NP-MRD: Showing NP-Card for methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate (NP0196879)

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Record Information

Version

2.0

Created at

2022-09-04 15:02:54 UTC

Updated at

2022-09-04 15:02:55 UTC

NP-MRD ID

NP0196879

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate

Description

Methyl 2-{[2-formyl-4,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate is found in Asclepias curassavica. Methyl 2-{[2-formyl-4,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161507452D          

 40 45  0  0  0  0            999 V2000
   -6.5877   -0.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7952   -0.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003   -0.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3980   -1.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4078   -0.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2626   -1.3564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7187    0.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0880    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1476    1.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    0.3162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3653   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1953   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4756    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1794    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -0.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416   -1.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1505    0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9211    1.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6040    1.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308    2.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2553    1.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926    0.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 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
 20 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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 18 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 19 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 13 37  1  0  0  0  0
 37 38  1  0  0  0  0
 35 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END

     RDKit          3D

 82 87  0  0  0  0  0  0  0  0999 V2000
   -5.4403    2.4238    2.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8566    2.0819    1.5585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6569    0.7927    1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1032   -0.0132    1.8556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0844    0.4441   -0.2965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6729    1.5542   -0.9274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1651   -0.6100   -0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6826   -1.7191   -1.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9824   -2.7879   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7486   -1.1356   -1.8743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0319   -0.1922   -1.1400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0476   -0.8566   -0.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7549   -0.5120   -0.8087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1836    0.1448    0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7435    0.4922    0.2927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5743    1.3493   -0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8538    1.7710   -1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7904    0.9973   -0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4712   -0.4547   -0.0002 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2629   -1.2531   -1.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7085   -1.1937   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1739    0.2058   -0.4434 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3142    0.3874   -1.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7457    0.4679    0.9370 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0951   -0.0361    1.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2009    0.5722    1.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3344   -0.3551    1.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5313   -0.0436    1.9009 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8341   -1.5960    1.3164 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4570   -1.5008    1.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6965    1.9515    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7547    2.4491    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1618    1.2780   -0.6626 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1549    1.6244   -2.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -0.7870    0.0458 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3241   -1.6965    1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2619   -2.8987    1.0347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -1.4601   -1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247   -1.6323   -1.3048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2016   -1.8288   -2.6617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3664    2.7151    2.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0264    3.2681    3.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5060    1.5234    3.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3991    1.4734   -1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1594   -0.2421   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2872   -0.9843    0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4855   -2.1672   -1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7902   -2.4561    0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0853   -3.1578   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6868   -3.6656   -0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6602    0.5460   -1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8244    0.2660   -1.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7645    1.1038    0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3865   -0.4507    1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035    1.0024    1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    2.2258   -0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786    0.8232   -1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    1.7371   -2.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8992    2.8505   -0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7140    1.4513    0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -0.7911    0.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9911   -2.3458   -0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455   -0.8791   -2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2772   -1.7910   -1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7993   -1.7694    0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2972    0.4721   -0.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3908   -0.4781   -2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128    1.2691   -2.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342    0.0258    1.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3424    1.6242    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8487   -2.0202    1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2495   -1.8692   -0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6857    2.4459    1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3385    2.2149    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1979    3.2014   -0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185    2.9963    0.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2638    2.5962   -2.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -1.3306    2.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0130   -0.9886   -2.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147   -2.5030   -1.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2143   -2.5483   -0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132   -1.8181   -3.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 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
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  6
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 19 35  1  0
 35 38  1  0
 38 39  1  0
 39 40  1  0
 35 36  1  1
 36 37  2  0
 11  5  1  0
 39 13  1  0
 35 15  1  0
 33 18  1  0
 30 25  1  0
 33 22  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  6
  9 48  1  0
  9 49  1  0
  9 50  1  0
 11 51  1  6
 13 52  1  6
 14 53  1  0
 14 54  1  0
 15 55  1  1
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 18 60  1  1
 19 61  1  1
 20 62  1  0
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 21 64  1  0
 21 65  1  0
 23 66  1  0
 23 67  1  0
 23 68  1  0
 24 69  1  1
 31 73  1  0
 31 74  1  0
 32 75  1  0
 32 76  1  0
 34 77  1  0
 26 70  1  0
 30 71  1  0
 30 72  1  0
 38 79  1  0
 38 80  1  0
 39 81  1  1
 40 82  1  0
 36 78  1  0
M  END


  Mrv1533004161507452D          

 40 45  0  0  0  0            999 V2000
   -6.5877   -0.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7952   -0.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003   -0.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3980   -1.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4078   -0.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2626   -1.3564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7187    0.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0880    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1476    1.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    0.3162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3653   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1953   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4756    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1794    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -0.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416   -1.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1505    0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9211    1.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6040    1.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308    2.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2553    1.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926    0.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 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
 20 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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 18 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 19 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 13 37  1  0  0  0  0
 37 38  1  0  0  0  0
 35 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0196879

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)CC(C)OC1OC1CC2CCC3C(CCC4(C)C(CCC34O)C3=CC(=O)OC3)C2(CC1O)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O10/c1-16-12-29(35,25(34)37-3)26(39-16)40-23-11-18-4-5-21-20(28(18,15-31)13-22(23)32)6-8-27(2)19(7-9-30(21,27)36)17-10-24(33)38-14-17/h10,15-16,18-23,26,32,35-36H,4-9,11-14H2,1-3H3

> <INCHI_KEY>
QLQSCJSKNAYZGB-UHFFFAOYSA-N

> <FORMULA>
C30H42O10

> <MOLECULAR_WEIGHT>
562.656

> <EXACT_MASS>
562.277797552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
60.197186472167324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-{[2-formyl-4,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
1.4742557839999975

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.640743693877786

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182484919997572

> <JCHEM_PKA_STRONGEST_BASIC>
0.26903050492235836

> <JCHEM_POLAR_SURFACE_AREA>
148.82000000000002

> <JCHEM_REFRACTIVITY>
140.49739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-{[2-formyl-4,11-dihydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0     -12.297  -0.805   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -10.818  -0.377   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -9.707  -1.444   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -10.076  -2.939   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -8.228  -1.016   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -7.957  -2.532   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -8.808   0.411   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.631   1.403   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.742   2.939   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.323   0.590   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.692  -0.905   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.699  -2.082   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.183  -1.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.191  -2.988   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.675  -2.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.682  -3.895   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.834  -3.624   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.357  -2.175   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.365  -0.998   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.888   0.451   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.404   0.722   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.396  -0.456   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.068   0.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.936  -0.506   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.364  -1.985   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.089  -2.849   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.873  -1.904   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.504  -3.399   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.881   0.710   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.453   2.189   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.727   3.054   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.777   4.593   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.943   2.108   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.420   0.660   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.151  -1.269   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.144  -0.092   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.660  -0.363   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.653   0.815   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.628   0.179   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.621   1.357   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   37                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20   35                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   27                                             
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   18   22   28                                             
CONECT   28   27                                                            
CONECT   29   24   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   29                                                       
CONECT   35   19   15   36   39                                             
CONECT   36   35   37                                                       
CONECT   37   36   13   38                                                  
CONECT   38   37                                                            
CONECT   39   35   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-{[2-formyl-4,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0,.0,]heptadecan-5-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylic acid	Generator
Methyl 2-{[2-formyl-4,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylic acid	Generator

Chemical Formula

C₃₀H₄₂O₁₀

Average Mass

562.6560 Da

Monoisotopic Mass

562.27780 Da

IUPAC Name

methyl 2-{[2-formyl-4,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate

Traditional Name

methyl 2-{[2-formyl-4,11-dihydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)CC(C)OC1OC1CC2CCC3C(CCC4(C)C(CCC34O)C3=CC(=O)OC3)C2(CC1O)C=O

InChI Identifier

InChI=1S/C30H42O10/c1-16-12-29(35,25(34)37-3)26(39-16)40-23-11-18-4-5-21-20(28(18,15-31)13-22(23)32)6-8-27(2)19(7-9-30(21,27)36)17-10-24(33)38-14-17/h10,15-16,18-23,26,32,35-36H,4-9,11-14H2,1-3H3

InChI Key

QLQSCJSKNAYZGB-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
Asclepias curassavica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolides and derivatives

Alternative Parents

Substituents

Cardanolide-skeleton
19-oxosteroid
2-hydroxysteroid
Oxosteroid
14-hydroxysteroid
Hydroxysteroid
2-furanone
Dicarboxylic acid or derivatives
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Aldehyde
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	0.71	ALOGPS
logP	1.47	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	140.5 m³·mol⁻¹	ChemAxon
Polarizability	60.2 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

75051804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate (NP0196879)

MOL for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)

3D MOL for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)

3D SDF for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)

3D-SDF for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)

PDB for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)

3D PDB for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)

SMILES for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)

INCHI for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)

Structure for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)

3D Structure for NP0196879 (methyl 2-{[9a-formyl-3a,8-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-3-hydroxy-5-methyloxolane-3-carboxylate)