NP-MRD: Showing NP-Card for cyclo(trans-10-hydroxy-L-Trp-L-Leu) (NP0333619)

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Record Information

Version

2.0

Created at

2024-07-17 14:45:43 UTC

Updated at

2025-12-20 03:41:05 UTC

NP-MRD ID

NP0333619

Natural Product DOI

https://doi.org/10.57994/3098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cyclo(trans-10-hydroxy-L-Trp-L-Leu)

Description

Cyclo(trans-10-hydroxy-L-Trp-L-Leu) belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on cyclo(trans-10-hydroxy-L-Trp-L-Leu).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03312317192D          

 23 25  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  1  0  0  0  0  0  0  0  0  0
    0.1536    1.3672    0.0000 O   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  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
  2 22  1  0  0  0  0
 16 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1NC(=O)[C@@H](NC1=O)[C@@H](O)C1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H21N3O3/c1-9(2)7-13-16(22)20-14(17(23)19-13)15(21)11-8-18-12-6-4-3-5-10(11)12/h3-6,8-9,13-15,18,21H,7H2,1-2H3,(H,19,23)(H,20,22)/t13-,14-,15-/m0/s1

> <INCHI_KEY>
PUEROZHOJKMEAR-KKUMJFAQSA-N

> <FORMULA>
C17H21N3O3

> <MOLECULAR_WEIGHT>
315.373

> <EXACT_MASS>
315.158291548

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.112504590130996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.017164375333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.038089543112

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.889035206864849

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3557950583803655

> <JCHEM_POLAR_SURFACE_AREA>
94.22

> <JCHEM_REFRACTIVITY>
85.1814

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S)-3-[(S)-hydroxy(1H-indol-3-yl)methyl]-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  O   UNK     0       0.287   2.552   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -3.281   0.583   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -4.787   0.904   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.263   2.368   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.769   2.688   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.245   4.153   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.751   4.473   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.215   5.297   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -4.232   3.513   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0      -5.817  -0.241   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    3   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17    2                                                       
CONECT   23   16                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₁N₃O₃

Average Mass

315.3730 Da

Monoisotopic Mass

315.15829 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1NC(=O)[C@@H](NC1=O)[C@@H](O)C1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C17H21N3O3/c1-9(2)7-13-16(22)20-14(17(23)19-13)15(21)11-8-18-12-6-4-3-5-10(11)12/h3-6,8-9,13-15,18,21H,7H2,1-2H3,(H,19,23)(H,20,22)/t13-,14-,15-/m0/s1

InChI Key

PUEROZHOJKMEAR-KKUMJFAQSA-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
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	daniel.ostendorff@pharmazie.uni-marburg.de	Philipps-Universität Marburg	Daniel Ostendorff	2024-07-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	daniel.ostendorff@pharmazie.uni-marburg.de	Philipps-Universität Marburg	Daniel Ostendorff	2024-07-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	daniel.ostendorff@pharmazie.uni-marburg.de	Philipps-Universität Marburg	Daniel Ostendorff	2024-07-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 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

This compound belongs to the class of organic compounds known as leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Leucine and derivatives

Alternative Parents

Substituents

Leucine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Indole or derivatives
Indole
2,5-dioxopiperazine
Dioxopiperazine
Fatty acyl
Benzenoid
Substituted pyrrole
Piperazine
N-acyl-amine
Fatty amide
1,4-diazinane
Heteroaromatic compound
Pyrrole
Secondary alcohol
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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	1.02	ChemAxon
pKa (Strongest Acidic)	10.89	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	94.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.18 m³·mol⁻¹	ChemAxon
Polarizability	32.11 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for cyclo(trans-10-hydroxy-L-Trp-L-Leu) (NP0333619)

MOL for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))

3D MOL for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))

3D SDF for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))

3D-SDF for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))

PDB for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))

3D PDB for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))

SMILES for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))

INCHI for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))

Structure for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))

3D Structure for NP0333619 (cyclo(trans-10-hydroxy-L-Trp-L-Leu))