NP-MRD: Showing NP-Card for Histidylalanine (NP0136487)

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Record Information

Version

2.0

Created at

2022-05-12 15:15:47 UTC

Updated at

2022-05-12 15:15:47 UTC

NP-MRD ID

NP0136487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Histidylalanine

Description

His-Ala, also known as histidinoalanine or HA, 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. His-Ala is a very strong basic compound (based on its pKa). Histidylalanine was first documented in 2011 (PMID: 21612224). A dipeptide formed from L-histidine and L-alanine residues.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    3.2870   -0.2471   -1.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269    0.2753   -0.4837 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9299   -0.1660   -0.8953 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1709   -1.0432   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249   -1.4478    0.9926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1614   -1.4721   -0.5617 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6694   -2.4301    0.4015 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0895   -0.2574   -0.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2176    0.3423    0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -0.0283    1.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0621    0.6848    2.7779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0135    1.5012    2.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074    1.2948    1.3430 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    1.7489   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758    2.3998   -0.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4345    2.3943   -0.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781   -0.1339   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0598   -1.3047   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194    0.3366   -2.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705   -0.1301    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696    0.1930   -1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0301   -1.9145   -1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6996   -3.3974    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303   -2.3438    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0768   -0.5684   -1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6722    0.4855   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9514   -0.7827    1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6631    2.2086    3.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959    1.7909    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065    2.0116    0.5209 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  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  2 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  1
  3 21  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv1652304062013472D          

 16 16  0  0  0  0            999 V2000
 9998.856310000.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5710 9999.7990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.284910000.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0006 9999.7990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.716310000.2111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.4320 9999.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.145710000.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4320 9998.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.716310001.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.284910001.0362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5710 9998.9737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.470710000.2930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8033 9999.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0582 9999.0234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8832 9999.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1381 9999.8080    0.0000 C   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
  2 11  1  1  0  0  0
  3  4  1  0  0  0  0
  3 10  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 15 16  2  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  1 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](NC(=O)[C@@H](N)CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N4O3/c1-5(9(15)16)13-8(14)7(10)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>
FRJIAZKQGSCKPQ-FSPLSTOPSA-N

> <FORMULA>
C9H14N4O3

> <MOLECULAR_WEIGHT>
226.236

> <EXACT_MASS>
226.106590327

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.202296766433424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-3-(1H-imidazol-5-yl)propanamido]propanoic acid

> <ALOGPS_LOGP>
-2.84

> <JCHEM_LOGP>
-3.9182224567181616

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.80936009749242

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3876704112606513

> <JCHEM_PKA_STRONGEST_BASIC>
8.022226429560167

> <JCHEM_POLAR_SURFACE_AREA>
121.10000000000001

> <JCHEM_REFRACTIVITY>
55.356399999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-(3H-imidazol-4-yl)propanamido]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    8664.5328667.061   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.8668666.291   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.1988667.061   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8668.5348666.291   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8669.8708667.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.2068666.291   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8672.5398667.061   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8671.2068664.751   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8669.8708668.601   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8667.1988668.601   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8665.8668664.751   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    8661.9458667.214   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8660.6998666.308   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8661.1758664.844   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8662.7158664.844   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.1918666.308   0.000  0.00  0.00           C+0
CONECT    1    2   16                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5                                                            
CONECT   10    3                                                            
CONECT   11    2                                                            
CONECT   12   13   16                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   16   14                                                       
CONECT   16   15   12    1                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
HA	ChEBI
Histidinoalanine	ChEBI
Histidinyl-alanine	ChEBI
Histidylalanine	ChEBI
L-His-L-ala	ChEBI
N-(2-Amino-2-carboxyethyl)histidine	ChEBI
Histidinylalanine	MeSH
Histidinoalanine, (beta)-isomer	MeSH
H-A dipeptide	HMDB
HA dipeptide	HMDB
His-Ala	HMDB
Histidine alanine dipeptide	HMDB
Histidine-alanine dipeptide	HMDB
Histidyl-alanine	HMDB
L-Histidinyl-L-alanine	HMDB
L-Histidyl-L-alanine	HMDB
N-Histidinylalanine	HMDB
N-Histidylalanine	HMDB
N-L-Histidinyl-L-alanine	HMDB
N-L-Histidyl-L-alanine	HMDB

Chemical Formula

C₉H₁₄N₄O₃

Average Mass

226.2360 Da

Monoisotopic Mass

226.10659 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-3-(1H-imidazol-5-yl)propanamido]propanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-(3H-imidazol-4-yl)propanamido]propanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](NC(=O)[C@@H](N)CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C9H14N4O3/c1-5(9(15)16)13-8(14)7(10)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

FRJIAZKQGSCKPQ-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 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
Alanine or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Aralkylamine
Azole
Imidazole
Heteroaromatic compound
Amino acid or derivatives
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Primary amine
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73924 )

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)	3.39	ChemAxon
pKa (Strongest Basic)	8.02	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	55.36 m³·mol⁻¹	ChemAxon
Polarizability	22.2 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

HMDB0028878

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

91418

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101180

PDB ID

Not Available

ChEBI ID

73924

Good Scents ID

Not Available

References

General References

Taylor CM, De Silva ST: Synthesis of histidinoalanine: a comparison of beta-lactone and sulfamidate electrophiles. J Org Chem. 2011 Jul 15;76(14):5703-8. doi: 10.1021/jo200744d. Epub 2011 Jun 14. [PubMed:21612224 ]

Showing NP-Card for Histidylalanine (NP0136487)

MOL for NP0136487 (Histidylalanine)

3D MOL for NP0136487 (Histidylalanine)

3D SDF for NP0136487 (Histidylalanine)

3D-SDF for NP0136487 (Histidylalanine)

PDB for NP0136487 (Histidylalanine)

3D PDB for NP0136487 (Histidylalanine)

SMILES for NP0136487 (Histidylalanine)

INCHI for NP0136487 (Histidylalanine)

Structure for NP0136487 (Histidylalanine)

3D Structure for NP0136487 (Histidylalanine)