NP-MRD: Showing NP-Card for 14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate (NP0163222)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 21:47:28 UTC

Updated at

2022-09-02 21:47:28 UTC

NP-MRD ID

NP0163222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate

Description

14-Formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]Pentacosan-20-yl acetate belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. 14-Formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]Pentacosan-20-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171520502D          

 43 49  0  0  0  0            999 V2000
    2.3538   -3.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1633   -3.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060   -2.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -4.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2394   -4.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8441   -3.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5647   -4.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6386   -3.2937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454   -3.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5048   -3.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2855   -2.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9068   -3.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6876   -3.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3089   -3.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0896   -3.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7109   -3.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4916   -3.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1129   -4.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8936   -3.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5149   -4.4199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9535   -4.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1727   -5.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0133   -6.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5515   -4.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3920   -5.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7707   -4.9438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1494   -4.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3687   -4.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7474   -4.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5880   -4.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2093   -5.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -4.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8073   -5.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0266   -5.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4053   -4.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1621   -5.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862   -5.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1844   -5.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5313   -6.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9265   -7.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0250   -7.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059   -6.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653   -5.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 29 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 38 43  1  0  0  0  0
M  END

     RDKit          3D

 85 91  0  0  0  0  0  0  0  0999 V2000
   -7.7497    1.7466    2.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5360    0.9081    2.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1916    0.0825    3.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7476    0.9979    1.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5906    0.2084    0.9425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4356    1.2186    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8520    1.0244   -0.4656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5204    1.7419   -1.4178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3917    1.2374   -0.6025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9678    2.6784   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841    2.7415   -1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608    1.4425   -1.1312 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6127    1.7874   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5718    0.8198   -0.7662 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7521   -0.3331   -1.5468 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9562   -0.9087   -1.0762 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9263    0.0549   -1.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0790   -0.1780   -0.5029 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3031    0.9777    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4773    0.7936    1.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1787   -1.5058    0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9816   -1.9104    0.9480 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9678   -3.3021    1.0654 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7097   -1.3813    0.3162 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8207   -2.4670    0.2433 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1689   -0.4499    1.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2232    0.3702    0.6166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8414   -0.2747    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893    0.8792    0.2301 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2044    1.9464    1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869    1.7184    2.3959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470    0.4668    0.3791 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7875   -0.9852    0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2760   -1.2526    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0823   -0.4985   -0.7110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8317   -0.8491   -2.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5659   -0.4776   -0.4007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2856   -1.7093   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8926   -2.8892   -0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0245   -3.8308   -0.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0042   -5.0673   -1.1798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1368   -3.1406   -0.4845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7582   -1.8212   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6302    1.1745    2.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5083    2.5691    3.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0082    2.2625    1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4694   -0.4625    1.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8044    2.2636    1.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7900    1.0007    1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9887    1.9782   -2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1044    0.8355   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678    3.1449    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197    3.2507   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9914    3.5821   -0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862    2.9238   -2.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9019    0.7026   -1.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8170    1.9015   -2.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7989    2.7858   -0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726    1.3338   -0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1671   -1.7711   -1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9280   -0.1152   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4450    1.9292   -0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4278    1.1172    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2538    0.6566    2.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4041   -2.2872   -0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0559   -1.4614    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1059   -1.5236    1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5238   -3.7211    0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3302   -3.2489   -0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1758    1.2961    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5547   -0.7733    1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8631   -0.9378   -0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6841    2.8818    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165    0.6650    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2808   -1.5963    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4779   -1.3109   -0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5540   -0.9506    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -2.3194    0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9838   -1.5701   -2.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5974    0.0516   -2.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7618   -1.2723   -2.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9968    0.2911   -1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141   -3.2578   -1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0059   -1.4679    0.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2916   -1.1608   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  1
 30 31  2  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  6
 35 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 40 42  1  0
 42 43  1  0
 37  5  1  0
 43 38  1  0
 35  7  1  0
 32  9  1  0
 29 12  1  0
 27 14  1  0
 24 16  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  5 47  1  1
  6 48  1  0
  6 49  1  0
  8 50  1  0
  9 51  1  6
 10 52  1  0
 10 53  1  0
 11 54  1  0
 11 55  1  0
 12 56  1  6
 13 57  1  0
 13 58  1  0
 14 59  1  1
 16 60  1  6
 18 61  1  6
 19 62  1  0
 19 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  1
 23 68  1  0
 25 69  1  0
 27 70  1  1
 28 71  1  0
 28 72  1  0
 30 73  1  0
 32 74  1  1
 33 75  1  0
 33 76  1  0
 34 77  1  0
 34 78  1  0
 36 79  1  0
 36 80  1  0
 36 81  1  0
 37 82  1  6
 39 83  1  0
 43 84  1  0
 43 85  1  0
M  END


  Mrv1533004171520502D          

 43 49  0  0  0  0            999 V2000
    2.3538   -3.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1633   -3.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060   -2.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -4.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2394   -4.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8441   -3.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5647   -4.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6386   -3.2937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454   -3.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5048   -3.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2855   -2.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9068   -3.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6876   -3.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3089   -3.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0896   -3.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7109   -3.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4916   -3.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1129   -4.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8936   -3.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5149   -4.4199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9535   -4.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1727   -5.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0133   -6.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5515   -4.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3920   -5.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7707   -4.9438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1494   -4.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3687   -4.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7474   -4.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5880   -4.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2093   -5.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -4.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8073   -5.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0266   -5.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4053   -4.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1621   -5.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862   -5.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1844   -5.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5313   -6.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9265   -7.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0250   -7.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059   -6.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653   -5.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 29 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 38 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2(O)C3CCC4CC5OC6OC(CO)CC(O)C6(O)OC5CC4(C=O)C3CCC2(C)C1C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C31H42O12/c1-15(34)40-23-11-30(37)20-4-3-17-8-21-22(43-31(38)24(35)9-18(12-32)41-27(31)42-21)10-29(17,14-33)19(20)5-6-28(30,2)26(23)16-7-25(36)39-13-16/h7,14,17-24,26-27,32,35,37-38H,3-6,8-13H2,1-2H3

> <INCHI_KEY>
VKBDXZRKAYVFOV-UHFFFAOYSA-N

> <FORMULA>
C31H42O12

> <MOLECULAR_WEIGHT>
606.665

> <EXACT_MASS>
606.267626792

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
63.8448735789525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate

> <ALOGPS_LOGP>
-0.15

> <JCHEM_LOGP>
-0.023427500000001142

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.460616248203237

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.818483880110244

> <JCHEM_PKA_STRONGEST_BASIC>
-2.944730495498864

> <JCHEM_POLAR_SURFACE_AREA>
178.28

> <JCHEM_REFRACTIVITY>
145.76770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.394  -5.927   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.905  -6.225   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.918  -5.065   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.403  -7.682   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.914  -7.980   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.042  -6.932   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.387  -7.682   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.525  -6.148   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.845  -7.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.142  -5.673   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.600  -5.176   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.759  -6.189   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.217  -5.691   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.377  -6.704   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      18.834  -6.206   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      19.994  -7.220   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      21.451  -6.722   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      22.611  -7.735   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.068  -7.237   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      25.228  -8.250   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      22.313  -9.246   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.856  -9.744   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      20.558 -11.255   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      19.696  -8.731   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      19.398 -10.242   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      18.239  -9.228   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.079  -8.215   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.622  -8.713   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.462  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.164  -9.211   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.324 -10.224   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.005  -8.198   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.707  -9.709   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.250 -10.206   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.090  -9.193   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.636 -10.665   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.561  -9.377   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.811 -10.722   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.458 -12.119   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.329 -13.167   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.513 -14.696   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       5.984 -12.417   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       6.282 -10.906   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   35                                             
CONECT    8    7                                                            
CONECT    9    7   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   16   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   14   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   12   30   32                                             
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29    9   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    7   36   37                                             
CONECT   36   35                                                            
CONECT   37   35    5   38                                                  
CONECT   38   37   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   38                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Value	Source
14-Formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0,.0,.0,.0,]pentacosan-20-yl acetic acid	Generator
14-Formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetic acid	Generator

Chemical Formula

C₃₁H₄₂O₁₂

Average Mass

606.6650 Da

Monoisotopic Mass

606.26763 Da

IUPAC Name

14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate

Traditional Name

14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2(O)C3CCC4CC5OC6OC(CO)CC(O)C6(O)OC5CC4(C=O)C3CCC2(C)C1C1=CC(=O)OC1

InChI Identifier

InChI=1S/C31H42O12/c1-15(34)40-23-11-30(37)20-4-3-17-8-21-22(43-31(38)24(35)9-18(12-32)41-27(31)42-21)10-29(17,14-33)19(20)5-6-28(30,2)26(23)16-7-25(36)39-13-16/h7,14,17-24,26-27,32,35,37-38H,3-6,8-13H2,1-2H3

InChI Key

VKBDXZRKAYVFOV-UHFFFAOYSA-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 cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroid ester
19-oxosteroid
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
Para-dioxane
2-furanone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Carboxylic acid ester
Secondary alcohol
Hemiacetal
Lactone
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Primary alcohol
Aldehyde
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.15	ALOGPS
logP	-0.023	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.82	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	178.28 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	145.77 m³·mol⁻¹	ChemAxon
Polarizability	63.84 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56680763

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate (NP0163222)

MOL for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)

3D MOL for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)

3D SDF for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)

3D-SDF for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)

PDB for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)

3D PDB for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)

SMILES for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)

INCHI for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)

Structure for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)

3D Structure for NP0163222 (14-formyl-9,10,22-trihydroxy-7-(hydroxymethyl)-18-methyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-20-yl acetate)