NP-MRD: Showing NP-Card for {[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid (NP0313541)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-11 11:10:13 UTC

Updated at

2022-09-11 11:10:13 UTC

NP-MRD ID

NP0313541

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid

Description

19-S-methylgeldanamycin 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. {[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid is found in Streptomyces hygroscopicus. It was first documented in 2011 (PMID: 21559026). Based on a literature review very few articles have been published on 19-s-methylgeldanamycin (PMID: 23591607).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112213102D          

 42 43  0  0  1  0            999 V2000
    0.0569   -1.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8116   -1.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4775   -1.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323   -1.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211   -0.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304   -0.0220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7245   -0.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4683    0.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886    0.6418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8425    1.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5901    2.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4575   -0.1658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9225   -0.7938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1624   -0.7299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9242   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0735   -1.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394   -2.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -1.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6506   -2.8573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4053   -2.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4942   -1.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -0.9185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2489   -1.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165   -3.3444    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0712   -3.0112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7371   -3.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2276   -4.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4729   -4.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070   -4.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0523   -4.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634   -5.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3864   -3.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -4.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4752   -3.0366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -2.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546   -2.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9657   -3.7029    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110   -4.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3887   -2.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339   -2.7288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -1.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529   -1.3962    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  4  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  1  0  0  0  0
  3 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 41  1  0  0  0  0
  4 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  END

     RDKit          3D

 84 85  0  0  0  0  0  0  0  0999 V2000
   -5.1491   -0.5019    2.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7036   -0.4455    1.1504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2755    0.0491    0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5640    0.5399    0.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5183    0.0265   -1.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1961   -0.0805   -1.2791 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3518    1.1199   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668    1.0703   -2.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415    2.2579   -0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6136    2.6025    0.6633 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1566    4.0472    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461    2.4851    1.6567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6062    1.3151    2.4253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1171    2.7495    1.1840 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0905    4.1063    1.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5295    4.6296   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7206    2.2215    2.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811    2.1252    2.1086 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9039    3.3971    2.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6563    1.6860    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479    0.2384    0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9608    0.1748   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604    1.3710   -0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4367    1.8196   -2.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4672   -1.0473   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4025   -1.0925   -1.7991 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226   -2.2910   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858   -3.7669   -1.1666 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745   -5.2495   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8291   -2.2609    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -3.5549    0.6695 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1457   -4.1176    0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6949   -4.9136    1.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588   -4.0531   -0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5136   -5.2833   -1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0570   -2.9732   -1.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325   -1.6113   -1.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1108   -1.0846   -0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -1.3295   -0.7821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6487   -2.3784   -1.6744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4670   -3.3949   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.9812    0.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677   -1.0130    1.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0797    0.5014    1.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2948   -0.3836   -2.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666    1.8885   -3.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131    0.1132   -3.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2650    1.1944   -2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0769    3.2056   -1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4785    1.9983    1.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184    4.0855    0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894    4.6697    0.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0928    4.4404    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7013    3.3000    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017    1.2291    2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0895    2.2917    0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120    4.4739   -0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5982    4.4287   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947    5.7621    0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5823    2.9844    3.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    1.2958    2.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    1.3518    2.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733    3.8147    3.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9957    4.0547    1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256    3.1535    2.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    2.1147   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080    2.3225    0.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0199    2.7815   -2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3735    2.1137   -2.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7819    1.1022   -2.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7568   -6.0950   -0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -5.6699   -0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8093   -5.2129    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0936   -5.8501    1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625   -5.4024   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0585   -6.2138   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -5.2503   -2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -3.1958   -2.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -0.8716   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8679   -0.4856    0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -1.6429    0.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5352   -4.1887   -1.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1647   -3.7962   -0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5280   -3.0212   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 39  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 30 42  1  0
 42 43  2  0
 12 14  1  0
 42 21  1  0
 16 57  1  0
 16 58  1  0
 16 59  1  0
 14 56  1  6
 17 60  1  0
 17 61  1  0
 18 62  1  1
 19 63  1  0
 19 64  1  0
 19 65  1  0
 20 66  1  0
 20 67  1  0
 24 68  1  0
 24 69  1  0
 24 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 33 74  1  0
 35 75  1  0
 35 76  1  0
 35 77  1  0
 36 78  1  0
 37 79  1  0
 38 80  1  0
 39 81  1  1
 41 82  1  0
 41 83  1  0
 41 84  1  0
  6 45  1  6
  4 44  1  0
  2  1  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  1
 11 51  1  0
 11 52  1  0
 11 53  1  0
 12 54  1  1
 13 55  1  0
M  END


  Mrv1652309112213102D          

 42 43  0  0  1  0            999 V2000
    0.0569   -1.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8116   -1.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4775   -1.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323   -1.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211   -0.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304   -0.0220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7245   -0.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4683    0.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886    0.6418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8425    1.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5901    2.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4575   -0.1658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9225   -0.7938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1624   -0.7299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9242   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0735   -1.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394   -2.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -1.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6506   -2.8573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4053   -2.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4942   -1.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -0.9185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2489   -1.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165   -3.3444    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0712   -3.0112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7371   -3.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2276   -4.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4729   -4.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070   -4.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0523   -4.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634   -5.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3864   -3.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -4.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4752   -3.0366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -2.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546   -2.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9657   -3.7029    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110   -4.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3887   -2.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339   -2.7288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -1.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529   -1.3962    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  4  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  1  0  0  0  0
  3 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 41  1  0  0  0  0
  4 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0313541

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@H](C)CC2=C(OC)C(=O)C(SC)=C(N=C(O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(O)=N)\C(C)=C\[C@H](C)[C@H]1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H42N2O9S/c1-15-12-19-24(34)22(28(42-8)25(35)27(19)40-7)32-29(36)16(2)10-9-11-20(38-5)26(41-30(31)37)18(4)14-17(3)23(33)21(13-15)39-6/h9-11,14-15,17,20-21,23,26,33H,12-13H2,1-8H3,(H2,31,37)(H,32,36)/b11-9-,16-10+,18-14+/t15-,17+,20+,21+,23-,26+/m1/s1

> <INCHI_KEY>
XGLOPHLGVPTCBN-WUNXPXPTSA-N

> <FORMULA>
C30H42N2O9S

> <MOLECULAR_WEIGHT>
606.73

> <EXACT_MASS>
606.261102114

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
62.921901494193776

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid

> <JCHEM_LOGP>
1.4918810636709052

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.706424496536436

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.9027877074463797

> <JCHEM_PKA_STRONGEST_BASIC>
11.5874285127556

> <JCHEM_POLAR_SURFACE_AREA>
167.95999999999995

> <JCHEM_REFRACTIVITY>
177.1519

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid

> <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       0.106  -2.654   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.515  -2.032   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.758  -2.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.167  -2.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.333  -0.788   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.843  -0.041   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.952  -1.110   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.474   1.364   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.005   1.198   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.039   2.339   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.568   3.805   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.321  -0.309   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.322  -1.482   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.636  -1.362   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.058  -0.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.471  -2.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.714  -3.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.488  -2.471   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.548  -5.334   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.957  -4.712   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.122  -3.181   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      11.651  -1.715   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0      13.531  -2.559   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.791  -6.243   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.200  -5.621   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.443  -6.530   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.625  -7.774   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.216  -8.396   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.973  -7.487   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.564  -8.108   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.398  -9.640   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.321  -7.199   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.912  -7.821   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       6.487  -5.668   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       5.244  -4.759   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.835  -5.381   0.000  0.00  0.00           C+0
HETATM   37  S   UNK     0       3.669  -6.912   0.000  0.00  0.00           S+0
HETATM   38  C   UNK     0       2.261  -7.534   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.592  -4.472   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.183  -5.094   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.410  -3.228   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.819  -2.606   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5   41                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36    3   40                                                  
CONECT   40   39                                                            
CONECT   41   35    4   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂N₂O₉S

Average Mass

606.7300 Da

Monoisotopic Mass

606.26110 Da

IUPAC Name

{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@H](C)CC2=C(OC)C(=O)C(SC)=C(N=C(O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(O)=N)\C(C)=C\[C@H](C)[C@H]1O)C2=O

InChI Identifier

InChI=1S/C30H42N2O9S/c1-15-12-19-24(34)22(28(42-8)25(35)27(19)40-7)32-29(36)16(2)10-9-11-20(38-5)26(41-30(31)37)18(4)14-17(3)23(33)21(13-15)39-6/h9-11,14-15,17,20-21,23,26,33H,12-13H2,1-8H3,(H2,31,37)(H,32,36)/b11-9-,16-10+,18-14+/t15-,17+,20+,21+,23-,26+/m1/s1

InChI Key

XGLOPHLGVPTCBN-WUNXPXPTSA-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 hygroscopicus	LOTUS Database	35616633

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
Vinylogous thioester
Carbamic acid ester
Vinylogous amide
Vinylogous ester
Carboxamide group
Ketone
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Thioenolether
Cyclic ketone
Azacycle
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Sulfenyl compound
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organosulfur compound
Organopnictogen compound
Organic oxide
Alcohol
Hydrocarbon derivative
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	1.49	ChemAxon
pKa (Strongest Acidic)	-2.9	ChemAxon
pKa (Strongest Basic)	11.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	167.96 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	177.15 m³·mol⁻¹	ChemAxon
Polarizability	62.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

78436312

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53392670

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu X, Li J, Ni S, Wu L, Wang H, Lin L, He W, Wang Y: A pair of sulfur-containing geldanamycin analogs, 19-S-methylgeldanamycin and 4,5-dihydro- 19-S-methylgeldanamycin, from Streptomyces hygroscopicus 17997. J Antibiot (Tokyo). 2011 Jul;64(7):519-22. doi: 10.1038/ja.2011.39. Epub 2011 May 11. [PubMed:21559026 ]
Li S, Cui J, Lu X, Zheng Z, Liu X, Ni S, Wang Y, Wu L: Methanethiol as a catabolite of methionine provides methylthio- group for chemical formation of 19-S-methylgeldanamycin and 17,19-dimethylthioherbimycin A. J Antibiot (Tokyo). 2013 Aug;66(8):499-503. doi: 10.1038/ja.2013.31. Epub 2013 Apr 17. [PubMed:23591607 ]
LOTUS database [Link]

Showing NP-Card for {[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid (NP0313541)

MOL for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D MOL for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D SDF for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D-SDF for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

PDB for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D PDB for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

SMILES for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

INCHI for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

Structure for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D Structure for NP0313541 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-21-(methylsulfanyl)-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)