NP-MRD: Showing NP-Card for Serylproline (NP0136633)

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Record Information

Version

2.0

Created at

2022-05-12 15:19:34 UTC

Updated at

2022-05-12 15:19:34 UTC

NP-MRD ID

NP0136633

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Serylproline

Description

Serylproline, also known as SP or L-ser-L-pro, 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. Serylproline is a very strong basic compound (based on its pKa). Serylproline was first documented in 1994 (PMID: 8000007). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 18838808) (PMID: 22038648).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062014122D          

 14 14  0  0  0  0            999 V2000
 2500.0338 2500.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3189 2500.8449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.5978 2500.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8829 2500.8573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3189 2501.6704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7487 2500.8449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4021 2499.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1170 2499.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4021 2500.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0162 2499.5959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3488 2499.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6037 2498.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.4287 2498.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.6836 2499.1109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  6  0  0  0
  3  4  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 14  7  1  6  0  0  0
  1 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136633

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CO)C(=O)N1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H14N2O4/c9-5(4-11)7(12)10-3-1-2-6(10)8(13)14/h5-6,11H,1-4,9H2,(H,13,14)/t5-,6-/m0/s1

> <INCHI_KEY>
WBAXJMCUFIXCNI-WDSKDSINSA-N

> <FORMULA>
C8H14N2O4

> <MOLECULAR_WEIGHT>
202.21

> <EXACT_MASS>
202.095356939

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
19.626530111066835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2-amino-3-hydroxypropanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.94

> <JCHEM_LOGP>
-4.155309731937008

> <ALOGPS_LOGS>
-0.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.917705206416738

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5254771335151474

> <JCHEM_PKA_STRONGEST_BASIC>
7.842197461334492

> <JCHEM_POLAR_SURFACE_AREA>
103.86

> <JCHEM_REFRACTIVITY>
47.02750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S)-2-amino-3-hydroxypropanoyl]pyrrolidine-2-carboxylic 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    4666.7304667.475   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4665.3954668.244   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4664.0494667.498   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4662.7154668.267   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0    4665.3954669.785   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0    4668.0644668.244   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    4669.2844665.762   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4670.6184664.990   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4669.2844667.303   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4666.6974665.912   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    4665.4514665.007   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4665.9274663.542   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4667.4674663.542   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4667.9434665.007   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2                                                            
CONECT    6    1                                                            
CONECT    7    8    9   14                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11   14    1                                                  
CONECT   11   12   10                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10    7                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
L-Ser-L-pro	ChEBI
SP	ChEBI
Ser-pro	HMDB
Seryl-proline	HMDB
1-L-Seryl-L-proline	HMDB
L-Seryl-L-proline	HMDB
S-p Dipeptide	HMDB
SP Dipeptide	HMDB
Serine proline dipeptide	HMDB
Serine-proline dipeptide	HMDB
Serinyl-proline	HMDB
Serinylproline	HMDB
Serylproline	ChEBI

Chemical Formula

C₈H₁₄N₂O₄

Average Mass

202.2100 Da

Monoisotopic Mass

202.09536 Da

IUPAC Name

(2S)-1-[(2S)-2-amino-3-hydroxypropanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-2-amino-3-hydroxypropanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CO)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C8H14N2O4/c9-5(4-11)7(12)10-3-1-2-6(10)8(13)14/h5-6,11H,1-4,9H2,(H,13,14)/t5-,6-/m0/s1

InChI Key

WBAXJMCUFIXCNI-WDSKDSINSA-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
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Alcohol
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Primary alcohol
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74820 )

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	-2.9	ALOGPS
logP	-4.2	ChemAxon
logS	-0.05	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	7.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.03 m³·mol⁻¹	ChemAxon
Polarizability	19.63 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

HMDB0029047

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

4369021

PDB ID

Not Available

ChEBI ID

74820

Good Scents ID

Not Available

References

General References

Oguri S, Amano K, Nakashita H, Nagata Y, Momonoki YS: Molecular structure and properties of lectin from tomato fruit. Biosci Biotechnol Biochem. 2008 Oct;72(10):2640-50. doi: 10.1271/bbb.80310. Epub 2008 Oct 7. [PubMed:18838808 ]
Woessner JP, Molendijk AJ, van Egmond P, Klis FM, Goodenough UW, Haring MA: Domain conservation in several volvocalean cell wall proteins. Plant Mol Biol. 1994 Nov;26(3):947-60. doi: 10.1007/BF00028861. [PubMed:8000007 ]
Gal M, Edmonds KA, Milbradt AG, Takeuchi K, Wagner G: Speeding up direct (15)N detection: hCaN 2D NMR experiment. J Biomol NMR. 2011 Dec;51(4):497-504. doi: 10.1007/s10858-011-9580-7. Epub 2011 Oct 30. [PubMed:22038648 ]

Showing NP-Card for Serylproline (NP0136633)

MOL for NP0136633 (Serylproline)

3D MOL for NP0136633 (Serylproline)

3D SDF for NP0136633 (Serylproline)

3D-SDF for NP0136633 (Serylproline)

PDB for NP0136633 (Serylproline)

3D PDB for NP0136633 (Serylproline)

SMILES for NP0136633 (Serylproline)

INCHI for NP0136633 (Serylproline)

Structure for NP0136633 (Serylproline)

3D Structure for NP0136633 (Serylproline)