NP-MRD: Showing NP-Card for 2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate (NP0229264)

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Record Information

Version

2.0

Created at

2022-09-06 09:14:32 UTC

Updated at

2022-09-06 09:14:32 UTC

NP-MRD ID

NP0229264

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate

Description

Acetylthevetin B 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. 2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate is found in Cerbera manghas. Acetylthevetin B is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241519462D          

 63 70  0  0  0  0            999 V2000
    6.7602    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1041    3.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6360    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875    0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6996    1.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9799    1.9145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2314    0.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4481    2.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7284    3.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3844    3.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8526    4.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1329    5.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6011    5.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7890    5.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5087    4.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    4.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6966    4.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4163    4.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041    3.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3239    3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    2.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    3.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2602    4.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0723    4.4872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284    4.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163    4.8275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678    3.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557    2.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2572    6.3295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8814    6.6199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9450    5.3585    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 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
 12 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
 17 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
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 22 32  1  0  0  0  0
 21 33  1  0  0  0  0
 12 34  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
  4 39  1  0  0  0  0
 39 40  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 42 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 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
 54 55  1  0  0  0  0
 50 55  1  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 53 58  1  0  0  0  0
 52 59  1  0  0  0  0
 51 60  1  0  0  0  0
 45 61  1  0  0  0  0
 44 62  1  0  0  0  0
 43 63  1  0  0  0  0
M  END

     RDKit          3D

131138  0  0  0  0  0  0  0  0999 V2000
    3.2669    2.0796   -3.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6506    1.1394   -2.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4487    1.5682   -0.9531 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9136    1.5362   -0.7801 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6678    1.9923    0.5359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934    3.0874    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990    3.6144    2.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    3.7342   -0.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5644    0.0395   -0.8107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7170   -0.0235   -1.2816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6419   -0.5773   -0.3503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2681   -1.7487   -0.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7100   -1.5939   -1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5042   -0.9559   -0.2068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3722   -1.7013    1.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9504   -0.8406   -0.6689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7292   -2.0801   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9694   -1.7485    0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8561   -0.7642   -0.2851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4241   -1.5092   -1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8885   -0.2897    0.6783 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.2452   -0.2198    0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2995   -0.8950    0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4344   -0.5867   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -13.0002    0.3050   -1.3027 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6560    0.6089   -1.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4718    1.1022    1.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6827    1.6570   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0422    0.4368   -0.6941 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0781    0.6614   -2.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6191    0.4032   -0.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9378    1.6300   -0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4824    1.3649   -1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9612    0.4163    0.0116 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4972    0.5591    0.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889   -0.6894   -1.5246 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765   -0.8261   -0.7671 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7973   -1.0453   -1.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    0.4992   -0.0468 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2750    0.6245    0.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4401    0.6369    1.7447 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1440   -0.4567    2.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5348   -0.3435    2.0567 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2361   -1.6356    2.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125   -1.6089    2.0919 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9584   -3.9931   -1.8222 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.2197   -1.7530   -0.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3255    1.1437   -1.0870 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0818   -0.1554    0.9384 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9638   -0.4806    1.9854 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8436    0.6551    3.1765 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1769    0.7775    3.4275 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966    2.0169    2.7301 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1495    2.4719    1.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775    1.9278    2.3041 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6508    3.0060    1.4264 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3987    1.6364   -4.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5294    2.9089   -3.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2343    2.4294   -2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8347    2.5741   -0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4296    2.1081   -1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2789    3.2580    2.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5626   -0.3719    0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0958   -2.6902    0.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9739   -2.7113   -1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7727   -1.2734    1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5023   -1.7460   -1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2215   -1.0225   -2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004241519462D          

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M  END
> <DATABASE_ID>
NP0229264

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(OC2OC(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C2O)C(C)OC(OC2CCC3(C)C(CCC4C3CCC3(C)C(CCC43O)C3=CC(=O)OC3)C2)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C44H68O19/c1-19-36(63-40-35(53)33(51)31(49)28(62-40)18-57-39-34(52)32(50)30(48)27(16-45)61-39)37(55-5)38(59-20(2)46)41(58-19)60-23-8-11-42(3)22(15-23)6-7-26-25(42)9-12-43(4)24(10-13-44(26,43)54)21-14-29(47)56-17-21/h14,19,22-28,30-41,45,48-54H,6-13,15-18H2,1-5H3

> <INCHI_KEY>
ILSCMGXPNCDKNU-UHFFFAOYSA-N

> <FORMULA>
C44H68O19

> <MOLECULAR_WEIGHT>
901.009

> <EXACT_MASS>
900.43547997

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
131

> <JCHEM_AVERAGE_POLARIZABILITY>
94.54618298542516

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
-0.11399046933332929

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.911357962014339

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182628112266389

> <JCHEM_PKA_STRONGEST_BASIC>
0.24220689832830977

> <JCHEM_POLAR_SURFACE_AREA>
279.05

> <JCHEM_REFRACTIVITY>
213.2395

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[11-hydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      12.619   6.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.612   5.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.128   5.657   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.597   3.032   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.089   3.938   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.590   1.854   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      18.106   2.125   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      18.629   3.574   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.099   0.948   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      17.636   4.751   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      18.160   6.199   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      15.651   7.106   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      14.658   8.283   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.181   9.731   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      14.189  10.909   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.673  10.638   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.150   9.189   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      13.142   8.012   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      10.634   8.918   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      10.110   7.470   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       8.594   7.199   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       8.071   5.750   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.555   5.479   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.563   6.657   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.086   8.105   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       7.602   8.376   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       5.093   9.282   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       3.577   9.011   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       4.047   6.386   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       6.032   4.031   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       9.064   4.573   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      11.680  11.815   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      14.712  12.357   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      16.697  10.002   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   41                                                  
CONECT    4    3    5   39                                                  
CONECT    5    4    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18   34                                             
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25   33                                             
CONECT   22   21   17   23   32                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26                                                       
CONECT   32   22                                                            
CONECT   33   21                                                            
CONECT   34   12                                                            
CONECT   35    5   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39    4   40                                                       
CONECT   40   39                                                            
CONECT   41    3   42                                                       
CONECT   42   41   43   47                                                  
CONECT   43   42   44   63                                                  
CONECT   44   43   45   62                                                  
CONECT   45   44   46   61                                                  
CONECT   46   45   47   48                                                  
CONECT   47   46   42                                                       
CONECT   48   46   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   55                                                  
CONECT   51   50   52   60                                                  
CONECT   52   51   53   59                                                  
CONECT   53   52   54   58                                                  
CONECT   54   53   55   56                                                  
CONECT   55   54   50                                                       
CONECT   56   54   57                                                       
CONECT   57   56                                                            
CONECT   58   53                                                            
CONECT   59   52                                                            
CONECT   60   51                                                            
CONECT   61   45                                                            
CONECT   62   44                                                            
CONECT   63   43                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  140    0
END

View in JSmol

Synonyms

Value	Source
2-{[11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0,.0,]heptadecan-5-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetic acid	Generator

Chemical Formula

C₄₄H₆₈O₁₉

Average Mass

901.0090 Da

Monoisotopic Mass

900.43548 Da

IUPAC Name

2-{[11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate

Traditional Name

2-{[11-hydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

COC1C(OC2OC(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C2O)C(C)OC(OC2CCC3(C)C(CCC4C3CCC3(C)C(CCC43O)C3=CC(=O)OC3)C2)C1OC(C)=O

InChI Identifier

InChI=1S/C44H68O19/c1-19-36(63-40-35(53)33(51)31(49)28(62-40)18-57-39-34(52)32(50)30(48)27(16-45)61-39)37(55-5)38(59-20(2)46)41(58-19)60-23-8-11-42(3)22(15-23)6-7-26-25(42)9-12-43(4)24(10-13-44(26,43)54)21-14-29(47)56-17-21/h14,19,22-28,30-41,45,48-54H,6-13,15-18H2,1-5H3

InChI Key

ILSCMGXPNCDKNU-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
Cerbera manghas	LOTUS Database	35616633

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
Steroidal glycoside
Oligosaccharide
14-hydroxysteroid
Hydroxysteroid
Glycosyl compound
O-glycosyl compound
2-furanone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Primary alcohol
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	0.43	ALOGPS
logP	-0.11	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	279.05 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	213.24 m³·mol⁻¹	ChemAxon
Polarizability	94.55 Å³	ChemAxon
Number of Rings	8	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

158042

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate (NP0229264)

MOL for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)

3D MOL for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)

3D SDF for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)

3D-SDF for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)

PDB for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)

3D PDB for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)

SMILES for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)

INCHI for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)

Structure for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)

3D Structure for NP0229264 (2-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-3-yl acetate)