NP-MRD: Showing NP-Card for (1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one (NP0308654)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 02:35:54 UTC

Updated at

2022-09-11 02:35:54 UTC

NP-MRD ID

NP0308654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one

Description

Griseoviridin belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group. (1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one is found in Streptomyces griseoviridis. Based on a literature review very few articles have been published on Griseoviridin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112204352D          

 33 35  0  0  1  0            999 V2000
    8.7259    1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1086    2.3265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4118    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1509    3.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4480    4.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6319    4.1873    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0845    3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620    2.7453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0539    2.3392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2327    2.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0253    1.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4765    2.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7086    2.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845    3.0846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286    3.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4271    3.5725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    4.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    5.6344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5451    5.8418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6734    6.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2208    7.0079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6967    7.6451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    7.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7377    7.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5588    7.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3150    7.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9323    6.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3503    5.9351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5279    5.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3515    5.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5749    2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431    1.3961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3831    1.9337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  4  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  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  4  0  0  0
 28 29  2  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -5.2542    0.6603   -1.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343    0.5143   -0.6426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8917   -0.7469    0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0882   -1.8074   -0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7508   -1.6663   -0.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223   -0.0465   -0.3430 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9576    0.3891    1.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6893    1.6547    1.6657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7874    2.5730    2.3233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1197    3.5242    1.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1152    4.7197    2.5954 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339    3.5519    0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9516    4.6485   -0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    4.2232   -1.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7904    2.9218   -1.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743    2.5072   -0.0126 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4877    1.9591   -2.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913    0.9610   -1.2521 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0464    1.1966    0.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9283   -0.4768   -1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894   -1.2254   -0.3209 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7993   -0.7675    0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -2.6882   -0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1828   -3.4742    0.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334   -3.1621    1.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2502   -2.8605    1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517   -3.5736    1.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0896   -3.1163   -0.3082 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9781   -2.8521   -0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -3.6522   -2.0246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4341    2.2454    0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007    3.3168    0.0410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522    1.6680    0.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2528    1.4823   -1.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0078    0.7587   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4344   -0.2844   -1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140    0.3262   -1.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9172   -1.1397    0.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4945   -0.5340    1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5867   -2.6656   -0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2612   -0.4671    2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1412    0.4988    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353    1.3837    2.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6327    5.4889    2.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856    5.6942   -0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6855    1.4227   -2.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1439    2.5008   -2.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3777    1.0910   -1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    1.7172    0.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0237   -0.5213   -2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447   -0.9423   -2.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7998   -0.9620    0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6622   -0.8564    0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -3.1205   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8350   -4.3744    0.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1031   -3.1879    2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9024   -2.0525    2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5137   -4.6806    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837   -3.5890    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845   -4.1059   -1.9310 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 15 16  2  0
  8 31  1  0
 31 32  2  0
 31 33  1  0
 33  2  1  0
 29  5  1  0
 16 12  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  6
  3 38  1  0
  3 39  1  0
  4 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  1
 11 44  1  0
 13 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  1
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  1
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 30 60  1  0
M  END


  Mrv1652309112204352D          

 33 35  0  0  1  0            999 V2000
    8.7259    1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1086    2.3265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4118    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1509    3.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4480    4.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6319    4.1873    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0845    3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620    2.7453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0539    2.3392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2327    2.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0253    1.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4765    2.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7086    2.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845    3.0846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286    3.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4271    3.5725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    4.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    5.6344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5451    5.8418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6734    6.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2208    7.0079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6967    7.6451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    7.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7377    7.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5588    7.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3150    7.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9323    6.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3503    5.9351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5279    5.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3515    5.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5749    2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431    1.3961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3831    1.9337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  4  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  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  4  0  0  0
 28 29  2  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C\C=C2/SC[C@@H](N=C(O)C3=COC(C[C@@H](O)C[C@H](O)\C=C/C=C\CN=C2O)=N3)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H27N3O7S/c1-13-6-7-18-21(29)23-8-4-2-3-5-14(26)9-15(27)10-19-24-16(11-31-19)20(28)25-17(12-33-18)22(30)32-13/h2-5,7,11,13-15,17,26-27H,6,8-10,12H2,1H3,(H,23,29)(H,25,28)/b4-2-,5-3-,18-7-/t13-,14-,15+,17-/m1/s1

> <INCHI_KEY>
UXWOXTQWVMFRSE-CPEQWFEASA-N

> <FORMULA>
C22H27N3O7S

> <MOLECULAR_WEIGHT>
477.53

> <EXACT_MASS>
477.156971395

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.4636055919439

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S,11S,12E,14E,19Z,22R)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1^{4,7}]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one

> <JCHEM_LOGP>
0.9954868786666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.55963319551281

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.402580469585985

> <JCHEM_PKA_STRONGEST_BASIC>
3.2815322608786306

> <JCHEM_POLAR_SURFACE_AREA>
157.97

> <JCHEM_REFRACTIVITY>
125.37209999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S,11S,12E,14E,19Z,22R)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1^{4,7}]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      16.288   3.321   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.136   4.343   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.702   5.775   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.215   7.236   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.903   8.042   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      12.380   7.816   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      11.358   6.664   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.316   5.125   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.434   4.367   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.901   4.516   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.514   3.025   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.490   5.131   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.056   4.569   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.078   5.758   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.907   7.056   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.397   6.669   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.225   8.985   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.375  10.518   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.884  10.905   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.990  11.929   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.012  13.081   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.034  14.271   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.340  13.862   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.844  14.193   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.376  14.044   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.788  13.428   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.940  12.407   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      13.720  11.079   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      14.052   9.575   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.589   9.667   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.273   3.918   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.467   2.606   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.782   3.610   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
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                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    5   30                                                  
CONECT   30   29                                                            
CONECT   31    8   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇N₃O₇S

Average Mass

477.5300 Da

Monoisotopic Mass

477.15697 Da

IUPAC Name

(1S,9S,11S,12E,14E,19Z,22R)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1^{4,7}]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one

Traditional Name

(1S,9S,11S,12E,14E,19Z,22R)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1^{4,7}]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C\C=C2/SC[C@@H](N=C(O)C3=COC(C[C@@H](O)C[C@H](O)\C=C/C=C\CN=C2O)=N3)C(=O)O1

InChI Identifier

InChI=1S/C22H27N3O7S/c1-13-6-7-18-21(29)23-8-4-2-3-5-14(26)9-15(27)10-19-24-16(11-31-19)20(28)25-17(12-33-18)22(30)32-13/h2-5,7,11,13-15,17,26-27H,6,8-10,12H2,1H3,(H,23,29)(H,25,28)/b4-2-,5-3-,18-7-/t13-,14-,15+,17-/m1/s1

InChI Key

UXWOXTQWVMFRSE-CPEQWFEASA-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
Streptomyces griseoviridis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolide lactams

Sub Class

Not Available

Direct Parent

Macrolide lactams

Alternative Parents

Substituents

Macrolide lactam
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
2-heteroaryl carboxamide
Azole
Heteroaromatic compound
Oxazole
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Thioenolether
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
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	1	ChemAxon
pKa (Strongest Acidic)	5.4	ChemAxon
pKa (Strongest Basic)	3.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	157.97 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	125.37 m³·mol⁻¹	ChemAxon
Polarizability	47.46 Å³	ChemAxon
Number of Rings	3	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

24827871

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73948073

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one (NP0308654)

MOL for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)

3D MOL for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)

3D SDF for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)

3D-SDF for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)

PDB for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)

3D PDB for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)

SMILES for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)

INCHI for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)

Structure for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)

3D Structure for NP0308654 ((1s,9s,11s,12e,14e,19z,22r)-3,9,11,18-tetrahydroxy-22-methyl-6,23-dioxa-26-thia-2,17,27-triazatricyclo[17.5.2.1⁴,⁷]heptacosa-2,4,7(27),12,14,17,19-heptaen-24-one)