MiMeDB: Showing metabocard for 4-(3-methylbut-2-enyl)-L-abrine (MMDBc0055451)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:52:25 UTC

Update Date

2022-08-12 20:09:22 UTC

Metabolite ID

MMDBc0055451

Metabolite Identification

Common Name

4-(3-methylbut-2-enyl)-L-abrine

Description

N-Methyl-4-dimethylallyltryptophan, also known as 4-(3-methylbut-2-enyl)-L-abrine or 4-dimethylallyl-L-abrine, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. N-Methyl-4-dimethylallyltryptophan is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on N-Methyl-4-dimethylallyltryptophan.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221522D          

 22 23  0  0  1  0            999 V2000
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    4.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    2.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    3.9312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    2.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203    1.7488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3317    2.3619    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  5  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  2  0  0  0  0
 15  9  1  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  3  1  0  0  0  0
 15 18  1  6  0  0  0
 19 10  1  0  0  0  0
 19 14  1  0  0  0  0
 20 17  2  0  0  0  0
 21 17  1  0  0  0  0
 15 22  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0055451

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](CC1=CNC2=CC=CC(CC=C(C)C)=C12)(NC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O2/c1-11(2)7-8-12-5-4-6-14-16(12)13(10-19-14)9-15(18-3)17(20)21/h4-7,10,15,18-19H,8-9H2,1-3H3,(H,20,21)/t15-/m0/s1

> <INCHI_KEY>
QQMWUGXCTSAHLX-HNNXBMFYSA-N

> <FORMULA>
C17H22N2O2

> <MOLECULAR_WEIGHT>
286.375

> <EXACT_MASS>
286.168127956

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.085887878053356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(methylamino)-3-[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid

> <JCHEM_LOGP>
0.8660600701510736

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.08715921551868

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.939292093682008

> <JCHEM_PKA_STRONGEST_BASIC>
10.639089580388852

> <JCHEM_POLAR_SURFACE_AREA>
65.12

> <JCHEM_REFRACTIVITY>
85.22019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(methylamino)-3-[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.839   7.658   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.143   5.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.887   4.729   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -0.333   7.338   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -2.393   5.049   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.411   3.264   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       0.619   4.409   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   18                                                            
CONECT    4    5    6                                                       
CONECT    5    4   12                                                       
CONECT    6    4   14                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9   13   15                                                       
CONECT   10   13   19                                                       
CONECT   11    1    2    7                                                  
CONECT   12    5    8   16                                                  
CONECT   13    9   10   16                                                  
CONECT   14    6   16   19                                                  
CONECT   15    9   17   18   22                                             
CONECT   16   12   13   14                                                  
CONECT   17   15   20   21                                                  
CONECT   18    3   15                                                       
CONECT   19   10   14                                                       
CONECT   20   17                                                            
CONECT   21   17                                                            
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

Synonyms

Value	Source
4-(3-Methylbut-2-enyl)-L-abrine	ChEBI
4-Dimethylallyl-L-abrine	ChEBI
4-Dimethylallyl-L-abrine zwitterion	ChEBI
4-Prenyl-L-abrine	Kegg

Molecular Formula

C₁₇H₂₂N₂O₂

Average Mass

286.375

Monoisotopic Mass

286.168127956

IUPAC Name

(2S)-2-(methylamino)-3-[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid

Traditional Name

(2S)-2-(methylamino)-3-[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](CC1=CNC2=CC=CC(CC=C(C)C)=C12)(NC)C(O)=O

InChI Identifier

InChI=1S/C17H22N2O2/c1-11(2)7-8-12-5-4-6-14-16(12)13(10-19-14)9-15(18-3)17(20)21/h4-7,10,15,18-19H,8-9H2,1-3H3,(H,20,21)/t15-/m0/s1

InChI Key

QQMWUGXCTSAHLX-HNNXBMFYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
3-alkylindole
Indole
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxylic acid salt
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Azacycle
Monocarboxylic acid or derivatives
Secondary amine
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic salt
Carbonyl group
Organic zwitterion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-methyl-L-alpha-amino acid (CHEBI:68464 )
L-tryptophan derivative (CHEBI:68464 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.87	ChemAxon
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	10.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.12 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.22 m³·mol⁻¹	ChemAxon
Polarizability	32.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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
Eukaryota/Fungi	Ascomycota	10	Human feces

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68294649

PDB ID

Not Available

ChEBI ID

67248

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 4-(3-methylbut-2-enyl)-L-abrine (MMDBc0055451)

MOL for #<Metabolite:0x00007fdb504ca878>

3D MOL for #<Metabolite:0x00007fdb504ca878>

3D SDF for #<Metabolite:0x00007fdb504ca878>

3D-SDF for #<Metabolite:0x00007fdb504ca878>

PDB for #<Metabolite:0x00007fdb504ca878>

3D PDB for #<Metabolite:0x00007fdb504ca878>

SMILES for #<Metabolite:0x00007fdb504ca878>

INCHI for #<Metabolite:0x00007fdb504ca878>

Structure for #<Metabolite:0x00007fdb504ca878>

3D Structure for #<Metabolite:0x00007fdb504ca878>