e8>

3D MOL for #<Metabolite:0x00007f25f04e83e8>

3D SDF for #<Metabolite:0x00007f25f04e83e8>

3D-SDF for #<Metabolite:0x00007f25f04e83e8>

PDB for #<Metabolite:0x00007f25f04e83e8>

3D PDB for #<Metabolite:0x00007f25f04e83e8>

SMILES for #<Metabolite:0x00007f25f04e83e8>

INCHI for #<Metabolite:0x00007f25f04e83e8>

Structure for #<Metabolite:0x00007f25f04e83e8>

3D Structure for #<Metabolite:0x00007f25f04e83e8>