NP-MRD: Showing NP-Card for Serylserine (NP0136634)

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Record Information

Version

2.0

Created at

2022-05-12 15:19:35 UTC

Updated at

2022-05-12 15:19:35 UTC

NP-MRD ID

NP0136634

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Serylserine

Description

Serylserine, also known as H-L-ser-L-ser-OH or S-S, 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. Serylserine is a very strong basic compound (based on its pKa). Serylserine is found in Trypanosoma brucei. Serylserine was first documented in 1990 (PMID: 2168981). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 19770837) (PMID: 15838284).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062014122D          

 13 12  0  0  0  0            999 V2000
 2497.7702 2498.9905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2497.7702 2497.9831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4847 2497.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1991 2497.9831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.9157 2497.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.6302 2497.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1991 2498.8081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4847 2496.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0557 2499.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.3413 2498.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0557 2500.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4847 2499.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4847 2500.2269    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 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  1  0  0  0
  5  6  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136634

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12N2O5/c7-3(1-9)5(11)8-4(2-10)6(12)13/h3-4,9-10H,1-2,7H2,(H,8,11)(H,12,13)/t3-,4-/m0/s1

> <INCHI_KEY>
XZKQVQKUZMAADP-IMJSIDKUSA-N

> <FORMULA>
C6H12N2O5

> <MOLECULAR_WEIGHT>
192.171

> <EXACT_MASS>
192.074621494

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.585256648878136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.40

> <JCHEM_LOGP>
-5.475871775932969

> <ALOGPS_LOGS>
-0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.503420826275487

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3032377154372656

> <JCHEM_PKA_STRONGEST_BASIC>
7.849237127049587

> <JCHEM_POLAR_SURFACE_AREA>
132.88

> <JCHEM_REFRACTIVITY>
40.8821

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.92e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-serine, N-L-seryl-

> <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    4662.5044664.782   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4662.5044662.902   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4663.8384662.130   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4665.1724662.902   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4666.5094662.130   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4667.8434662.902   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    4665.1724664.442   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    4663.8384660.590   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4661.1714665.550   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    4659.8374664.782   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    4661.1714667.090   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4663.8384665.550   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4663.8384667.090   0.000  0.00  0.00           O+0
CONECT    1    2    9   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4                                                            
CONECT    8    3                                                            
CONECT    9    1   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
H-L-Ser-L-ser-OH	ChEBI
H-Ser-ser-OH	ChEBI
L-Ser-L-ser	ChEBI
S-S	ChEBI
SS	ChEBI
(2S)-2-{[(2S)-2-amino-1,3-dihydroxypropylidene]amino}-3-hydroxypropanoate	HMDB
L-Seryl-L-serine	HMDB
N-L-Seryl-L-serine	HMDB
N-Serylserine	HMDB
S-S Dipeptide	HMDB
SS Dipeptide	HMDB
Ser-ser	HMDB
Serine serine dipeptide	HMDB
Serine-serine dipeptide	HMDB
Serinyl-serine	HMDB
Serinylserine	HMDB
Seryl-serine	HMDB
Serylserine	ChEBI

Chemical Formula

C₆H₁₂N₂O₅

Average Mass

192.1710 Da

Monoisotopic Mass

192.07462 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-hydroxypropanoic acid

Traditional Name

L-serine, N-L-seryl-

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H12N2O5/c7-3(1-9)5(11)8-4(2-10)6(12)13/h3-4,9-10H,1-2,7H2,(H,8,11)(H,12,13)/t3-,4-/m0/s1

InChI Key

XZKQVQKUZMAADP-IMJSIDKUSA-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

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

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
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Serine or derivatives
Alpha-amino acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Amino acid or derivatives
Amino acid
Carboxamide group
Carboxylic acid salt
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organonitrogen compound
Organooxygen compound
Primary alcohol
Primary aliphatic amine
Primary amine
Organic zwitterion
Organic salt
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

dipeptide (CHEBI:73653 )

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	-3.4	ALOGPS
logP	-5.5	ChemAxon
logS	-0.33	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	132.88 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.88 m³·mol⁻¹	ChemAxon
Polarizability	17.59 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

HMDB0029048

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

7019104

PDB ID

Not Available

ChEBI ID

73653

Good Scents ID

Not Available

References

General References

Golimbet VE, Lebedeva IS, Monakhov MV, Korovaitseva GI, Lezheiko TV, Abramova LI, Kaleda VG, Karpov VL: [The Cys allele of the DRD2 (Ser311Cys polymorphism) is associated with schizophrenia and worse sustained attention in patients]. Zh Nevrol Psikhiatr Im S S Korsakova. 2009;109(9):67-70. [PubMed:19770837 ]
Kawanabe Y, Okamoto Y, Hashimoto N, Masaki T: Molecular mechanisms for activation of voltage-independent Ca2+ channels by endothelin-1/endothelin-A receptors. J Cardiovasc Pharmacol. 2004 Nov;44 Suppl 1:S219-23. doi: 10.1097/01.fjc.0000166252.66486.06. [PubMed:15838284 ]
Dupraz P, Oertle S, Meric C, Damay P, Spahr PF: Point mutations in the proximal Cys-His box of Rous sarcoma virus nucleocapsid protein. J Virol. 1990 Oct;64(10):4978-87. doi: 10.1128/JVI.64.10.4978-4987.1990. [PubMed:2168981 ]

Showing NP-Card for Serylserine (NP0136634)

MOL for NP0136634 (Serylserine)

3D MOL for NP0136634 (Serylserine)

3D SDF for NP0136634 (Serylserine)

3D-SDF for NP0136634 (Serylserine)

PDB for NP0136634 (Serylserine)

3D PDB for NP0136634 (Serylserine)

SMILES for NP0136634 (Serylserine)

INCHI for NP0136634 (Serylserine)

Structure for NP0136634 (Serylserine)

3D Structure for NP0136634 (Serylserine)