NP-MRD: Showing NP-Card for (1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione (NP0323164)

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Record Information

Version

2.0

Created at

2022-09-12 02:25:05 UTC

Updated at

2022-09-12 02:25:06 UTC

NP-MRD ID

NP0323164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione

Description

Lyngbyabellin B belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. (1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione was first documented in 2013 (PMID: 24016099). Based on a literature review very few articles have been published on Lyngbyabellin B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122204252D          

 43 45  0  0  1  0            999 V2000
    2.6147    2.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3132    3.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2823    4.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0427    3.0372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7412    3.4762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706    3.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4396    3.9153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    3.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8986    3.1445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9295    2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2310    1.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6590    1.9347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4589    2.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8980    1.4379    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4194    0.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6900    1.1103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4504   -0.0995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1880   -0.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9257   -0.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8186   -1.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5575    0.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7076   -0.6127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4823   -1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9920   -2.0551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6579   -1.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8579   -1.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7749   -2.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3737   -0.6628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7409   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9661   -0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3332   -1.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584   -1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419   -0.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -1.9293    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7836   -0.8711    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5945   -0.2068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5635    0.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2620    1.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8341    1.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341    0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    1.4998    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737    2.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031    1.8274    0.0000 N   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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  6  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 15 16  2  0  0  0  0
 12 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  4 42  1  0  0  0  0
 42 43  2  0  0  0  0
 39 43  1  0  0  0  0
M  END


  Mrv1652309122204252D          

 43 45  0  0  1  0            999 V2000
    2.6147    2.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3132    3.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2823    4.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0427    3.0372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7412    3.4762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706    3.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4396    3.9153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    3.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8986    3.1445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9295    2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2310    1.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6590    1.9347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4589    2.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8980    1.4379    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4194    0.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6900    1.1103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4504   -0.0995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1880   -0.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9257   -0.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8186   -1.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5575    0.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7076   -0.6127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4823   -1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9920   -2.0551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6579   -1.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8579   -1.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7749   -2.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3737   -0.6628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7409   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9661   -0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3332   -1.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584   -1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419   -0.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -1.9293    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7836   -0.8711    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5945   -0.2068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5635    0.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2620    1.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8341    1.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341    0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    1.4998    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737    2.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031    1.8274    0.0000 N   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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  6  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 15 16  2  0  0  0  0
 12 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  4 42  1  0  0  0  0
 42 43  2  0  0  0  0
 39 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1N=C(O)CN=C(O)[C@@H]2CSC(=N2)[C@@H](OC(=O)C(C)(C)[C@H](CCCC(C)(Cl)Cl)OC(=O)C2=CSC1=N2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40Cl2N4O7S2/c1-14(2)19-22-33-16(13-42-22)24(37)40-17(9-8-10-28(7,29)30)26(3,4)25(38)41-20(27(5,6)39)23-32-15(12-43-23)21(36)31-11-18(35)34-19/h13-15,17,19-20,39H,8-12H2,1-7H3,(H,31,36)(H,34,35)/t15-,17-,19-,20+/m0/s1

> <INCHI_KEY>
XZRCVAJXDSWDNB-LWCVALJOSA-N

> <FORMULA>
C28H40Cl2N4O7S2

> <MOLECULAR_WEIGHT>
679.67

> <EXACT_MASS>
678.1715474

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
68.1304259448766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,7S,14S,18S)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-15,15-dimethyl-7-(propan-2-yl)-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1^{8,11}]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione

> <JCHEM_LOGP>
4.805487756921195

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.231212044896757

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7340646742356398

> <JCHEM_PKA_STRONGEST_BASIC>
3.941747441876499

> <JCHEM_POLAR_SURFACE_AREA>
163.26

> <JCHEM_REFRACTIVITY>
166.0579

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7S,14S,18S)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1^{8,11}]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione

> <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       4.881   5.569   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.185   6.389   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.127   7.928   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.546   5.669   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       8.850   6.489   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      10.212   5.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.154   7.309   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.516   6.589   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      12.877   5.870   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      12.935   4.331   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.631   3.511   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      14.297   3.611   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.790   3.988   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0      16.610   2.684   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0      15.716   1.353   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      14.355   2.073   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      15.774  -0.186   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.151  -0.875   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.528  -1.565   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.461  -2.252   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.841   0.502   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      14.388  -1.144   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.967  -2.625   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.918  -3.836   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.428  -2.683   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.935  -3.059   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.646  -4.207   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.898  -1.237   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.716  -2.225   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.270  -1.696   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.089  -2.684   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.642  -2.155   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.171  -0.709   0.000  0.00  0.00           C+0
HETATM   34 Cl   UNK     0       6.113  -3.601   0.000  0.00  0.00          Cl+0
HETATM   35 Cl   UNK     0       5.196  -1.626   0.000  0.00  0.00          Cl+0
HETATM   36  O   UNK     0      10.443  -0.386   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.385   1.153   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.689   1.972   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.024   1.872   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.530   1.496   0.000  0.00  0.00           C+0
HETATM   41  S   UNK     0       6.711   2.800   0.000  0.00  0.00           S+0
HETATM   42  C   UNK     0       7.604   4.131   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0       8.966   3.411   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   42                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   12                                                       
CONECT   17   15   18   22                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   28   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   43                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41    4   43                                                  
CONECT   43   42   39                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀Cl₂N₄O₇S₂

Average Mass

679.6700 Da

Monoisotopic Mass

678.17155 Da

IUPAC Name

(1R,7S,14S,18S)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-15,15-dimethyl-7-(propan-2-yl)-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1^{8,11}]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione

Traditional Name

(1R,7S,14S,18S)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1^{8,11}]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1N=C(O)CN=C(O)[C@@H]2CSC(=N2)[C@@H](OC(=O)C(C)(C)[C@H](CCCC(C)(Cl)Cl)OC(=O)C2=CSC1=N2)C(C)(C)O

InChI Identifier

InChI=1S/C28H40Cl2N4O7S2/c1-14(2)19-22-33-16(13-42-22)24(37)40-17(9-8-10-28(7,29)30)26(3,4)25(38)41-20(27(5,6)39)23-32-15(12-43-23)21(36)31-11-18(35)34-19/h13-15,17,19-20,39H,8-12H2,1-7H3,(H,31,36)(H,34,35)/t15-,17-,19-,20+/m0/s1

InChI Key

XZRCVAJXDSWDNB-LWCVALJOSA-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 cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolactam
Macrolide
Thiazolecarboxylic acid or derivatives
Dicarboxylic acid or derivatives
Imidothiolactone
Azole
Tertiary alcohol
Thiazole
Meta-thiazoline
Cyclic carboximidic acid
Heteroaromatic compound
Carboxylic acid ester
Lactone
Propargyl-type 1,3-dipolar organic compound
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Carboxylic acid derivative
Alkyl halide
Organohalogen compound
Organic oxide
Organopnictogen compound
Organochloride
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Alkyl chloride
Alcohol
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.81	ChemAxon
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	3.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	163.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	166.06 m³·mol⁻¹	ChemAxon
Polarizability	68.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

23326375

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44558912

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Thornburg CC, Cowley ES, Sikorska J, Shaala LA, Ishmael JE, Youssef DT, McPhail KL: Apratoxin H and apratoxin A sulfoxide from the Red Sea cyanobacterium Moorea producens. J Nat Prod. 2013 Sep 27;76(9):1781-8. doi: 10.1021/np4004992. Epub 2013 Sep 9. [PubMed:24016099 ]
LOTUS database [Link]

Showing NP-Card for (1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione (NP0323164)

MOL for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)

3D MOL for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)

3D SDF for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)

3D-SDF for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)

PDB for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)

3D PDB for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)

SMILES for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)

INCHI for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)

Structure for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)

3D Structure for NP0323164 ((1r,7s,14s,18s)-14-(4,4-dichloropentyl)-2,5-dihydroxy-18-(2-hydroxypropan-2-yl)-7-isopropyl-15,15-dimethyl-13,17-dioxa-9,20-dithia-3,6,22,23-tetraazatricyclo[17.2.1.1⁸,¹¹]tricosa-2,5,8(23),10,19(22)-pentaene-12,16-dione)