NP-MRD: Showing NP-Card for Venturamide A (NP0006950)

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Record Information

Version

2.0

Created at

2020-12-09 03:52:04 UTC

Updated at

2021-07-15 16:56:14 UTC

NP-MRD ID

NP0006950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Venturamide A

Provided By

NPAtlas

Description

Venturamide A belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. Venturamide 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. Venturamide A is found in Oscillataria sp. and Oscillatoria sp.. Venturamide A was first documented in 2007 (PMID: 17328572). Based on a literature review very few articles have been published on venturamide A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118363D          

 57 60  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118363D          

 57 60  0  0  0  0            999 V2000
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    1.1695    3.6225   -0.6365 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9727    2.6960   -1.3990 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2271    1.8802   -2.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2333    1.5277    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0555   -0.2542    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990    0.5201    2.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -2.1012    2.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939   -3.6140    0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1621   -1.3785   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9661   -1.5737   -0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992   -2.8253   -1.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262   -5.0675    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3077   -0.8694   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5191   -0.4961    0.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5039    0.2491    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2975    1.9798    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7423    0.8325    2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661    0.8203    2.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -1.6549    1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3448   -1.1527    2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2181   -2.1633    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    4.2535   -2.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6276    4.0356    0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310    3.2984   -1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643    1.5886   -3.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4873    2.5001   -2.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543    0.9158   -2.0001 H   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  1  0  0  0  0
  4  5  2  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  6  2  2  0  0  0  0
 16 12  1  0  0  0  0
 28 24  1  0  0  0  0
 32  4  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  1  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
 15 42  1  0  0  0  0
 19 43  1  0  0  0  0
 20 44  1  1  0  0  0
 21 45  1  6  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 23 49  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 27 52  1  0  0  0  0
 31 53  1  0  0  0  0
 32 54  1  6  0  0  0
 33 55  1  0  0  0  0
 33 56  1  0  0  0  0
 33 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=O)C2=C([H])SC(=N2)[C@]([H])(N([H])C(=O)C2=C([H])SC(=N2)[C@]([H])(N([H])C(=O)C2=C(OC(=N2)[C@@]1([H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N6O4S2/c1-8(2)14-21-25-12(7-33-21)16(28)22-9(3)19-27-15(11(5)31-19)18(30)23-10(4)20-24-13(6-32-20)17(29)26-14/h6-10,14H,1-5H3,(H,22,28)(H,23,30)(H,26,29)/t9-,10-,14-/m1/s1

> <INCHI_KEY>
OJMSNONHTSXZKM-GPCCPHFNSA-N

> <FORMULA>
C21H24N6O4S2

> <MOLECULAR_WEIGHT>
488.58

> <EXACT_MASS>
488.130045625

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
49.21405659519932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,11R,18R)-4,7,11-trimethyl-18-(propan-2-yl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1^{5,8}.1^{12,15}]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaene-2,9,16-trione

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
1.8262449816666662

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.819942374438806

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.527413921806271

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8175648620986095

> <JCHEM_POLAR_SURFACE_AREA>
139.11

> <JCHEM_REFRACTIVITY>
121.38129999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,11R,18R)-18-isopropyl-4,7,11-trimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1^{5,8}.1^{12,15}]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaene-2,9,16-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    5.5983    0.6484    1.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0236    1.8561   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604    1.8565   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1899    0.8738    0.2680 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    0.2626    1.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7736   -0.8411    1.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166   -0.8617    3.0370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390   -1.8779    1.7210 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7063   -2.7168    0.5582 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9967   -2.0621   -0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191   -3.3084    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6546   -2.7686   -0.1965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8376   -3.3030   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0123   -4.4600    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519   -4.6766    1.1784 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8864   -2.6217   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7695   -3.3925   -1.5604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -1.2197   -1.2327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4769   -0.2239   -0.2874 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5484   -0.0875    0.8017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1155    0.9611    1.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7381   -1.3697    1.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172    1.1194   -0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657    1.9590   -0.6823 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2593    3.1074   -1.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138    3.3744   -2.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1709    1.9534   -2.1987 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1529    4.0305   -0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4643    5.2744   -0.8739 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695    3.6225   -0.6365 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9727    2.6960   -1.3990 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2271    1.8802   -2.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2333    1.5277    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0555   -0.2542    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990    0.5201    2.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -2.1012    2.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939   -3.6140    0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1621   -1.3785   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9661   -1.5737   -0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992   -2.8253   -1.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262   -5.0675    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3077   -0.8694   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5191   -0.4961    0.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5039    0.2491    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2975    1.9798    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7423    0.8325    2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661    0.8203    2.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -1.6549    1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3448   -1.1527    2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2181   -2.1633    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    4.2535   -2.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6276    4.0356    0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310    3.2984   -1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643    1.5886   -3.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4873    2.5001   -2.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543    0.9158   -2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 20 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 26 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
  6  2  2  0
 16 12  1  0
 28 24  1  0
 32  4  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  0
 11 40  1  0
 11 41  1  0
 15 42  1  0
 19 43  1  0
 20 44  1  1
 21 45  1  6
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 27 52  1  0
 31 53  1  0
 32 54  1  6
 33 55  1  0
 33 56  1  0
 33 57  1  0
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       5.598   0.648   1.379  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.276   0.945   0.763  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.024   1.856  -0.109  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.760   1.857  -0.447  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.190   0.874   0.268  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.093   0.263   1.049  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.774  -0.841   1.940  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.417  -0.862   3.037  0.00  0.00           O+0
HETATM    9  N   UNK     0       1.839  -1.878   1.721  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.706  -2.717   0.558  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.997  -2.062  -0.742  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.319  -3.308   0.499  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.655  -2.769  -0.197  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.838  -3.303  -0.227  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.012  -4.460   0.507  0.00  0.00           C+0
HETATM   16  S   UNK     0      -0.452  -4.677   1.178  0.00  0.00           S+0
HETATM   17  C   UNK     0      -2.886  -2.622  -1.039  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.769  -3.393  -1.560  0.00  0.00           O+0
HETATM   19  N   UNK     0      -2.922  -1.220  -1.233  0.00  0.00           N+0
HETATM   20  C   UNK     0      -2.477  -0.224  -0.287  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.548  -0.088   0.802  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.115   0.961   1.819  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.738  -1.370   1.562  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.317   1.119  -0.974  0.00  0.00           C+0
HETATM   25  N   UNK     0      -1.366   1.959  -0.682  0.00  0.00           N+0
HETATM   26  C   UNK     0      -1.259   3.107  -1.290  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.214   3.374  -2.255  0.00  0.00           C+0
HETATM   28  S   UNK     0      -3.171   1.953  -2.199  0.00  0.00           S+0
HETATM   29  C   UNK     0      -0.153   4.030  -0.923  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.464   5.274  -0.874  0.00  0.00           O+0
HETATM   31  N   UNK     0       1.169   3.623  -0.637  0.00  0.00           N+0
HETATM   32  C   UNK     0       1.973   2.696  -1.399  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.227   1.880  -2.398  0.00  0.00           C+0
HETATM   34  H   UNK     0       6.233   1.528   1.273  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.056  -0.254   0.965  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.399   0.520   2.474  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.128  -2.101   2.489  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.394  -3.614   0.629  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.162  -1.379  -1.021  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.966  -1.574  -0.817  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.999  -2.825  -1.578  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.926  -5.067   0.616  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.308  -0.869  -2.148  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.519  -0.496   0.184  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.504   0.249   0.372  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.297   1.980   1.447  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.742   0.833   2.729  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.066   0.820   2.141  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.736  -1.655   1.966  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.345  -1.153   2.479  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.218  -2.163   0.969  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.345   4.253  -2.896  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.628   4.036   0.213  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.731   3.298  -1.988  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.964   1.589  -3.207  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.487   2.500  -2.904  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.854   0.916  -2.000  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    2                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   37                                                  
CONECT   10    9   11   12   38                                             
CONECT   11   10   39   40   41                                             
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16   42                                                  
CONECT   16   15   12                                                       
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   43                                                  
CONECT   20   19   21   24   44                                             
CONECT   21   20   22   23   45                                             
CONECT   22   21   46   47   48                                             
CONECT   23   21   49   50   51                                             
CONECT   24   20   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28   52                                                  
CONECT   28   27   24                                                       
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   53                                                  
CONECT   32   31   33    4   54                                             
CONECT   33   32   55   56   57                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   15                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   27                                                            
CONECT   53   31                                                            
CONECT   54   32                                                            
CONECT   55   33                                                            
CONECT   56   33                                                            
CONECT   57   33                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

RDKit          3D

57 60  0  0  0  0  0  0  0  0999 V2000
    5.5983    0.6484    1.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2760    0.9448    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0236    1.8561   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604    1.8565   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1899    0.8738    0.2680 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    0.2626    1.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7736   -0.8411    1.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166   -0.8617    3.0370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390   -1.8779    1.7210 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7063   -2.7168    0.5582 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9967   -2.0621   -0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191   -3.3084    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6546   -2.7686   -0.1965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8376   -3.3030   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0123   -4.4600    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519   -4.6766    1.1784 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8864   -2.6217   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7695   -3.3925   -1.5604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -1.2197   -1.2327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4769   -0.2239   -0.2874 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5484   -0.0875    0.8017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1155    0.9611    1.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7381   -1.3697    1.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172    1.1194   -0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657    1.9590   -0.6823 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2593    3.1074   -1.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138    3.3744   -2.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1709    1.9534   -2.1987 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1529    4.0305   -0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4643    5.2744   -0.8739 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695    3.6225   -0.6365 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9727    2.6960   -1.3990 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2271    1.8802   -2.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2333    1.5277    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0555   -0.2542    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990    0.5201    2.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -2.1012    2.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939   -3.6140    0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1621   -1.3785   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9661   -1.5737   -0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992   -2.8253   -1.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262   -5.0675    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3077   -0.8694   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5191   -0.4961    0.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5039    0.2491    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2975    1.9798    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7423    0.8325    2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661    0.8203    2.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -1.6549    1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3448   -1.1527    2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2181   -2.1633    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    4.2535   -2.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6276    4.0356    0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310    3.2984   -1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643    1.5886   -3.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4873    2.5001   -2.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8543    0.9158   -2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 20 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 26 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
  6  2  2  0
 16 12  1  0
 28 24  1  0
 32  4  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  0
 11 40  1  0
 11 41  1  0
 15 42  1  0
 19 43  1  0
 20 44  1  1
 21 45  1  6
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 27 52  1  0
 31 53  1  0
 32 54  1  6
 33 55  1  0
 33 56  1  0
 33 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄N₆O₄S₂

Average Mass

488.5800 Da

Monoisotopic Mass

488.13005 Da

IUPAC Name

(4R,11R,18R)-4,7,11-trimethyl-18-(propan-2-yl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1^{5,8}.1^{12,15}]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaene-2,9,16-trione

Traditional Name

(4R,11R,18R)-18-isopropyl-4,7,11-trimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1^{5,8}.1^{12,15}]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaene-2,9,16-trione

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1NC(=O)C2=CSC(=N2)[C@@H](C)NC(=O)C2=C(C)OC(=N2)[C@@H](C)NC(=O)C2=CSC1=N2

InChI Identifier

InChI=1S/C21H24N6O4S2/c1-8(2)14-21-25-12(7-33-21)16(28)22-9(3)19-27-15(11(5)31-19)18(30)23-10(4)20-24-13(6-32-20)17(29)26-14/h6-10,14H,1-5H3,(H,22,28)(H,23,30)(H,26,29)/t9-,10-,14-/m1/s1

InChI Key

OJMSNONHTSXZKM-GPCCPHFNSA-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
Oscillataria sp.	-	KNApSAcK
Oscillatoria sp.	NPAtlas	17328572

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
2-heteroaryl carboxamide
Thiazolecarboxylic acid or derivatives
Azole
Oxazole
Thiazole
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Lactam
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1,3-oxazoles (CHEBI:66353 )
1,3-thiazole (CHEBI:66353 )
homodetic cyclic peptide (CHEBI:66353 )
macrocycle (CHEBI:66353 )

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	2.42	ALOGPS
logP	1.83	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.53	ChemAxon
pKa (Strongest Basic)	-0.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.11 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	121.38 m³·mol⁻¹	ChemAxon
Polarizability	49.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA018289

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040633

Chemspider ID

23280565

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11225555

PDB ID

Not Available

ChEBI ID

66353

Good Scents ID

Not Available

References

General References

Linington RG, Gonzalez J, Urena LD, Romero LI, Ortega-Barria E, Gerwick WH: Venturamides A and B: antimalarial constituents of the panamanian marine Cyanobacterium Oscillatoria sp. J Nat Prod. 2007 Mar;70(3):397-401. doi: 10.1021/np0605790. Epub 2007 Mar 1. [PubMed:17328572 ]

Showing NP-Card for Venturamide A (NP0006950)

MOL for NP0006950 (Venturamide A)

3D MOL for NP0006950 (Venturamide A)

3D SDF for NP0006950 (Venturamide A)

3D-SDF for NP0006950 (Venturamide A)

PDB for NP0006950 (Venturamide A)

3D PDB for NP0006950 (Venturamide A)

SMILES for NP0006950 (Venturamide A)

INCHI for NP0006950 (Venturamide A)

Structure for NP0006950 (Venturamide A)

3D Structure for NP0006950 (Venturamide A)