NP-MRD: Showing NP-Card for Histidylserine (NP0136503)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-12 15:16:12 UTC

Updated at

2022-05-12 15:16:12 UTC

NP-MRD ID

NP0136503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Histidylserine

Description

His-Ser, also known as histidinyl-serine or HS, 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. His-Ser is a very strong basic compound (based on its pKa). A dipeptide formed from L-histidine and L-serine residues.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -0.1713   -2.3594    1.2832 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7005   -1.6621    0.0858 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0221   -1.0979    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259   -0.3704   -0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9509    0.2607   -0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3383    0.8179   -1.5633 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    0.5462   -2.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4035   -0.1632   -1.8718 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3119   -0.6041   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1183    0.1119   -1.2230 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600   -0.4032    0.5900 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058    0.6334    0.2493 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5234    1.6298    1.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4298    2.6147    1.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302    0.0446   -0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -1.1908    0.0284 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7922    0.8467   -0.3922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552   -3.1388    1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3102   -1.6805    2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7305   -2.3671   -0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6680   -1.9624    0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8415   -0.4407    1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795    0.2660    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304    1.3559   -1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4397    0.8995   -3.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360   -0.9914    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0729    1.1672   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8312    1.0915    2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5285    2.1183    1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0086    3.5113    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.5165   -1.0186 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
  5  6  1  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 17  1  0
 15 16  2  0
  8  4  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 12 27  1  6
 13 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
M  END


  Mrv1652304062013492D          

 17 17  0  0  0  0            999 V2000
 9998.880610000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5954 9999.7892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.309310000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0248 9999.7892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.742510000.2013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.4560 9999.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.171610000.2013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.309310001.0261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5954 9998.9638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.494910000.2836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8275 9999.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0824 9999.0140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9074 9999.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1623 9999.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.743510001.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.458510001.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4555 9998.9642    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  0  0  0  0
  2  9  1  1  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
 13 14  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 11  2  0  0  0  0
 10 14  1  0  0  0  0
  1 14  1  0  0  0  0
  5 15  1  1  0  0  0
 15 16  1  0  0  0  0
  6 17  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136503

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N4O4/c10-6(1-5-2-11-4-12-5)8(15)13-7(3-14)9(16)17/h2,4,6-7,14H,1,3,10H2,(H,11,12)(H,13,15)(H,16,17)/t6-,7-/m0/s1

> <INCHI_KEY>
KRBMQYPTDYSENE-BQBZGAKWSA-N

> <FORMULA>
C9H14N4O4

> <MOLECULAR_WEIGHT>
242.235

> <EXACT_MASS>
242.101504947

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.21718689302793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanoic acid

> <ALOGPS_LOGP>
-2.98

> <JCHEM_LOGP>
-4.8015213268207075

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.366120869915274

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.227276888166671

> <JCHEM_PKA_STRONGEST_BASIC>
7.838422795626286

> <JCHEM_POLAR_SURFACE_AREA>
141.33

> <JCHEM_REFRACTIVITY>
56.3344

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanoic 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    8664.5778667.042   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.9118666.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.2448667.042   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8668.5808666.273   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8669.9198667.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.2518666.273   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8672.5878667.042   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8667.2448668.582   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8665.9118664.732   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0    8661.9908667.196   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8660.7458666.291   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8661.2208664.826   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8662.7608664.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.2368666.291   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.9218668.582   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8671.2568669.351   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8671.2508664.733   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5   17    7                                                  
CONECT    7    6                                                            
CONECT    8    3                                                            
CONECT    9    2                                                            
CONECT   10   11   14                                                       
CONECT   11   12   10                                                       
CONECT   12   11   13                                                       
CONECT   13   14   12                                                       
CONECT   14   13   10    1                                                  
CONECT   15    5   16                                                       
CONECT   16   15                                                            
CONECT   17    6                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
Histidinyl-serine	ChEBI
Histidylserine	ChEBI
HS	ChEBI
L-His-L-ser	ChEBI
H-S dipeptide	HMDB
HS dipeptide	HMDB
His-Ser	HMDB
Histidine serine dipeptide	HMDB
Histidine-serine dipeptide	HMDB
Histidinylserine	HMDB
Histidyl-serine	HMDB
L-Histidinyl-L-serine	HMDB
L-Histidyl-L-serine	HMDB
N-Histidinylserine	HMDB
N-Histidylserine	HMDB
N-L-Histidinyl-L-serine	HMDB
N-L-Histidyl-L-serine	HMDB

Chemical Formula

C₉H₁₄N₄O₄

Average Mass

242.2350 Da

Monoisotopic Mass

242.10150 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H14N4O4/c10-6(1-5-2-11-4-12-5)8(15)13-7(3-14)9(16)17/h2,4,6-7,14H,1,3,10H2,(H,11,12)(H,13,15)(H,16,17)/t6-,7-/m0/s1

InChI Key

KRBMQYPTDYSENE-BQBZGAKWSA-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-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Serine or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Beta-hydroxy acid
Aralkylamine
Fatty amide
Hydroxy acid
Fatty acyl
Heteroaromatic compound
Azole
Imidazole
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Primary aliphatic amine
Organic salt
Hydrocarbon derivative
Amine
Organic zwitterion
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Primary alcohol
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74056 )

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	ALOGPS
logP	-4.8	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	7.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	141.33 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	56.33 m³·mol⁻¹	ChemAxon
Polarizability	23.22 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

HMDB0028894

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5360951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6992829

PDB ID

Not Available

ChEBI ID

74056

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Histidylserine (NP0136503)

MOL for NP0136503 (Histidylserine)

3D MOL for NP0136503 (Histidylserine)

3D SDF for NP0136503 (Histidylserine)

3D-SDF for NP0136503 (Histidylserine)

PDB for NP0136503 (Histidylserine)

3D PDB for NP0136503 (Histidylserine)

SMILES for NP0136503 (Histidylserine)

INCHI for NP0136503 (Histidylserine)

Structure for NP0136503 (Histidylserine)

3D Structure for NP0136503 (Histidylserine)