NP-MRD: Showing NP-Card for (2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid (NP0299038)

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Record Information

Version

2.0

Created at

2022-09-10 10:38:38 UTC

Updated at

2022-09-10 10:38:39 UTC

NP-MRD ID

NP0299038

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid

Description

Ile-Ala, also known as isoleucyl-alanine or IA, 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-Ala is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid is found in Trypanosoma brucei. (2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid was first documented in 2021 (PMID: 34681729). Based on a literature review a small amount of articles have been published on Ile-Ala (PMID: 36027851) (PMID: 35030435) (PMID: 34416878) (PMID: 34268766).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.6013    0.4361    2.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315   -0.5986    0.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945   -0.0140   -0.4134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4178   -1.1107   -1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559    0.8705   -0.8199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2292    1.3754   -2.1690 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3551    0.2344   -0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6561   -0.8549   -1.6259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2872    0.6927   -0.0691 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6079    0.1370   -0.0069 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6665    1.1854    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7204   -0.8970    1.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8195   -1.4669    1.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6358   -1.2247    1.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083    0.4611    2.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0714    0.1260    2.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274    1.4293    1.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218   -1.0486    1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992   -1.4316    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0017    0.6576   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5620   -1.5007   -1.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420   -0.7233   -2.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9656   -1.9295   -0.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9556    1.7441   -0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    0.8944   -2.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915    2.4181   -2.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8079   -1.7802   -1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878   -0.3232   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6707    1.5337    1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599    2.0308   -0.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6640    0.7473    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5491   -2.0703    2.3682 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  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 14  1  0
 12 13  2  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  1
  4 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  1
  6 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END


  Mrv1652309102212382D          

 14 13  0  0  1  0            999 V2000
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  4  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299038

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H18N2O3/c1-4-5(2)7(10)8(12)11-6(3)9(13)14/h5-7H,4,10H2,1-3H3,(H,11,12)(H,13,14)/t5-,6-,7-/m0/s1

> <INCHI_KEY>
RCFDOSNHHZGBOY-ACZMJKKPSA-N

> <FORMULA>
C9H18N2O3

> <MOLECULAR_WEIGHT>
202.254

> <EXACT_MASS>
202.131742448

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
21.590713628150894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid

> <JCHEM_LOGP>
-1.4220188178321775

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.56491168105637

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6042330469127144

> <JCHEM_PKA_STRONGEST_BASIC>
9.672826700102215

> <JCHEM_POLAR_SURFACE_AREA>
95.91000000000001

> <JCHEM_REFRACTIVITY>
51.91300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.540   2.667   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
IA	ChEBI
Isoleucyl-alanine	ChEBI
Isoleucylalanine	ChEBI
L-Ile-L-ala	ChEBI

Chemical Formula

C₉H₁₈N₂O₃

Average Mass

202.2540 Da

Monoisotopic Mass

202.13174 Da

IUPAC Name

(2S)-2-{[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid

Traditional Name

(2S)-2-{[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H18N2O3/c1-4-5(2)7(10)8(12)11-6(3)9(13)14/h5-7H,4,10H2,1-3H3,(H,11,12)(H,13,14)/t5-,6-,7-/m0/s1

InChI Key

RCFDOSNHHZGBOY-ACZMJKKPSA-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-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
Alpha-amino acid or derivatives
Fatty acyl
Fatty amide
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid salt
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Organic zwitterion
Organic nitrogen compound
Primary aliphatic amine
Organic salt
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:74062 )

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	-1.4	ChemAxon
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.91 m³·mol⁻¹	ChemAxon
Polarizability	21.59 Å³	ChemAxon
Number of Rings	0	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5373156

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7009576

PDB ID

Not Available

ChEBI ID

74062

Good Scents ID

Not Available

References

General References

Lin L, He YL, Tang Y, Hong P, Zhou C, Sun S, Qian ZJ: Mechanism analysis of octapeptide from microalgae, Isochrysis zhanjiangensis for suppressing vascular injury and angiogenesis in human umbilical vein endothelial cell. Int Immunopharmacol. 2022 Oct;111:109149. doi: 10.1016/j.intimp.2022.109149. Epub 2022 Aug 23. [PubMed:36027851 ]
Ren Q, Jiang X, Zhang S, Gao X, Paudel YN, Zhang P, Wang R, Liu K, Jin M: Neuroprotective effect of YIAEDAER peptide against Parkinson's disease like pathology in zebrafish. Biomed Pharmacother. 2022 Mar;147:112629. doi: 10.1016/j.biopha.2022.112629. Epub 2022 Jan 11. [PubMed:35030435 ]
Silva M, Philadelpho B, Santos J, Souza V, Souza C, Santiago V, Silva J, Souza C, Azeredo F, Castilho M, Cilli E, Ferreira E: IAF, QGF, and QDF Peptides Exhibit Cholesterol-Lowering Activity through a Statin-like HMG-CoA Reductase Regulation Mechanism: In Silico and In Vitro Approach. Int J Mol Sci. 2021 Oct 14;22(20):11067. doi: 10.3390/ijms222011067. [PubMed:34681729 ]
Yu Y, Tan P, Zhuang Z, Wang Z, Zhu L, Qiu R, Xu H: Untargeted metabolomic approach to study the serum metabolites in women with polycystic ovary syndrome. BMC Med Genomics. 2021 Aug 20;14(1):206. doi: 10.1186/s12920-021-01058-y. [PubMed:34416878 ]
Zhang X, Li H, Wang L, Zhang S, Wang F, Lin H, Gao S, Li X, Liu K: Anti-inflammatory peptides and metabolomics-driven biomarkers discovery from sea cucumber protein hydrolysates. J Food Sci. 2021 Aug;86(8):3540-3549. doi: 10.1111/1750-3841.15834. Epub 2021 Jul 15. [PubMed:34268766 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid (NP0299038)

MOL for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)

3D MOL for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)

3D SDF for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)

3D-SDF for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)

PDB for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)

3D PDB for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)

SMILES for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)

INCHI for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)

Structure for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)

3D Structure for NP0299038 ((2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}propanoic acid)