MiMeDB: Showing metabocard for Cyclo-(L-Pro-L-Tyr) (MMDBc0004564)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:30:34 UTC

Update Date

2024-04-30 19:33:53 UTC

Metabolite ID

MMDBc0004564

Metabolite Identification

Common Name

Cyclo-(L-Pro-L-Tyr)

Description

(3s,8ar)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-a]Pyrazine-1,4-Dione, also known as cyclo(L-pro-L-tyr) or cyclo-(L-tyrosine-L-proline) inhibitor, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. A homodetic cyclic peptide that is a dipeptide composed of L-proline and L-tyrosine joined by peptide linkages (3s,8ar)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-a]Pyrazine-1,4-Dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

TYP
  Mrv0541 02231217442D          

 21 23  0  0  0  0            999 V2000
   -0.0748    0.4300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748   -0.3950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7893   -0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893   -1.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6397   -0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3541   -0.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3541    0.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    0.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -0.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686   -0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831    0.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975    0.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038   -0.3950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038    0.4300    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7893    0.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    1.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2884    0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733    0.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2884   -0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4309   -0.1031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5648    1.0107    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  1  0  0  0
  2 20  1  6  0  0  0
  3  4  2  0  0  0  0
  3 13  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 14 21  1  6  0  0  0
 15 16  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0004564

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=C(O)C=C1)NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1

> <INCHI_KEY>
LSGOTAXPWMCUCK-RYUDHWBXSA-N

> <FORMULA>
C14H16N2O3

> <MOLECULAR_WEIGHT>
260.2884

> <EXACT_MASS>
260.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.771614413787546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-octahydropyrrolo[1,2-a]piperazine-1,4-dione

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.5523886290000003

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.36828125993004

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.489836669811092

> <JCHEM_PKA_STRONGEST_BASIC>
-4.042931337632337

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
68.88380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-hexahydropyrrolo[1,2-a]piperazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: TYP                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      -0.140   0.803   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.140  -0.737   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.473  -1.507   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.473  -3.047   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.194  -1.507   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.528  -0.737   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.528   0.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.861   1.573   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.195  -0.737   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.861  -1.507   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.195   0.803   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.529   1.573   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -2.807  -0.737   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -2.807   0.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.473   1.573   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.473   3.113   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.272   1.278   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.177   0.033   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.272  -1.213   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       0.804  -0.192   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.921   1.887   0.000  0.00  0.00           H+0
CONECT    1    2   15                                                       
CONECT    2    1    3    5   20                                             
CONECT    3    2    4   13                                                  
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7   11                                                       
CONECT    9   10   11                                                       
CONECT   10    6    9                                                       
CONECT   11    8    9   12                                                  
CONECT   12   11                                                            
CONECT   13    3   14   19                                                  
CONECT   14   13   15   17   21                                             
CONECT   15    1   14   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   13   18                                                       
CONECT   20    2                                                            
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

Synonyms

Value	Source
Cyclo(L-pro-L-tyr)	ChEBI
CYCLO-(L-tyrosine-L-proline) inhibitor	ChEBI

Molecular Formula

C₁₄H₁₆N₂O₃

Average Mass

260.2884

Monoisotopic Mass

260.116092388

IUPAC Name

(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-octahydropyrrolo[1,2-a]piperazine-1,4-dione

Traditional Name

(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-hexahydropyrrolo[1,2-a]piperazine-1,4-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=C(O)C=C1)NC2=O

InChI Identifier

InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1

InChI Key

LSGOTAXPWMCUCK-RYUDHWBXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Carboxamide group
Lactam
Propargyl-type 1,3-dipolar organic compound
Azacycle
Organic 1,3-dipolar compound
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:6631 )
dipeptide (CHEBI:6631 )
homodetic cyclic peptide (CHEBI:6631 )
pyrrolopyrazine (CHEBI:6631 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	11.2 g/L	ALOGPS
logP	0.44	ALOGPS
logP	0.55	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.88 m³·mol⁻¹	ChemAxon
Polarizability	26.77 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	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-015d-9230000000-5e6f3638cf711617ed3c	2017-08-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-85bb681387aeaf3bae71	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0390000000-abbc3a064d1f3559322e	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05tf-9300000000-39654fe19b51dad8c608	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1290000000-7ae825d9c6b3987da875	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ku7-8930000000-a0c23e898d117ea89149	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uxr-9400000000-6880092386ae81ab0690	2017-07-26	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

Not Available

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	Actinobacteria	3	Human	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	3	Human feces; Human supragingival plaque

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

DB04520

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00030074

Chemspider ID

Not Available

KEGG Compound ID

C10605

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119404

PDB ID

Not Available

ChEBI ID

6631

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for Cyclo-(L-Pro-L-Tyr) (MMDBc0004564)

MOL for #<Metabolite:0x00007f46c800a940>

3D MOL for #<Metabolite:0x00007f46c800a940>

3D SDF for #<Metabolite:0x00007f46c800a940>

3D-SDF for #<Metabolite:0x00007f46c800a940>

PDB for #<Metabolite:0x00007f46c800a940>

3D PDB for #<Metabolite:0x00007f46c800a940>

SMILES for #<Metabolite:0x00007f46c800a940>

INCHI for #<Metabolite:0x00007f46c800a940>

Structure for #<Metabolite:0x00007f46c800a940>

3D Structure for #<Metabolite:0x00007f46c800a940>