NP-MRD: Showing NP-Card for (1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione (NP0311364)

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Record Information

Version

2.0

Created at

2022-09-11 07:18:28 UTC

Updated at

2022-09-11 07:18:28 UTC

NP-MRD ID

NP0311364

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione

Description

Gliotoxin G 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. (1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione is found in Aspergillus fumigatus. (1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione was first documented in 2012 (PMID: 22978674). Based on a literature review a small amount of articles have been published on Gliotoxin G (PMID: 25766916) (PMID: 23537878).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -2.7971   -0.3194   -2.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785    0.3229   -1.2659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    1.1084   -1.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7947    1.6982   -2.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3293    1.2698   -0.7238 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6613    1.2069   -1.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640    0.5281   -0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.7364    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0618   -0.1743    1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2925   -1.1477    1.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9529   -1.4534    1.1153 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0267   -2.7982    0.6611 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -0.5958   -0.0055 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2887    0.0634    0.1222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9430   -0.1363    0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9730   -0.6071    1.9624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    0.2080    0.1512 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2311   -0.9366    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4088   -0.7035   -0.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9990    1.6902    0.8502 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823    2.2803    2.6664 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0226    2.4150    2.3159 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3100    2.7800    0.2318 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744   -0.3849   -3.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344    0.2483   -2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -1.3677   -1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1057    2.2048   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332    0.6181   -2.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381    1.5421   -0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0368    0.0016    1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7183   -1.7655    2.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2326   -1.4104    1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9419   -3.3524    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883   -1.2425   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7772   -1.9185    0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517   -0.8966    1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5758    0.2884   -0.2172 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  6
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 17  2  1  0
 14  5  1  0
 23  5  1  0
 13  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  1
 12 33  1  0
 13 34  1  6
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv1652309112209182D          

 23 26  0  0  1  0            999 V2000
   -1.0659   -0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2763   -0.5438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046    0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686    0.8055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949    0.6227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7859    1.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6112    0.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3824    1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0218    0.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8901   -0.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1189   -0.4328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9872   -1.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4795    0.0885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6287   -0.0136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3279   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8535   -1.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723   -0.9681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3287   -1.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9605   -2.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766   -0.1230    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2318    0.7781    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0177    1.5895    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7966    1.4856    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  6  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
  5 14  1  1  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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311364

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@]23CC4=CC=C[C@H](O)[C@H]4N2C(=O)[C@@]1(CO)SSSS3

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O4S4/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-23-22-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1

> <INCHI_KEY>
TZBWGHOEGGDHNR-RBJBARPLSA-N

> <FORMULA>
C13H14N2O4S4

> <MOLECULAR_WEIGHT>
390.51

> <EXACT_MASS>
389.983641635

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
35.60893832879821

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0^{1,9}.0^{3,8}]heptadeca-3,5-diene-10,16-dione

> <JCHEM_LOGP>
1.1703335053333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.39905167418419

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.795204360743522

> <JCHEM_PKA_STRONGEST_BASIC>
-3.181536426589509

> <JCHEM_POLAR_SURFACE_AREA>
81.07999999999998

> <JCHEM_REFRACTIVITY>
93.19919999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0^{1,9}.0^{3,8}]heptadeca-3,5-diene-10,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.990  -1.462   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.516  -1.015   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.195   0.396   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.875   1.504   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.857   1.162   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.334   1.900   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.874   1.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.314   2.233   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.507   1.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.262  -0.261   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.822  -0.808   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.576  -2.328   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.628   0.165   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.040  -0.025   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.479  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.460  -2.727   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.882  -1.807   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.614  -3.324   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.793  -4.314   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       1.076  -0.230   0.000  0.00  0.00           S+0
HETATM   21  S   UNK     0       0.433   1.452   0.000  0.00  0.00           S+0
HETATM   22  S   UNK     0      -0.033   2.967   0.000  0.00  0.00           S+0
HETATM   23  S   UNK     0       1.487   2.773   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   23                                             
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   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    5                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄N₂O₄S₄

Average Mass

390.5100 Da

Monoisotopic Mass

389.98364 Da

IUPAC Name

(1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0^{1,9}.0^{3,8}]heptadeca-3,5-diene-10,16-dione

Traditional Name

(1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0^{1,9}.0^{3,8}]heptadeca-3,5-diene-10,16-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@]23CC4=CC=C[C@H](O)[C@H]4N2C(=O)[C@@]1(CO)SSSS3

InChI Identifier

InChI=1S/C13H14N2O4S4/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-23-22-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1

InChI Key

TZBWGHOEGGDHNR-RBJBARPLSA-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
Aspergillus fumigatus	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
Indole or derivatives
Thiodioxopiperazine
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Piperazine
Pyrrolidine
Tertiary carboxylic acid amide
Secondary alcohol
Lactam
Carboxamide group
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Organic oxide
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	1.17	ChemAxon
pKa (Strongest Acidic)	13.8	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	93.2 m³·mol⁻¹	ChemAxon
Polarizability	35.61 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

2276741

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3007092

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rodrigues BS, Sahm BD, Jimenez PC, Pinto FC, Mafezoli J, Mattos MC, Rodrigues-Filho E, Pfenning LH, Abreu LM, Costa-Lotufo LV, Oliveira MC: Bioprospection of cytotoxic compounds in fungal strains recovered from sediments of the Brazilian coast. Chem Biodivers. 2015 Mar;12(3):432-42. doi: 10.1002/cbdv.201400193. [PubMed:25766916 ]
Nicolaou KC, Lu M, Totokotsopoulos S, Heretsch P, Giguere D, Sun YP, Sarlah D, Nguyen TH, Wolf IC, Smee DF, Day CW, Bopp S, Winzeler EA: Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8'-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents. J Am Chem Soc. 2012 Oct 17;134(41):17320-32. doi: 10.1021/ja308429f. Epub 2012 Oct 4. [PubMed:22978674 ]
Kang D, Son GH, Park HM, Kim J, Choi JN, Kim HY, Lee S, Hong SB, Lee CH: Culture condition-dependent metabolite profiling of Aspergillus fumigatus with antifungal activity. Fungal Biol. 2013 Mar;117(3):211-9. doi: 10.1016/j.funbio.2013.01.009. Epub 2013 Feb 14. [PubMed:23537878 ]
LOTUS database [Link]

Showing NP-Card for (1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione (NP0311364)

MOL for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)

3D MOL for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)

3D SDF for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)

3D-SDF for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)

PDB for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)

3D PDB for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)

SMILES for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)

INCHI for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)

Structure for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)

3D Structure for NP0311364 ((1r,7s,8s,11r)-7-hydroxy-11-(hydroxymethyl)-17-methyl-12,13,14,15-tetrathia-9,17-diazatetracyclo[9.4.2.0¹,⁹.0³,⁸]heptadeca-3,5-diene-10,16-dione)