NP-MRD: Showing NP-Card for Alanylmethionine (NP0136334)

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Record Information

Version

2.0

Created at

2022-05-12 15:11:52 UTC

Updated at

2022-05-12 15:11:52 UTC

NP-MRD ID

NP0136334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alanylmethionine

Description

Alanylmethionine, also known as AM or L-ala-L-met, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Alanylmethionine is a very strong basic compound (based on its pKa). Alanylmethionine was first documented in 1975 (PMID: 1238384). It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
    3.9239    2.2978    0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7534    0.7122    1.2186 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -0.4843    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064    0.0736    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4465   -0.7350   -0.6823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8285   -0.0758   -0.6676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508    0.0087    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1149   -0.4778    1.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8861    0.6709    0.6402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8497   -0.4022    1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3008    1.2119   -0.6179 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2477   -2.1264   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902   -2.5469    0.1352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978   -3.0311   -0.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0258    2.6265   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1677    3.0609    1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209    2.2352   -0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531   -1.4602    0.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543   -0.6065   -0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    1.0561   -0.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095    0.2729    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729   -0.8498   -1.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075    0.3305   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8257    1.4662    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2797   -1.0814    1.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004    0.0542    1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1839   -0.9463    0.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2295    0.4813   -1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511    2.0557   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3040   -3.7910   -0.6965 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  5 12  1  0
 12 14  1  0
 12 13  2  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  6
  6 23  1  0
  9 24  1  1
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 14 30  1  0
M  END


  Mrv1652304062013202D          

 14 13  0  0  0  0            999 V2000
 2502.4349 2502.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.4349 2501.5092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2503.1560 2501.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.8710 2501.5215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.1560 2500.2843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2502.4411 2499.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.8710 2499.8706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7201 2502.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0053 2502.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.2905 2502.7464    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 2499.5713 2502.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.1498 2502.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.8648 2502.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.1498 2503.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  8  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136334

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O3S/c1-5(9)7(11)10-6(8(12)13)3-4-14-2/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t5-,6-/m0/s1

> <INCHI_KEY>
FSHURBQASBLAPO-WDSKDSINSA-N

> <FORMULA>
C8H16N2O3S

> <MOLECULAR_WEIGHT>
220.29

> <EXACT_MASS>
220.088163557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.600415094100388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-aminopropanamido]-4-(methylsulfanyl)butanoic acid

> <ALOGPS_LOGP>
-1.33

> <JCHEM_LOGP>
-2.72828458936582

> <ALOGPS_LOGS>
-1.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.735474284109074

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.80437848897365

> <JCHEM_PKA_STRONGEST_BASIC>
8.388623163124928

> <JCHEM_POLAR_SURFACE_AREA>
92.42000000000002

> <JCHEM_REFRACTIVITY>
54.88340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-aminopropanamido]-4-(methylsulfanyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    4671.2124671.025   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4671.2124669.484   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4672.5584668.738   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4673.8934669.507   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4672.5584667.197   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4671.2234666.425   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    4673.8934666.425   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    4669.8784671.793   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4668.5434671.025   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0    4667.2094671.793   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0    4665.8664671.021   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4672.5464671.793   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4673.8814671.025   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    4672.5464673.334   0.000  0.00  0.00           O+0
CONECT    1    2    8   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    1   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
AM	ChEBI
L-Ala-L-met	ChEBI
Copoly(alanine, methionine)	HMDB
Poly(ala, met)	HMDB
Copoly(L-alanine, L-methionine)	HMDB
a-m Dipeptide	HMDB
AM dipeptide	HMDB
Ala-met	HMDB
Alanine methionine dipeptide	HMDB
Alanine-methionine dipeptide	HMDB
Alanyl-methionine	HMDB
L-Alanyl-L-methionine	HMDB
N-Alanylmethionine	HMDB
N-L-Alanyl-L-methionine	HMDB
Alanylmethionine	ChEBI

Chemical Formula

C₈H₁₆N₂O₃S

Average Mass

220.2900 Da

Monoisotopic Mass

220.08816 Da

IUPAC Name

(2S)-2-[(2S)-2-aminopropanamido]-4-(methylsulfanyl)butanoic acid

Traditional Name

(2S)-2-[(2S)-2-aminopropanamido]-4-(methylsulfanyl)butanoic acid

CAS Registry Number

Not Available

SMILES

CSCC[C@H](NC(=O)[C@H](C)N)C(O)=O

InChI Identifier

InChI=1S/C8H16N2O3S/c1-5(9)7(11)10-6(8(12)13)3-4-14-2/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t5-,6-/m0/s1

InChI Key

FSHURBQASBLAPO-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Thia fatty acid
Fatty acyl
Fatty acid
Amino acid or derivatives
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Dialkylthioether
Thioether
Sulfenyl compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Primary amine
Carbonyl group
Organic nitrogen compound
Amine
Primary aliphatic amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73806 )

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	-1.3	ALOGPS
logP	-2.7	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	8.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	54.88 m³·mol⁻¹	ChemAxon
Polarizability	22.6 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

HMDB0028693

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

85744

PDB ID

Not Available

ChEBI ID

73806

Good Scents ID

Not Available

References

General References

Drew SW, Demain AL: Stimulation of cephalosporin production by methionine peptides in a mutant blocked in reverse transsulfuration. J Antibiot (Tokyo). 1975 Nov;28(11):889-95. doi: 10.7164/antibiotics.28.889. [PubMed:1238384 ]

Showing NP-Card for Alanylmethionine (NP0136334)

MOL for NP0136334 (Alanylmethionine)

3D MOL for NP0136334 (Alanylmethionine)

3D SDF for NP0136334 (Alanylmethionine)

3D-SDF for NP0136334 (Alanylmethionine)

PDB for NP0136334 (Alanylmethionine)

3D PDB for NP0136334 (Alanylmethionine)

SMILES for NP0136334 (Alanylmethionine)

INCHI for NP0136334 (Alanylmethionine)

Structure for NP0136334 (Alanylmethionine)

3D Structure for NP0136334 (Alanylmethionine)