NP-MRD: Showing NP-Card for 6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate (NP0197220)

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Record Information

Version

2.0

Created at

2022-09-04 15:26:28 UTC

Updated at

2022-09-04 15:26:29 UTC

NP-MRD ID

NP0197220

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

3-Hydroxy-6-({4-hydroxy-6-[(4-hydroxy-6-{[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}-2-methyloxan-3-yl)oxy]-2-methyloxan-3-yl}oxy)-2-methyloxan-4-yl acetate 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. 6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate is found in Digitalis obscura. 3-Hydroxy-6-({4-hydroxy-6-[(4-hydroxy-6-{[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}-2-methyloxan-3-yl)oxy]-2-methyloxan-3-yl}oxy)-2-methyloxan-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161513532D          

 57 64  0  0  0  0            999 V2000
   14.8238    0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0117    0.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7314   -0.3179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9193   -0.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3875    0.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6678    0.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1360    1.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4163    2.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8844    2.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2284    2.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4799    1.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7602    1.8647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6390   -1.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8269   -1.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5466   -2.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0784   -2.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7345   -2.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2026   -1.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7663   -2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   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
    4.5466   -0.5086    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
    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
    2.0307   -0.9107    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
    1.3367    0.6509    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
    2.6708    0.6076    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
    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
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4829   -0.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2951   -0.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5754    0.0224    0.0000 C   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  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 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
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 34 43  1  0  0  0  0
 38 43  1  0  0  0  0
 43 44  1  0  0  0  0
 40 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
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 45 50  1  0  0  0  0
 31 51  1  0  0  0  0
 26 51  1  0  0  0  0
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 20 53  1  0  0  0  0
 53 54  1  0  0  0  0
 18 55  1  0  0  0  0
 55 56  1  0  0  0  0
 14 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END

     RDKit          3D

123130  0  0  0  0  0  0  0  0999 V2000
   14.2154    0.1267    2.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5423    0.7297    1.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9940    1.7602    1.0552 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4007    0.1473    1.0390 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7442    0.6886   -0.0717 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3218    1.0242    0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4771   -0.2595    0.3439 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6102   -0.1418    1.4240 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2860   -0.0874    1.0902 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5521   -1.2552    1.7103 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2864   -2.1785    0.7126 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2077   -0.7828    2.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5988    0.0645    1.1646 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2899    0.4217    1.4611 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380   -0.1590    0.5421 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4055   -1.0583    1.1812 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0459   -2.1341    0.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1992   -0.2528    1.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3493    0.4743    0.4589 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5898   -0.0196    0.0995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134    0.9252    0.1381 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6540    0.6666    1.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166   -0.2890    0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9165   -0.3930   -0.7326 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.3539   -0.7136   -1.0799 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0608   -1.5620   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2803   -0.9212    0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2488   -0.4578   -0.5140 C   0  0  1  0  0  0  0  0  0  0  0  0
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  -11.8687    0.7403    3.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.5988    1.3380   -1.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5614    0.0786   -1.7717 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.4852   -0.8834   -2.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1456    0.5444   -1.4278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5729    1.0995   -2.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0739    0.9514   -2.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5780    0.9432   -1.3341 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1218    1.2027   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4734    0.5345   -0.6594 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3831    1.4615    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9797   -0.2857   -0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2026   -0.1657   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1334   -1.6639    2.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112   -3.0769    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184   -1.6240    2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3137   -0.1755    3.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6164   -0.5794    0.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395   -0.7802   -0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8595   -1.4644    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177   -2.0146   -0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435    0.4768    2.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0498   -0.1488    1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004161513532D          

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M  END
> <DATABASE_ID>
NP0197220

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CC(OC(C)=O)C1O)OC1C(O)CC(OC2C(O)CC(OC3CCC4(C)C(CCC5C4CCC4(C)C(CCC54O)C4=CC(=O)OC4)C3)OC2C)OC1C

> <INCHI_IDENTIFIER>
InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3

> <INCHI_KEY>
HPMZBILYSWLILX-UHFFFAOYSA-N

> <FORMULA>
C43H66O14

> <MOLECULAR_WEIGHT>
806.987

> <EXACT_MASS>
806.445256805

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
89.61766362330786

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-6-({4-hydroxy-6-[(4-hydroxy-6-{[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}-2-methyloxan-3-yl)oxy]-2-methyloxan-3-yl}oxy)-2-methyloxan-4-yl acetate

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
4.0386171493333345

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.05997602246958

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182635647025093

> <JCHEM_PKA_STRONGEST_BASIC>
0.24222921557030686

> <JCHEM_POLAR_SURFACE_AREA>
188.89999999999998

> <JCHEM_REFRACTIVITY>
200.86880000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      27.671   1.126   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.155   0.855   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      25.632  -0.593   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      24.116  -0.864   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.123   0.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.647   1.761   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      22.654   2.939   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      23.177   4.387   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      22.184   5.564   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      24.693   4.658   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.162   2.032   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      25.686   3.481   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      23.593  -2.313   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      22.077  -2.584   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.554  -4.032   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      22.546  -5.210   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      20.038  -4.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.045  -3.126   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.497  -3.939   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      16.067   0.406   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      18.575  -0.500   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      19.568  -1.678   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      21.084  -1.407   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      21.607   0.042   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6    2   12                                                  
CONECT   12   11                                                            
CONECT   13    4   14                                                       
CONECT   14   13   15   56                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   55                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   53                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   52                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   51                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   35                                             
CONECT   30   29                                                            
CONECT   31   29   32   51                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   43                                                  
CONECT   35   34   29   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40   43                                             
CONECT   39   38                                                            
CONECT   40   38   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   34   38   44                                             
CONECT   44   43                                                            
CONECT   45   40   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49   45                                                       
CONECT   51   31   26                                                       
CONECT   52   24   53                                                       
CONECT   53   52   20   54                                                  
CONECT   54   53                                                            
CONECT   55   18   56                                                       
CONECT   56   55   14   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  128    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₄₃H₆₆O₁₄

Average Mass

806.9870 Da

Monoisotopic Mass

806.44526 Da

IUPAC Name

3-hydroxy-6-({4-hydroxy-6-[(4-hydroxy-6-{[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}-2-methyloxan-3-yl)oxy]-2-methyloxan-3-yl}oxy)-2-methyloxan-4-yl acetate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1OC(CC(OC(C)=O)C1O)OC1C(O)CC(OC2C(O)CC(OC3CCC4(C)C(CCC5C4CCC4(C)C(CCC54O)C4=CC(=O)OC4)C3)OC2C)OC1C

InChI Identifier

InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3

InChI Key

HPMZBILYSWLILX-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
Digitalis obscura	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
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.87	ALOGPS
logP	4.04	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	188.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	200.87 m³·mol⁻¹	ChemAxon
Polarizability	89.62 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

1997

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate (NP0197220)

MOL for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)

3D MOL for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)

3D SDF for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)

3D-SDF for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)

PDB for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)

3D PDB for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)

SMILES for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)

INCHI for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)

Structure for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)

3D Structure for NP0197220 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-3-hydroxy-2-methyloxan-4-yl acetate)