NP-MRD: Showing NP-Card for (4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid (NP0183780)

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Record Information

Version

2.0

Created at

2022-09-03 22:44:43 UTC

Updated at

2022-09-03 22:44:43 UTC

NP-MRD ID

NP0183780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid

Description

(+)-(S)-Dihydroaeruginoic Acid belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. (4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid is found in Zymoseptoria tritici. Based on a literature review very few articles have been published on (+)-(S)-Dihydroaeruginoic Acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042200442D          

 15 16  0  0  1  0            999 V2000
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390   -2.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 15  2  0  0  0  0
  4 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@H]1CSC(=N1)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO3S/c12-8-4-2-1-3-6(8)9-11-7(5-15-9)10(13)14/h1-4,7,12H,5H2,(H,13,14)/t7-/m1/s1

> <INCHI_KEY>
CECDPVOEINSAQG-SSDOTTSWSA-N

> <FORMULA>
C10H9NO3S

> <MOLECULAR_WEIGHT>
223.25

> <EXACT_MASS>
223.030314328

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
21.624499856668194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid

> <JCHEM_LOGP>
2.3728537726666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.62262626002677

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.363657706281193

> <JCHEM_PKA_STRONGEST_BASIC>
0.8714866536292362

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
57.377800000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       2.104  -4.680   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.499  -4.358   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       0.088  -3.215   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    7    4                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
(+)-(S)-Dihydroaeruginoate	Generator

Chemical Formula

C₁₀H₉NO₃S

Average Mass

223.2500 Da

Monoisotopic Mass

223.03031 Da

IUPAC Name

(4S)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid

Traditional Name

(4S)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@H]1CSC(=N1)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C10H9NO3S/c12-8-4-2-1-3-6(8)9-11-7(5-15-9)10(13)14/h1-4,7,12H,5H2,(H,13,14)/t7-/m1/s1

InChI Key

CECDPVOEINSAQG-SSDOTTSWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Zymoseptoria tritici	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Imidothiolactone
Meta-thiazoline
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.37	ChemAxon
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	0.87	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.38 m³·mol⁻¹	ChemAxon
Polarizability	21.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23110944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135482070

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid (NP0183780)

MOL for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)

3D MOL for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)

3D SDF for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)

3D-SDF for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)

PDB for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)

3D PDB for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)

SMILES for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)

INCHI for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)

Structure for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)

3D Structure for NP0183780 ((4s)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid)