NP-MRD: Showing NP-Card for Alanylhistidine (NP0136330)

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Record Information

Version

2.0

Created at

2022-05-12 15:11:46 UTC

Updated at

2022-05-12 15:11:46 UTC

NP-MRD ID

NP0136330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alanylhistidine

Description

Alanylhistidine, also known as AH or L-ala-L-his, 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. Alanylhistidine is a very strong basic compound (based on its pKa). Alanylhistidine was first documented in 1990 (PMID: 2302959). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 11989761) (PMID: 11033076) (PMID: 19162328) (PMID: 8797080).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    2.6892   -1.9443    0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262   -0.4459   -0.1259 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9225    0.2336    1.1438 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449    0.0429   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0914   -0.4247   -1.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356    1.0043   -0.0323 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5903    1.4478   -0.6158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7993    1.1341    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9983   -0.2954    0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435   -1.1125   -0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7541   -2.3557    0.1134 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0151   -2.3347    1.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5556   -1.0890    1.4634 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6010    2.8912   -0.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3964    3.5840   -0.6419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7101    3.4720   -1.4708 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -2.2136    1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9433   -2.3433   -0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6915   -2.3521   -0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5894   -0.1946   -0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4443   -0.3619    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821    1.1025    0.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533    1.3719    0.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7594    0.9296   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117    1.5490   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063    1.6398    1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2616   -0.8210   -1.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2457   -3.1883   -0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542   -3.2320    1.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    4.3062   -1.0258 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  7 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  6
  3 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
M  END


  Mrv1652304062013192D          

 16 16  0  0  0  0            999 V2000
 2501.2716 2501.2194    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.2716 2500.3942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.9922 2499.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7067 2500.4066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.9922 2499.1700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.2778 2498.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7067 2498.7564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.5571 2501.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.9860 2501.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7005 2501.2194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.9860 2502.4560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1707 2501.7138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5031 2501.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.7581 2500.4439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.5833 2500.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.8382 2501.2287    0.0000 C   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  9  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
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 15 16  2  0  0  0  0
 12 13  2  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](N)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N4O3/c1-5(10)8(14)13-7(9(15)16)2-6-3-11-4-12-6/h3-5,7H,2,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/t5-,7-/m0/s1

> <INCHI_KEY>
XZWXFWBHYRFLEF-FSPLSTOPSA-N

> <FORMULA>
C9H14N4O3

> <MOLECULAR_WEIGHT>
226.236

> <EXACT_MASS>
226.106590327

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.75683002378748

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-aminopropanamido]-3-(1H-imidazol-4-yl)propanoic acid

> <ALOGPS_LOGP>
-2.80

> <JCHEM_LOGP>
-3.8904554251929073

> <ALOGPS_LOGS>
-1.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.81260742332292

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3603239928007707

> <JCHEM_PKA_STRONGEST_BASIC>
8.394797122252138

> <JCHEM_POLAR_SURFACE_AREA>
121.10000000000002

> <JCHEM_REFRACTIVITY>
54.7907

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-aminopropanamido]-3-(1H-imidazol-4-yl)propanoic 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    4669.0404668.943   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4669.0404667.403   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4670.3854666.657   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4671.7194667.426   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4670.3854665.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4669.0524664.345   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    4671.7194664.345   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    4667.7074669.711   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4670.3744669.711   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    4671.7084668.943   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    4670.3744671.251   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0    4665.1194669.866   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    4663.8724668.960   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    4664.3484667.495   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    4665.8894667.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4666.3654668.960   0.000  0.00  0.00           C+0
CONECT    1    2    8    9                                                  
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   16                                                       
CONECT    9    1   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   16                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   16   14                                                       
CONECT   16   15   12    8                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
AH	ChEBI
Alanyl-histidine	ChEBI
L-Ala-L-his	ChEBI
N-L-Alanyl-L-histidine	ChEBI
Alanylhistidine, (D-his-L-ala)-isomer	HMDB
a-H Dipeptide	HMDB
AH dipeptide	HMDB
Ala-his	HMDB
Alanine histidine dipeptide	HMDB
Alanine-histidine dipeptide	HMDB
L-Alanyl-L-histidine	HMDB
N-Alanylhistidine	HMDB
Alanylhistidine	ChEBI

Chemical Formula

C₉H₁₄N₄O₃

Average Mass

226.2360 Da

Monoisotopic Mass

226.10659 Da

IUPAC Name

(2S)-2-[(2S)-2-aminopropanamido]-3-(1H-imidazol-4-yl)propanoic acid

Traditional Name

(2S)-2-[(2S)-2-aminopropanamido]-3-(1H-imidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](N)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O

InChI Identifier

InChI=1S/C9H14N4O3/c1-5(10)8(14)13-7(9(15)16)2-6-3-11-4-12-6/h3-5,7H,2,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/t5-,7-/m0/s1

InChI Key

XZWXFWBHYRFLEF-FSPLSTOPSA-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 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
Histidine 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
Imidazolyl carboxylic acid derivative
Azole
Heteroaromatic compound
Imidazole
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary aliphatic amine
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73771 )

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	-2.8	ALOGPS
logP	-3.9	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	8.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.1 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	54.79 m³·mol⁻¹	ChemAxon
Polarizability	21.76 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

HMDB0028689

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

CPD-13401

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9837455

PDB ID

Not Available

ChEBI ID

73771

Good Scents ID

Not Available

References

General References

Kuroda M, Harada T: Increase of gamma-glutamyl-beta-alanyl-histidine isopeptide in the macromolecular fraction of model chicken extract during heating and distribution in commercial chicken extracts. Poult Sci. 2002 Apr;81(4):590-4. doi: 10.1093/ps/81.4.590. [PubMed:11989761 ]
Mastrolorenzo A, Scozzafava A, Supuran CT: 4-toluenesulfonylureido derivatives of amines, amino acids and dipeptides: a novel class of potential antitumor agents. Eur J Pharm Sci. 2000 Oct;11(4):325-32. doi: 10.1016/s0928-0987(00)00122-6. [PubMed:11033076 ]
Gorzsas A, Andersson I, Pettersson L: Speciation in aqueous vanadate-ligand and peroxovanadate-ligand systems. J Inorg Biochem. 2009 Apr;103(4):517-26. doi: 10.1016/j.jinorgbio.2008.12.006. Epub 2008 Dec 24. [PubMed:19162328 ]
Brotman DN, Flancbaum L, Kang YH, Merrill GF, Fisher H: Positive inotropic effect of carcinine in the isolated perfused guinea pig heart. Crit Care Med. 1990 Mar;18(3):317-21. doi: 10.1097/00003246-199003000-00015. [PubMed:2302959 ]
Shimizu M: Detection of the peptidyltransferase activity of a dipeptide, alanylhistidine, in the absence of ribosomes. J Biochem. 1996 May;119(5):832-4. doi: 10.1093/oxfordjournals.jbchem.a021318. [PubMed:8797080 ]

Showing NP-Card for Alanylhistidine (NP0136330)

MOL for NP0136330 (Alanylhistidine)

3D MOL for NP0136330 (Alanylhistidine)

3D SDF for NP0136330 (Alanylhistidine)

3D-SDF for NP0136330 (Alanylhistidine)

PDB for NP0136330 (Alanylhistidine)

3D PDB for NP0136330 (Alanylhistidine)

SMILES for NP0136330 (Alanylhistidine)

INCHI for NP0136330 (Alanylhistidine)

Structure for NP0136330 (Alanylhistidine)

3D Structure for NP0136330 (Alanylhistidine)