NP-MRD: Showing NP-Card for 1,4-Benzothiazine-o-quinonimine (NP0339016)

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Record Information

Version

2.0

Created at

2024-09-11 19:15:44 UTC

Updated at

2024-09-11 19:15:45 UTC

NP-MRD ID

NP0339016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4-Benzothiazine-o-quinonimine

Description

1,4-Benzothiazine-O-quinonimine, also known as QI, belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom). 1,4-Benzothiazine-O-quinonimine is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208052D          

 20 21  0  0  1  0            999 V2000
   11.9958  -14.6802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9958  -13.8552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.7103  -13.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4248  -13.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1393  -13.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8537  -13.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5682  -13.4427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8537  -14.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5682  -15.0927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5682  -15.9177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8537  -16.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1393  -15.9177    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.1393  -15.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4248  -14.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2827  -16.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2827  -17.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9971  -15.9177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2813  -13.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2813  -12.6177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5669  -13.8552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@H](CC1=CC(=O)C2=N[C@H](CSC2=C1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O5S/c13-6(11(16)17)1-5-2-8(15)10-9(3-5)20-4-7(14-10)12(18)19/h2-3,6-7H,1,4,13H2,(H,16,17)(H,18,19)/t6-,7-/m1/s1

> <INCHI_KEY>
NANJICKTJNNTGA-RNFRBKRXSA-N

> <FORMULA>
C12H12N2O5S

> <MOLECULAR_WEIGHT>
296.299

> <EXACT_MASS>
296.046692194

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.279142890684767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-7-[(2R)-2-amino-2-carboxyethyl]-5-oxo-3,5-dihydro-2H-1,4-benzothiazine-3-carboxylic acid

> <ALOGPS_LOGP>
-2.12

> <JCHEM_LOGP>
-2.3398871820118154

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.5953277672011796

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.858710756594534

> <JCHEM_PKA_STRONGEST_BASIC>
9.2637323311402

> <JCHEM_POLAR_SURFACE_AREA>
130.05

> <JCHEM_REFRACTIVITY>
73.2414

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-7-[(2R)-2-amino-2-carboxyethyl]-5-oxo-2,3-dihydro-1,4-benzothiazine-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  N   UNK     0      22.392 -27.403   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      22.392 -25.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.726 -25.093   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.060 -25.863   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.393 -25.093   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.727 -25.863   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      29.061 -25.093   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      27.727 -27.403   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      29.061 -28.173   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      29.061 -29.713   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.727 -30.483   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      26.393 -29.713   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      26.393 -28.173   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.060 -27.403   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.394 -30.483   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      30.394 -32.023   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      31.728 -29.713   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      21.058 -25.093   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      21.058 -23.553   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      19.725 -25.863   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    8   12   14                                                  
CONECT   14    4   13                                                       
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    2   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
QI	HMDB
(3S)-7-[(2R)-2-Amino-2-carboxyethyl]-5-oxo-3,5-dihydro-2H-1,4-benzothiazine-3-carboxylate	Generator

Chemical Formula

C₁₂H₁₂N₂O₅S

Average Mass

296.2990 Da

Monoisotopic Mass

296.04669 Da

IUPAC Name

(3S)-7-[(2R)-2-amino-2-carboxyethyl]-5-oxo-3,5-dihydro-2H-1,4-benzothiazine-3-carboxylic acid

Traditional Name

(3S)-7-[(2R)-2-amino-2-carboxyethyl]-5-oxo-2,3-dihydro-1,4-benzothiazine-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

N[C@H](CC1=CC(=O)C2=N[C@H](CSC2=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C12H12N2O5S/c13-6(11(16)17)1-5-2-8(15)10-9(3-5)20-4-7(14-10)12(18)19/h2-3,6-7H,1,4,13H2,(H,16,17)(H,18,19)/t6-,7-/m1/s1

InChI Key

NANJICKTJNNTGA-RNFRBKRXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Not Available

Direct Parent

Benzothiazines

Alternative Parents

Substituents

Alpha-amino acid
Alpha-amino acid or derivatives
Benzothiazine
D-alpha-amino acid
Dicarboxylic acid or derivatives
Amino acid or derivatives
Amino acid
Ketimine
Ketone
Thioenolether
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Organic oxygen compound
Imine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-2.1	ALOGPS
logP	-2.3	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	9.26	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.24 m³·mol⁻¹	ChemAxon
Polarizability	28.28 Å³	ChemAxon
Number of Rings	2	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

HMDB0012491

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029098

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

53481441

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1,4-Benzothiazine-o-quinonimine (NP0339016)

MOL for NP0339016 (1,4-Benzothiazine-o-quinonimine)

3D MOL for NP0339016 (1,4-Benzothiazine-o-quinonimine)

3D SDF for NP0339016 (1,4-Benzothiazine-o-quinonimine)

3D-SDF for NP0339016 (1,4-Benzothiazine-o-quinonimine)

PDB for NP0339016 (1,4-Benzothiazine-o-quinonimine)

3D PDB for NP0339016 (1,4-Benzothiazine-o-quinonimine)

SMILES for NP0339016 (1,4-Benzothiazine-o-quinonimine)

INCHI for NP0339016 (1,4-Benzothiazine-o-quinonimine)

Structure for NP0339016 (1,4-Benzothiazine-o-quinonimine)

3D Structure for NP0339016 (1,4-Benzothiazine-o-quinonimine)