NP-MRD: Showing NP-Card for (1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione (NP0186046)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 01:43:30 UTC

Updated at

2022-09-04 01:43:30 UTC

NP-MRD ID

NP0186046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione

Description

Deacetylsirodesmin PL belongs to the class of organic compounds known as epipolythiodioxopiperazines. Epipolythiodioxopiperazines are compounds containing an epipolythiodioxopiperazine moiety, which consists of a 2,3-dithia-5,7-diazabicyclo[2.2.2]Octane-6,8-dione ring system. One distinct characteristics of Epipolythiodioxopiperazines is the presence of unique di- or polysulfide bridges. (1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione is found in Leptosphaeria maculans. (1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione was first documented in 2008 (PMID: 18701303). Based on a literature review very few articles have been published on deacetylsirodesmin PL.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042203432D          

 29 33  0  0  1  0            999 V2000
    6.8446   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921    0.3502    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4717    0.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356    1.0168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5229    0.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8082    0.8764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9459    0.7855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -0.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864   -0.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866   -0.1016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1832   -0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -1.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1402    0.4027    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9267    1.1189    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5099    1.5897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2181    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9791    1.6835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1253    2.4955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7996    1.7703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2116    2.4850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756    2.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582    0.6899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337    0.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7484    1.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6616    2.3897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4631    1.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9545    1.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15  7  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  6  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -4.9948   -0.5924    1.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367   -0.5605    0.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6439   -0.2162    1.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7722   -0.0142    0.2565 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5593    0.7988    0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5248   -0.1990    0.9830 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7883    0.1042    0.3773 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7693    1.0953    0.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    1.9611    1.5295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0523    1.1219   -0.1434 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0423    2.0281    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2059    2.0610   -0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386    1.6473   -1.8282 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    0.1930   -2.2436 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0388   -0.8234   -0.7151 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0563   -1.9002   -0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0919   -1.5300    0.4316 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1085   -2.4883    1.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2629   -1.3493   -0.1914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2551   -1.5020   -1.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4657   -1.2414   -0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399   -2.4523   -0.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4577   -0.2540   -0.2619 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -0.6995   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    0.6713   -0.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398    1.1943   -1.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9922    0.5677   -0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615    1.8502    0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9786    0.2430   -1.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9259   -0.5036    1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0122   -1.6304    2.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9133    0.1588    2.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8229   -1.5032    0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857    1.5019    1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424    1.3545   -0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5767   -0.2231    2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6187    3.0586    0.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1959    1.7520    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5418    2.9767   -0.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5835   -2.0751   -1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5705   -2.8623   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1992   -3.3904    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9033   -2.1917    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772   -0.6973   -1.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9174   -1.7842   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5340   -0.1960   -0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1043   -0.5674    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4686    1.9388    0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0085    2.6896   -0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682    1.9070    1.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9915    0.5694   -1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7916    0.8470   -2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0558   -0.8439   -1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  1
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
  4 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 27  2  1  0
 19  4  1  0
 17  6  1  0
 15  7  1  0
 23 10  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  5 34  1  0
  5 35  1  0
  6 36  1  1
 11 37  1  0
 11 38  1  0
 12 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  1
 20 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 28 48  1  0
 28 49  1  0
 28 50  1  0
 29 51  1  0
 29 52  1  0
 29 53  1  0
M  END


  Mrv1652309042203432D          

 29 33  0  0  1  0            999 V2000
    6.8446   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921    0.3502    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4717    0.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356    1.0168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5229    0.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8082    0.8764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9459    0.7855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -0.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864   -0.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866   -0.1016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1832   -0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -1.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1402    0.4027    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9267    1.1189    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5099    1.5897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2181    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9791    1.6835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1253    2.4955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7996    1.7703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2116    2.4850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756    2.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582    0.6899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337    0.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7484    1.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6616    2.3897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4631    1.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9545    1.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15  7  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  6  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@]2(C[C@@H]3N4C(=O)[C@]5(CO)SS[C@@]4(C[C@]3(O)[C@@H]2O)C(=O)N5C)C(=O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H24N2O7S2/c1-8-14(2,3)10(22)16(27-8)5-9-15(26,11(16)23)6-17-12(24)19(4)18(7-21,29-28-17)13(25)20(9)17/h8-9,11,21,23,26H,5-7H2,1-4H3/t8-,9-,11-,15+,16+,17-,18-/m0/s1

> <INCHI_KEY>
ODGGLAWTFMFKDG-RSMYJANASA-N

> <FORMULA>
C18H24N2O7S2

> <MOLECULAR_WEIGHT>
444.52

> <EXACT_MASS>
444.102493469

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.404535077774796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,3'R,4'S,5S,7'S,10'S)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0^{1,8}.0^{3,7}]tetradecane]-3,9',13'-trione

> <JCHEM_LOGP>
0.3406147426666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.750734469218944

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.522956651462781

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1958775509401454

> <JCHEM_POLAR_SURFACE_AREA>
127.61000000000001

> <JCHEM_REFRACTIVITY>
103.6137

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,3'R,4'S,5S,7'S,10'S)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0^{1,8}.0^{3,7}]tetradecane]-3,9',13'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      12.776  -0.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.745   0.654   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.214   0.492   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.587   1.898   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.443   0.867   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.109   1.636   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.499   1.466   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.727  -0.096   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.575  -1.382   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.962  -0.190   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.209  -1.533   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.996  -2.857   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0       3.995   0.752   0.000  0.00  0.00           S+0
HETATM   14  S   UNK     0       3.597   2.089   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       4.685   2.967   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.007   3.849   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.428   3.143   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.701   4.658   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.959   3.305   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.728   4.639   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.880   2.854   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.008   4.123   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       2.162   1.288   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       0.623   1.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.730   2.929   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.568   4.461   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.064   2.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.982   3.397   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.598   2.016   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19   25                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13   23                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   16   21                                             
CONECT   16   15   17                                                       
CONECT   17   16    6   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    4   20                                                  
CONECT   20   19                                                            
CONECT   21   15   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   10   24                                                  
CONECT   24   23                                                            
CONECT   25    4   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    2   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₄N₂O₇S₂

Average Mass

444.5200 Da

Monoisotopic Mass

444.10249 Da

IUPAC Name

(1'S,2S,3'R,4'S,5S,7'S,10'S)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0^{1,8}.0^{3,7}]tetradecane]-3,9',13'-trione

Traditional Name

(1'S,2S,3'R,4'S,5S,7'S,10'S)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0^{1,8}.0^{3,7}]tetradecane]-3,9',13'-trione

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@]2(C[C@@H]3N4C(=O)[C@]5(CO)SS[C@@]4(C[C@]3(O)[C@@H]2O)C(=O)N5C)C(=O)C1(C)C

InChI Identifier

InChI=1S/C18H24N2O7S2/c1-8-14(2,3)10(22)16(27-8)5-9-15(26,11(16)23)6-17-12(24)19(4)18(7-21,29-28-17)13(25)20(9)17/h8-9,11,21,23,26H,5-7H2,1-4H3/t8-,9-,11-,15+,16+,17-,18-/m0/s1

InChI Key

ODGGLAWTFMFKDG-RSMYJANASA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Leptosphaeria maculans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epipolythiodioxopiperazines. Epipolythiodioxopiperazines are compounds containing an epipolythiodioxopiperazine moiety, which consists of a 2,3-dithia-5,7-diazabicyclo[2.2.2]Octane-6,8-dione ring system. One distinct characteristics of Epipolythiodioxopiperazines is the presence of unique di- or polysulfide bridges.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Epipolythiodioxopiperazines

Alternative Parents

Substituents

Epipolythiodioxopiperazine
Alpha-amino acid or derivatives
N-alkylpiperazine
N-methylpiperazine
Dithiazinane
3-furanone
Tetrahydrofuran
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Secondary alcohol
Organic disulfide
Lactam
Ketone
Carboxamide group
Oxacycle
Azacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.34	ChemAxon
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	127.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	103.61 m³·mol⁻¹	ChemAxon
Polarizability	42.4 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101588056

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pedras MS, Yu Y: Stress-driven discovery of metabolites from the phytopathogenic fungus Leptosphaeria maculans: structure and activity of leptomaculins A-E. Bioorg Med Chem. 2008 Sep 1;16(17):8063-71. doi: 10.1016/j.bmc.2008.07.060. Epub 2008 Jul 26. [PubMed:18701303 ]
LOTUS database [Link]

Showing NP-Card for (1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione (NP0186046)

MOL for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)

3D MOL for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)

3D SDF for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)

3D-SDF for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)

PDB for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)

3D PDB for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)

SMILES for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)

INCHI for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)

Structure for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)

3D Structure for NP0186046 ((1's,2s,3'r,4's,5s,7's,10's)-3',4'-dihydroxy-10'-(hydroxymethyl)-4,4,5,14'-tetramethyl-11',12'-dithia-8',14'-diazaspiro[oxolane-2,5'-tetracyclo[8.2.2.0¹,⁸.0³,⁷]tetradecane]-3,9',13'-trione)