MiMeDB: Showing metabocard for Cyclo-[isoleucyl-prolyl-leucyl-alanyl] (MMDBc0005152)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:51:49 UTC

Update Date

2025-10-07 16:04:58 UTC

Metabolite ID

MMDBc0005152

Metabolite Identification

Common Name

Cyclo-[isoleucyl-prolyl-leucyl-alanyl]

Description

Cyclo-[isoleucyl-prolyl-leucyl-alanyl] is a cyclic peptide, a class of compounds characterized by a circular structure formed by amino acid residues. There is limited literature available on this metabolite, and further research is needed to elucidate its biological significance and potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100512D          

 33 34  0  0  1  0            999 V2000
    0.9337    0.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804   -6.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3355   -4.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2490   -0.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0804   -3.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311    0.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7003   -2.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942   -3.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824   -4.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779   -5.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -0.3551    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2618   -3.2506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1849   -4.1262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6907   -2.0493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3862   -1.1737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7637   -3.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1926   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0439   -1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728   -3.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413   -2.4904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451   -3.8057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -1.4941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702   -2.8095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -4.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5131   -0.6314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8041   -1.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2330   -3.9485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913    0.4635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5823   -4.0108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426   -4.6243    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0889   -1.3267    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286   -0.6755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11 10  1  0  0  0  0
 12  4  1  6  0  0  0
 12  6  1  0  0  0  0
 13  5  1  1  0  0  0
 14 10  1  1  0  0  0
 15  8  1  0  0  0  0
 16 12  1  1  0  0  0
 17 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 21 13  1  0  0  0  0
 21 19  2  0  0  0  0
 22 14  1  0  0  0  0
 22 17  2  0  0  0  0
 23 16  1  0  0  0  0
 23 18  2  0  0  0  0
 24  9  1  0  0  0  0
 24 15  1  0  0  0  0
 24 20  1  0  0  0  0
 17 25  1  4  0  0  0
 18 26  1  4  0  0  0
 19 27  1  4  0  0  0
 28 20  2  0  0  0  0
 12 29  1  1  0  0  0
 13 30  1  6  0  0  0
 14 31  1  6  0  0  0
 15 32  1  6  0  0  0
 16 33  1  6  0  0  0
M  END


  Mrv1652305152100512D          

 33 34  0  0  1  0            999 V2000
    0.9337    0.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804   -6.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3355   -4.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2490   -0.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0804   -3.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311    0.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7003   -2.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942   -3.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824   -4.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779   -5.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -0.3551    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2618   -3.2506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1849   -4.1262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6907   -2.0493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3862   -1.1737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7637   -3.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1926   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0439   -1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728   -3.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413   -2.4904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451   -3.8057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -1.4941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702   -2.8095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -4.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5131   -0.6314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8041   -1.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2330   -3.9485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913    0.4635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5823   -4.0108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426   -4.6243    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0889   -1.3267    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286   -0.6755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11 10  1  0  0  0  0
 12  4  1  6  0  0  0
 12  6  1  0  0  0  0
 13  5  1  1  0  0  0
 14 10  1  1  0  0  0
 15  8  1  0  0  0  0
 16 12  1  1  0  0  0
 17 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 21 13  1  0  0  0  0
 21 19  2  0  0  0  0
 22 14  1  0  0  0  0
 22 17  2  0  0  0  0
 23 16  1  0  0  0  0
 23 18  2  0  0  0  0
 24  9  1  0  0  0  0
 24 15  1  0  0  0  0
 24 20  1  0  0  0  0
 17 25  1  4  0  0  0
 18 26  1  4  0  0  0
 19 27  1  4  0  0  0
 28 20  2  0  0  0  0
 12 29  1  1  0  0  0
 13 30  1  6  0  0  0
 14 31  1  6  0  0  0
 15 32  1  6  0  0  0
 16 33  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0005152

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(CC)[C@]1([H])N=C(O)[C@]2([H])CCCN2C(=O)[C@]([H])(CC(C)C)N=C(O)[C@]([H])(C)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34N4O4/c1-6-12(4)16-19(27)21-13(5)17(25)22-14(10-11(2)3)20(28)24-9-7-8-15(24)18(26)23-16/h11-16H,6-10H2,1-5H3,(H,21,27)(H,22,25)(H,23,26)/t12-,13-,14-,15-,16-/m0/s1

> <INCHI_KEY>
DDXULJFDBNIPEQ-QXKUPLGCSA-N

> <FORMULA>
C20H34N4O4

> <MOLECULAR_WEIGHT>
394.516

> <EXACT_MASS>
394.258005591

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.76263581626675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S,9S,14aS)-3-[(2S)-butan-2-yl]-1,4,7-trihydroxy-6-methyl-9-(2-methylpropyl)-3H,6H,9H,10H,12H,13H,14H,14aH-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.3223168659675508

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.316751775100308

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.38624980021305433

> <JCHEM_PKA_STRONGEST_BASIC>
5.7644676638641545

> <JCHEM_POLAR_SURFACE_AREA>
118.08000000000001

> <JCHEM_REFRACTIVITY>
105.714

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,9S,14aS)-3-[(2S)-butan-2-yl]-1,4,7-trihydroxy-6-methyl-9-(2-methylpropyl)-3H,6H,9H,12H,13H,14H,14aH-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       1.743   1.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.457 -11.357   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.493  -8.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.198  -0.065   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.750  -6.259   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.551   0.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.174  -5.455   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.824  -3.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.856  -6.252   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.154  -9.230   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.265  -9.828   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.779  -0.663   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.222  -6.068   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.345  -7.702   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.289  -3.825   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.588  -2.191   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.292  -7.295   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.359  -2.598   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.815  -3.121   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.882  -6.772   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.624  -4.649   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       1.764  -7.104   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       1.169  -2.789   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      -0.691  -5.244   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       3.891  -8.714   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.958  -1.179   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.234  -2.522   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.302  -7.371   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       2.970   0.865   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.820  -7.487   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.573  -8.632   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.033  -2.477   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.360  -1.261   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6    1   12                                                       
CONECT    7    8    9                                                       
CONECT    8    7   15                                                       
CONECT    9    7   24                                                       
CONECT   10   11   14                                                       
CONECT   11    2    3   10                                                  
CONECT   12    4    6   16   29                                             
CONECT   13    5   17   21   30                                             
CONECT   14   10   20   22   31                                             
CONECT   15    8   18   24   32                                             
CONECT   16   12   19   23   33                                             
CONECT   17   13   22   25                                                  
CONECT   18   15   23   26                                                  
CONECT   19   16   21   27                                                  
CONECT   20   14   24   28                                                  
CONECT   21   13   19                                                       
CONECT   22   14   17                                                       
CONECT   23   16   18                                                       
CONECT   24    9   15   20                                                  
CONECT   25   17                                                            
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   16                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

Synonyms

Not Available

Molecular Formula

C₂₀H₃₄N₄O₄

Average Mass

394.516

Monoisotopic Mass

394.258005591

IUPAC Name

(3S,6S,9S,14aS)-3-[(2S)-butan-2-yl]-1,4,7-trihydroxy-6-methyl-9-(2-methylpropyl)-3H,6H,9H,10H,12H,13H,14H,14aH-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one

Traditional Name

(3S,6S,9S,14aS)-3-[(2S)-butan-2-yl]-1,4,7-trihydroxy-6-methyl-9-(2-methylpropyl)-3H,6H,9H,12H,13H,14H,14aH-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one

CAS Registry Number

Not Available

SMILES

[H][C@](C)(CC)[C@]1([H])N=C(O)[C@]2([H])CCCN2C(=O)[C@]([H])(CC(C)C)N=C(O)[C@]([H])(C)N=C1O

InChI Identifier

InChI=1S/C20H34N4O4/c1-6-12(4)16-19(27)21-13(5)17(25)22-14(10-11(2)3)20(28)24-9-7-8-15(24)18(26)23-16/h11-16H,6-10H2,1-5H3,(H,21,27)(H,22,25)(H,23,26)/t12-,13-,14-,15-,16-/m0/s1

InChI Key

DDXULJFDBNIPEQ-QXKUPLGCSA-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
Cyclic alpha peptide
Macrolactam
Alpha-amino acid or derivatives
Pyrrolidine
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Lactam
Carboxamide group
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2	ALOGPS
logP	1.32	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	-0.39	ChemAxon
pKa (Strongest Basic)	5.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.08 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.71 m³·mol⁻¹	ChemAxon
Polarizability	42.76 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Proteobacteria	1	Human feces; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439630

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24851292

PDB ID

Not Available

ChEBI ID

Not Available

CMMC Knowledgebase

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Cyclo-[isoleucyl-prolyl-leucyl-alanyl] (MMDBc0005152)

MOL for #<Metabolite:0x00007fd448df15f0>

3D MOL for #<Metabolite:0x00007fd448df15f0>

3D SDF for #<Metabolite:0x00007fd448df15f0>

3D-SDF for #<Metabolite:0x00007fd448df15f0>

PDB for #<Metabolite:0x00007fd448df15f0>

3D PDB for #<Metabolite:0x00007fd448df15f0>

SMILES for #<Metabolite:0x00007fd448df15f0>

INCHI for #<Metabolite:0x00007fd448df15f0>

Structure for #<Metabolite:0x00007fd448df15f0>

3D Structure for #<Metabolite:0x00007fd448df15f0>