NP-MRD: Showing NP-Card for 7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one (NP0007847)

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Record Information

Version

2.0

Created at

2020-12-09 05:25:16 UTC

Updated at

2021-07-15 16:58:43 UTC

NP-MRD ID

NP0007847

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one

Provided By

NPAtlas

Description

7-Hydroxy-5-hydroxymethyl-2h-benzo[1,4]thiazin-3-one is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one is found in Ampelomyces sp. 7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one was first documented in 2008 (PMID: 18603789). Based on a literature review very few articles have been published on 7-hydroxy-5-hydroxymethyl-2h-benzo[1,4]thiazin-3-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106043D          

 23 24  0  0  0  0            999 V2000
   -2.5973   -2.9414    0.8696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109   -1.9674    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0818   -1.2225   -0.6386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8267    0.5593   -0.4589 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689    0.8098   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020    2.0513   -0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420    2.3211   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    3.5947   -0.5411 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6298    1.2501    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0942    0.0164    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9578   -1.1445    0.6278 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2651   -0.6733    0.7082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2798   -0.2545    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7562   -1.5749    0.3419 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1299   -1.4226   -0.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617   -1.5442   -1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454    2.8870   -0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4367    4.2370    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    1.4105    0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313   -1.9490   -0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909   -1.5018    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103   -0.6267   -0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0662   -2.3143    0.6096 H   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14  2  1  0  0  0  0
 13  5  1  0  0  0  0
  3 15  1  0  0  0  0
  3 16  1  0  0  0  0
  6 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
 11 20  1  0  0  0  0
 11 21  1  0  0  0  0
 12 22  1  0  0  0  0
 14 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007847

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C2N([H])C(=O)C([H])([H])SC2=C1[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO3S/c11-3-5-1-6(12)2-7-9(5)10-8(13)4-14-7/h1-2,11-12H,3-4H2,(H,10,13)

> <INCHI_KEY>
CZXYFHNORNVRJZ-UHFFFAOYSA-N

> <FORMULA>
C9H9NO3S

> <MOLECULAR_WEIGHT>
211.24

> <EXACT_MASS>
211.030314328

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
20.539301891444804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-5-(hydroxymethyl)-3,4-dihydro-2H-1,4-benzothiazin-3-one

> <ALOGPS_LOGP>
0.33

> <JCHEM_LOGP>
0.1582533623333332

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.343326438407942

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.40732841789352

> <JCHEM_PKA_STRONGEST_BASIC>
-2.948720418574376

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
56.065200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-5-(hydroxymethyl)-2,4-dihydro-1,4-benzothiazin-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.597  -2.941   0.870  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.111  -1.967   0.244  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.082  -1.222  -0.639  0.00  0.00           C+0
HETATM    4  S   UNK     0      -2.827   0.559  -0.459  0.00  0.00           S+0
HETATM    5  C   UNK     0      -1.069   0.810  -0.256  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.502   2.051  -0.458  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.842   2.321  -0.326  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.371   3.595  -0.541  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.630   1.250   0.033  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.094   0.016   0.238  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.958  -1.145   0.628  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.265  -0.673   0.708  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.280  -0.255   0.102  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.756  -1.575   0.342  0.00  0.00           N+0
HETATM   15  H   UNK     0      -4.130  -1.423  -0.341  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.962  -1.544  -1.679  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.145   2.887  -0.742  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.437   4.237   0.226  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.697   1.411   0.150  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.931  -1.949  -0.126  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.691  -1.502   1.646  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.610  -0.627  -0.229  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.066  -2.314   0.610  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   15   16                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   18                                                       
CONECT    9    7   10   19                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12   20   21                                             
CONECT   12   11   22                                                       
CONECT   13   10   14    5                                                  
CONECT   14   13    2   23                                                  
CONECT   15    3                                                            
CONECT   16    3                                                            
CONECT   17    6                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   11                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
CONECT   23   14                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₉H₉NO₃S

Average Mass

211.2400 Da

Monoisotopic Mass

211.03031 Da

IUPAC Name

7-hydroxy-5-(hydroxymethyl)-3,4-dihydro-2H-1,4-benzothiazin-3-one

Traditional Name

7-hydroxy-5-(hydroxymethyl)-2,4-dihydro-1,4-benzothiazin-3-one

CAS Registry Number

Not Available

SMILES

OCC1=CC(O)=CC2=C1NC(=O)CS2

InChI Identifier

InChI=1S/C9H9NO3S/c11-3-5-1-6(12)2-7-9(5)10-8(13)4-14-7/h1-2,11-12H,3-4H2,(H,10,13)

InChI Key

CZXYFHNORNVRJZ-UHFFFAOYSA-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
Ampelomyces sp.	NPAtlas	18603789

Chemical Taxonomy

Description

This compound 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

Benzothiazine
Aryl thioether
1-hydroxy-2-unsubstituted benzenoid
Alkylarylthioether
Para-thiazine
Benzenoid
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Thioether
Azacycle
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Alcohol
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:66030 )
benzyl alcohols (CHEBI:66030 )
lactam (CHEBI:66030 )
benzothiazine (CHEBI:66030 )

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	0.33	ALOGPS
logP	0.16	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.07 m³·mol⁻¹	ChemAxon
Polarizability	20.54 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

NPAtlas ID

NPA016472

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28533009

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70678753

PDB ID

Not Available

ChEBI ID

66030

Good Scents ID

Not Available

References

General References

Zhang H, Xie H, Qiu SX, Xue J, Wei X: Heteroatom-containing antibacterial phenolic metabolites from a terrestrial Ampelomyces fungus. Biosci Biotechnol Biochem. 2008 Jul;72(7):1746-9. doi: 10.1271/bbb.80043. Epub 2008 Jul 7. [PubMed:18603789 ]

Showing NP-Card for 7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one (NP0007847)

MOL for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)

3D MOL for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)

3D SDF for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)

3D-SDF for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)

PDB for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)

3D PDB for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)

SMILES for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)

INCHI for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)

Structure for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)

3D Structure for NP0007847 (7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one)