NP-MRD: Showing NP-Card for ile-pro (NP0309865)

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Record Information

Version

2.0

Created at

2022-09-11 04:44:53 UTC

Updated at

2022-09-11 04:44:53 UTC

NP-MRD ID

NP0309865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ile-pro

Description

Isoleucylproline, also known as ip dipeptide or L-ile-L-pro, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. ile-pro is found in Trypanosoma brucei. ile-pro was first documented in 1986 (PMID: 3782411). Isoleucylproline is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.8572   -1.1075   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4225   -0.3404    0.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1296    1.1031    0.6148 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3087    1.8987    0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8544    1.3866   -0.1369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8075    0.8595   -1.4408 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2975    0.8783    0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821    1.3699    1.8272 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506   -0.0521    0.2126 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3642   -0.7436   -1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018   -1.9276   -0.7784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4717   -1.9432    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -0.4690    1.0522 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5962    0.2653    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682    0.0492    1.2609 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669    1.1989   -0.3807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5668   -0.5883   -1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3751   -2.0382    0.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0010   -1.5053   -0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1804   -0.4552    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -0.8078    1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9422    1.5159    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359    1.7364    0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5784    1.6848   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9893    2.9810    0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117    2.5041   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294    0.6797   -1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1219    1.3030   -2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3787   -1.1330   -1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095   -0.0731   -1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8057   -2.8417   -1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -1.7440   -1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169   -2.4588    1.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4548   -2.3351    1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -0.3317    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4074    1.4813   -0.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  1
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  1
 16 36  1  0
M  END

      
  Mrv1652305161919552D          

 16 16  0  0  0  0            999 V2000
 2500.3943 2500.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6794 2500.8449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9582 2500.4454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.2434 2500.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5223 2500.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9582 2499.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6794 2501.6704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.1093 2500.8449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7627 2499.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4776 2499.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7627 2500.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3766 2499.5958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.7093 2499.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9642 2498.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7892 2498.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0441 2499.1109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  6  0  0  0
  3  4  1  0  0  0  0
  3  6  1  1  0  0  0
  4  5  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  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
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 16  9  1  6  0  0  0
  1 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H20N2O3/c1-3-7(2)9(12)10(14)13-6-4-5-8(13)11(15)16/h7-9H,3-6,12H2,1-2H3,(H,15,16)/t7-,8-,9-/m0/s1

> <INCHI_KEY>
BBIXOODYWPFNDT-CIUDSAMLSA-N

> <FORMULA>
C11H20N2O3

> <MOLECULAR_WEIGHT>
228.292

> <EXACT_MASS>
228.147392512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.283770819739253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-1.7752702079774902

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9154771752947966

> <JCHEM_PKA_STRONGEST_BASIC>
8.49948149969245

> <JCHEM_POLAR_SURFACE_AREA>
83.63000000000001

> <JCHEM_REFRACTIVITY>
59.08040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-19         0                                  
HETATM    1  C   UNK     0    4667.4034667.475   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4666.0684668.244   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4664.7224667.498   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4663.3884668.267   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4662.0424667.521   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4664.7224665.957   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    4666.0684669.785   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    4668.7374668.244   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4669.9574665.762   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    4671.2924664.990   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    4669.9574667.303   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0    4667.3704665.912   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    4666.1244665.007   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4666.6004663.542   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4668.1404663.542   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4668.6164665.007   0.000  0.00  0.00           C+0
CONECT    1    2    8   12                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    2                                                            
CONECT    8    1                                                            
CONECT    9   10   11   16                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   16    1                                                  
CONECT   13   14   12                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12    9                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
IP	HMDB
Isoleucyl-proline	HMDB
L-Ile-L-pro	HMDB
1-L-Isoleucyl-L-proline	HMDB
1-L-Isoleucyl-proline	HMDB
I-p dipeptide	HMDB
IP dipeptide	HMDB
Ile-pro	HMDB
Isoleucine proline dipeptide	HMDB
Isoleucine-proline dipeptide	HMDB
L-Isoleucyl-L-proline	HMDB
Isoleucylproline	ChEBI
IP dipeptide	HMDB

Chemical Formula

C₁₁H₂₀N₂O₃

Average Mass

228.2920 Da

Monoisotopic Mass

228.14739 Da

IUPAC Name

(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C11H20N2O3/c1-3-7(2)9(12)10(14)13-6-4-5-8(13)11(15)16/h7-9H,3-6,12H2,1-2H3,(H,15,16)/t7-,8-,9-/m0/s1

InChI Key

BBIXOODYWPFNDT-CIUDSAMLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Isoleucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Proline or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organoheterocyclic compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74076 )

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	-0.45	ALOGPS
logP	-1.8	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.08 m³·mol⁻¹	ChemAxon
Polarizability	24.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0011174

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

444876

PDB ID

Not Available

ChEBI ID

74076

Good Scents ID

Not Available

References

General References

Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. doi: 10.1016/s0378-4347(00)83502-1. [PubMed:3782411 ]
LOTUS database [Link]

Showing NP-Card for ile-pro (NP0309865)

MOL for NP0309865 (ile-pro)

3D MOL for NP0309865 (ile-pro)

3D SDF for NP0309865 (ile-pro)

3D-SDF for NP0309865 (ile-pro)

PDB for NP0309865 (ile-pro)

3D PDB for NP0309865 (ile-pro)

SMILES for NP0309865 (ile-pro)

INCHI for NP0309865 (ile-pro)

Structure for NP0309865 (ile-pro)

3D Structure for NP0309865 (ile-pro)