MiMeDB: Showing metabocard for Crotonobetaine (MMDBc0031651)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:42:55 UTC

Update Date

2022-08-31 18:22:48 UTC

Metabolite ID

MMDBc0031651

Metabolite Identification

Common Name

Crotonobetaine

Description

Crotonobetaine is a member of the chemical class known as Quaternary Ammonium Salts. These are compounds containing positively charged polyatomic ion of the structure NR4+, R being an alkyl group or an aryl groupCrotonobetaine is invovled in Carnitine metabolism, and ABC transporters. Crotonobetaine is involved in carnitine metabolism. Carnitine dehydratase from Escherichia coli O44 K74 is an inducible enzyme detectable in cells grown anaerobically in the presence of L-(-)-carnitine or crotonobetaine. (PMID 8188598 ).

Structure

MOL SDF PDB SMILES InChI

5462194
  Mrv0541 07101212512D          

 23 22  0  0  0  0            999 V2000
    5.9370    0.3630    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0495    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.0790    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078    0.7548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502    0.7548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943   -0.0191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -0.7178    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058   -0.9050    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950    0.9207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962    1.1080    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5090    0.4092    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -1.0197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0328   -1.2070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.5082    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.5610    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.8745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  5 15  1  0  0  0  0
  6 16  1  0  0  0  0
  6 17  1  0  0  0  0
  6 18  1  0  0  0  0
  7 19  1  0  0  0  0
  7 20  1  0  0  0  0
  7 21  1  0  0  0  0
  8  9  2  0  0  0  0
  8 22  1  0  0  0  0
  9 10  1  0  0  0  0
  9 23  1  0  0  0  0
M  CHG  2   1  -1   3   1
M  END
> <DATABASE_ID>
MMDBc0031651

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO2/c1-8(2,3)6-4-5-7(9)10/h4-5H,6H2,1-3H3/b5-4+

> <INCHI_KEY>
GUYHPGUANSLONG-SNAWJCMRSA-N

> <FORMULA>
C7H13NO2

> <MOLECULAR_WEIGHT>
143.1836

> <EXACT_MASS>
143.094628665

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
15.555731447518657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-(trimethylazaniumyl)but-2-enoate

> <ALOGPS_LOGP>
-2.81

> <JCHEM_LOGP>
-3.8147789514717454

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4913706175167265

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
63.21710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
crotonobetaine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5462194                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUL-12         0                                  
HETATM    1  O   UNK     0      11.082   0.678   0.000  0.00  0.00           O-1
HETATM    2  O   UNK     0       9.749  -1.632   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.414  -0.092   0.000  0.00  0.00           N+1
HETATM    4  C   UNK     0       5.747   0.678   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.080  -0.862   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644   1.241   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.184  -1.426   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -0.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   0.678   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.749  -0.092   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       6.361   1.409   0.000  0.00  0.00           H+0
HETATM   12  H   UNK     0       5.134   1.409   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       2.603  -0.036   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.253  -1.340   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.557  -1.689   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       4.471   1.719   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.166   2.068   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.817   0.764   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       4.357  -1.903   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       5.661  -2.253   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       6.011  -0.949   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       7.081  -1.047   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       8.415   1.632   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    4    5    6    7                                             
CONECT    4    3    8   11   12                                             
CONECT    5    3   13   14   15                                             
CONECT    6    3   16   17   18                                             
CONECT    7    3   19   20   21                                             
CONECT    8    4    9   22                                                  
CONECT    9    8   10   23                                                  
CONECT   10    1    2    9                                                  
CONECT   11    4                                                            
CONECT   12    4                                                            
CONECT   13    5                                                            
CONECT   14    5                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
CONECT   17    6                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    7                                                            
CONECT   21    7                                                            
CONECT   22    8                                                            
CONECT   23    9                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

Synonyms

Value	Source
(3-Carboxyallyl)trimethylammonium hydroxide, inner salt	ChEBI
Croton betaine	ChEBI
Crotonic acid betaine	ChEBI
Crotonsaeurebetain	ChEBI
Crotono-betaine	Kegg
Crotonate betaine	Generator
Crotonic acid betaine, inner salt, (e)-isomer	MeSH
Crotonobetaine	ChEBI
(e)-4-(Trimethylammonio)but-2-enoic acid	Generator

Molecular Formula

C₇H₁₃NO₂

Average Mass

143.1836

Monoisotopic Mass

143.094628665

IUPAC Name

(2E)-4-(trimethylazaniumyl)but-2-enoate

Traditional Name

crotonobetaine

CAS Registry Number

927-89-9

SMILES

[H]\C(=C(\[H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([O-])=O

InChI Identifier

InChI=1S/C7H13NO2/c1-8(2,3)6-4-5-7(9)10/h4-5H,6H2,1-3H3/b5-4+

InChI Key

GUYHPGUANSLONG-SNAWJCMRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight chain fatty acids

Alternative Parents

Substituents

Straight chain fatty acid
Unsaturated fatty acid
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic salt
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

4-(trimethylammonio)but-2-enoate (CHEBI:17237 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.087 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-3.8	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.22 m³·mol⁻¹	ChemAxon
Polarizability	15.56 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002g-4900000000-c8b03fae018b169a2e01	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002e-9800000000-ccc6940cd5c2b86b325f	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000m-9000000000-79a28749b01de1e2632f	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-f5fdddf4dc2a31fd3ddc	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-5900000000-bc7d04ce2d48f7eb839d	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05n0-9000000000-51e7dcf4e8df7057eca3	2019-02-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	72	Human feces; Human ; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	140	Human feces; Human ; Human subgingival plaque; Cattle ; Human saliva	Metabolic reconstruction
Bacteria	Bacteroidetes	45	Human feces; Human ; Human stool; Human saliva	Metabolic reconstruction
Bacteria	Actinobacteria	7	Human feces; Human	Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction

Exposure Sources

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

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

Not Available

KEGG Compound ID

C04114

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17237

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Crotonobetaine (MMDBc0031651)

MOL for #<Metabolite:0x00007fdb716e6780>

3D MOL for #<Metabolite:0x00007fdb716e6780>

3D SDF for #<Metabolite:0x00007fdb716e6780>

3D-SDF for #<Metabolite:0x00007fdb716e6780>

PDB for #<Metabolite:0x00007fdb716e6780>

3D PDB for #<Metabolite:0x00007fdb716e6780>

SMILES for #<Metabolite:0x00007fdb716e6780>

INCHI for #<Metabolite:0x00007fdb716e6780>

Structure for #<Metabolite:0x00007fdb716e6780>

3D Structure for #<Metabolite:0x00007fdb716e6780>