NP-MRD: Showing NP-Card for dehydrogliotoxin (NP0168738)

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Record Information

Version

2.0

Created at

2022-09-03 04:35:41 UTC

Updated at

2022-09-03 04:35:41 UTC

NP-MRD ID

NP0168738

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dehydrogliotoxin

Description

Dehydrogliotoxin belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. dehydrogliotoxin is found in Trichoderma virens. dehydrogliotoxin was first documented in 2003 (PMID: 12948196). Based on a literature review very few articles have been published on Dehydrogliotoxin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.6127   -1.1835   -0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2577   -0.7016   -0.2926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1463   -1.5557   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523   -2.7979   -0.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1159   -0.9152   -0.9825 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2921   -1.7703   -1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522   -0.8698   -0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7334   -0.9976   -0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793   -0.0003    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059    1.1273    0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5425    1.2636    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8959    2.3721    1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7765    0.2552    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    0.1832   -0.0643 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7432    0.9218    0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367    1.6918    1.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0692    0.7478   -0.1931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1799    1.4521    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3259    0.9756    1.7494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205    1.2883   -1.9344 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2874   -0.1005   -2.5815 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7153   -2.2476   -0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9498   -1.1809    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3124   -0.6083   -0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133   -2.0936   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2069   -2.6199   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2066   -1.8856   -0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5597   -0.0710    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158    1.9074    1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693    3.1223    1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959    1.3076   -0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9649    2.5391    0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532    0.4441    2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  6
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  1
 18 19  1  0
 17 20  1  0
 20 21  1  0
 17  2  1  0
 14  5  1  0
 21  5  1  0
 13  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv1652309032206352D          

 21 24  0  0  1  0            999 V2000
   -1.0582    0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    0.1969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605    0.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454    1.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1622    0.7496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8649    1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6044    0.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4086    1.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699    0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268   -0.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226   -0.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6795   -1.3441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613    0.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158   -0.1004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920   -0.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -1.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057   -0.6333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4376   -1.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1716   -2.0351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -0.2822    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4603    0.3954    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0168738

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@]23CC4=CC=CC(O)=C4N2C(=O)[C@@]1(CO)SS3

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,16-17H,5-6H2,1H3/t12-,13-/m1/s1

> <INCHI_KEY>
BNNLUYCZQNYABS-CHWSQXEVSA-N

> <FORMULA>
C13H12N2O4S2

> <MOLECULAR_WEIGHT>
324.37

> <EXACT_MASS>
324.023849222

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
30.46275240025178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0^{1,9}.0^{3,8}]pentadeca-3,5,7-triene-10,14-dione

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
1.2936511313333334

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.091342045969451

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.523349510772528

> <JCHEM_PKA_STRONGEST_BASIC>
-3.196249020210063

> <JCHEM_POLAR_SURFACE_AREA>
81.08000000000001

> <JCHEM_REFRACTIVITY>
79.90440000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0^{1,9}.0^{3,8}]pentadeca-3,5,7-triene-10,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.975   0.506   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.442   0.368   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.486   1.810   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.085   3.241   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.169   1.399   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.481   2.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.861   1.563   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.363   1.906   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.410   0.777   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.957  -0.694   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.455  -1.037   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.002  -2.509   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.408   0.091   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.829  -0.187   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.852  -1.619   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.390  -3.062   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.197  -1.182   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.817  -2.341   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.320  -3.799   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       1.491  -0.527   0.000  0.00  0.00           S+0
HETATM   21  S   UNK     0       0.859   0.738   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14   21                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13    5   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18   20                                             
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20    5                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₂N₂O₄S₂

Average Mass

324.3700 Da

Monoisotopic Mass

324.02385 Da

IUPAC Name

(1R,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0^{1,9}.0^{3,8}]pentadeca-3,5,7-triene-10,14-dione

Traditional Name

(1R,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0^{1,9}.0^{3,8}]pentadeca-3,5,7-triene-10,14-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@]23CC4=CC=CC(O)=C4N2C(=O)[C@@]1(CO)SS3

InChI Identifier

InChI=1S/C13H12N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,16-17H,5-6H2,1H3/t12-,13-/m1/s1

InChI Key

BNNLUYCZQNYABS-CHWSQXEVSA-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
Trichoderma virens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
Alpha-amino acid or derivatives
Epipolythiodioxopiperazine
Thiodioxopiperazine
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
N-methylpiperazine
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dithiazinane
Benzenoid
1,4-diazinane
Piperazine
Tertiary carboxylic acid amide
Carboxamide group
Organic disulfide
Lactam
Azacycle
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Alcohol
Primary alcohol
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.63	ALOGPS
logP	1.29	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.52	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.08 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.9 m³·mol⁻¹	ChemAxon
Polarizability	30.46 Å³	ChemAxon
Number of Rings	4	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

28288612

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13989137

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Moody CJ, Slawin AM, Willows D: Dirhodium(II) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomunchnones), an approach to analogues of dehydrogliotoxin. Org Biomol Chem. 2003 Aug 7;1(15):2716-22. doi: 10.1039/b305698h. [PubMed:12948196 ]
LOTUS database [Link]

Showing NP-Card for dehydrogliotoxin (NP0168738)

MOL for NP0168738 (dehydrogliotoxin)

3D MOL for NP0168738 (dehydrogliotoxin)

3D SDF for NP0168738 (dehydrogliotoxin)

3D-SDF for NP0168738 (dehydrogliotoxin)

PDB for NP0168738 (dehydrogliotoxin)

3D PDB for NP0168738 (dehydrogliotoxin)

SMILES for NP0168738 (dehydrogliotoxin)

INCHI for NP0168738 (dehydrogliotoxin)

Structure for NP0168738 (dehydrogliotoxin)

3D Structure for NP0168738 (dehydrogliotoxin)