NP-MRD: Showing NP-Card for {[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid (NP0302555)

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Record Information

Version

1.0

Created at

2022-09-10 16:13:41 UTC

Updated at

2022-09-10 16:13:41 UTC

NP-MRD ID

NP0302555

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid

Description

Ala-Ala-Gly, also known as a-a-g or L-ala-L-ala-gly, 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. Ala-Ala-Gly 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)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid is found in Trypanosoma brucei. It was first documented in 2017 (PMID: 28238440). Based on a literature review a significant number of articles have been published on Ala-Ala-Gly (PMID: 35724928) (PMID: 35700447) (PMID: 34251190) (PMID: 29950075).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
   -3.0370   -0.6722    2.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3050    0.4485    1.4064 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2628    1.5008    1.1144 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7465   -0.0062    0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5727   -0.4940   -0.8667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859    0.0531   -0.0807 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014   -0.3839   -1.3312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2782    0.5398   -2.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5732   -0.4994   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2829   -0.9090   -2.3378 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1757   -0.2286   -0.1186 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6016   -0.3485   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0840   -0.3335    1.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3423   -0.4353    1.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -0.2170    2.4659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4889   -0.9973    3.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -1.5492    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187   -0.3230    2.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5339    0.8150    2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8898    1.2017    0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322    2.4241    0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    0.1708   -1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741   -1.4006   -1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594    0.2206   -2.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527    0.5271   -3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3777    1.5730   -2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3418   -0.3076   -3.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9225   -1.3053   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574    0.5233   -0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -0.6835    3.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
  5 22  1  0
  7 23  1  6
  8 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
M  END


  Mrv1652309102218132D          

 15 14  0  0  1  0            999 V2000
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 N   0  0  0  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
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   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  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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  4  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302555

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H15N3O4/c1-4(9)7(14)11-5(2)8(15)10-3-6(12)13/h4-5H,3,9H2,1-2H3,(H,10,15)(H,11,14)(H,12,13)/t4-,5-/m0/s1

> <INCHI_KEY>
RLMISHABBKUNFO-WHFBIAKZSA-N

> <FORMULA>
C8H15N3O4

> <MOLECULAR_WEIGHT>
217.225

> <EXACT_MASS>
217.106255975

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.132482761197366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid

> <JCHEM_LOGP>
-3.208264854132494

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.915090307644752

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.237600606007804

> <JCHEM_PKA_STRONGEST_BASIC>
9.569644648186058

> <JCHEM_POLAR_SURFACE_AREA>
128.5

> <JCHEM_REFRACTIVITY>
51.641600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic 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       6.930  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.930   1.334   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       3.850   1.334   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
a-a-g	ChEBI
AAG	ChEBI
L-Ala-L-ala-gly	ChEBI

Chemical Formula

C₈H₁₅N₃O₄

Average Mass

217.2250 Da

Monoisotopic Mass

217.10626 Da

IUPAC Name

2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid

Traditional Name

{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H15N3O4/c1-4(9)7(14)11-5(2)8(15)10-3-6(12)13/h4-5H,3,9H2,1-2H3,(H,10,15)(H,11,14)(H,12,13)/t4-,5-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tripeptide (CHEBI:73318 )

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	-3.2	ChemAxon
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.5 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.64 m³·mol⁻¹	ChemAxon
Polarizability	21.13 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

5374156

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7010589

PDB ID

Not Available

ChEBI ID

73318

Good Scents ID

Not Available

References

General References

Yaeger JDW, Krupp KT, Summers TR, Summers CH: Contextual generalization of social stress learning is modulated by orexin receptors in basolateral amygdala. Neuropharmacology. 2022 Sep 1;215:109168. doi: 10.1016/j.neuropharm.2022.109168. Epub 2022 Jun 17. [PubMed:35724928 ]
Sherman SL, Fischer KC, Garand E: Conformational Changes Induced by Methyl Side-Chains in Protonated Tripeptides Containing Glycine and Alanine Residues. J Phys Chem A. 2022 Jun 30;126(25):4036-4045. doi: 10.1021/acs.jpca.2c02584. Epub 2022 Jun 14. [PubMed:35700447 ]
Onofrei D, Stengel D, Jia D, Johnson HR, Trescott S, Soni A, Addison B, Muthukumar M, Holland GP: Investigating the Atomic and Mesoscale Interactions that Facilitate Spider Silk Protein Pre-Assembly. Biomacromolecules. 2021 Aug 9;22(8):3377-3385. doi: 10.1021/acs.biomac.1c00473. Epub 2021 Jul 12. [PubMed:34251190 ]
Ren Y, Zhang YF, Liu WJ, Zhao YF, Song YL, He LQ, Xia RX, Tu PF, Li J: [Two new polypeptides from extract of deer bone extract]. Zhongguo Zhong Yao Za Zhi. 2018 Jun;43(12):2556-2562. doi: 10.19540/j.cnki.cjcmm.20180208.001. [PubMed:29950075 ]
Matagne A, Bolle L, El Mahyaoui R, Baeyens-Volant D, Azarkan M: The proteolytic system of pineapple stems revisited: Purification and characterization of multiple catalytically active forms. Phytochemistry. 2017 Jun;138:29-51. doi: 10.1016/j.phytochem.2017.02.019. Epub 2017 Feb 23. [PubMed:28238440 ]
LOTUS database [Link]

Showing NP-Card for {[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid (NP0302555)

MOL for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D MOL for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D SDF for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D-SDF for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

PDB for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D PDB for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

SMILES for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

INCHI for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

Structure for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D Structure for NP0302555 ({[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}acetic acid)