NP-MRD: Showing NP-Card for ala-pro (NP0318365)

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Record Information

Version

2.0

Created at

2022-09-11 18:49:07 UTC

Updated at

2022-09-11 18:49:07 UTC

NP-MRD ID

NP0318365

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ala-pro

Description

Alanylproline, also known as A-P or L-ala-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. Alanylproline is a very strong basic compound (based on its pKa). ala-pro is found in Trypanosoma brucei. ala-pro was first documented in 1997 (PMID: 9200606). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 26686724) (PMID: 18672677) (PMID: 23062344) (PMID: 10543577).

Structure

MOL 3D MOL SDF PDB SMILES InChI

      
  Mrv1652304032018422D          

 13 13  0  0  0  0            999 V2000
 2499.6746 2500.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9602 2500.8467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.2354 2500.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9602 2501.6740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3911 2500.8467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0479 2499.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7644 2499.0998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0479 2500.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6578 2499.5934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9904 2499.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2453 2498.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0703 2498.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3252 2499.1085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 13  6  1  6  0  0  0
  1  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318365

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H14N2O3/c1-5(9)7(11)10-4-2-3-6(10)8(12)13/h5-6H,2-4,9H2,1H3,(H,12,13)/t5-,6-/m0/s1

> <INCHI_KEY>
WPWUFUBLGADILS-WDSKDSINSA-N

> <FORMULA>
C8H14N2O3

> <MOLECULAR_WEIGHT>
186.211

> <EXACT_MASS>
186.100442319

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.66480904082092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-1.99

> <JCHEM_LOGP>
-3.107002794240429

> <ALOGPS_LOGS>
0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.706322612953283

> <JCHEM_PKA_STRONGEST_BASIC>
8.381476455934987

> <JCHEM_POLAR_SURFACE_AREA>
83.63000000000001

> <JCHEM_REFRACTIVITY>
45.48380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0    4666.0594667.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4664.7264668.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4663.3734667.500   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    4664.7264669.791   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0    4667.3974668.247   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    4668.6234665.760   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4669.9604664.986   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4668.6234667.305   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    4666.0284665.908   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    4664.7824665.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4665.2584663.538   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4666.7984663.538   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4667.2744665.003   0.000  0.00  0.00           C+0
CONECT    1    2    5    9                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1                                                            
CONECT    6    7    8   13                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10   13    1                                                  
CONECT   10   11    9                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9    6                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
A-P	ChEBI
AP	ChEBI
L-Ala-L-pro	ChEBI
L-Alanyl-L-proline	HMDB
1-L-Alanyl-L-proline	HMDB
1-L-Alanylproline	HMDB
a-p Dipeptide	HMDB
AP dipeptide	HMDB
Ala-pro	HMDB
Alanine proline dipeptide	HMDB
Alanine-proline dipeptide	HMDB
Alanyl-proline	HMDB
L-alpha-Alanyl-L-proline	HMDB
L-Α-alanyl-L-proline	HMDB
N-Alanylproline	HMDB
N-L-Alanyl-L-proline	HMDB
NSC 97932	HMDB
Alanylproline	ChEBI

Chemical Formula

C₈H₁₄N₂O₃

Average Mass

186.2110 Da

Monoisotopic Mass

186.10044 Da

IUPAC Name

(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H14N2O3/c1-5(9)7(11)10-4-2-3-6(10)8(12)13/h5-6H,2-4,9H2,1H3,(H,12,13)/t5-,6-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73393 )

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	-2	ALOGPS
logP	-3.1	ChemAxon
logS	0.12	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	8.38	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	2	ChemAxon
Refractivity	45.48 m³·mol⁻¹	ChemAxon
Polarizability	18.66 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

HMDB0028695

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

75359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83525

PDB ID

Not Available

ChEBI ID

73393

Good Scents ID

Not Available

References

General References

Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]
Ranganathan R, Lu KP, Hunter T, Noel JP: Structural and functional analysis of the mitotic rotamase Pin1 suggests substrate recognition is phosphorylation dependent. Cell. 1997 Jun 13;89(6):875-86. doi: 10.1016/s0092-8674(00)80273-1. [PubMed:9200606 ]
Goptar' IA, Kulemzina IA, Filippova IIu, Lysogorskaia EN, Oksenoit ES, Zhuzhikov DP, Dunaevskii IaE, Belozerskii MA, Elpidina EN: [Properties of post-proline cleaving enzymes from Tenebrio molitor]. Bioorg Khim. 2008 May-Jun;34(3):310-6. doi: 10.1134/s1068162008030047. [PubMed:18672677 ]
Daidone I, Iacobucci C, McLain SE, Smith JC: Alteration of water structure by peptide clusters revealed by neutron scattering in the small-angle region (below 1 A(-1)). Biophys J. 2012 Oct 3;103(7):1518-24. doi: 10.1016/j.bpj.2012.08.010. Epub 2012 Oct 2. [PubMed:23062344 ]
Ishikawa H, Matsuda Y, Katayama M, Hara I, Sato H, Kaneko S, Hirakawa S, Matsushima M: Amidolytic activities and prostate-specific antigen in human seminal plasma. Arch Androl. 1999 Sep-Oct;43(2):141-51. doi: 10.1080/014850199262652. [PubMed:10543577 ]
LOTUS database [Link]

Showing NP-Card for ala-pro (NP0318365)

MOL for NP0318365 (ala-pro)

3D MOL for NP0318365 (ala-pro)

3D SDF for NP0318365 (ala-pro)

3D-SDF for NP0318365 (ala-pro)

PDB for NP0318365 (ala-pro)

3D PDB for NP0318365 (ala-pro)

SMILES for NP0318365 (ala-pro)

INCHI for NP0318365 (ala-pro)

Structure for NP0318365 (ala-pro)

3D Structure for NP0318365 (ala-pro)