NP-MRD: Showing NP-Card for 4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde (NP0258499)

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Record Information

Version

2.0

Created at

2022-09-07 23:59:15 UTC

Updated at

2022-09-07 23:59:15 UTC

NP-MRD ID

NP0258499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde

Description

9-Hydroxy-14-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-6,6,11,15-tetramethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-1-carbaldehyde belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde is found in Momordica charantia. 9-Hydroxy-14-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-6,6,11,15-tetramethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-1-carbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502022D          

 57 62  0  0  0  0            999 V2000
   -2.6962    0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8244   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1353   -1.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3307   -0.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1480   -0.3044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4589   -1.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9525   -1.7199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2634   -2.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7571   -3.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0680   -3.8996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0807   -2.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3915   -3.3612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5870   -1.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4043   -2.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2761   -1.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7825   -0.5301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0198    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5262    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2153    1.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3434    1.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1983   -2.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8353   -3.6824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -2.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4768   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2253   -4.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6935   -5.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738   -5.8151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374   -4.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3177   -5.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5692   -3.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3813   -4.0682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8207   -2.5163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643   -3.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -3.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995   -0.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 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
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 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
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 39 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 37 46  1  0  0  0  0
 46 47  1  0  0  0  0
 35 48  1  0  0  0  0
 31 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 32 51  1  0  0  0  0
 27 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 22 54  1  0  0  0  0
 25 54  1  0  0  0  0
 54 55  1  0  0  0  0
 51 56  1  0  0  0  0
 56 57  2  0  0  0  0
M  END

     RDKit          3D

125130  0  0  0  0  0  0  0  0999 V2000
   -7.0967   -1.0669   -3.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9628   -2.1538   -2.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4540   -3.5123   -2.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4496   -1.9644   -0.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9478   -0.6572   -0.4287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8022    0.3211   -1.0071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5490    1.0067   -0.0587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8868    0.6474   -0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6788    1.3149    0.8094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.3859    0.8874    2.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6387   -0.5018    2.2787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6100    2.8144    0.6493 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.8379    3.3308    0.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5027    3.2586   -0.2321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9517    3.1531   -1.5702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2555    2.4495   -0.1289 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5541    2.6969   -1.3410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5352   -0.4398   -0.8197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2797    0.9075   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167   -1.3165   -0.0374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6761   -2.7026   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2730   -0.5963   -0.0705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5430   -0.3699   -1.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151    0.6512   -0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3823    0.4198    0.6492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2128    1.4238    1.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    0.4586    1.1831 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6743    1.7234    0.6874 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1647    2.8826    1.2864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1399    1.7466    0.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8685    0.6627    0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2270   -0.6306    0.6045 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5881   -0.9022   -0.8372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9445   -0.3224   -1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8887   -0.2111   -0.0050 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0153    0.4505   -0.4934 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1668   -0.3485   -0.4606 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0516    0.2198    0.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3792    0.1006    0.1138 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1404    1.0731    0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6763    2.3556    0.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7507    0.3859   -1.3165 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1414    0.2329   -1.4341 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0385   -0.6975   -2.1347 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4760   -1.9402   -1.7213 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5849   -0.5492   -1.8714 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1203    0.5318   -2.6607 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    0.6184    1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414    1.9978    1.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5808   -0.0673    2.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145   -0.7626    0.9891 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8077   -1.4940    2.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0480   -2.6845    2.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2656   -2.0726    0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1077   -0.9222    0.8018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5294   -1.1285    2.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2558   -1.4829   -4.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2403   -0.3727   -3.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0031   -0.4389   -2.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0076   -3.7026   -3.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1431   -4.3003   -1.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5619   -3.4661   -2.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4210   -2.8557   -0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1326   -0.6002    0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1996    0.6197    0.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7274    1.0265    0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3583    1.0319    2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1356    1.3300    2.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1675   -0.9546    1.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4695    3.2507    1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2467    2.5773   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2331    4.3351   -0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5479    3.8917   -1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5593    2.8163    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8167    3.3169   -1.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -0.4856   -1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4957    0.9930    0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9369   -1.2237    1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2973   -2.8833   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7428   -3.3279   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2369   -3.2740    0.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5589    0.4863    0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1008   -1.2226   -1.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1355    0.1771   -2.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858    0.5581   -1.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9101    1.6851   -0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5604    2.2402    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004201502022D          

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 56 57  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0258499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C(O)C(OC1OC(CO)C(O)C(O)C1O)C=C(C)C)C1CCC2(C)C3C(O)C=C4C(CCC(OC5OC(CO)C(O)C(O)C5O)C4(C)C)C3(CCC12C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H68O15/c1-19(2)14-25(54-37-34(52)32(50)30(48)26(16-43)55-37)29(47)20(3)21-10-11-41(7)36-24(46)15-23-22(42(36,18-45)13-12-40(21,41)6)8-9-28(39(23,4)5)57-38-35(53)33(51)31(49)27(17-44)56-38/h14-15,18,20-22,24-38,43-44,46-53H,8-13,16-17H2,1-7H3

> <INCHI_KEY>
ZCVDJGDEHWAVSV-UHFFFAOYSA-N

> <FORMULA>
C42H68O15

> <MOLECULAR_WEIGHT>
812.991

> <EXACT_MASS>
812.45582149

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
87.82347309780104

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-hydroxy-14-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-6,6,11,15-tetramethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

> <ALOGPS_LOGP>
0.33

> <JCHEM_LOGP>
-0.13888288000000015

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.421620237340047

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.905429731631655

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0106934627970405

> <JCHEM_POLAR_SURFACE_AREA>
256.28999999999996

> <JCHEM_REFRACTIVITY>
204.66820000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-14-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-6,6,11,15-tetramethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -5.033   0.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.139  -1.573   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -7.719  -3.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -8.084  -0.358   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -9.610  -0.568   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0     -10.190  -1.995   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -9.245  -3.211   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -9.825  -4.637   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.880  -5.853   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -9.460  -7.279   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -11.351  -4.848   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -11.931  -6.274   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0     -12.296  -3.632   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -13.821  -3.843   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -11.715  -2.205   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -12.661  -0.990   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -7.504   1.069   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.449   2.285   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.869   3.711   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.974   2.074   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.237  -5.472   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.559  -6.874   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.490  -5.603   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.497  -6.781   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.021  -8.229   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.028  -9.406   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.551 -10.855   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       7.536  -8.500   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       8.060  -9.949   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.529  -7.323   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      10.045  -7.594   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       8.006  -5.874   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       8.999  -4.697   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.600  -6.094   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       3.240  -6.586   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       0.372  -0.445   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    7   17                                                  
CONECT   17   16                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    2   23   54                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   54                                             
CONECT   26   25                                                            
CONECT   27   25   28   51                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   48                                                  
CONECT   32   31   33   51                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   48                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   46                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   39   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   37   47                                                  
CONECT   47   46                                                            
CONECT   48   35   31   49   50                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   32   27   52   56                                             
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   22   25   55                                             
CONECT   55   54                                                            
CONECT   56   51   57                                                       
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₆₈O₁₅

Average Mass

812.9910 Da

Monoisotopic Mass

812.45582 Da

IUPAC Name

9-hydroxy-14-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-6,6,11,15-tetramethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C(O)C(OC1OC(CO)C(O)C(O)C1O)C=C(C)C)C1CCC2(C)C3C(O)C=C4C(CCC(OC5OC(CO)C(O)C(O)C5O)C4(C)C)C3(CCC12C)C=O

InChI Identifier

InChI=1S/C42H68O15/c1-19(2)14-25(54-37-34(52)32(50)30(48)26(16-43)55-37)29(47)20(3)21-10-11-41(7)36-24(46)15-23-22(42(36,18-45)13-12-40(21,41)6)8-9-28(39(23,4)5)57-38-35(53)33(51)31(49)27(17-44)56-38/h14-15,18,20-22,24-38,43-44,46-53H,8-13,16-17H2,1-7H3

InChI Key

ZCVDJGDEHWAVSV-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

Species Name	Source	Reference
Momordica charantia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Cucurbitacin skeleton
Triterpenoid
22-hydroxysteroid
19-oxosteroid
7-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-5-steroid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty acyl
Oxane
Monosaccharide
Secondary alcohol
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Primary alcohol
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Aldehyde
Hydrocarbon derivative
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	0.33	ALOGPS
logP	-0.14	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	256.29 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	204.67 m³·mol⁻¹	ChemAxon
Polarizability	87.82 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

75214647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde (NP0258499)

MOL for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)

3D MOL for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)

3D SDF for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)

3D-SDF for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)

PDB for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)

3D PDB for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)

SMILES for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)

INCHI for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)

Structure for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)

3D Structure for NP0258499 (4-hydroxy-1-(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-5-en-2-yl)-3a,6,6,11a-tetramethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthrene-9b-carbaldehyde)