NP-MRD: Showing NP-Card for 8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid (NP0320931)

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Record Information

Version

2.0

Created at

2022-09-11 22:51:16 UTC

Updated at

2022-09-11 22:51:16 UTC

NP-MRD ID

NP0320931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid

Description

Thiomarinol A belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group. Thiomarinol A 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. 8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid was first documented in 1995 (PMID: 7592043). Based on a literature review a small amount of articles have been published on thiomarinol A (PMID: 34342433) (PMID: 30270573) (PMID: 29363252) (PMID: 24723119).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122200512D          

 43 45  0  0  1  0            999 V2000
    5.0386    6.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4675    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4675    6.8385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1820    5.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8965    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6109    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3254    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0399    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7544    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4688    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1833    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8978    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6122    6.0135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8978    4.7760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6122    4.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3659    4.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5374    5.5060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9179    4.0859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5054    3.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5917    2.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8380    2.2154    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.2860    2.8285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.6985    3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3241    5.6010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3241    4.7760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6096    6.0135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8952    5.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807    6.8385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4662    7.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518    6.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    7.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772    6.8385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6772    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    7.2510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1061    6.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    8.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8952    7.2510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8952    8.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6096    6.8385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3241    7.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  4  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 25  2  0  0  0  0
 21 25  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 26  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  6  0  0  0
 31 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 28 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END


  Mrv1652309122200512D          

 43 45  0  0  1  0            999 V2000
    5.0386    6.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4675    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4675    6.8385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1820    5.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8965    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6109    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3254    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0399    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7544    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4688    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1833    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8978    5.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6122    6.0135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8978    4.7760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6122    4.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3659    4.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5374    5.5060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9179    4.0859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5054    3.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5917    2.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8380    2.2154    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.2860    2.8285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.6985    3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3241    5.6010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3241    4.7760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6096    6.0135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8952    5.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807    6.8385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4662    7.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518    6.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    7.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772    6.8385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6772    6.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    7.2510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1061    6.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    8.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8952    7.2510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8952    8.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6096    6.8385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3241    7.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  4  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 25  2  0  0  0  0
 21 25  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 26  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  6  0  0  0
 31 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 28 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0320931

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@H](C)\C=C\C[C@H]1CO[C@@H]([C@H](O)C(\C)=C\C(=O)OCCCCCCCC(O)=NC2=C3SSC=C3N=C2O)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44N2O9S2/c1-17(19(3)33)10-9-11-20-15-41-28(27(38)26(20)37)25(36)18(2)14-23(35)40-13-8-6-4-5-7-12-22(34)32-24-29-21(16-42-43-29)31-30(24)39/h9-10,14,16-17,19-20,25-28,33,36-38H,4-8,11-13,15H2,1-3H3,(H,31,39)(H,32,34)/b10-9+,18-14+/t17-,19+,20+,25-,26-,27-,28+/m1/s1

> <INCHI_KEY>
JIEMCPGFAXNCQW-XVYZEKPJSA-N

> <FORMULA>
C30H44N2O9S2

> <MOLECULAR_WEIGHT>
640.81

> <EXACT_MASS>
640.248823353

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
69.553986545241

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-{[(2E,4R)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2E,4R,5S)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-N-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid

> <JCHEM_LOGP>
5.030199999999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.871983282946998

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.70807610956739

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2811709278031498

> <JCHEM_POLAR_SURFACE_AREA>
182.16

> <JCHEM_REFRACTIVITY>
166.90290000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
8-{[(2E,4R)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2E,4R,5S)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-N-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.405  12.765   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.405  11.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.739  10.455   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.073  11.225   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.073  12.765   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.406  10.455   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      14.740  11.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.074  10.455   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.407  11.225   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.741  10.455   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.075  11.225   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.408  10.455   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.742  11.225   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.076  10.455   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      25.410  11.225   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      24.076   8.915   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      25.410   8.145   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.816   8.772   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      27.137  10.278   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      27.847   7.627   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      27.077   6.293   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.238   4.762   0.000  0.00  0.00           C+0
HETATM   23  S   UNK     0      25.831   4.135   0.000  0.00  0.00           S+0
HETATM   24  S   UNK     0      24.800   5.280   0.000  0.00  0.00           S+0
HETATM   25  C   UNK     0      25.570   6.614   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.072  10.455   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.072   8.915   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.738  11.225   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.404  10.455   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.071  11.225   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.071  12.765   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.737  13.535   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.403  12.765   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.070  13.535   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.264  12.765   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.264  11.225   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.598  13.535   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.931  12.765   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.598  15.075   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.404  13.535   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.404  15.075   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.738  12.765   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       8.072  13.535   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   17   21                                                  
CONECT   26    2   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   42                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   31   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   28   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
Thiomarinol	ChEBI

Chemical Formula

C₃₀H₄₄N₂O₉S₂

Average Mass

640.8100 Da

Monoisotopic Mass

640.24882 Da

IUPAC Name

8-{[(2E,4R)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2E,4R,5S)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-N-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid

Traditional Name

8-{[(2E,4R)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2E,4R,5S)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-N-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@H](C)\C=C\C[C@H]1CO[C@@H]([C@H](O)C(\C)=C\C(=O)OCCCCCCCC(O)=NC2=C3SSC=C3N=C2O)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C30H44N2O9S2/c1-17(19(3)33)10-9-11-20-15-41-28(27(38)26(20)37)25(36)18(2)14-23(35)40-13-8-6-4-5-7-12-22(34)32-24-29-21(16-42-43-29)31-30(24)39/h9-10,14,16-17,19-20,25-28,33,36-38H,4-8,11-13,15H2,1-3H3,(H,31,39)(H,32,34)/b10-9+,18-14+/t17-,19+,20+,25-,26-,27-,28+/m1/s1

InChI Key

JIEMCPGFAXNCQW-XVYZEKPJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

N-arylamides

Direct Parent

N-arylamides

Alternative Parents

Substituents

N-arylamide
Fatty acid ester
Fatty amide
Oxane
Substituted pyrrole
Fatty acyl
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dithiole
1,2-dithiole
Pyrrole
Carboxamide group
Carboxylic acid ester
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Azacycle
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organopnictogen compound
Organic oxide
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

lactam (CHEBI:66220 )
organosulfur heterocyclic compound (CHEBI:66220 )
cyclic ether (CHEBI:66220 )
enoate ester (CHEBI:66220 )

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	5.03	ChemAxon
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	182.16 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	166.9 m³·mol⁻¹	ChemAxon
Polarizability	69.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8093067

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9917420

PDB ID

Not Available

ChEBI ID

66220

Good Scents ID

Not Available

References

General References

Shiozawa H, Kagasaki T, Torikata A, Tanaka N, Fujimoto K, Hata T, Furukawa Y, Takahashi S: Thiomarinols B and C, new antimicrobial antibiotics produced by a marine bacterium. J Antibiot (Tokyo). 1995 Aug;48(8):907-9. doi: 10.7164/antibiotics.48.907. [PubMed:7592043 ]
Johnson RA, Chan AN, Ward RD, McGlade CA, Hatfield BM, Peters JM, Li B: Inhibition of Isoleucyl-tRNA Synthetase by the Hybrid Antibiotic Thiomarinol. J Am Chem Soc. 2021 Aug 11;143(31):12003-12013. doi: 10.1021/jacs.1c02622. Epub 2021 Aug 3. [PubMed:34342433 ]
Timmermans ML, Picott KJ, Ucciferri L, Ross AC: Culturing marine bacteria from the genus Pseudoalteromonas on a cotton scaffold alters secondary metabolite production. Microbiologyopen. 2019 May;8(5):e00724. doi: 10.1002/mbo3.724. Epub 2018 Oct 1. [PubMed:30270573 ]
Mohammad HH, Connolly JA, Song Z, Hothersall J, Race PR, Willis CL, Simpson TJ, Winn PJ, Thomas CM: Fine Tuning of Antibiotic Activity by a Tailoring Hydroxylase in a Trans-AT Polyketide Synthase Pathway. Chembiochem. 2018 Apr 16;19(8):836-841. doi: 10.1002/cbic.201800036. Epub 2018 Mar 13. [PubMed:29363252 ]
Brock NL, Nikolay A, Dickschat JS: Biosynthesis of the antibiotic tropodithietic acid by the marine bacterium Phaeobacter inhibens. Chem Commun (Camb). 2014 May 28;50(41):5487-9. doi: 10.1039/c4cc01924e. [PubMed:24723119 ]
LOTUS database [Link]

Showing NP-Card for 8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid (NP0320931)

MOL for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)

3D MOL for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)

3D SDF for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)

3D-SDF for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)

PDB for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)

3D PDB for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)

SMILES for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)

INCHI for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)

Structure for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)

3D Structure for NP0320931 (8-{[(2e,4r)-4-[(2s,3r,4r,5s)-3,4-dihydroxy-5-[(2e,4r,5s)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl]-4-hydroxy-3-methylbut-2-enoyl]oxy}-n-{5-hydroxy-[1,2]dithiolo[4,3-b]pyrrol-6-yl}octanimidic acid)