NP-MRD: Showing NP-Card for 3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid (NP0188694)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 05:03:47 UTC

Updated at

2022-09-04 05:03:47 UTC

NP-MRD ID

NP0188694

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid

Description

Oleficin belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid was first documented in 1982 (PMID: 6818995). Based on a literature review very few articles have been published on Oleficin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042207032D          

 44 45  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6687  -11.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4534  -11.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138  -12.4070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8987  -13.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632  -13.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0481  -14.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7125  -15.2493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8686  -14.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888  -12.4070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1039  -13.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3339  -11.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5492  -11.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  4  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 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  2  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  2  0  0  0  0
  2 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 33 32  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 33 41  1  0  0  0  0
 31 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
M  END

     RDKit          3D

 91 92  0  0  0  0  0  0  0  0999 V2000
   -3.7976   -1.0966    0.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5363    0.3276    0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2888    1.0491    0.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164    0.4924    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8213   -0.8962    0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -1.2855    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -0.3621    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655   -0.8983    0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256    0.0033    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1506   -0.4660   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3264    0.3833   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5367   -0.1362   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7340    0.6549   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6212    2.0316   -0.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9197    0.1024   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1854    0.8298   -0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4243    1.9631   -0.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1182   -0.1228   -1.3014 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.4886    0.3210   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6160   -0.4253   -1.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8986    0.1995   -1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8994    1.1624   -0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0980   -0.3224   -1.5763 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7075   -1.3804   -0.7304 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5170   -2.5062   -0.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2687   -1.3043   -0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5414   -2.3147   -0.5390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619    1.0633    1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0082    0.5893    1.1414 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5594    1.0516    2.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9699    0.9722    0.0908 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1987    0.2862    0.2663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5284   -0.5170   -0.7946 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3911   -1.9755   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4878   -2.2248    0.6387 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.3150   -1.3983    1.7378 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7903   -1.9080   -0.0252 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.8090   -1.9746    0.9402 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8486   -0.5987   -0.7237 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.2863    0.4722    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7121   -0.2346   -1.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3218    2.3965   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1770    3.3424   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3201    2.9445    0.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5603   -1.7707    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822   -1.2844    0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2776   -1.4052   -0.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2797    2.1610    0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2358    1.2038    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327   -1.7039    0.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6399   -2.3731    0.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    0.7123    0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877   -1.9561    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056    1.0742    0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2781   -1.5353   -0.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2671    1.4639   -0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5776   -1.2343   -0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0290    2.5642   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8865   -0.0423   -2.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6129    1.4034   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6064    0.3365    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6078   -0.2851   -2.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6226   -1.5032   -1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3558   -0.3777   -2.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9099   -3.0569   -1.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8598   -3.2493    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3053   -2.2338    0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4714    2.1339    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1432   -0.5347    1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5039    0.5690    2.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5500    2.1300    2.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7979    0.6506    3.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5859    0.6187   -0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7141   -0.3948   -1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6397   -2.5688   -1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3822   -2.1410    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5168   -3.2990    0.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5714   -1.6629    2.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0041   -2.7320   -0.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4419   -2.1960    1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6704   -0.6559   -1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2259    1.4767   -0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7016    0.3984    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3524    0.3417    0.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8927    2.4175   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5035    4.1666   -1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3579    2.8523   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9003    3.9047    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8796    3.7627    1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7694    2.1267    1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1883    3.4375    0.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
 43 42  1  0
 42 44  1  0
 42 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 31 29  1  0
 29 30  1  0
 29 28  1  0
 28  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 23  1  0
 21 22  2  0
 18 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 41 33  1  0
 26 15  1  0
 43 86  1  0
 43 87  1  0
 43 88  1  0
 42 85  1  0
 44 89  1  0
 44 90  1  0
 44 91  1  0
 31 73  1  6
 33 74  1  6
 34 75  1  0
 34 76  1  0
 35 77  1  1
 36 78  1  0
 37 79  1  6
 38 80  1  0
 39 81  1  6
 40 82  1  0
 40 83  1  0
 40 84  1  0
 29 69  1  1
 30 70  1  0
 30 71  1  0
 30 72  1  0
 28 68  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  3 48  1  0
  4 49  1  0
  5 50  1  0
  6 51  1  0
  7 52  1  0
  8 53  1  0
  9 54  1  0
 10 55  1  0
 11 56  1  0
 12 57  1  0
 14 58  1  0
 18 59  1  6
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
M  END


  Mrv1652309042207032D          

 44 45  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6687  -11.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4534  -11.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138  -12.4070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8987  -13.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632  -13.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0481  -14.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7125  -15.2493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8686  -14.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888  -12.4070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1039  -13.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3339  -11.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5492  -11.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  4  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 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  2  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  2  0  0  0  0
  2 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 33 32  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 33 41  1  0  0  0  0
 31 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188694

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](O[C@H]1C[C@@H](O)[C@@H](O)[C@@H](C)O1)[C@H](C)\C=C(/C)\C=C/C=C\C=C\C=C\C=C\C(O)=C1C(=O)[C@@H](CCC(O)=O)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H47NO9/c1-21(2)33(44-29-20-27(37)31(40)24(5)43-29)23(4)19-22(3)15-13-11-9-7-8-10-12-14-16-26(36)30-32(41)25(17-18-28(38)39)35(6)34(30)42/h7-16,19,21,23-25,27,29,31,33,36-37,40H,17-18,20H2,1-6H3,(H,38,39)/b8-7+,11-9-,12-10+,15-13-,16-14+,22-19+,30-26?/t23-,24-,25-,27-,29+,31+,33+/m1/s1

> <INCHI_KEY>
UZDYIIINJYOXLQ-YIKHYYSESA-N

> <FORMULA>
C34H47NO9

> <MOLECULAR_WEIGHT>
613.748

> <EXACT_MASS>
613.325082097

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
69.89558435826885

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2R)-4-[(2E,4E,6E,8Z,10Z,12E,14R,15S)-15-{[(2R,4R,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid

> <JCHEM_LOGP>
3.9832568933333303

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.515554690760595

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.072526835391175

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0173582116724078

> <JCHEM_POLAR_SURFACE_AREA>
153.82999999999998

> <JCHEM_REFRACTIVITY>
174.7916000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2R)-4-[(2E,4E,6E,8Z,10Z,12E,14R,15S)-15-{[(2R,4R,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.669 -18.480   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.582 -21.695   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.046 -21.219   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.106 -23.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.011 -24.406   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.385 -25.813   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.290 -27.058   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.663 -28.465   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.821 -26.897   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       8.566 -23.160   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       7.661 -24.406   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.090 -21.695   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.625 -21.219   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   26                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   15   27                                                  
CONECT   27   26                                                            
CONECT   28    2   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   42                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   41                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   33                                                       
CONECT   42   31   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₇NO₉

Average Mass

613.7480 Da

Monoisotopic Mass

613.32508 Da

IUPAC Name

3-[(2R)-4-[(2E,4E,6E,8Z,10Z,12E,14R,15S)-15-{[(2R,4R,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](O[C@H]1C[C@@H](O)[C@@H](O)[C@@H](C)O1)[C@H](C)\C=C(/C)\C=C/C=C\C=C\C=C\C=C\C(O)=C1C(=O)[C@@H](CCC(O)=O)N(C)C1=O

InChI Identifier

InChI=1S/C34H47NO9/c1-21(2)33(44-29-20-27(37)31(40)24(5)43-29)23(4)19-22(3)15-13-11-9-7-8-10-12-14-16-26(36)30-32(41)25(17-18-28(38)39)35(6)34(30)42/h7-16,19,21,23-25,27,29,31,33,36-37,40H,17-18,20H2,1-6H3,(H,38,39)/b8-7+,11-9-,12-10+,15-13-,16-14+,22-19+,30-26?/t23-,24-,25-,27-,29+,31+,33+/m1/s1

InChI Key

UZDYIIINJYOXLQ-YIKHYYSESA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
N-alkylpyrrolidine
3-pyrrolidone
2-pyrrolidone
Pyrrolidone
Oxane
Monosaccharide
Vinylogous acid
Tertiary carboxylic acid amide
Pyrrolidine
Cyclic ketone
Secondary alcohol
Lactam
Ketone
Carboxamide group
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.98	ChemAxon
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	153.83 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	174.79 m³·mol⁻¹	ChemAxon
Polarizability	69.9 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

C00018806

Chemspider ID

78443181

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139589208

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kovac L, Poliachova V, Horvath I: Ionophores and intact cells. II. Oleficin acts on mitochondria and induces disintegration of the mitochondrial genome in yeast Saccharomyces cerevisiae. Biochim Biophys Acta. 1982 Dec 30;721(4):349-56. doi: 10.1016/0167-4889(82)90089-1. [PubMed:6818995 ]
LOTUS database [Link]

Showing NP-Card for 3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid (NP0188694)

MOL for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)

3D MOL for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)

3D SDF for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)

3D-SDF for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)

PDB for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)

3D PDB for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)

SMILES for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)

INCHI for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)

Structure for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)

3D Structure for NP0188694 (3-[(2r)-4-[(2e,4e,6e,8z,10z,12e,14r,15s)-15-{[(2r,4r,5r,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-12,14,16-trimethylheptadeca-2,4,6,8,10,12-hexaen-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid)