NP-MRD: Showing NP-Card for 4'-O-Demethylsordarin (NP0004007)

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Record Information

Version

1.0

Created at

2020-12-09 01:31:46 UTC

Updated at

2021-07-15 16:47:59 UTC

NP-MRD ID

NP0004007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-O-Demethylsordarin

Provided By

NPAtlas

Description

(4R,5R,8R)-9-formyl-5-methyl-13-(propan-2-yl)-2-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}tetracyclo[7.4.0.0²,¹¹.0⁴,⁸]Tridec-12-ene-1-carboxylic acid belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 4'-O-Demethylsordarin is found in Streptomyces. It was first documented in 2001 (PMID: 11827037). Based on a literature review very few articles have been published on (4R,5R,8R)-9-formyl-5-methyl-13-(propan-2-yl)-2-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}tetracyclo[7.4.0.0²,¹¹.0⁴,⁸]Tridec-12-ene-1-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118033D          

 72 76  0  0  0  0            999 V2000
   -2.8634   -3.6652    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.2283    0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7099   -4.0979   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -1.8012   -0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350   -1.4024   -1.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950    0.0673   -1.4753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3798    0.1540   -1.6965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9314    0.0182   -0.2948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1968   -0.7512   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9534   -0.7969    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660    1.4013    0.2216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3067    2.1529   -0.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0041    3.5732    0.1557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5124    3.5991    0.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2275    3.7514    1.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144    2.3356   -0.1379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7955    1.7322    0.4416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6518    0.3421    0.0122 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6596   -0.2353    0.4633 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6737    0.3549   -0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201   -0.1308    0.0734 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5389   -0.7233   -1.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.3377   -0.5937 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2996   -2.2458   -1.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -0.2267   -0.3574 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8386    0.5152   -1.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2110    0.6417    0.7478 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9895    1.7867    0.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7636    1.0320    0.5441 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6334    2.0637   -0.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7965   -0.5977    0.4362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9425   -0.7750    1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0446   -0.6365    2.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510   -1.1156    2.6394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9376   -4.7752    0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3519   -3.4249   -0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981   -3.2405    0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9419   -3.4591    1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9835   -3.7911   -2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958   -4.0590   -0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0464   -5.1477   -0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -1.9720   -2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2759    0.6192   -2.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7336    1.0059   -2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7829   -0.7477   -2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544   -1.3123   -1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2509    1.4364    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2865    2.2241   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3041    1.8561    0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5270    3.7496    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    4.3343   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0835    4.4709   -0.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709    4.0894    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4736    2.8857    2.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423    4.6142    2.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8763    2.5016   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1264    2.2749    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119    1.7207    1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7939    0.1009    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6961   -1.3322    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653   -0.8875    0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631   -1.8591    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7290   -3.1576   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3193   -2.5325   -1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220   -1.6792   -2.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7065   -0.6250   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    1.1964   -1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771    0.0611    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2732    1.9456    1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3683    1.3118    1.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4721    1.7554   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587   -1.9060    3.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
 11 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 31  4  1  0  0  0  0
 18  6  1  0  0  0  0
 29 21  1  0  0  0  0
 31  8  1  0  0  0  0
 16 11  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  2 38  1  1  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  3 41  1  0  0  0  0
  5 42  1  0  0  0  0
  6 43  1  6  0  0  0
  7 44  1  0  0  0  0
  7 45  1  0  0  0  0
  9 46  1  0  0  0  0
 11 47  1  1  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 13 50  1  0  0  0  0
 13 51  1  0  0  0  0
 14 52  1  6  0  0  0
 15 53  1  0  0  0  0
 15 54  1  0  0  0  0
 15 55  1  0  0  0  0
 16 56  1  6  0  0  0
 17 57  1  0  0  0  0
 17 58  1  0  0  0  0
 19 59  1  0  0  0  0
 19 60  1  0  0  0  0
 21 61  1  1  0  0  0
 23 62  1  1  0  0  0
 24 63  1  0  0  0  0
 24 64  1  0  0  0  0
 24 65  1  0  0  0  0
 25 66  1  1  0  0  0
 26 67  1  0  0  0  0
 27 68  1  1  0  0  0
 28 69  1  0  0  0  0
 29 70  1  1  0  0  0
 30 71  1  0  0  0  0
 34 72  1  0  0  0  0
M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
   -2.8634   -3.6652    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.2283    0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7099   -4.0979   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -1.8012   -0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350   -1.4024   -1.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950    0.0673   -1.4753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3798    0.1540   -1.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    0.0182   -0.2948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1968   -0.7512   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9534   -0.7969    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660    1.4013    0.2216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3067    2.1529   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041    3.5732    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5124    3.5991    0.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2275    3.7514    1.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144    2.3356   -0.1379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7955    1.7322    0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518    0.3421    0.0122 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6596   -0.2353    0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.3549   -0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201   -0.1308    0.0734 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5389   -0.7233   -1.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.3377   -0.5937 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2996   -2.2458   -1.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -0.2267   -0.3574 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8386    0.5152   -1.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3519   -3.4249   -0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2865    2.2241   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3041    1.8561    0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2771    0.0611    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2732    1.9456    1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3683    1.3118    1.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4721    1.7554   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587   -1.9060    3.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  2  0
  8 11  1  0
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 12 13  1  0
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 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  1  0
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 29 30  1  0
 18 31  1  0
 31 32  1  1
 32 33  2  0
 32 34  1  0
 31  4  1  0
 18  6  1  0
 29 21  1  0
 31  8  1  0
 16 11  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  3 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  6 43  1  6
  7 44  1  0
  7 45  1  0
  9 46  1  0
 11 47  1  1
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 15 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  6
 17 57  1  0
 17 58  1  0
 19 59  1  0
 19 60  1  0
 21 61  1  1
 23 62  1  1
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  1
 26 67  1  0
 27 68  1  1
 28 69  1  0
 29 70  1  1
 30 71  1  0
 34 72  1  0
M  END


  Mrv1652306242118033D          

 72 76  0  0  0  0            999 V2000
   -2.8634   -3.6652    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.2283    0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7099   -4.0979   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -1.8012   -0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350   -1.4024   -1.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950    0.0673   -1.4753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3798    0.1540   -1.6965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9314    0.0182   -0.2948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1968   -0.7512   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9534   -0.7969    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660    1.4013    0.2216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3067    2.1529   -0.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0041    3.5732    0.1557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5124    3.5991    0.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2275    3.7514    1.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144    2.3356   -0.1379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7955    1.7322    0.4416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6518    0.3421    0.0122 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6596   -0.2353    0.4633 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6737    0.3549   -0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201   -0.1308    0.0734 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5389   -0.7233   -1.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.3377   -0.5937 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2996   -2.2458   -1.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -0.2267   -0.3574 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8386    0.5152   -1.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2110    0.6417    0.7478 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9895    1.7867    0.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7636    1.0320    0.5441 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6334    2.0637   -0.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7965   -0.5977    0.4362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9425   -0.7750    1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0446   -0.6365    2.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510   -1.1156    2.6394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9376   -4.7752    0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3519   -3.4249   -0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981   -3.2405    0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9419   -3.4591    1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9835   -3.7911   -2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958   -4.0590   -0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0464   -5.1477   -0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -1.9720   -2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2759    0.6192   -2.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7336    1.0059   -2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7829   -0.7477   -2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544   -1.3123   -1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2509    1.4364    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2865    2.2241   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3041    1.8561    0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5270    3.7496    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    4.3343   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0835    4.4709   -0.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709    4.0894    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4736    2.8857    2.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423    4.6142    2.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8763    2.5016   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1264    2.2749    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119    1.7207    1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7939    0.1009    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6961   -1.3322    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653   -0.8875    0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631   -1.8591    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7290   -3.1576   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3193   -2.5325   -1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220   -1.6792   -2.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7065   -0.6250   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    1.1964   -1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771    0.0611    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2732    1.9456    1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3683    1.3118    1.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4721    1.7554   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587   -1.9060    3.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
 11 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  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
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 31  4  1  0  0  0  0
 18  6  1  0  0  0  0
 29 21  1  0  0  0  0
 31  8  1  0  0  0  0
 16 11  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  2 38  1  1  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  3 41  1  0  0  0  0
  5 42  1  0  0  0  0
  6 43  1  6  0  0  0
  7 44  1  0  0  0  0
  7 45  1  0  0  0  0
  9 46  1  0  0  0  0
 11 47  1  1  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 13 50  1  0  0  0  0
 13 51  1  0  0  0  0
 14 52  1  6  0  0  0
 15 53  1  0  0  0  0
 15 54  1  0  0  0  0
 15 55  1  0  0  0  0
 16 56  1  6  0  0  0
 17 57  1  0  0  0  0
 17 58  1  0  0  0  0
 19 59  1  0  0  0  0
 19 60  1  0  0  0  0
 21 61  1  1  0  0  0
 23 62  1  1  0  0  0
 24 63  1  0  0  0  0
 24 64  1  0  0  0  0
 24 65  1  0  0  0  0
 25 66  1  1  0  0  0
 26 67  1  0  0  0  0
 27 68  1  1  0  0  0
 28 69  1  0  0  0  0
 29 70  1  1  0  0  0
 30 71  1  0  0  0  0
 34 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]12C(=C([H])[C@@]3([H])C([H])([H])[C@]1(C([H])=O)[C@]1([H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]1([H])C([H])([H])[C@@]23C([H])([H])O[C@@]1([H])O[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])[C@@]([H])(O[H])[C@@]1([H])O[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O8/c1-12(2)18-7-15-8-24(10-27)17-6-5-13(3)16(17)9-25(15,26(18,24)23(31)32)11-33-22-21(30)20(29)19(28)14(4)34-22/h7,10,12-17,19-22,28-30H,5-6,8-9,11H2,1-4H3,(H,31,32)/t13-,14+,15+,16-,17-,19-,20-,21-,22+,24+,25+,26+/m1/s1

> <INCHI_KEY>
YTWDSZAPPKUSFS-RMPMTSDOSA-N

> <FORMULA>
C26H38O8

> <MOLECULAR_WEIGHT>
478.582

> <EXACT_MASS>
478.256668184

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.912856770872466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4R,5R,8R,9S,11R)-9-formyl-5-methyl-13-(propan-2-yl)-2-({[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
1.4631774676666662

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.22477482333843

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1791157705755815

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612182335029072

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
121.7674

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,5R,8R,9S,11R)-9-formyl-13-isopropyl-5-methyl-2-({[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
   -2.8634   -3.6652    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.2283    0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7099   -4.0979   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -1.8012   -0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350   -1.4024   -1.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950    0.0673   -1.4753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3798    0.1540   -1.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    0.0182   -0.2948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1968   -0.7512   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9534   -0.7969    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660    1.4013    0.2216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3067    2.1529   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041    3.5732    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5124    3.5991    0.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2275    3.7514    1.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144    2.3356   -0.1379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7955    1.7322    0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518    0.3421    0.0122 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6596   -0.2353    0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.3549   -0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201   -0.1308    0.0734 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5389   -0.7233   -1.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.3377   -0.5937 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2996   -2.2458   -1.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -0.2267   -0.3574 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8386    0.5152   -1.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2110    0.6417    0.7478 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9895    1.7867    0.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7636    1.0320    0.5441 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6334    2.0637   -0.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7965   -0.5977    0.4362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9425   -0.7750    1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0446   -0.6365    2.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510   -1.1156    2.6394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9376   -4.7752    0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3519   -3.4249   -0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981   -3.2405    0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9419   -3.4591    1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9835   -3.7911   -2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958   -4.0590   -0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0464   -5.1477   -0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -1.9720   -2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2759    0.6192   -2.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7336    1.0059   -2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7829   -0.7477   -2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544   -1.3123   -1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2509    1.4364    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2865    2.2241   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3041    1.8561    0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5270    3.7496    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    4.3343   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0835    4.4709   -0.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709    4.0894    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4736    2.8857    2.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423    4.6142    2.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8763    2.5016   -1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1264    2.2749    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119    1.7207    1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7939    0.1009    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6961   -1.3322    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653   -0.8875    0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631   -1.8591    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7290   -3.1576   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3193   -2.5325   -1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220   -1.6792   -2.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7065   -0.6250   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    1.1964   -1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771    0.0611    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2732    1.9456    1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3683    1.3118    1.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4721    1.7554   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587   -1.9060    3.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 18 31  1  0
 31 32  1  1
 32 33  2  0
 32 34  1  0
 31  4  1  0
 18  6  1  0
 29 21  1  0
 31  8  1  0
 16 11  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  3 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  6 43  1  6
  7 44  1  0
  7 45  1  0
  9 46  1  0
 11 47  1  1
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
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 15 55  1  0
 16 56  1  6
 17 57  1  0
 17 58  1  0
 19 59  1  0
 19 60  1  0
 21 61  1  1
 23 62  1  1
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  1
 26 67  1  0
 27 68  1  1
 28 69  1  0
 29 70  1  1
 30 71  1  0
 34 72  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.863  -3.665   0.058  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.409  -3.228   0.064  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.710  -4.098  -0.960  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.292  -1.801  -0.297  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.635  -1.402  -1.414  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.895   0.067  -1.475  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.380   0.154  -1.696  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.931   0.018  -0.295  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.197  -0.751  -0.275  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.953  -0.797   0.654  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.166   1.401   0.222  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.307   2.153  -0.348  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.004   3.573   0.156  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.512   3.599   0.476  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.228   3.751   1.923  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.014   2.336  -0.138  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.796   1.732   0.442  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.652   0.342   0.012  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.660  -0.235   0.463  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.674   0.355  -0.289  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.920  -0.131   0.073  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.539  -0.723  -1.026  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.708  -1.338  -0.594  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.300  -2.246  -1.646  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.728  -0.227  -0.357  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.839   0.515  -1.532  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.211   0.642   0.748  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.989   1.787   0.840  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.764   1.032   0.544  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.633   2.064  -0.367  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.797  -0.598   0.436  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.942  -0.775   1.854  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.045  -0.637   2.463  0.00  0.00           O+0
HETATM   34  O   UNK     0      -0.851  -1.116   2.639  0.00  0.00           O+0
HETATM   35  H   UNK     0      -2.938  -4.775   0.184  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.352  -3.425  -0.895  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.398  -3.240   0.913  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.942  -3.459   1.045  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.984  -3.791  -2.001  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.396  -4.059  -0.796  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.046  -5.148  -0.841  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.063  -1.972  -2.104  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.276   0.619  -2.136  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.734   1.006  -2.255  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.783  -0.748  -2.252  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.454  -1.312  -1.166  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.251   1.436   1.338  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.287   2.224  -1.448  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.304   1.856   0.027  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.527   3.750   1.121  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.283   4.334  -0.591  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.083   4.471  -0.061  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.171   4.089   2.035  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.474   2.886   2.545  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.842   4.614   2.301  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.876   2.502  -1.198  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.126   2.275   0.247  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.912   1.721   1.565  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.794   0.101   1.531  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.696  -1.332   0.478  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.765  -0.888   0.896  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.563  -1.859   0.352  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.729  -3.158  -1.818  0.00  0.00           H+0
HETATM   64  H   UNK     0       6.319  -2.533  -1.310  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.422  -1.679  -2.595  0.00  0.00           H+0
HETATM   66  H   UNK     0       6.707  -0.625  -0.047  0.00  0.00           H+0
HETATM   67  H   UNK     0       6.545   1.196  -1.445  0.00  0.00           H+0
HETATM   68  H   UNK     0       5.277   0.061   1.690  0.00  0.00           H+0
HETATM   69  H   UNK     0       6.273   1.946   1.776  0.00  0.00           H+0
HETATM   70  H   UNK     0       3.368   1.312   1.556  0.00  0.00           H+0
HETATM   71  H   UNK     0       3.472   1.755  -1.279  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.859  -1.906   3.281  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3    4   38                                             
CONECT    3    2   39   40   41                                             
CONECT    4    2    5   31                                                  
CONECT    5    4    6   42                                                  
CONECT    6    5    7   18   43                                             
CONECT    7    6    8   44   45                                             
CONECT    8    7    9   11   31                                             
CONECT    9    8   10   46                                                  
CONECT   10    9                                                            
CONECT   11    8   12   16   47                                             
CONECT   12   11   13   48   49                                             
CONECT   13   12   14   50   51                                             
CONECT   14   13   15   16   52                                             
CONECT   15   14   53   54   55                                             
CONECT   16   14   17   11   56                                             
CONECT   17   16   18   57   58                                             
CONECT   18   17   19   31    6                                             
CONECT   19   18   20   59   60                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   29   61                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   25   62                                             
CONECT   24   23   63   64   65                                             
CONECT   25   23   26   27   66                                             
CONECT   26   25   67                                                       
CONECT   27   25   28   29   68                                             
CONECT   28   27   69                                                       
CONECT   29   27   30   21   70                                             
CONECT   30   29   71                                                       
CONECT   31   18   32    4    8                                             
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   72                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    2                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    7                                                            
CONECT   45    7                                                            
CONECT   46    9                                                            
CONECT   47   11                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   17                                                            
CONECT   58   17                                                            
CONECT   59   19                                                            
CONECT   60   19                                                            
CONECT   61   21                                                            
CONECT   62   23                                                            
CONECT   63   24                                                            
CONECT   64   24                                                            
CONECT   65   24                                                            
CONECT   66   25                                                            
CONECT   67   26                                                            
CONECT   68   27                                                            
CONECT   69   28                                                            
CONECT   70   29                                                            
CONECT   71   30                                                            
CONECT   72   34                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  152    0
END

RDKit          3D

72 76  0  0  0  0  0  0  0  0999 V2000
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   -1.4092   -3.2283    0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.2915   -1.8012   -0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350   -1.4024   -1.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3798    0.1540   -1.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    0.0182   -0.2948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1968   -0.7512   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9534   -0.7969    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660    1.4013    0.2216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3067    2.1529   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041    3.5732    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5124    3.5991    0.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.6334    2.0637   -0.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7965   -0.5977    0.4362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9425   -0.7750    1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0446   -0.6365    2.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510   -1.1156    2.6394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9376   -4.7752    0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3519   -3.4249   -0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9835   -3.7911   -2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7939    0.1009    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6961   -1.3322    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653   -0.8875    0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631   -1.8591    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7290   -3.1576   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3193   -2.5325   -1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220   -1.6792   -2.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7065   -0.6250   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    1.1964   -1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771    0.0611    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2732    1.9456    1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3683    1.3118    1.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4721    1.7554   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587   -1.9060    3.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 18 31  1  0
 31 32  1  1
 32 33  2  0
 32 34  1  0
 31  4  1  0
 18  6  1  0
 29 21  1  0
 31  8  1  0
 16 11  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  3 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  6 43  1  6
  7 44  1  0
  7 45  1  0
  9 46  1  0
 11 47  1  1
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 15 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  6
 17 57  1  0
 17 58  1  0
 19 59  1  0
 19 60  1  0
 21 61  1  1
 23 62  1  1
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  1
 26 67  1  0
 27 68  1  1
 28 69  1  0
 29 70  1  1
 30 71  1  0
 34 72  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(4R,5R,8R)-9-Formyl-5-methyl-13-(propan-2-yl)-2-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}tetracyclo[7.4.0.0,.0,]tridec-12-ene-1-carboxylate	Generator

Chemical Formula

C₂₆H₃₈O₈

Average Mass

478.5820 Da

Monoisotopic Mass

478.25667 Da

IUPAC Name

(1R,2S,4R,5R,8R,9S,11R)-9-formyl-5-methyl-13-(propan-2-yl)-2-({[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

Traditional Name

(1R,2S,4R,5R,8R,9S,11R)-9-formyl-13-isopropyl-5-methyl-2-({[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2CC3(C=O)[C@@H]4CC[C@@H](C)[C@H]4CC2(COC2OC(C)C(O)C(O)C2O)C13C(O)=O

InChI Identifier

InChI=1S/C26H38O8/c1-12(2)18-7-15-8-24(10-27)17-6-5-13(3)16(17)9-25(15,26(18,24)23(31)32)11-33-22-21(30)20(29)19(28)14(4)34-22/h7,10,12-17,19-22,28-30H,5-6,8-9,11H2,1-4H3,(H,31,32)/t13-,14?,15?,16-,17-,19?,20?,21?,22?,24?,25?,26?/m1/s1

InChI Key

YTWDSZAPPKUSFS-RMPMTSDOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces	NPAtlas	11827037

Species Where Detected

Species Name	Source	Reference
Streptomyces avermitilis ATCC31272	KNApSAcK Database	22123792
Streptomyces capreolus ATCC31963	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Polyol
Carbonyl group
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
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	1.68	ALOGPS
logP	1.46	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.18	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.77 m³·mol⁻¹	ChemAxon
Polarizability	50.91 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA014753

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78445433

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587202

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hall RM, Dawson MJ, Jones CA, Roberts AD, Sidebottom PJ, Stead P, Taylor NL: The production of novel sordarin analogues by biotransformation. J Antibiot (Tokyo). 2001 Nov;54(11):948-57. doi: 10.7164/antibiotics.54.948. [PubMed:11827037 ]

Showing NP-Card for 4'-O-Demethylsordarin (NP0004007)

MOL for NP0004007 (4'-O-Demethylsordarin)

3D MOL for NP0004007 (4'-O-Demethylsordarin)

3D SDF for NP0004007 (4'-O-Demethylsordarin)

3D-SDF for NP0004007 (4'-O-Demethylsordarin)

PDB for NP0004007 (4'-O-Demethylsordarin)

3D PDB for NP0004007 (4'-O-Demethylsordarin)

SMILES for NP0004007 (4'-O-Demethylsordarin)

INCHI for NP0004007 (4'-O-Demethylsordarin)

Structure for NP0004007 (4'-O-Demethylsordarin)

3D Structure for NP0004007 (4'-O-Demethylsordarin)