NP-MRD: Showing NP-Card for {6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate (NP0227272)

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Record Information

Version

2.0

Created at

2022-09-06 06:32:45 UTC

Updated at

2022-09-06 06:32:46 UTC

NP-MRD ID

NP0227272

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate

Description

[3,4,5-Tris(acetyloxy)-6-[(8-{2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-4,7-dien-14-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]Nonan-4-yl)methoxy]oxan-2-yl]methyl acetate belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. {6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate is found in Datura metel. [3,4,5-Tris(acetyloxy)-6-[(8-{2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-4,7-dien-14-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]Nonan-4-yl)methoxy]oxan-2-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261511222D          

 56 62  0  0  0  0            999 V2000
   -2.8475   -4.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5366   -5.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7193   -5.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429   -5.6941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -6.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9148   -6.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4085   -5.9198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -6.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849   -5.3813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324   -5.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -4.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343   -5.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1368   -5.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513   -4.6534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9699   -3.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -4.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8308   -4.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122   -4.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0493   -3.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7664   -2.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803   -6.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5369   -6.9097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8478   -7.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6651   -7.7867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -8.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7867   -7.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4758   -8.2123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9821   -8.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6712   -9.6278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994   -8.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -7.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103   -7.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9275   -7.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4339   -8.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2384   -7.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  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  2  0  0  0  0
 12 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
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 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
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 26 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
 22 40  1  0  0  0  0
 25 40  1  0  0  0  0
 40 41  1  0  0  0  0
  8 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
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 42 47  1  0  0  0  0
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 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 47 52  1  0  0  0  0
  6 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
M  END

     RDKit          3D

112118  0  0  0  0  0  0  0  0999 V2000
   -3.7237    4.0644    1.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9247    3.4251    2.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6026    4.0837    2.8608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2898    2.1438    1.7150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4053    1.4772    2.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5516    0.0980    1.7215 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5435   -0.7778    1.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6268   -0.9264    0.8451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8871    0.2261    0.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638    0.2230    1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5834   -0.6546    0.8668 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3672   -0.5225    1.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5088   -0.0808    2.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893   -0.8913    1.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727   -0.8501   -0.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0668   -1.2198   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0727   -0.3004   -0.5146 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1772   -0.5894   -1.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562    0.9695   -0.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779    1.4201   -0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232    0.5532   -0.3132 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7197    1.1355    0.6170 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9222    2.5934    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3903    2.8940    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9354    1.5857    0.0358 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3814    1.4119    0.0051 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1640    1.7845    1.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5219    1.1726    1.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9286    0.2388    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3234   -0.2732    0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8958   -0.2403   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1689   -0.0919   -1.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7295    0.0522   -1.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0803   -0.3642   -0.6140 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2002   -1.8821   -0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6715    0.0149   -0.4849 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9040   -1.0217    0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3906   -0.7538    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0723    0.5936    0.7484 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3351    0.5336    2.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2782   -1.5023   -0.3362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0634   -2.8973   -0.5381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6936   -3.4772   -1.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4932   -4.9422   -1.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5214   -2.7735   -2.7327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8149   -1.3383   -0.1914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4874   -1.6535   -1.3707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4198   -2.6910   -1.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1520   -3.0511   -2.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.4615   -0.3420    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9173   -1.6881    1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8727    0.0823    2.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695    1.2932    1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -1.6996    0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9810   -1.6486   -0.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2335   -2.2477   -0.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446   -1.1786   -1.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835    0.1625   -1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7749   -0.6415   -2.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5876   -1.5842   -1.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    2.4457   -0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4017    1.6209    0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150    0.6578   -1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699    1.2756    1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9392    2.6252   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3393    2.8930    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6920    1.5134    2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3066   -1.2890    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9676   -0.3434   -0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7178   -0.0857   -2.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3070   -2.0990   -0.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0227272

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1OC(OCC2C(=O)OC3CC2(C)OCC3C2CCC3C4CC=C5CC=CC(=O)C5(C)C4CCC23C)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H56O14/c1-21(43)49-20-33-35(52-22(2)44)36(53-23(3)45)37(54-24(4)46)39(56-33)50-19-31-38(48)55-32-17-41(31,6)51-18-27(32)29-14-13-28-26-12-11-25-9-8-10-34(47)42(25,7)30(26)15-16-40(28,29)5/h8,10-11,26-33,35-37,39H,9,12-20H2,1-7H3

> <INCHI_KEY>
HSJHZZIGCYJXGO-UHFFFAOYSA-N

> <FORMULA>
C42H56O14

> <MOLECULAR_WEIGHT>
784.896

> <EXACT_MASS>
784.367006483

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
82.85022857515152

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3,4,5-tris(acetyloxy)-6-[(8-{2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,7-dien-14-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
3.578027547666663

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.050864499590602

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7926766117380404

> <JCHEM_POLAR_SURFACE_AREA>
176.26

> <JCHEM_REFRACTIVITY>
195.74900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4,5-tris(acetyloxy)-6-[(8-{2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,7-dien-14-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -5.315  -7.987   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.735  -9.413   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.209  -9.624   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -5.680 -10.629   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.100 -12.055   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.574 -12.266   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.629 -11.050   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.104 -11.261   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.158 -10.045   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.367 -10.256   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.312  -9.040   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.797  -9.448   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.989 -10.976   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.136  -8.686   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.544  -7.201   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.610  -7.951   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.551  -7.701   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.023  -7.893   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.959  -6.216   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.297  -5.455   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.284  -6.510   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.523 -12.687   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.002 -12.898   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.583 -14.325   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       3.108 -14.535   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       0.637 -15.540   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -1.468 -13.903   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -0.888 -15.330   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -1.833 -16.546   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -1.253 -17.972   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -3.359 -16.335   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -2.994 -13.693   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -3.939 -14.908   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -5.465 -14.698   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -6.410 -15.914   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -6.045 -13.271   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   52                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   42                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23   40                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   40                                                  
CONECT   26   25   27   37                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   29   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   26   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   22   25   41                                             
CONECT   41   40                                                            
CONECT   42    8   43   47                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   42   48   52                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   47    6   53                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Value	Source
[3,4,5-Tris(acetyloxy)-6-[(8-{2,15-dimethyl-3-oxotetracyclo[8.7.0.0,.0,]heptadeca-4,7-dien-14-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]oxan-2-yl]methyl acetic acid	Generator
[3,4,5-Tris(acetyloxy)-6-[(8-{2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,7-dien-14-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₄₂H₅₆O₁₄

Average Mass

784.8960 Da

Monoisotopic Mass

784.36701 Da

IUPAC Name

[3,4,5-tris(acetyloxy)-6-[(8-{2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,7-dien-14-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]oxan-2-yl]methyl acetate

Traditional Name

[3,4,5-tris(acetyloxy)-6-[(8-{2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,7-dien-14-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1OC(OCC2C(=O)OC3CC2(C)OCC3C2CCC3C4CC=C5CC=CC(=O)C5(C)C4CCC23C)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

InChI Identifier

InChI=1S/C42H56O14/c1-21(43)49-20-33-35(52-22(2)44)36(53-23(3)45)37(54-24(4)46)39(56-33)50-19-31-38(48)55-32-17-41(31,6)51-18-27(32)29-14-13-28-26-12-11-25-9-8-10-34(47)42(25,7)30(26)15-16-40(28,29)5/h8,10-11,26-33,35-37,39H,9,12-20H2,1-7H3

InChI Key

HSJHZZIGCYJXGO-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
Datura metel	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
Steroid lactone
Androstane-skeleton
1-oxosteroid
Oxosteroid
Pentacarboxylic acid or derivatives
Glycosyl compound
O-glycosyl compound
Delta valerolactone
Cyclohexenone
Delta_valerolactone
Oxane
Monosaccharide
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Acetal
Ether
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
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	4.23	ALOGPS
logP	3.58	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	19.05	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	176.26 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	195.75 m³·mol⁻¹	ChemAxon
Polarizability	82.85 Å³	ChemAxon
Number of Rings	7	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

14428169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate (NP0227272)

MOL for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)

3D MOL for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)

3D SDF for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)

3D-SDF for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)

PDB for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)

3D PDB for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)

SMILES for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)

INCHI for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)

Structure for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)

3D Structure for NP0227272 ({6-[(8-{9a,11a-dimethyl-9-oxo-1h,2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-5-methyl-3-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl)methoxy]-3,4,5-tris(acetyloxy)oxan-2-yl}methyl acetate)