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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:14:56 UTC

Update Date

2022-09-22 18:35:02 UTC

HMDB ID

HMDB0341132

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Arg-Thr-Arg

Description

Arg-Thr-Arg, also known as RTR tripeptide, 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 a small amount of articles have been published on Arg-Thr-Arg.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092221532D          

 34 33  0  0  1  0            999 V2000
    8.2587    5.1315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485    5.2874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9886    5.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186    4.5078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    5.4433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1785    6.0669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683    6.2228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9084    6.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186    6.6906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    7.6260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0983    7.0024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283    7.7819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785    8.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9084    9.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485    9.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785   10.4324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186   11.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485   11.8356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5287   10.9001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983    4.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683    4.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    4.9755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481    4.3519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4780    5.1315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    4.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    3.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476    3.4164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6974    2.9487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675    4.3519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283    3.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4780    2.9487    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  0  0  0  0
  2  4  1  1  0  0  0
  2  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  4  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  4  0  0  0
 20 22  2  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END


  Mrv1652309092221532D          

 34 33  0  0  1  0            999 V2000
    8.2587    5.1315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485    5.2874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9886    5.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186    4.5078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    5.4433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1785    6.0669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683    6.2228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9084    6.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186    6.6906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    7.6260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0983    7.0024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283    7.7819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785    8.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9084    9.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485    9.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785   10.4324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186   11.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485   11.8356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5287   10.9001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983    4.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683    4.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    4.9755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481    4.3519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4780    5.1315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    4.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    3.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476    3.4164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6974    2.9487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675    4.3519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283    3.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4780    2.9487    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  0  0  0  0
  2  4  1  1  0  0  0
  2  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  4  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  4  0  0  0
 20 22  2  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341132

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H33N9O5/c1-8(26)11(25-12(27)9(17)4-2-6-22-15(18)19)13(28)24-10(14(29)30)5-3-7-23-16(20)21/h8-11,26H,2-7,17H2,1H3,(H,24,28)(H,25,27)(H,29,30)(H4,18,19,22)(H4,20,21,23)/t8-,9+,10+,11+/m1/s1

> <INCHI_KEY>
AIFHRTPABBBHKU-RCWTZXSCSA-N

> <FORMULA>
C16H33N9O5

> <MOLECULAR_WEIGHT>
431.498

> <EXACT_MASS>
431.260465199

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.804821768310504

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1,3-dihydroxybutylidene]amino}-5-carbamimidamidopentanoic acid

> <JCHEM_LOGP>
-8.012466349821931

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
3.607226848207092

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.005894108872845

> <JCHEM_PKA_STRONGEST_BASIC>
12.323771031988068

> <JCHEM_POLAR_SURFACE_AREA>
272.53

> <JCHEM_REFRACTIVITY>
128.94959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1,3-dihydroxybutylidene]amino}-5-carbamimidamidopentanoic 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      15.416   9.579   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      13.904   9.870   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.912  11.034   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      14.408   8.415   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.392  10.161   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      13.400  11.325   0.000  0.00  0.00           H+0
HETATM    7  N   UNK     0      11.888  11.616   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      12.896  12.780   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.408  12.489   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.392  14.235   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      11.383  13.071   0.000  0.00  0.00           H+0
HETATM   12  N   UNK     0      10.879  14.526   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      13.400  15.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.896  16.855   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.904  18.019   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      13.400  19.474   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      14.408  20.638   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      13.904  22.093   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      15.920  20.347   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      11.383   8.997   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.888   7.541   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       9.871   9.288   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       8.863   8.124   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       8.359   9.579   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       7.351   8.415   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.343   7.250   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.830   7.541   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       3.822   6.377   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       2.310   6.668   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       1.302   5.504   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       1.806   8.124   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       9.367   6.668   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.879   6.377   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.359   5.504   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6    7   20                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    5   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25   32                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   23   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
RTR Tripeptide	MeSH
Arginyl-threonyl-arginine	MeSH

Chemical Formula

C₁₆H₃₃N₉O₅

Average Molecular Weight

431.498

Monoisotopic Molecular Weight

431.260465199

IUPAC Name

(2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1,3-dihydroxybutylidene]amino}-5-carbamimidamidopentanoic acid

Traditional Name

(2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1,3-dihydroxybutylidene]amino}-5-carbamimidamidopentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](C)(O)[C@]([H])(N=C(O)[C@@]([H])(N)CCCNC(N)=N)C(O)=N[C@@]([H])(CCCNC(N)=N)C(O)=O

InChI Identifier

InChI=1S/C16H33N9O5/c1-8(26)11(25-12(27)9(17)4-2-6-22-15(18)19)13(28)24-10(14(29)30)5-3-7-23-16(20)21/h8-11,26H,2-7,17H2,1H3,(H,24,28)(H,25,27)(H,29,30)(H4,18,19,22)(H4,20,21,23)/t8-,9+,10+,11+/m1/s1

InChI Key

AIFHRTPABBBHKU-RCWTZXSCSA-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
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Fatty acid
Amino acid or derivatives
Carboxamide group
Amino acid
Guanidine
Secondary alcohol
Secondary carboxylic acid amide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboximidamide
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Primary aliphatic amine
Carbonyl group
Alcohol
Organonitrogen compound
Organooxygen compound
Primary amine
Organic oxide
Amine
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	ChemAxon
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	12.32	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	272.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	128.95 m³·mol⁻¹	ChemAxon
Polarizability	44.8 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

8335348

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10159840

PDB ID

Not Available

ChEBI ID

159320

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 Arg-Thr-Arg (HMDB0341132)

MOL for HMDB0341132 (Arg-Thr-Arg)

3D MOL for HMDB0341132 (Arg-Thr-Arg)

3D SDF for HMDB0341132 (Arg-Thr-Arg)

3D-SDF for HMDB0341132 (Arg-Thr-Arg)

PDB for HMDB0341132 (Arg-Thr-Arg)

3D PDB for HMDB0341132 (Arg-Thr-Arg)

SMILES for HMDB0341132 (Arg-Thr-Arg)

INCHI for HMDB0341132 (Arg-Thr-Arg)

Structure for HMDB0341132 (Arg-Thr-Arg)

3D Structure for HMDB0341132 (Arg-Thr-Arg)

Predicted Kovats Retention Indices