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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:20:17 UTC

Update Date

2022-09-22 18:35:02 UTC

HMDB ID

HMDB0341146

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cys-Gln-Gln

Description

Cys-Gln-Gln, also known as C-Q-Q or H-cys-GLN-GLN-OH, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Based on a literature review very few articles have been published on Cys-Gln-Gln.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309092221582D          

 28 27  0  0  1  0            999 V2000
    4.1250    7.1447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    6.4302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7125    6.4302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    7.8592    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    5.0013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.2868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3625    5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8875    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  4  0  0  0
  6  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  4  0  0  0
 16 18  2  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END

  Mrv1652309092221582D          

 28 27  0  0  1  0            999 V2000
    4.1250    7.1447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    6.4302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7125    6.4302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    7.8592    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    5.0013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.2868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3625    5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8875    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  4  0  0  0
  6  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  4  0  0  0
 16 18  2  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341146

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](N)(CS)C(O)=N[C@@]([H])(CCC(O)=N)C(O)=N[C@@]([H])(CCC(O)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H23N5O6S/c14-6(5-25)11(21)17-7(1-3-9(15)19)12(22)18-8(13(23)24)2-4-10(16)20/h6-8,25H,1-5,14H2,(H2,15,19)(H2,16,20)(H,17,21)(H,18,22)(H,23,24)/t6-,7-,8-/m0/s1

> <INCHI_KEY>
BPHKULHWEIUDOB-FXQIFTODSA-N

> <FORMULA>
C13H23N5O6S

> <MOLECULAR_WEIGHT>
377.42

> <EXACT_MASS>
377.136904655

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.91676104821489

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-{[(2R)-2-amino-1-hydroxy-3-sulfanylpropylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

> <JCHEM_LOGP>
-8.460560224564594

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
-0.22965731449219629

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.8674232918114217

> <JCHEM_PKA_STRONGEST_BASIC>
13.140534226880911

> <JCHEM_POLAR_SURFACE_AREA>
216.65999999999997

> <JCHEM_REFRACTIVITY>
110.96019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2R)-2-amino-1-hydroxy-3-sulfanylpropylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  H   UNK     0       7.700  13.337   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       8.470  12.003   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.930  12.003   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.240  13.337   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0       8.470  14.670   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0       9.240  10.669   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.780  10.669   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       8.470   9.336   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.240   8.002   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      10.010   9.336   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      10.780   8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.090   6.668   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.860   8.002   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      13.860   5.335   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.240   5.335   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       6.930   6.668   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       5.390   6.668   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       1.540   5.335   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.470   4.001   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   19   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
C-Q-Q	ChEBI
CQQ	ChEBI
Cysteinyl-glutaminyl-glutamine	ChEBI
H-Cys-GLN-GLN-OH	ChEBI
L-Cys-L-GLN-L-GLN	ChEBI

Chemical Formula

C₁₃H₂₃N₅O₆S

Average Molecular Weight

377.42

Monoisotopic Molecular Weight

377.136904655

IUPAC Name

(2S)-2-{[(2S)-2-{[(2R)-2-amino-1-hydroxy-3-sulfanylpropylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

Traditional Name

(2S)-2-{[(2S)-2-{[(2R)-2-amino-1-hydroxy-3-sulfanylpropylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CS)C(O)=N[C@@]([H])(CCC(O)=N)C(O)=N[C@@]([H])(CCC(O)=N)C(O)=O

InChI Identifier

InChI=1S/C13H23N5O6S/c14-6(5-25)11(21)17-7(1-3-9(15)19)12(22)18-8(13(23)24)2-4-10(16)20/h6-8,25H,1-5,14H2,(H2,15,19)(H2,16,20)(H,17,21)(H,18,22)(H,23,24)/t6-,7-,8-/m0/s1

InChI Key

BPHKULHWEIUDOB-FXQIFTODSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
N-acyl-l-glutamine
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
N-acyl-amine
Fatty acyl
Fatty acid
Fatty amide
Amino acid
Amino acid or derivatives
Secondary carboxylic acid amide
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid
Monocarboxylic acid or derivatives
Alkylthiol
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Organosulfur compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-8.5	ChemAxon
pKa (Strongest Acidic)	-0.87	ChemAxon
pKa (Strongest Basic)	13.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	216.66 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	110.96 m³·mol⁻¹	ChemAxon
Polarizability	36.92 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

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

71471965

PDB ID

Not Available

ChEBI ID

156079

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

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for Cys-Gln-Gln (HMDB0341146)

MOL for HMDB0341146 (Cys-Gln-Gln)

3D MOL for HMDB0341146 (Cys-Gln-Gln)

3D SDF for HMDB0341146 (Cys-Gln-Gln)

3D-SDF for HMDB0341146 (Cys-Gln-Gln)

PDB for HMDB0341146 (Cys-Gln-Gln)

3D PDB for HMDB0341146 (Cys-Gln-Gln)

SMILES for HMDB0341146 (Cys-Gln-Gln)

INCHI for HMDB0341146 (Cys-Gln-Gln)

Structure for HMDB0341146 (Cys-Gln-Gln)

3D Structure for HMDB0341146 (Cys-Gln-Gln)

Predicted Kovats Retention Indices