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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:17:31 UTC

Update Date

2022-09-22 18:34:46 UTC

HMDB ID

HMDB0341304

Secondary Accession Numbers

None

Metabolite Identification

Common Name

cyclo(pro-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>
HMDB0341304

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₁₄H₁₆N₂O₃

Average Molecular Weight

260.2884

Monoisotopic Molecular Weight

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 )

Ontology

Not Available

Exogenous (DrugBank: DB04520)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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

Predicted Chromatographic Properties

Predicted Retention Times

Not Available

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cyclo(pro-tyr) GC-MS (Non-derivatized) - 70eV, Positive	splash10-015d-9230000000-5e6f3638cf711617ed3c	2017-08-28	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclo(pro-tyr) 10V, Positive-QTOF	splash10-03di-0090000000-85bb681387aeaf3bae71	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclo(pro-tyr) 20V, Positive-QTOF	splash10-03di-0390000000-abbc3a064d1f3559322e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclo(pro-tyr) 40V, Positive-QTOF	splash10-05tf-9300000000-39654fe19b51dad8c608	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclo(pro-tyr) 10V, Negative-QTOF	splash10-0a4i-1290000000-7ae825d9c6b3987da875	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclo(pro-tyr) 20V, Negative-QTOF	splash10-0ku7-8930000000-a0c23e898d117ea89149	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclo(pro-tyr) 40V, Negative-QTOF	splash10-0uxr-9400000000-6880092386ae81ab0690	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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(pro-tyr) (HMDB0341304)

MOL for HMDB0341304 (cyclo(pro-tyr))

3D MOL for HMDB0341304 (cyclo(pro-tyr))

3D SDF for HMDB0341304 (cyclo(pro-tyr))

3D-SDF for HMDB0341304 (cyclo(pro-tyr))

PDB for HMDB0341304 (cyclo(pro-tyr))

3D PDB for HMDB0341304 (cyclo(pro-tyr))

SMILES for HMDB0341304 (cyclo(pro-tyr))

INCHI for HMDB0341304 (cyclo(pro-tyr))

Structure for HMDB0341304 (cyclo(pro-tyr))

3D Structure for HMDB0341304 (cyclo(pro-tyr))

Predicted Retention Times

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra