MiMeDB: Showing metabocard for Tiglylcarnitine (MMDBc0033540)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:52:48 UTC

Update Date

2024-04-30 20:12:13 UTC

Metabolite ID

MMDBc0033540

Metabolite Identification

Common Name

Tiglylcarnitine

Description

Tiglylcarnitine is an acylcarnitine. More specifically, it is an tiglic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review [Dambrova et al. 2021, Physiological Reviews], acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. Tiglylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine Tiglylcarnitine is a member of the most abundant group of carnitines in the body, comprising more than 50% of all acylcarnitines quantified in tissues and biofluids (PMID: 31920980 ). Some short-chain carnitines have been studied as supplements or treatments for a number of diseases, including neurological disorders and inborn errors of metabolism. In particular Tiglylcarnitine is elevated in the blood or plasma of individuals with beta ketothiolase deficiency/acat1 gene mutation (PMID: 27264805 , PMID: 14518824 , PMID: 3435793 ), and ECHS1 deficiency (PMID: 31908952 ). It is also decreased in the blood or plasma of individuals with familial mediterranean fever (PMID: 29900937 ), carcinoma, lewis lung (PMID: 30839735 ), metabolic syndrome, type 2 diabetes mellitus, and cardiovascular diseases (PMID: 24710945 ). Tiglylcarnitine is also detected in the urinary organic acid and blood spot acylcarnitine profiles in patients with mitochondrial acetoacetyl-CoA thiolase (T2) deficiency, an inborn error of metabolism affecting isoleucine and ketone bodies in the catabolic process (PMID: 14518824 ). Tiglylcarnitine is found to be associated with celiac disease, which is also an inborn error of metabolism. Tiglylcarnitine has been identified in the human placenta (PMID: 32033212 ). Carnitine acetyltransferase (CrAT, EC:2.3.1.7) is responsible for the synthesis of all short-chain and short branched-chain acylcarnitines (PMID: 23485643 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available at [Dambrova et al. 2021, Physiological Reviews].

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311192105522D          

 17 16  0  0  0  0            999 V2000
    2.9684   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
M  CHG  2  11  -1  14   1
M  END
> <DATABASE_ID>
MMDBc0033540

> <DATABASE_NAME>
MIME

> <SMILES>
CC=C(C)C(=O)OC(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h6,10H,7-8H2,1-5H3

> <INCHI_KEY>
WURBQCVBQNMUQT-UHFFFAOYSA-N

> <FORMULA>
C12H21NO4

> <MOLECULAR_WEIGHT>
243.303

> <EXACT_MASS>
243.14705816

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.137418449428356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2-methylbut-2-enoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.89

> <JCHEM_LOGP>
-2.674568813471746

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.295140408588241

> <JCHEM_PKA_STRONGEST_BASIC>
-6.863909891770237

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
87.3151

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2-methylbut-2-enoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-NOV-21         0                                  
HETATM    1  C   UNK     0       5.541  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.207  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.207  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.541  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.540  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.206  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.461  -2.310   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0      -1.127  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.874   0.770   0.000  0.00  0.00           N+1
HETATM   15  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.207   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

Synonyms

Value	Source
3-[(2-Methylbut-2-enoyl)oxy]-4-(trimethylazaniumyl)butanoic acid	Generator

Molecular Formula

C₁₂H₂₁NO₄

Average Mass

243.303

Monoisotopic Mass

243.14705816

IUPAC Name

3-[(2-methylbut-2-enoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

3-[(2-methylbut-2-enoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

64191-86-2

SMILES

CC=C(C)C(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C12H21NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h6,10H,7-8H2,1-5H3

InChI Key

WURBQCVBQNMUQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Branched fatty acid
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.7	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.32 m³·mol⁻¹	ChemAxon
Polarizability	26.14 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	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0005105	Tiglyl-CoA	Tiglylcarnitine	carnitine palmitoyltransferase 1A (liver)		VMH	8930414 14518824
MMDBr0005369	Tiglylcarnitine	Tiglylcarnitine	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Celiac disease	Decreased	Association	Human Blood	HMDB	16425363

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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 Blood	Detected and Quantified	0.034	0.002			uM	Adult (>18 years old)	Both	Celiac disease	HMDB	16425363
Human Blood	Detected and Quantified	<0.0400				uM	Not Specified	Not Specified	Normal	HMDB	16148061
Human Urine	Detected and Quantified			0.03	0.16	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.033	0.003			uM	Adult (>18 years old)	Both	Normal	HMDB	16425363
Human Blood	Detected and Quantified	0.05	0.01			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Urine	Detected and Quantified	0.07	0.022			umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.08	0.03			umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.10		0.05	0.20	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected and Quantified	0.15	0.08			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.24	0.12			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified			0.040	0.080	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Blood	Detected and Quantified			0.040	0.080	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21239116

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74000427

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Millington DS, Roe CR, Maltby DA: Characterization of new diagnostic acylcarnitines in patients with beta-ketothiolase deficiency and glutaric aciduria type I using mass spectrometry. Biomed Environ Mass Spectrom. 1987 Dec;14(12):711-6. doi: 10.1002/bms.1200141204. [PubMed:3435793 ]
Fontaine M, Briand G, Ser N, Armelin I, Rolland MO, Degand P, Vamecq J: Metabolic studies in twin brothers with 2-methylacetoacetyl-CoA thiolase deficiency. Clin Chim Acta. 1996 Nov 15;255(1):67-83. doi: 10.1016/0009-8981(96)06391-7. [PubMed:8930414 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Fukao T, Zhang GX, Sakura N, Kubo T, Yamaga H, Hazama A, Kohno Y, Matsuo N, Kondo M, Yamaguchi S, Shigematsu Y, Kondo N: The mitochondrial acetoacetyl-CoA thiolase (T2) deficiency in Japanese patients: urinary organic acid and blood acylcarnitine profiles under stable conditions have subtle abnormalities in T2-deficient patients with some residual T2 activity. J Inherit Metab Dis. 2003;26(5):423-31. doi: 10.1023/a:1025117226051. [PubMed:14518824 ]
Violante S, Ijlst L, Ruiter J, Koster J, van Lenthe H, Duran M, de Almeida IT, Wanders RJ, Houten SM, Ventura FV: Substrate specificity of human carnitine acetyltransferase: Implications for fatty acid and branched-chain amino acid metabolism. Biochim Biophys Acta. 2013 Jun;1832(6):773-9. doi: 10.1016/j.bbadis.2013.02.012. Epub 2013 Feb 24. [PubMed:23485643 ]
Yu ZR, Ning Y, Yu H, Tang NJ: A HPLC-Q-TOF-MS-based urinary metabolomic approach to identification of potential biomarkers of metabolic syndrome. J Huazhong Univ Sci Technolog Med Sci. 2014 Apr;34(2):276-283. doi: 10.1007/s11596-014-1271-7. Epub 2014 Apr 8. [PubMed:24710945 ]
Wen P, Chen Z, Wang G, Su Z, Zhang X, Tang G, Cui D, Liu X, Li C: [Analysis of clinical phenotype and ACAT1 gene mutation in a family affected with beta-ketothiolase deficiency]. Zhonghua Yi Xue Yi Chuan Xue Za Zhi. 2016 Jun;33(3):286-91. doi: 10.3760/cma.j.issn.1003-9406.2016.03.002. [PubMed:27264805 ]
Kiykim E, Aktuglu Zeybek AC, Barut K, Zubarioglu T, Cansever MS, Alsancak S, Kasapcopur O: Screening of Free Carnitine and Acylcarnitine Status in Children With Familial Mediterranean Fever. Arch Rheumatol. 2016 Mar 10;31(2):133-138. doi: 10.5606/ArchRheumatol.2016.5696. eCollection 2016 Jun. [PubMed:29900937 ]
Wu H, Chen Y, Li Z, Liu X: Untargeted metabolomics profiles delineate metabolic alterations in mouse plasma during lung carcinoma development using UPLC-QTOF/MS in MS(E) mode. R Soc Open Sci. 2018 Sep 19;5(9):181143. doi: 10.1098/rsos.181143. eCollection 2018 Sep. [PubMed:30839735 ]
Pajares S, Lopez RM, Gort L, Argudo-Ramirez A, Marin JL, Gonzalez de Aledo-Castillo JM, Garcia-Villoria J, Arranz JA, Del Toro M, Tort F, Ugarteburu O, Casellas MD, Fernandez R, Ribes A: An incidental finding in newborn screening leading to the diagnosis of a patient with ECHS1 mutations. Mol Genet Metab Rep. 2020 Jan 2;22:100553. doi: 10.1016/j.ymgmr.2019.100553. eCollection 2020 Mar. [PubMed:31908952 ]
Makarova E, Makrecka-Kuka M, Vilks K, Volska K, Sevostjanovs E, Grinberga S, Zarkova-Malkova O, Dambrova M, Liepinsh E: Decreases in Circulating Concentrations of Long-Chain Acylcarnitines and Free Fatty Acids During the Glucose Tolerance Test Represent Tissue-Specific Insulin Sensitivity. Front Endocrinol (Lausanne). 2019 Dec 17;10:870. doi: 10.3389/fendo.2019.00870. eCollection 2019. [PubMed:31920980 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Tiglylcarnitine (MMDBc0033540)

MOL for #<Metabolite:0x00005634c2c13f98>

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3D Structure for #<Metabolite:0x00005634c2c13f98>