NP-MRD: Showing NP-Card for 16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate (NP0283568)

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Record Information

Version

2.0

Created at

2022-09-09 10:53:03 UTC

Updated at

2022-09-09 10:53:04 UTC

NP-MRD ID

NP0283568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate

Description

16-{[6-(Hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane-6,2'-piperidin]-18-en-5'-yl acetate belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. 16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate is found in Solanum robustum. 16-{[6-(Hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane-6,2'-piperidin]-18-en-5'-yl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231515192D          

 74 83  0  0  0  0            999 V2000
   -0.3582    2.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819    2.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    1.3840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757    1.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7460    0.5988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2927   -0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691   -0.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0158   -0.7319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0848   -1.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381   -2.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1441   -2.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6670   -2.8344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3442   -2.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2097   -1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5800   -2.2543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4036   -2.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738   -3.0394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9677   -3.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4866   -0.8757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5696    0.5508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0230    1.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8466    1.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2168    0.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0405    0.4070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635   -0.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4964   -0.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    2.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527    1.9774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4588    2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9121    3.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352    2.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649    3.5477    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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
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 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  1  0  0  0  0
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 23 41  1  0  0  0  0
 18 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
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 44 45  1  0  0  0  0
 13 45  1  0  0  0  0
 11 46  1  0  0  0  0
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 47 48  1  0  0  0  0
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 48 56  1  0  0  0  0
 56 57  1  0  0  0  0
 46 58  1  0  0  0  0
  6 58  1  0  0  0  0
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  4 69  1  0  0  0  0
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 71 72  1  0  0  0  0
 71 73  1  0  0  0  0
  2 73  1  0  0  0  0
 73 74  1  0  0  0  0
M  END

     RDKit          3D

157166  0  0  0  0  0  0  0  0999 V2000
   13.6676    2.9416    1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5360    2.0696    0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4777    2.5953    0.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6232    0.6918    0.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5882   -0.1402    0.2730 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9628   -1.6065    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3097    0.0522    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1167    0.2771    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9960   -0.7407   -0.9514 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2930   -0.9166   -1.5585 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2623    0.0856   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5918   -1.9596   -0.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3118   -2.2215   -0.8385 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3226   -1.8213    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5979   -0.6611   -0.3385 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1571   -0.5278    0.1115 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2227   -0.2911    1.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533    0.0209    2.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    0.5162    1.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832    0.8039    1.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    0.3375    0.8658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5230   -0.3231    1.5984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7130    0.3790    1.4592 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.8628   -0.2141   -2.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6420   -0.1383   -3.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0620   -0.5000   -2.9464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1070   -1.8275   -2.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5300    0.3582   -1.7888 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.6576    1.0527   -2.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6409   -1.3068   -0.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5652   -3.3304    0.1945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2809   -4.0189   -0.9443 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0335   -3.1707   -2.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818   -5.1374   -1.2034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6330   -5.0721   -2.5453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5391   -4.8780   -0.3790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6203   -5.6114   -0.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8393   -3.3770   -0.4266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9504   -3.1160   -1.8052 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0944   -0.6425   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2106   -0.0642   -0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231515192D          

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   -6.0405    0.4070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635   -0.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4964   -0.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    2.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527    1.9774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4588    2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9121    3.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352    2.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649    3.5477    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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 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
 21 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  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 33  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 21 40  1  0  0  0  0
 25 40  1  0  0  0  0
 23 41  1  0  0  0  0
 18 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 16 44  1  0  0  0  0
 44 45  1  0  0  0  0
 13 45  1  0  0  0  0
 11 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 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
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 48 56  1  0  0  0  0
 56 57  1  0  0  0  0
 46 58  1  0  0  0  0
  6 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 63 65  1  0  0  0  0
 65 66  1  0  0  0  0
 65 67  1  0  0  0  0
 60 67  1  0  0  0  0
 67 68  1  0  0  0  0
  4 69  1  0  0  0  0
 69 70  1  0  0  0  0
 69 71  1  0  0  0  0
 71 72  1  0  0  0  0
 71 73  1  0  0  0  0
  2 73  1  0  0  0  0
 73 74  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(C)C(O)C(O)C3O)C(OC3OCC(O)C(O)C3O)C2OC2OC(C)C(O)C(O)C2O)OC11CCC(C)(CN1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C52H83NO21/c1-21-33-31(74-52(21)15-14-49(5,20-53-52)73-24(4)55)17-29-27-9-8-25-16-26(10-12-50(25,6)28(27)11-13-51(29,33)7)68-48-44(72-47-41(64)38(61)35(58)23(3)67-47)43(71-45-39(62)36(59)30(56)19-65-45)42(32(18-54)69-48)70-46-40(63)37(60)34(57)22(2)66-46/h8,21-23,26-48,53-54,56-64H,9-20H2,1-7H3

> <INCHI_KEY>
RBTOZVQNRSYMKC-UHFFFAOYSA-N

> <FORMULA>
C52H83NO21

> <MOLECULAR_WEIGHT>
1058.222

> <EXACT_MASS>
1057.545758697

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
157

> <JCHEM_AVERAGE_POLARIZABILITY>
114.11717132826325

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
-0.4674845146666665

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.241355852562252

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.784522674887056

> <JCHEM_PKA_STRONGEST_BASIC>
8.529155299583525

> <JCHEM_POLAR_SURFACE_AREA>
323.7

> <JCHEM_REFRACTIVITY>
253.22970000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
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HETATM    2  C   UNK     0      -2.206   3.960   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.897   2.583   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.435   2.494   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.126   1.118   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.280  -0.169   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.742  -0.079   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.051   1.297   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.514   1.386   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.896  -1.366   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.587  -2.742   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.741  -4.029   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.204  -3.939   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.487  -2.563   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.025  -2.474   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.871  -3.761   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.562  -2.384   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.408  -3.671   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.100  -2.295   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.637  -2.205   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.483  -3.492   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.315  -2.196   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.792  -4.868   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.887  -5.951   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.255  -5.244   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.778  -5.476   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.469  -4.100   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.013  -2.659   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.532  -2.409   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.508  -3.600   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.512  -2.432   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.965  -5.041   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      12.445  -5.291   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0      15.833  -4.386   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      17.175  -3.631   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      17.193  -2.092   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      18.500  -4.417   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.374  -3.017   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.606  -1.495   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.006  -3.724   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.255  -4.958   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.563  -6.334   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.026  -6.423   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.180  -5.137   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.642  -5.226   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -4.125  -2.832   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -4.816  -4.208   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -6.353  -4.297   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -7.045  -5.674   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -8.582  -5.763   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -9.273  -7.139   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -9.428  -4.476   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0     -10.966  -4.566   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -8.737  -3.100   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -9.583  -1.814   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -7.200  -3.011   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -7.449  -1.491   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      -4.971  -1.545   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -6.508  -1.635   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -7.355  -0.348   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -6.663   1.028   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      -7.510   2.315   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -9.047   2.225   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      -9.893   3.512   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      -9.738   0.849   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0     -11.276   0.760   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      -8.892  -0.437   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0     -10.260  -1.144   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      -5.281   3.781   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      -6.818   3.691   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      -4.590   5.157   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      -5.436   6.443   0.000  0.00  0.00           O+0
HETATM   73  C   UNK     0      -3.052   5.246   0.000  0.00  0.00           C+0
HETATM   74  O   UNK     0      -2.361   6.622   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   73                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   69                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   58                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   46                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   45                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   44                                             
CONECT   17   16                                                            
CONECT   18   16   19   41                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   40                                             
CONECT   22   21                                                            
CONECT   23   21   24   41                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   40                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33   38                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   34                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27                                                       
CONECT   34   30   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   27   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   21   25                                                  
CONECT   41   23   18   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   16   45                                                  
CONECT   45   44   13                                                       
CONECT   46   11   47   58                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   56                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   48   57                                                  
CONECT   57   56                                                            
CONECT   58   46    6   59                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61   67                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63   66   67                                                  
CONECT   66   65                                                            
CONECT   67   65   60   68                                                  
CONECT   68   67                                                            
CONECT   69    4   70   71                                                  
CONECT   70   69                                                            
CONECT   71   69   72   73                                                  
CONECT   72   71                                                            
CONECT   73   71    2   74                                                  
CONECT   74   73                                                            
MASTER        0    0    0    0    0    0    0    0   74    0  166    0
END

View in JSmol

Synonyms

Value	Source
16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0,.0,.0,]icosane-6,2'-piperidin]-18-en-5'-yl acetic acid	Generator
16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetic acid	Generator

Chemical Formula

C₅₂H₈₃NO₂₁

Average Mass

1058.2220 Da

Monoisotopic Mass

1057.54576 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(C)C(O)C(O)C3O)C(OC3OCC(O)C(O)C3O)C2OC2OC(C)C(O)C(O)C2O)OC11CCC(C)(CN1)OC(C)=O

InChI Identifier

InChI=1S/C52H83NO21/c1-21-33-31(74-52(21)15-14-49(5,20-53-52)73-24(4)55)17-29-27-9-8-25-16-26(10-12-50(25,6)28(27)11-13-51(29,33)7)68-48-44(72-47-41(64)38(61)35(58)23(3)67-47)43(71-45-39(62)36(59)30(56)19-65-45)42(32(18-54)69-48)70-46-40(63)37(60)34(57)22(2)66-46/h8,21-23,26-48,53-54,56-64H,9-20H2,1-7H3

InChI Key

RBTOZVQNRSYMKC-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
Solanum robustum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Substituents

Steroidal saponin
Diterpene glycoside
Spirosolane skeleton
Oligosaccharide
Diterpenoid
Steroidal alkaloid
Azasteroid
Delta-5-steroid
Terpene glycoside
Glycosyl compound
O-glycosyl compound
Azaspirodecane
Alkaloid or derivatives
Piperidine
Oxane
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Hemiaminal
Azacycle
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Secondary aliphatic amine
Secondary amine
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Alcohol
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Amine
Primary alcohol
Carbonyl group
Organopnictogen compound
Organonitrogen 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	0.5	ALOGPS
logP	-0.47	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.78	ChemAxon
pKa (Strongest Basic)	8.53	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	323.7 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	253.23 m³·mol⁻¹	ChemAxon
Polarizability	114.12 Å³	ChemAxon
Number of Rings	10	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate (NP0283568)

MOL for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)

3D MOL for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)

3D SDF for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)

3D-SDF for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)

PDB for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)

3D PDB for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)

SMILES for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)

INCHI for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)

Structure for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)

3D Structure for NP0283568 (16-{[6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-5'-yl acetate)