NP-MRD: Showing NP-Card for cyclo-L-Trp-L-Leu (NP0333618)

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Record Information

Version

2.0

Created at

2024-07-17 14:45:13 UTC

Updated at

2025-12-20 03:41:05 UTC

NP-MRD ID

NP0333618

Natural Product DOI

https://doi.org/10.57994/3097

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cyclo-L-Trp-L-Leu

Description

Cyclo(L-leucyl-L-tryptophyl), also known as cyclo(leu-TRP), 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. Based on a literature review very few articles have been published on Cyclo(L-leucyl-L-tryptophyl).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03312317192D          

 22 24  0  0  1  0            999 V2000
   -0.9083    2.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    0.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8194    1.2687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6263    1.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8813    2.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6882    2.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292    2.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673    1.8818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1165   -0.1290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
  2 21  1  0  0  0  0
 15 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1NC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H21N3O2/c1-10(2)7-14-16(21)20-15(17(22)19-14)8-11-9-18-13-6-4-3-5-12(11)13/h3-6,9-10,14-15,18H,7-8H2,1-2H3,(H,19,22)(H,20,21)/t14-,15-/m0/s1

> <INCHI_KEY>
BZUNCDPEEKFTCX-GJZGRUSLSA-N

> <FORMULA>
C17H21N3O2

> <MOLECULAR_WEIGHT>
299.374

> <EXACT_MASS>
299.163376928

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.37678281781773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S)-3-[(1H-indol-3-yl)methyl]-6-(2-methylpropyl)piperazine-2,5-dione

> <JCHEM_LOGP>
1.9361605223333322

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.359858896019952

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.247359488419566

> <JCHEM_PKA_STRONGEST_BASIC>
-3.776408541538762

> <JCHEM_POLAR_SURFACE_AREA>
73.99000000000001

> <JCHEM_REFRACTIVITY>
83.9739

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S)-3-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)piperazine-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-23         0                                  
HETATM    1  O   UNK     0      -1.696   4.337   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.726   3.192   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -3.281   0.583   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -4.787   0.904   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.263   2.368   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.769   2.688   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.245   4.153   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.751   4.473   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.215   5.297   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -4.232   3.513   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -5.817  -0.241   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    3   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16    2                                                       
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Cyclo(leu-TRP)	MeSH

Chemical Formula

C₁₇H₂₁N₃O₂

Average Mass

299.3740 Da

Monoisotopic Mass

299.16338 Da

IUPAC Name

(3S,6S)-3-[(1H-indol-3-yl)methyl]-6-(2-methylpropyl)piperazine-2,5-dione

Traditional Name

(3S,6S)-3-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)piperazine-2,5-dione

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1NC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC1=O

InChI Identifier

InChI=1S/C17H21N3O2/c1-10(2)7-14-16(21)20-15(17(22)19-14)8-11-9-18-13-6-4-3-5-12(11)13/h3-6,9-10,14-15,18H,7-8H2,1-2H3,(H,19,22)(H,20,21)/t14-,15-/m0/s1

InChI Key

BZUNCDPEEKFTCX-GJZGRUSLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)	daniel.ostendorff@pharmazie.uni-marburg.de	Philipps-Universität Marburg	Daniel Ostendorff	2024-07-17	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces albofaciens		Not Available

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
1,4-diazinane
Piperazine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Lactam
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.94	ChemAxon
pKa (Strongest Acidic)	11.25	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.97 m³·mol⁻¹	ChemAxon
Polarizability	32.38 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2339563

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3082081

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for cyclo-L-Trp-L-Leu (NP0333618)

MOL for NP0333618 (cyclo-L-Trp-L-Leu)

3D MOL for NP0333618 (cyclo-L-Trp-L-Leu)

3D SDF for NP0333618 (cyclo-L-Trp-L-Leu)

3D-SDF for NP0333618 (cyclo-L-Trp-L-Leu)

PDB for NP0333618 (cyclo-L-Trp-L-Leu)

3D PDB for NP0333618 (cyclo-L-Trp-L-Leu)

SMILES for NP0333618 (cyclo-L-Trp-L-Leu)

INCHI for NP0333618 (cyclo-L-Trp-L-Leu)

Structure for NP0333618 (cyclo-L-Trp-L-Leu)

3D Structure for NP0333618 (cyclo-L-Trp-L-Leu)