MiMeDB: Showing metabocard for cyclo-acetoacetyl-L-tryptophan (MMDBc0055834)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:08:13 UTC

Update Date

2022-08-12 20:09:28 UTC

Metabolite ID

MMDBc0055834

Metabolite Identification

Common Name

cyclo-acetoacetyl-L-tryptophan

Description

cAATrp belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Based on a literature review a small amount of articles have been published on cAATrp.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222082D          

 21 23  0  0  1  0            999 V2000
   -2.0907    1.1949    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
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    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
   -2.0044    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2508    0.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363    0.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587   -0.8543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6719   -0.1105    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.4500    1.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -1.3812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903    0.6962    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  6  0  0  0
 13  8  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18  8  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  1  0  0  0  0
 12 21  1  1  0  0  0
M  CHG  1  18  -1
M  END
> <DATABASE_ID>
MMDBc0055834

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC2=CNC3=CC=CC=C23)N=C(O)\C(=C(\C)[O-])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14N2O3/c1-8(18)13-14(19)12(17-15(13)20)6-9-7-16-11-5-3-2-4-10(9)11/h2-5,7,12,16,18H,6H2,1H3,(H,17,20)/p-1/b13-8-/t12-/m0/s1

> <INCHI_KEY>
ADTDXFWSOBUFSD-OEMOTLHWSA-M

> <FORMULA>
C15H13N2O3

> <MOLECULAR_WEIGHT>
269.281

> <EXACT_MASS>
269.093165867

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.410787716211505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2S,4E)-5-hydroxy-2-[(1H-indol-3-yl)methyl]-3-oxo-3,4-dihydro-2H-pyrrol-4-ylidene]ethan-1-olate

> <JCHEM_LOGP>
2.1932620139999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.752452760158867

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.23538672917122

> <JCHEM_PKA_STRONGEST_BASIC>
1.0297871047456184

> <JCHEM_POLAR_SURFACE_AREA>
88.51

> <JCHEM_REFRACTIVITY>
86.1448

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(3E,5S)-2-hydroxy-5-(1H-indol-3-ylmethyl)-4-oxo-5H-pyrrol-3-ylidene]ethanolate

> <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      -3.903   2.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.742   0.699   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.335   0.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.001   0.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.015  -1.434   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -0.483  -1.595   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      -4.987  -0.206   0.000  0.00  0.00           O-1
HETATM   19  O   UNK     0      -0.840   2.374   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.045  -2.578   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       0.542   1.300   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   11                                                       
CONECT    6    9   12                                                       
CONECT    7    9   16                                                       
CONECT    8    1   13   18                                                  
CONECT    9    6    7   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11    5   10   16                                                  
CONECT   12    6   14   17   21                                             
CONECT   13    8   14   15                                                  
CONECT   14   12   13   19                                                  
CONECT   15   13   17   20                                                  
CONECT   16    7   11                                                       
CONECT   17   12   15                                                       
CONECT   18    8                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   12                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

Synonyms

Value	Source
Cyclo-acetoacetyl-L-tryptophan	MeSH

Molecular Formula

C₁₅H₁₃N₂O₃

Average Mass

269.281

Monoisotopic Mass

269.093165867

IUPAC Name

1-[(2S,4E)-5-hydroxy-2-[(1H-indol-3-yl)methyl]-3-oxo-3,4-dihydro-2H-pyrrol-4-ylidene]ethan-1-olate

Traditional Name

1-[(3E,5S)-2-hydroxy-5-(1H-indol-3-ylmethyl)-4-oxo-5H-pyrrol-3-ylidene]ethanolate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC2=CNC3=CC=CC=C23)N=C(O)\C(=C(\C)[O-])C1=O

InChI Identifier

InChI=1S/C15H14N2O3/c1-8(18)13-14(19)12(17-15(13)20)6-9-7-16-11-5-3-2-4-10(9)11/h2-5,7,12,16,18H,6H2,1H3,(H,17,20)/p-1/b13-8-/t12-/m0/s1

InChI Key

ADTDXFWSOBUFSD-OEMOTLHWSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Vinylogous acid
Cyclic carboximidic acid
Pyrroline
Pyrrole
Cyclic ketone
Lactim
Ketone
Azacycle
Enolate
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.19	ChemAxon
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	1.03	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.51 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.14 m³·mol⁻¹	ChemAxon
Polarizability	27.41 Å³	ChemAxon
Number of Rings	3	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	Deposition Date	View
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

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	1	Human feces

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

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155802573

PDB ID

Not Available

ChEBI ID

Not Available

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 cyclo-acetoacetyl-L-tryptophan (MMDBc0055834)

MOL for #<Metabolite:0x00007fecf47b7378>

3D MOL for #<Metabolite:0x00007fecf47b7378>

3D SDF for #<Metabolite:0x00007fecf47b7378>

3D-SDF for #<Metabolite:0x00007fecf47b7378>

PDB for #<Metabolite:0x00007fecf47b7378>

3D PDB for #<Metabolite:0x00007fecf47b7378>

SMILES for #<Metabolite:0x00007fecf47b7378>

INCHI for #<Metabolite:0x00007fecf47b7378>

Structure for #<Metabolite:0x00007fecf47b7378>

3D Structure for #<Metabolite:0x00007fecf47b7378>