NP-MRD: Showing NP-Card for Serylisoleucine (NP0136629)

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Record Information

Version

2.0

Created at

2022-05-12 15:19:27 UTC

Updated at

2022-05-12 15:19:27 UTC

NP-MRD ID

NP0136629

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Serylisoleucine

Description

Serylisoleucine, also known as SI or L-ser-L-ile, 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. Serylisoleucine is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.8106    0.0214   -1.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0100    0.5593   -0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214    0.0294   -0.4070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6319   -1.4809   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385    0.6489    0.5346 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6428    0.0208    0.3000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    0.6944   -0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    1.9143   -0.5044 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0420   -0.0505   -0.4077 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0938    0.7746   -0.9264 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -0.5688    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6383   -1.3025    0.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0423    0.6191    1.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    0.0958    2.8625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426    1.1795    2.3659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5867    0.7904   -1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097   -0.0488   -2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -0.9381   -1.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0212    1.6608   -0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4848    0.2095    0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564    0.2908   -1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3881   -1.8172   -1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9233   -1.8070    0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658   -1.9035   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254    1.7173    0.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826   -0.9957    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239   -0.9306   -1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659    1.5238   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7202    0.1541   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6099    0.2833    1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6611   -1.2466    1.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -2.2616    0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592    2.1645    2.2437 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
  3  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
 11 12  1  0
  5 13  1  0
 13 15  1  0
 13 14  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  6
  4 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  6
  6 26  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
M  END


  Mrv1652304062014112D          

 15 14  0  0  0  0            999 V2000
 2501.4720 2500.4940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.4720 2501.3195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1849 2501.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8998 2501.3195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1849 2502.5588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.4720 2502.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7572 2502.5588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8998 2502.9703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7572 2500.0822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2500.0424 2500.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3253 2500.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7572 2499.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1869 2500.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.9019 2500.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1869 2499.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  9  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  1  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136629

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H18N2O4/c1-3-5(2)7(9(14)15)11-8(13)6(10)4-12/h5-7,12H,3-4,10H2,1-2H3,(H,11,13)(H,14,15)/t5-,6-,7-/m0/s1

> <INCHI_KEY>
BXLYSRPHVMCOPS-ACZMJKKPSA-N

> <FORMULA>
C9H18N2O4

> <MOLECULAR_WEIGHT>
218.253

> <EXACT_MASS>
218.126657068

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.41194909295308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-methylpentanoic acid

> <ALOGPS_LOGP>
-2.43

> <JCHEM_LOGP>
-3.093997432237988

> <ALOGPS_LOGS>
-0.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.532435858489169

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.767420306931801

> <JCHEM_PKA_STRONGEST_BASIC>
7.849374451812914

> <JCHEM_POLAR_SURFACE_AREA>
112.65

> <JCHEM_REFRACTIVITY>
52.935

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-methylpentanoic 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    4669.4144667.589   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4669.4144669.130   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4670.7454669.902   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4672.0804669.130   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4670.7454671.443   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4669.4144672.211   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4668.0804671.443   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    4672.0804672.211   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    4668.0804666.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4666.7464667.589   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4665.4074666.820   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4668.0804665.279   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4670.7494666.820   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    4672.0844667.589   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    4670.7494665.279   0.000  0.00  0.00           O+0
CONECT    1    2    9   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    1   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    1   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
L-Ser-L-ile	ChEBI
Seryl-isoleucine	ChEBI
SI	ChEBI
L-Seryl-L-isoleucine	HMDB
N-L-Seryl-L-isoleucine	HMDB
N-Serylisoleucine	HMDB
S-I dipeptide	HMDB
SI dipeptide	HMDB
Ser-ile	HMDB
Serine isoleucine dipeptide	HMDB
Serine-isoleucine dipeptide	HMDB
Serinyl-isoleucine	HMDB
Serinylisoleucine	HMDB
Serylisoleucine	ChEBI

Chemical Formula

C₉H₁₈N₂O₄

Average Mass

218.2530 Da

Monoisotopic Mass

218.12666 Da

IUPAC Name

(2S,3S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-methylpentanoic acid

Traditional Name

(2S,3S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H](NC(=O)[C@@H](N)CO)C(O)=O

InChI Identifier

InChI=1S/C9H18N2O4/c1-3-5(2)7(9(14)15)11-8(13)6(10)4-12/h5-7,12H,3-4,10H2,1-2H3,(H,11,13)(H,14,15)/t5-,6-,7-/m0/s1

InChI Key

BXLYSRPHVMCOPS-ACZMJKKPSA-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
Isoleucine 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
Methyl-branched fatty acid
Hydroxy fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Amino acid
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary alcohol
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	-2.4	ALOGPS
logP	-3.1	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.65 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	52.94 m³·mol⁻¹	ChemAxon
Polarizability	22.41 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

HMDB0029042

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

71429009

PDB ID

Not Available

ChEBI ID

90326

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Serylisoleucine (NP0136629)

MOL for NP0136629 (Serylisoleucine)

3D MOL for NP0136629 (Serylisoleucine)

3D SDF for NP0136629 (Serylisoleucine)

3D-SDF for NP0136629 (Serylisoleucine)

PDB for NP0136629 (Serylisoleucine)

3D PDB for NP0136629 (Serylisoleucine)

SMILES for NP0136629 (Serylisoleucine)

INCHI for NP0136629 (Serylisoleucine)

Structure for NP0136629 (Serylisoleucine)

3D Structure for NP0136629 (Serylisoleucine)