NP-MRD: Showing NP-Card for ascidiathiazone B (NP0033003)

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Record Information

Version

2.0

Created at

2021-06-19 23:40:00 UTC

Updated at

2021-06-30 00:02:32 UTC

NP-MRD ID

NP0033003

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ascidiathiazone B

Provided By

JEOL Database JEOL Logo

Description

Ascidiathiazone B 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. ascidiathiazone B is found in Aplidium sp. ascidiathiazone B was first documented in 2007 (Pearce, A. N., et al.). Based on a literature review very few articles have been published on ascidiathiazone B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101403D          

 27 29  0  0  0  0            999 V2000
    0.6427   -6.7847    1.1524 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256   -5.6359    0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -5.1827   -0.3217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1644   -4.5364    1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524   -4.7768    2.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686   -3.7086    3.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710   -2.4459    2.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -2.2982    1.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494   -3.3201    0.7722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6243   -0.9828    0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964   -0.8686   -0.3257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807    0.1426    1.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707    0.0242    2.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8969    1.0490    2.8680 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9206    2.3352    2.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2421    2.7912    1.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2403    1.6910    0.4698 S   0  0  2  0  0  6  0  0  0  0  0  0
   -1.8275    1.6102   -0.8562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226    2.1639    0.6391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3104   -1.3018    2.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0307   -1.4255    3.9587 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -4.2193   -0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079   -5.7693    2.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964   -3.8643    3.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4555    0.7963    3.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5559    2.9983    3.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    3.8176    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 17  1  0  0  0  0
 12 13  2  0  0  0  0
 16 15  2  0  0  0  0
  8  9  2  0  0  0  0
  5  4  2  0  0  0  0
  4  9  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  2  0  0  0  0
 15 14  1  0  0  0  0
 20 21  2  0  0  0  0
 12 10  1  0  0  0  0
 17 18  2  0  0  0  0
 13 20  1  0  0  0  0
 17 19  2  0  0  0  0
 20  7  1  0  0  0  0
  4  2  1  0  0  0  0
  8 10  1  0  0  0  0
  2  3  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  2  0  0  0  0
 14 13  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  2  0  0  0  0
 16 27  1  0  0  0  0
 15 26  1  0  0  0  0
 14 25  1  0  0  0  0
  5 23  1  0  0  0  0
  3 22  1  0  0  0  0
  6 24  1  0  0  0  0
M  END


  Mrv1652306202101403D          

 27 29  0  0  0  0            999 V2000
    0.6427   -6.7847    1.1524 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256   -5.6359    0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -5.1827   -0.3217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1644   -4.5364    1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524   -4.7768    2.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686   -3.7086    3.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710   -2.4459    2.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -2.2982    1.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494   -3.3201    0.7722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6243   -0.9828    0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964   -0.8686   -0.3257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807    0.1426    1.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707    0.0242    2.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8969    1.0490    2.8680 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9206    2.3352    2.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2421    2.7912    1.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2403    1.6910    0.4698 S   0  0  2  0  0  6  0  0  0  0  0  0
   -1.8275    1.6102   -0.8562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226    2.1639    0.6391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3104   -1.3018    2.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0307   -1.4255    3.9587 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -4.2193   -0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079   -5.7693    2.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964   -3.8643    3.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4555    0.7963    3.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5559    2.9983    3.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    3.8176    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 17  1  0  0  0  0
 12 13  2  0  0  0  0
 16 15  2  0  0  0  0
  8  9  2  0  0  0  0
  5  4  2  0  0  0  0
  4  9  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  2  0  0  0  0
 15 14  1  0  0  0  0
 20 21  2  0  0  0  0
 12 10  1  0  0  0  0
 17 18  2  0  0  0  0
 13 20  1  0  0  0  0
 17 19  2  0  0  0  0
 20  7  1  0  0  0  0
  4  2  1  0  0  0  0
  8 10  1  0  0  0  0
  2  3  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  2  0  0  0  0
 14 13  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  2  0  0  0  0
 16 27  1  0  0  0  0
 15 26  1  0  0  0  0
 14 25  1  0  0  0  0
  5 23  1  0  0  0  0
  3 22  1  0  0  0  0
  6 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033003

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C2C(=O)C3=C(C(=O)C2=N1)[S](=O)(=O)C([H])=C([H])N3[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H6N2O6S/c15-9-5-1-2-6(12(17)18)14-7(5)10(16)11-8(9)13-3-4-21(11,19)20/h1-4,13H,(H,17,18)

> <INCHI_KEY>
GDXFAPJBCPQOTL-UHFFFAOYSA-N

> <FORMULA>
C12H6N2O6S

> <MOLECULAR_WEIGHT>
306.25

> <EXACT_MASS>
305.994657095

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
26.35995998960137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,4,5,10-tetraoxo-1H,4H,5H,10H-4lambda6-[1,4]thiazino[3,2-g]quinoline-7-carboxylic acid

> <ALOGPS_LOGP>
0.20

> <JCHEM_LOGP>
-1.2618995773333328

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.809093802958458

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6376897236856816

> <JCHEM_PKA_STRONGEST_BASIC>
0.2953221656007493

> <JCHEM_POLAR_SURFACE_AREA>
130.49999999999997

> <JCHEM_REFRACTIVITY>
70.18109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4,5,10-tetraoxo-1H-4lambda6-[1,4]thiazino[3,2-g]quinoline-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       0.643  -6.785   1.152  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.626  -5.636   0.749  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.318  -5.183  -0.322  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.164  -4.536   1.373  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.952  -4.777   2.489  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.669  -3.709   3.028  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.571  -2.446   2.433  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.761  -2.298   1.322  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.049  -3.320   0.772  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.624  -0.983   0.657  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.096  -0.869  -0.326  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.381   0.143   1.226  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.171   0.024   2.300  0.00  0.00           C+0
HETATM   14  N   UNK     0      -2.897   1.049   2.868  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.921   2.335   2.423  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.242   2.791   1.369  0.00  0.00           C+0
HETATM   17  S   UNK     0      -1.240   1.691   0.470  0.00  0.00           S+0
HETATM   18  O   UNK     0      -1.827   1.610  -0.856  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.123   2.164   0.639  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.310  -1.302   2.974  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.031  -1.426   3.959  0.00  0.00           O+0
HETATM   22  H   UNK     0       1.149  -4.219  -0.457  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.008  -5.769   2.929  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.296  -3.864   3.904  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.455   0.796   3.690  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.556   2.998   3.006  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.278   3.818   1.036  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    3    1                                                  
CONECT    3    2   22                                                       
CONECT    4    5    9    2                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7   24                                                  
CONECT    7   20    8    6                                                  
CONECT    8    9   10    7                                                  
CONECT    9    8    4                                                       
CONECT   10   11   12    8                                                  
CONECT   11   10                                                            
CONECT   12   17   13   10                                                  
CONECT   13   12   20   14                                                  
CONECT   14   15   13   25                                                  
CONECT   15   16   14   26                                                  
CONECT   16   15   17   27                                                  
CONECT   17   12   16   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   21   13    7                                                  
CONECT   21   20                                                            
CONECT   22    3                                                            
CONECT   23    5                                                            
CONECT   24    6                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
CONECT   27   16                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₆N₂O₆S

Average Mass

306.2500 Da

Monoisotopic Mass

305.99466 Da

IUPAC Name

4,4,5,10-tetraoxo-1H,4H,5H,10H-4lambda6-[1,4]thiazino[3,2-g]quinoline-7-carboxylic acid

Traditional Name

4,4,5,10-tetraoxo-1H-4lambda6-[1,4]thiazino[3,2-g]quinoline-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C([H])=C2C(=O)C3=C(C(=O)C2=N1)[S](=O)(=O)C([H])=C([H])N3[H]

InChI Identifier

InChI=1S/C12H6N2O6S/c15-9-5-1-2-6(12(17)18)14-7(5)10(16)11-8(9)13-3-4-21(11,19)20/h1-4,13H,(H,17,18)

InChI Key

GDXFAPJBCPQOTL-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aplidium sp.	JEOL database	Pearce, A. N., et al, J. Nat. Prod. 70, 936 (2007)

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-2-carboxylic acid
Quinoline quinone
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Aryl ketone
Para-thiazine
Pyridine
Heteroaromatic compound
Vinylogous amide
Sulfone
Amino acid or derivatives
Ketone
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Enamine
Monocarboxylic acid or derivatives
Azacycle
Secondary amine
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfone (CHEBI:65449 )
monocarboxylic acid (CHEBI:65449 )
organic heterotricyclic compound (CHEBI:65449 )
alkaloid (CHEBI:65449 )
quinone (CHEBI:65449 )

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	0.2	ALOGPS
logP	-1.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	0.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	130.5 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.18 m³·mol⁻¹	ChemAxon
Polarizability	26.36 Å³	ChemAxon
Number of Rings	3	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038518

Chemspider ID

20568304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

65449

Good Scents ID

Not Available

References

General References

Pearce, A. N., et al. (2007). Pearce, A. N., et al, J. Nat. Prod. 70, 936 (2007). J. Nat. Prod..

Showing NP-Card for ascidiathiazone B (NP0033003)

MOL for NP0033003 (ascidiathiazone B)

3D MOL for NP0033003 (ascidiathiazone B)

3D SDF for NP0033003 (ascidiathiazone B)

3D-SDF for NP0033003 (ascidiathiazone B)

PDB for NP0033003 (ascidiathiazone B)

3D PDB for NP0033003 (ascidiathiazone B)

SMILES for NP0033003 (ascidiathiazone B)

INCHI for NP0033003 (ascidiathiazone B)

Structure for NP0033003 (ascidiathiazone B)

3D Structure for NP0033003 (ascidiathiazone B)