NP-MRD: Showing NP-Card for Cladosporin A (NP0013691)

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Record Information

Version

2.0

Created at

2021-01-05 22:59:01 UTC

Updated at

2021-07-15 17:15:12 UTC

NP-MRD ID

NP0013691

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cladosporin A

Provided By

NPAtlas

Description

Cladosporin A is found in Cladosporium sp. Cladosporin A was first documented in 2015 (PMID: 25584683). Based on a literature review very few articles have been published on (1R,4S,5S,11R,14S,15S)-15-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-3,13-diazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁴,¹⁹]Icosa-6,8,16,18-tetraen-5-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119493D          

 55 59  0  0  0  0            999 V2000
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   -3.8472    2.5822    3.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5099    3.1175    3.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242119493D          

 55 59  0  0  0  0            999 V2000
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   -2.7155   -1.3923    0.4097 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8818    1.9479   -0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8607    2.1734    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    2.9500    3.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7448    2.8845    4.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    1.2073    3.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839    3.7626    2.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9266    2.5804    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5695   -4.5122    0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -3.6985   -1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0834   -4.9926   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3928   -2.5847    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7123   -0.7794    1.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -3.4072   -0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006   -3.1924   -2.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457   -1.4500   -4.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761   -0.6236   -3.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006    3.4340   -4.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6646    3.5236   -3.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7194    2.8725   -4.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078    0.2743   -0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 12  3  1  0  0  0  0
 29 15  1  0  0  0  0
 30  3  1  0  0  0  0
 11  5  1  0  0  0  0
 28 19  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  6 37  1  0  0  0  0
  7 38  1  0  0  0  0
  8 39  1  0  0  0  0
  9 40  1  1  0  0  0
 10 41  1  0  0  0  0
 11 42  1  6  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 20 48  1  0  0  0  0
 21 49  1  0  0  0  0
 22 50  1  0  0  0  0
 23 51  1  6  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
 26 54  1  0  0  0  0
 28 55  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0013691

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])=C([H])C([H])=C2C([H])([H])[C@]3(SC([H])([H])[H])N(C(=O)[C@@]4(SC([H])([H])[H])N(C3=O)[C@@]3([H])C(=C([H])C([H])=C([H])[C@]3([H])OC(=O)C([H])([H])[H])C4([H])[H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O5S2/c1-12(25)29-16-9-5-7-14-11-22(31-3)19(27)23-17-13(6-4-8-15(17)26)10-21(23,30-2)20(28)24(22)18(14)16/h4-9,15-18,26H,10-11H2,1-3H3/t15-,16-,17-,18-,21+,22+/m0/s1

> <INCHI_KEY>
FPGPKYXTPXMJHN-NEEVBFIGSA-N

> <FORMULA>
C22H24N2O5S2

> <MOLECULAR_WEIGHT>
460.56

> <EXACT_MASS>
460.112664229

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
46.39679621283325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
1.5954102523333336

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.125014835912438

> <JCHEM_PKA_STRONGEST_BASIC>
-3.181518510771898

> <JCHEM_POLAR_SURFACE_AREA>
87.15

> <JCHEM_REFRACTIVITY>
122.60669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -3.7471   -1.1426    1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155   -1.3923    0.4097 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6584    0.0118    0.0972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5239    1.2003   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8161    1.7235    1.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047    2.1431    1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    2.5822    3.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7085    2.5333    3.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173    2.0536    3.1473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5099    3.1175    3.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4511    1.7371    1.7105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9268    0.4660    1.2961 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012   -0.4058    1.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715   -0.3776    2.9359 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439   -1.3567    0.8147 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1065   -2.9322    0.8079 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -4.1206   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2076   -1.6037    1.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938   -1.7818   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849   -2.6176   -0.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350   -2.4975   -2.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1454   -1.5264   -3.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267   -0.5297   -2.4530 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7436    0.7506   -2.8019 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    1.6057   -3.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919    2.9515   -4.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0304    1.2041   -4.1969 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0425   -0.6054   -0.9934 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7104   -0.6795   -0.4944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6019   -0.2739   -0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8228   -0.1696   -2.1271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0495   -2.1545    2.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7194   -0.6479    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2864   -0.5629    2.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347    0.9276   -0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818    1.9479   -0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8607    2.1734    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    2.9500    3.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7448    2.8845    4.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    1.2073    3.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839    3.7626    2.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9266    2.5804    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5695   -4.5122    0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -3.6985   -1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0834   -4.9926   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3928   -2.5847    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7123   -0.7794    1.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -3.4072   -0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006   -3.1924   -2.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457   -1.4500   -4.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761   -0.6236   -3.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006    3.4340   -4.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6646    3.5236   -3.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7194    2.8725   -4.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078    0.2743   -0.5255 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  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  6
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 12  3  1  0
 29 15  1  0
 30  3  1  0
 11  5  1  0
 28 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  1
 10 41  1  0
 11 42  1  6
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  6
 26 52  1  0
 26 53  1  0
 26 54  1  0
 28 55  1  1
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.747  -1.143   1.851  0.00  0.00           C+0
HETATM    2  S   UNK     0      -2.716  -1.392   0.410  0.00  0.00           S+0
HETATM    3  C   UNK     0      -1.658   0.012   0.097  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.524   1.200  -0.289  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.816   1.724   1.094  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.905   2.143   1.658  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.847   2.582   3.050  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.708   2.533   3.699  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.417   2.054   3.147  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.510   3.118   3.362  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.451   1.737   1.710  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.927   0.466   1.296  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.101  -0.406   1.748  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.472  -0.378   2.936  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.744  -1.357   0.815  0.00  0.00           C+0
HETATM   16  S   UNK     0      -0.107  -2.932   0.808  0.00  0.00           S+0
HETATM   17  C   UNK     0       0.618  -4.121  -0.316  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.208  -1.604   1.093  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.694  -1.782  -0.329  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.485  -2.618  -0.959  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.735  -2.498  -2.376  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.145  -1.526  -3.043  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.227  -0.530  -2.453  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.744   0.751  -2.802  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.103   1.606  -3.696  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.692   2.951  -4.032  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.030   1.204  -4.197  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.042  -0.605  -0.993  0.00  0.00           C+0
HETATM   29  N   UNK     0       0.710  -0.680  -0.494  0.00  0.00           N+0
HETATM   30  C   UNK     0      -0.602  -0.274  -0.904  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.823  -0.170  -2.127  0.00  0.00           O+0
HETATM   32  H   UNK     0      -4.050  -2.155   2.252  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.719  -0.648   1.601  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.286  -0.563   2.654  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.435   0.928  -0.816  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.882   1.948  -0.791  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.861   2.173   1.112  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.766   2.950   3.536  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.745   2.885   4.738  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.023   1.207   3.780  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.684   3.763   2.615  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.927   2.580   1.156  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.569  -4.512   0.096  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.825  -3.699  -1.319  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.083  -4.993  -0.382  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.393  -2.585   1.586  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.712  -0.779   1.592  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.952  -3.407  -0.395  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.401  -3.192  -2.905  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.346  -1.450  -4.102  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.276  -0.624  -3.035  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.001   3.434  -4.750  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.665   3.524  -3.079  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.719   2.873  -4.384  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.608   0.274  -0.526  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   12   30                                             
CONECT    4    3    5   35   36                                             
CONECT    5    4    6   11                                                  
CONECT    6    5    7   37                                                  
CONECT    7    6    8   38                                                  
CONECT    8    7    9   39                                                  
CONECT    9    8   10   11   40                                             
CONECT   10    9   41                                                       
CONECT   11    9   12    5   42                                             
CONECT   12   11   13    3                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   18   29                                             
CONECT   16   15   17                                                       
CONECT   17   16   43   44   45                                             
CONECT   18   15   19   46   47                                             
CONECT   19   18   20   28                                                  
CONECT   20   19   21   48                                                  
CONECT   21   20   22   49                                                  
CONECT   22   21   23   50                                                  
CONECT   23   22   24   28   51                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   52   53   54                                             
CONECT   27   25                                                            
CONECT   28   23   29   19   55                                             
CONECT   29   28   30   15                                                  
CONECT   30   29   31    3                                                  
CONECT   31   30                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   28                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

RDKit          3D

55 59  0  0  0  0  0  0  0  0999 V2000
   -3.7471   -1.1426    1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155   -1.3923    0.4097 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6584    0.0118    0.0972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5239    1.2003   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8161    1.7235    1.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047    2.1431    1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8472    2.5822    3.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7085    2.5333    3.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173    2.0536    3.1473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5099    3.1175    3.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4511    1.7371    1.7105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9268    0.4660    1.2961 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012   -0.4058    1.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715   -0.3776    2.9359 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439   -1.3567    0.8147 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1065   -2.9322    0.8079 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -4.1206   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2076   -1.6037    1.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938   -1.7818   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849   -2.6176   -0.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350   -2.4975   -2.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1454   -1.5264   -3.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267   -0.5297   -2.4530 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7436    0.7506   -2.8019 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    1.6057   -3.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919    2.9515   -4.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0304    1.2041   -4.1969 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0425   -0.6054   -0.9934 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7104   -0.6795   -0.4944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6019   -0.2739   -0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8228   -0.1696   -2.1271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0495   -2.1545    2.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7194   -0.6479    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2864   -0.5629    2.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347    0.9276   -0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818    1.9479   -0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8607    2.1734    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    2.9500    3.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7448    2.8845    4.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    1.2073    3.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839    3.7626    2.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9266    2.5804    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5695   -4.5122    0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -3.6985   -1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0834   -4.9926   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3928   -2.5847    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7123   -0.7794    1.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -3.4072   -0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006   -3.1924   -2.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457   -1.4500   -4.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761   -0.6236   -3.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006    3.4340   -4.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6646    3.5236   -3.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7194    2.8725   -4.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078    0.2743   -0.5255 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  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  6
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 12  3  1  0
 29 15  1  0
 30  3  1  0
 11  5  1  0
 28 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  1
 10 41  1  0
 11 42  1  6
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  6
 26 52  1  0
 26 53  1  0
 26 54  1  0
 28 55  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1R,4S,5S,11R,14S,15S)-15-Hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-3,13-diazapentacyclo[11.7.0.0,.0,.0,]icosa-6,8,16,18-tetraen-5-yl acetic acid	Generator
(1R,4S,5S,11R,14S,15S)-15-Hydroxy-1,11-bis(methylsulphanyl)-2,12-dioxo-3,13-diazapentacyclo[11.7.0.0,.0,.0,]icosa-6,8,16,18-tetraen-5-yl acetate	Generator
(1R,4S,5S,11R,14S,15S)-15-Hydroxy-1,11-bis(methylsulphanyl)-2,12-dioxo-3,13-diazapentacyclo[11.7.0.0,.0,.0,]icosa-6,8,16,18-tetraen-5-yl acetic acid	Generator

Chemical Formula

C₂₂H₂₄N₂O₅S₂

Average Mass

460.5600 Da

Monoisotopic Mass

460.11266 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H24N2O5S2/c1-12(25)29-16-9-5-7-14-11-22(31-3)19(27)23-17-13(6-4-8-15(17)26)10-21(23,30-2)20(28)24(22)18(14)16/h4-9,15-18,26H,10-11H2,1-3H3/t15-,16-,17-,18-,21+,22+/m0/s1

InChI Key

FPGPKYXTPXMJHN-NEEVBFIGSA-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
Cladosporium sp.	NPAtlas	25584683

Chemical Taxonomy

Classification

Not classified

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	1.4	ALOGPS
logP	1.6	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	87.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.61 m³·mol⁻¹	ChemAxon
Polarizability	46.4 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

NPAtlas ID

NPA014074

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35516719

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86290883

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gu B, Zhang Y, Ding L, He S, Wu B, Dong J, Zhu P, Chen J, Zhang J, Yan X: Preparative separation of sulfur-containing diketopiperazines from marine fungus Cladosporium sp. using high-speed counter-current chromatography in stepwise elution mode. Mar Drugs. 2015 Jan 9;13(1):354-65. doi: 10.3390/md13010354. [PubMed:25584683 ]

Showing NP-Card for Cladosporin A (NP0013691)

MOL for NP0013691 (Cladosporin A)

3D MOL for NP0013691 (Cladosporin A)

3D SDF for NP0013691 (Cladosporin A)

3D-SDF for NP0013691 (Cladosporin A)

PDB for NP0013691 (Cladosporin A)

3D PDB for NP0013691 (Cladosporin A)

SMILES for NP0013691 (Cladosporin A)

INCHI for NP0013691 (Cladosporin A)

Structure for NP0013691 (Cladosporin A)

3D Structure for NP0013691 (Cladosporin A)