NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid (NP0240508)

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Record Information

Version

2.0

Created at

2022-09-07 00:21:09 UTC

Updated at

2022-09-07 00:21:09 UTC

NP-MRD ID

NP0240508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

Description

N-[(2S)-3-Phenyl-2-sulfanylpropanoyl]-L-phenylalanyl-L-tyrosine 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. (2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid is found in Coix lacryma-jobi. N-[(2S)-3-Phenyl-2-sulfanylpropanoyl]-L-phenylalanyl-L-tyrosine is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041412022D          

 38 40  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv0541 05041412022D          

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 24 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0240508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](S)(CC1=CC=CC=C1)C(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=N[C@@]([H])(CC1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28N2O5S/c30-21-13-11-20(12-14-21)16-23(27(33)34)29-25(31)22(15-18-7-3-1-4-8-18)28-26(32)24(35)17-19-9-5-2-6-10-19/h1-14,22-24,30,35H,15-17H2,(H,28,32)(H,29,31)(H,33,34)/t22-,23-,24-/m0/s1

> <INCHI_KEY>
GIVBBFGMRNXKPE-HJOGWXRNSA-N

> <FORMULA>
C27H28N2O5S

> <MOLECULAR_WEIGHT>
492.587

> <EXACT_MASS>
492.171892706

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
50.34084561062899

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
5.80356799

> <ALOGPS_LOGS>
-5.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.503550761692094

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.785129356160117

> <JCHEM_PKA_STRONGEST_BASIC>
1.5969719519846957

> <JCHEM_POLAR_SURFACE_AREA>
122.71000000000002

> <JCHEM_REFRACTIVITY>
136.44289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.55e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   36  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   18                                                       
CONECT    8    4   18                                                       
CONECT    9    5   19                                                       
CONECT   10    6   19                                                       
CONECT   11   13   20                                                       
CONECT   12   14   20                                                       
CONECT   13   11   21                                                       
CONECT   14   12   21                                                       
CONECT   15   18   22                                                       
CONECT   16   20   23                                                       
CONECT   17   19   24                                                       
CONECT   18    7    8   15                                                  
CONECT   19    9   10   17                                                  
CONECT   20   11   12   16                                                  
CONECT   21   13   14   30                                                  
CONECT   22   15   25   28   36                                             
CONECT   23   16   27   29   37                                             
CONECT   24   17   26   35   38                                             
CONECT   25   22   29   31                                                  
CONECT   26   24   28   32                                                  
CONECT   27   23   33   34                                                  
CONECT   28   22   26                                                       
CONECT   29   23   25                                                       
CONECT   30   21                                                            
CONECT   31   25                                                            
CONECT   32   26                                                            
CONECT   33   27                                                            
CONECT   34   27                                                            
CONECT   35   24                                                            
CONECT   36   22                                                            
CONECT   37   23                                                            
CONECT   38   24                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
N-[(2S)-3-Phenyl-2-sulphanylpropanoyl]-L-phenylalanyl-L-tyrosine	Generator
(2S)-2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoate	Generator
(2S)-2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-3-phenyl-2-sulphanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoate	Generator
(2S)-2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-3-phenyl-2-sulphanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid	Generator
(2-Sulphanyl-3-phenylpropanoyl)-phe-tyr	Generator

Chemical Formula

C₂₇H₂₈N₂O₅S

Average Mass

492.5870 Da

Monoisotopic Mass

492.17189 Da

IUPAC Name

(2S)-2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

Traditional Name

(2S)-2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](S)(CC1=CC=CC=C1)C(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=N[C@@]([H])(CC1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C27H28N2O5S/c30-21-13-11-20(12-14-21)16-23(27(33)34)29-25(31)22(15-18-7-3-1-4-8-18)28-26(32)24(35)17-19-9-5-2-6-10-19/h1-14,22-24,30,35H,15-17H2,(H,28,32)(H,29,31)(H,33,34)/t22-,23-,24-/m0/s1

InChI Key

GIVBBFGMRNXKPE-HJOGWXRNSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Coix lacryma-jobi	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
Tyrosine or derivatives
Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
3-phenylpropanoic-acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty amide
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Alkylthiol
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.02	ALOGPS
logP	5.8	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	122.71 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	136.44 m³·mol⁻¹	ChemAxon
Polarizability	50.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB03949

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

5289470

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid (NP0240508)

MOL for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D MOL for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D SDF for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D-SDF for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

PDB for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D PDB for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

SMILES for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

INCHI for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

Structure for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D Structure for NP0240508 ((2s)-2-{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-3-phenyl-2-sulfanylpropylidene]amino}-3-phenylpropylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)