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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:17:49 UTC

Update Date

2022-09-22 18:34:46 UTC

HMDB ID

HMDB0341305

Secondary Accession Numbers

None

Metabolite Identification

Common Name

cyclo(trp-tyr)

Description

Cyclo(-Trp-Tyr) 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. Cyclo(-Trp-Tyr) is a strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05031419592D          

 28 31  0  0  1  0            999 V2000
    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
    4.4509   -2.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1538   -1.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2579   -2.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -1.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -2.3815    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
    3.8989   -2.2100    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
    5.5128   -1.8669    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
    2.5399   -1.7684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7948   -0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    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
    1.7329   -1.9399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.3707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3198   -1.6954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -0.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469   -1.5969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -0.7137    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  3  2  0  0  0  0
 15 13  1  0  0  0  0
 16  4  2  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  6  0  0  0
 18 10  1  6  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 22 20  2  0  0  0  0
 23 18  1  0  0  0  0
 23 19  2  0  0  0  0
 24 14  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 17 27  1  1  0  0  0
 18 28  1  1  0  0  0
M  END


  Mrv0541 05031419592D          

 28 31  0  0  1  0            999 V2000
    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
    4.4509   -2.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1538   -1.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2579   -2.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -1.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -2.3815    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
    3.8989   -2.2100    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
    5.5128   -1.8669    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
    2.5399   -1.7684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7948   -0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    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
    1.7329   -1.9399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.3707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3198   -1.6954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -0.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469   -1.5969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -0.7137    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  3  2  0  0  0  0
 15 13  1  0  0  0  0
 16  4  2  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  6  0  0  0
 18 10  1  6  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 22 20  2  0  0  0  0
 23 18  1  0  0  0  0
 23 19  2  0  0  0  0
 24 14  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 17 27  1  1  0  0  0
 18 28  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0341305

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC2=CNC3=CC=CC=C23)N=C(O)[C@]([H])(CC2=CC=C(O)C=C2)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H19N3O3/c24-14-7-5-12(6-8-14)9-17-19(25)23-18(20(26)22-17)10-13-11-21-16-4-2-1-3-15(13)16/h1-8,11,17-18,21,24H,9-10H2,(H,22,26)(H,23,25)/t17-,18-/m0/s1

> <INCHI_KEY>
ZJDMXAAEAVGGSK-ROUUACIJSA-N

> <FORMULA>
C20H19N3O3

> <MOLECULAR_WEIGHT>
349.3832

> <EXACT_MASS>
349.142641489

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.561283365885316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S)-3-[(4-hydroxyphenyl)methyl]-6-(1H-indol-3-ylmethyl)-3,6-dihydropyrazine-2,5-diol

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.2594083378619407

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.2551811746198736

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.449224120965689

> <JCHEM_PKA_STRONGEST_BASIC>
3.7367561199729673

> <JCHEM_POLAR_SURFACE_AREA>
101.2

> <JCHEM_REFRACTIVITY>
97.94360000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S)-3-[(4-hydroxyphenyl)methyl]-6-(1H-indol-3-ylmethyl)-3,6-dihydropyrazine-2,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   15                                                       
CONECT    4    2   16                                                       
CONECT    5    7   12                                                       
CONECT    6    8   12                                                       
CONECT    7    5   14                                                       
CONECT    8    6   14                                                       
CONECT    9   12   17                                                       
CONECT   10   13   18                                                       
CONECT   11   13   21                                                       
CONECT   12    5    6    9                                                  
CONECT   13   10   11   15                                                  
CONECT   14    7    8   24                                                  
CONECT   15    3   13   16                                                  
CONECT   16    4   15   21                                                  
CONECT   17    9   19   22   27                                             
CONECT   18   10   20   23   28                                             
CONECT   19   17   23   25                                                  
CONECT   20   18   22   26                                                  
CONECT   21   11   16                                                       
CONECT   22   17   20                                                       
CONECT   23   18   19                                                       
CONECT   24   14                                                            
CONECT   25   19                                                            
CONECT   26   20                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₁₉N₃O₃

Average Molecular Weight

349.3832

Monoisotopic Molecular Weight

349.142641489

IUPAC Name

(3S,6S)-3-[(4-hydroxyphenyl)methyl]-6-(1H-indol-3-ylmethyl)-3,6-dihydropyrazine-2,5-diol

Traditional Name

(3S,6S)-3-[(4-hydroxyphenyl)methyl]-6-(1H-indol-3-ylmethyl)-3,6-dihydropyrazine-2,5-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC2=CNC3=CC=CC=C23)N=C(O)[C@]([H])(CC2=CC=C(O)C=C2)N=C1O

InChI Identifier

InChI=1S/C20H19N3O3/c24-14-7-5-12(6-8-14)9-17-19(25)23-18(20(26)22-17)10-13-11-21-16-4-2-1-3-15(13)16/h1-8,11,17-18,21,24H,9-10H2,(H,22,26)(H,23,25)/t17-,18-/m0/s1

InChI Key

ZJDMXAAEAVGGSK-ROUUACIJSA-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
3-alkylindole
Indole
Indole or derivatives
Dioxopiperazine
2,5-dioxopiperazine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
1,4-diazinane
Benzenoid
Substituted pyrrole
Piperazine
Heteroaromatic compound
Pyrrole
Lactam
Carboxamide group
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

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	2.63	ALOGPS
logP	3.26	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	5.45	ChemAxon
pKa (Strongest Basic)	3.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	101.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.94 m³·mol⁻¹	ChemAxon
Polarizability	36.56 Å³	ChemAxon
Number of Rings	4	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 Kovats Retention Indices

Not Available

Spectra

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

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

7408259

PDB ID

Not Available

ChEBI ID

Not Available

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(trp-tyr) (HMDB0341305)

MOL for HMDB0341305 (cyclo(trp-tyr))

3D MOL for HMDB0341305 (cyclo(trp-tyr))

3D SDF for HMDB0341305 (cyclo(trp-tyr))

3D-SDF for HMDB0341305 (cyclo(trp-tyr))

PDB for HMDB0341305 (cyclo(trp-tyr))

3D PDB for HMDB0341305 (cyclo(trp-tyr))

SMILES for HMDB0341305 (cyclo(trp-tyr))

INCHI for HMDB0341305 (cyclo(trp-tyr))

Structure for HMDB0341305 (cyclo(trp-tyr))

3D Structure for HMDB0341305 (cyclo(trp-tyr))

Predicted Kovats Retention Indices