NP-MRD: Showing NP-Card for Exserohilone (NP0051360)

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Record Information

Version

2.0

Created at

2022-04-27 22:45:24 UTC

Updated at

2022-04-27 22:45:24 UTC

NP-MRD ID

NP0051360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Exserohilone

Description

Exserohilone 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. Exserohilone is found in Dactyloctenium aegyptium and Exserohilum holmii. Exserohilone was first documented in 2010 (PMID: 20809554). Based on a literature review very few articles have been published on Exserohilone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200452D          

 30 34  0  0  1  0            999 V2000
    3.7054    1.0256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7854    0.2410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0403    1.0256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3729    1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8473    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1022    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3993    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1444   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374   -0.3721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0825   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2243    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729   -1.0076    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598   -1.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5339    1.8326    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470    2.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  1  5  1  0  0  0  0
  4  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
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 14 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 15 25  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  2  0  0  0  0
 14 27  1  6  0  0  0
 27 28  1  0  0  0  0
  1 29  1  6  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    1.2758   -1.1995    3.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733    0.1127    2.2271 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1086   -0.5055    0.5917 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0741   -1.6198    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2826   -0.7928   -0.0328 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3677   -1.4091   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186   -2.6151   -0.9058 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2462   -0.4289   -1.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024    0.8475   -1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216    1.3892   -0.9738 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2163    2.5294   -1.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637    0.2596   -0.9785 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3624    0.4652   -0.4637 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116    1.3722   -0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054    2.4788   -1.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    1.1018   -0.4968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8697    2.3221    0.6096 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    2.2672    2.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762    1.1231   -1.7559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184    0.6127   -1.1357 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2784    0.1090   -1.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4545    0.3229   -3.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2450   -0.7464   -1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9299   -1.2149   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534   -0.9422    0.6263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3013   -2.0173    1.4367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6413   -0.6346   -0.4205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3462   -0.2631   -0.0422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011   -0.9209    0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5863   -1.9231    1.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1732   -1.3512    4.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0662   -2.1764    2.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4414   -0.9576    4.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2001   -2.3528    1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6850   -2.0775   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -0.2984    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1913   -0.7596   -1.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355    1.5477   -2.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8987    1.6657    0.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    2.4444   -2.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6927   -0.1958   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8722    2.8823    2.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    2.7238    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340    1.2469    2.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    0.4152   -2.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654    2.1594   -2.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6406    1.3125   -0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2155   -1.0083   -1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6255   -1.8643    0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144   -0.0047    1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8760   -1.9395    2.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6874   -1.4920   -1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5 12  1  0
 12 10  1  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 19  1  0
 19 20  1  0
 20 27  1  0
 27 25  1  0
 25 26  1  0
 25 24  1  0
 24 23  2  0
 23 21  1  0
 21 22  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 16 17  1  1
 17 18  1  0
 13  3  1  0
 28 16  1  0
 29  3  1  0
  6  5  1  0
 21 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
 12 41  1  6
 10 39  1  1
 11 40  1  0
  9 38  1  0
  8 37  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  1
 27 52  1  6
 25 50  1  1
 26 51  1  0
 24 49  1  0
 23 48  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
M  END


  Mrv1652304282200452D          

 30 34  0  0  1  0            999 V2000
    3.7054    1.0256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7854    0.2410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0403    1.0256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3729    1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8473    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1022    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3993    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1444   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374   -0.3721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0825   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2243    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729   -1.0076    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598   -1.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5339    1.8326    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470    2.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  1  5  1  0  0  0  0
  4  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
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 14 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 15 25  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  2  0  0  0  0
 14 27  1  6  0  0  0
 27 28  1  0  0  0  0
  1 29  1  6  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS[C@]12C[C@@H]3[C@H]([C@H](O)C=CC3=O)N1C(=O)[C@]1(C[C@@H]3[C@H]([C@H](O)C=CC3=O)N1C2=O)SC

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O6S2/c1-29-19-7-9-11(23)3-5-13(25)15(9)21(19)18(28)20(30-2)8-10-12(24)4-6-14(26)16(10)22(20)17(19)27/h3-6,9-10,13-16,25-26H,7-8H2,1-2H3/t9-,10-,13+,14+,15+,16+,19-,20-/m0/s1

> <INCHI_KEY>
FWPMSYUTOOUASJ-GFIYPFTLSA-N

> <FORMULA>
C20H22N2O6S2

> <MOLECULAR_WEIGHT>
450.52

> <EXACT_MASS>
450.091928784

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
44.17165752551564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,5R,9R,11S,14R,15R,19R)-5,15-dihydroxy-1,11-bis(methylsulfanyl)-3,13-diazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{14,19}]icosa-6,16-diene-2,8,12,18-tetrone

> <ALOGPS_LOGP>
-0.07

> <JCHEM_LOGP>
0.8384330106666666

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.35220033628293

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.765367537626684

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1780427724617537

> <JCHEM_POLAR_SURFACE_AREA>
115.22000000000003

> <JCHEM_REFRACTIVITY>
113.04319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5R,9R,11S,14R,15R,19R)-5,15-dihydroxy-1,11-bis(methylsulfanyl)-3,13-diazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{14,19}]icosa-6,16-diene-2,8,12,18-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.393   0.450   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       8.933   0.450   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.409   1.914   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.163   2.820   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.915   2.235   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.391   3.699   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.945   1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.470  -0.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.963  -0.695   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.487  -2.159   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.838  -2.159   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.380   1.090   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.610  -1.280   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.382  -2.159   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.285   3.699   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.935   3.699   0.000  0.00  0.00           O+0
HETATM   27  S   UNK     0       5.176  -1.881   0.000  0.00  0.00           S+0
HETATM   28  C   UNK     0       4.032  -2.911   0.000  0.00  0.00           C+0
HETATM   29  S   UNK     0       6.597   3.421   0.000  0.00  0.00           S+0
HETATM   30  C   UNK     0       7.741   4.451   0.000  0.00  0.00           C+0
CONECT    1    2    5   25   29                                             
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10                                                            
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   18   27                                             
CONECT   15   14   16   25                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   14                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23                                                            
CONECT   25   15    1   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28                                                       
CONECT   28   27                                                            
CONECT   29    1   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₆S₂

Average Mass

450.5200 Da

Monoisotopic Mass

450.09193 Da

IUPAC Name

(1S,4R,5R,9R,11S,14R,15R,19R)-5,15-dihydroxy-1,11-bis(methylsulfanyl)-3,13-diazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{14,19}]icosa-6,16-diene-2,8,12,18-tetrone

Traditional Name

(1S,4R,5R,9R,11S,14R,15R,19R)-5,15-dihydroxy-1,11-bis(methylsulfanyl)-3,13-diazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{14,19}]icosa-6,16-diene-2,8,12,18-tetrone

CAS Registry Number

Not Available

SMILES

CS[C@]12C[C@@H]3[C@H]([C@H](O)C=CC3=O)N1C(=O)[C@]1(C[C@@H]3[C@H]([C@H](O)C=CC3=O)N1C2=O)SC

InChI Identifier

InChI=1S/C20H22N2O6S2/c1-29-19-7-9-11(23)3-5-13(25)15(9)21(19)18(28)20(30-2)8-10-12(24)4-6-14(26)16(10)22(20)17(19)27/h3-6,9-10,13-16,25-26H,7-8H2,1-2H3/t9-,10-,13+,14+,15+,16+,19-,20-/m0/s1

InChI Key

FWPMSYUTOOUASJ-GFIYPFTLSA-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
Dactyloctenium aegyptium	Plant	KNApSAcK
Exserohilum holmii	-	KNApSAcK

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
Cyclohexenone
N-alkylpiperazine
1,4-diazinane
Piperazine
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Ketone
Lactam
Secondary alcohol
Organoheterocyclic compound
Sulfenyl compound
Azacycle
Hemithioaminal
Thioether
Dialkylthioether
Carbonyl group
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:4954 )

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	-0.07	ALOGPS
logP	0.84	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	115.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	113.04 m³·mol⁻¹	ChemAxon
Polarizability	44.17 Å³	ChemAxon
Number of Rings	5	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

C00002338

Chemspider ID

391169

KEGG Compound ID

C10593

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442856

PDB ID

Not Available

ChEBI ID

4954

Good Scents ID

Not Available

References

General References

Gross U, Nieger M, Brase S: A unified strategy targeting the thiodiketopiperazine mycotoxins exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin A and aranotin. Chemistry. 2010 Oct 11;16(38):11624-31. doi: 10.1002/chem.201001169. Epub 2010 Aug 31. [PubMed:20809554 ]

Showing NP-Card for Exserohilone (NP0051360)

MOL for NP0051360 (Exserohilone)

3D MOL for NP0051360 (Exserohilone)

3D SDF for NP0051360 (Exserohilone)

3D-SDF for NP0051360 (Exserohilone)

PDB for NP0051360 (Exserohilone)

3D PDB for NP0051360 (Exserohilone)

SMILES for NP0051360 (Exserohilone)

INCHI for NP0051360 (Exserohilone)

Structure for NP0051360 (Exserohilone)

3D Structure for NP0051360 (Exserohilone)