NP-MRD: Showing NP-Card for 4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one (NP0217834)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-05 18:17:55 UTC

Updated at

2022-09-05 18:17:55 UTC

NP-MRD ID

NP0217834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one

Description

Neoconvallatoxoloside 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. Neoconvallatoxoloside is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one is found in Convallaria majalis. It was first documented in 2000 (PMID: 11413487). Convallaria majalis is banned by the FDA from food use in the USA (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305212D          

 50 56  0  0  0  0            999 V2000
    3.4813   -1.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4555    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4843    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6404    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7934   -0.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900    3.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0131   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2193    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7130    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7358    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5131    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3242    3.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8252   -0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0449    0.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7646    1.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3570   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9525    1.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0767    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4207    0.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2646    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6081    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6055   -0.9184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1167    3.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055   -1.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8570    0.4883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2964    2.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1692   -0.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6722    2.3306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1086    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4104    0.6540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6728    4.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -0.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7010    0.1480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6086    1.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 16  1  1  0  0  0  0
 17 11  2  0  0  0  0
 17 14  1  0  0  0  0
 18  3  1  0  0  0  0
 18 12  1  0  0  0  0
 19  6  1  0  0  0  0
 19 17  1  0  0  0  0
 20  4  1  0  0  0  0
 21  5  1  0  0  0  0
 21 20  1  0  0  0  0
 22 13  1  0  0  0  0
 23 11  1  0  0  0  0
 24 16  1  0  0  0  0
 25 22  1  0  0  0  0
 26 25  1  0  0  0  0
 27 24  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 29  1  0  0  0  0
 32  2  1  0  0  0  0
 32  7  1  0  0  0  0
 32 19  1  0  0  0  0
 33  8  1  0  0  0  0
 33 15  1  0  0  0  0
 33 20  1  0  0  0  0
 34  9  1  0  0  0  0
 34 12  1  0  0  0  0
 34 33  1  0  0  0  0
 35 10  1  0  0  0  0
 35 21  1  0  0  0  0
 35 32  1  0  0  0  0
 36 13  1  0  0  0  0
 37 15  1  0  0  0  0
 38 23  2  0  0  0  0
 39 24  1  0  0  0  0
 40 25  1  0  0  0  0
 41 26  1  0  0  0  0
 42 27  1  0  0  0  0
 43 28  1  0  0  0  0
 44 34  1  0  0  0  0
 45 35  1  0  0  0  0
 46 14  1  0  0  0  0
 46 23  1  0  0  0  0
 47 16  1  0  0  0  0
 47 31  1  0  0  0  0
 48 18  1  0  0  0  0
 48 31  1  0  0  0  0
 49 22  1  0  0  0  0
 49 30  1  0  0  0  0
 50 29  1  0  0  0  0
 50 30  1  0  0  0  0
M  END


  Mrv0541 05061305212D          

 50 56  0  0  0  0            999 V2000
    3.4813   -1.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4555    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4843    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6404    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7934   -0.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900    3.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0131   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2193    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7130    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7358    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5131    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3242    3.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8252   -0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0449    0.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7646    1.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3570   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9525    1.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0767    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4207    0.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2646    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6081    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6055   -0.9184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1167    3.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055   -1.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8570    0.4883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2964    2.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1692   -0.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6722    2.3306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1086    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4104    0.6540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6728    4.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -0.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7010    0.1480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6086    1.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 16  1  1  0  0  0  0
 17 11  2  0  0  0  0
 17 14  1  0  0  0  0
 18  3  1  0  0  0  0
 18 12  1  0  0  0  0
 19  6  1  0  0  0  0
 19 17  1  0  0  0  0
 20  4  1  0  0  0  0
 21  5  1  0  0  0  0
 21 20  1  0  0  0  0
 22 13  1  0  0  0  0
 23 11  1  0  0  0  0
 24 16  1  0  0  0  0
 25 22  1  0  0  0  0
 26 25  1  0  0  0  0
 27 24  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 29  1  0  0  0  0
 32  2  1  0  0  0  0
 32  7  1  0  0  0  0
 32 19  1  0  0  0  0
 33  8  1  0  0  0  0
 33 15  1  0  0  0  0
 33 20  1  0  0  0  0
 34  9  1  0  0  0  0
 34 12  1  0  0  0  0
 34 33  1  0  0  0  0
 35 10  1  0  0  0  0
 35 21  1  0  0  0  0
 35 32  1  0  0  0  0
 36 13  1  0  0  0  0
 37 15  1  0  0  0  0
 38 23  2  0  0  0  0
 39 24  1  0  0  0  0
 40 25  1  0  0  0  0
 41 26  1  0  0  0  0
 42 27  1  0  0  0  0
 43 28  1  0  0  0  0
 44 34  1  0  0  0  0
 45 35  1  0  0  0  0
 46 14  1  0  0  0  0
 46 23  1  0  0  0  0
 47 16  1  0  0  0  0
 47 31  1  0  0  0  0
 48 18  1  0  0  0  0
 48 31  1  0  0  0  0
 49 22  1  0  0  0  0
 49 30  1  0  0  0  0
 50 29  1  0  0  0  0
 50 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2CCC3(CO)C4CCC5(C)C(CCC5(O)C4CCC3(O)C2)C2=CC(=O)OC2)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C35H54O15/c1-16-24(39)27(42)29(50-30-28(43)26(41)25(40)22(13-36)49-30)31(47-16)48-18-3-8-33(15-37)20-4-7-32(2)19(17-11-23(38)46-14-17)6-10-35(32,45)21(20)5-9-34(33,44)12-18/h11,16,18-22,24-31,36-37,39-45H,3-10,12-15H2,1-2H3

> <INCHI_KEY>
DGPZFZCNZRLKLF-UHFFFAOYSA-N

> <FORMULA>
C35H54O15

> <MOLECULAR_WEIGHT>
714.7943

> <EXACT_MASS>
714.346271058

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
75.02420957269237

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{5-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-7,11-dihydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
-1.48

> <JCHEM_LOGP>
-1.9402716653333323

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.098088228674373

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182630944011895

> <JCHEM_PKA_STRONGEST_BASIC>
0.24213160687322455

> <JCHEM_POLAR_SURFACE_AREA>
245.28999999999994

> <JCHEM_REFRACTIVITY>
170.18270000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{5-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-7,11-dihydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.498  -2.714   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.330   5.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.398   4.257   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.850   5.071   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.904   0.996   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.626   2.635   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.666   5.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.882   4.528   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.420   0.725   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.351   1.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.682   5.280   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.929   1.632   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.548  -1.443   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.715   6.809   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.366   4.799   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.491  -1.536   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.143   5.330   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.921   2.809   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.198   4.114   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.373   3.622   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.381   2.445   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.024   0.005   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.205   6.728   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.007  -1.807   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.017   1.183   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.494   2.631   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.000  -0.630   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.978   2.902   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.477   0.818   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.985   1.725   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.961   1.089   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.658   4.164   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.890   3.351   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.413   1.903   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.135   2.716   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      16.064  -1.714   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       3.359   5.977   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -7.685   7.156   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       9.530  -3.256   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      16.533   0.911   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      15.487   3.808   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      11.516  -0.901   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      12.455   4.350   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       3.936   0.454   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -0.766   1.221   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -4.989   7.674   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       6.968  -0.088   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       7.437   2.538   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      12.509   0.276   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      10.469   1.996   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   32                                                            
CONECT    3    8   18                                                       
CONECT    4    7   20                                                       
CONECT    5    9   21                                                       
CONECT    6   10   19                                                       
CONECT    7    4   32                                                       
CONECT    8    3   33                                                       
CONECT    9    5   34                                                       
CONECT   10    6   35                                                       
CONECT   11   17   23                                                       
CONECT   12   18   34                                                       
CONECT   13   22   36                                                       
CONECT   14   17   46                                                       
CONECT   15   33   37                                                       
CONECT   16    1   24   47                                                  
CONECT   17   11   14   19                                                  
CONECT   18    3   12   48                                                  
CONECT   19    6   17   32                                                  
CONECT   20    4   21   33                                                  
CONECT   21    5   20   35                                                  
CONECT   22   13   25   49                                                  
CONECT   23   11   38   46                                                  
CONECT   24   16   27   39                                                  
CONECT   25   22   26   40                                                  
CONECT   26   25   28   41                                                  
CONECT   27   24   29   42                                                  
CONECT   28   26   30   43                                                  
CONECT   29   27   31   50                                                  
CONECT   30   28   49   50                                                  
CONECT   31   29   47   48                                                  
CONECT   32    2    7   19   35                                             
CONECT   33    8   15   20   34                                             
CONECT   34    9   12   33   44                                             
CONECT   35   10   21   32   45                                             
CONECT   36   13                                                            
CONECT   37   15                                                            
CONECT   38   23                                                            
CONECT   39   24                                                            
CONECT   40   25                                                            
CONECT   41   26                                                            
CONECT   42   27                                                            
CONECT   43   28                                                            
CONECT   44   34                                                            
CONECT   45   35                                                            
CONECT   46   14   23                                                       
CONECT   47   16   31                                                       
CONECT   48   18   31                                                       
CONECT   49   22   30                                                       
CONECT   50   29   30                                                       
MASTER        0    0    0    0    0    0    0    0   50    0  112    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₅₄O₁₅

Average Mass

714.7943 Da

Monoisotopic Mass

714.34627 Da

IUPAC Name

4-{5-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-7,11-dihydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-2,5-dihydrofuran-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(OC2CCC3(CO)C4CCC5(C)C(CCC5(O)C4CCC3(O)C2)C2=CC(=O)OC2)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O

InChI Identifier

InChI=1S/C35H54O15/c1-16-24(39)27(42)29(50-30-28(43)26(41)25(40)22(13-36)49-30)31(47-16)48-18-3-8-33(15-37)20-4-7-32(2)19(17-11-23(38)46-14-17)6-10-35(32,45)21(20)5-9-34(33,44)12-18/h11,16,18-22,24-31,36-37,39-45H,3-10,12-15H2,1-2H3

InChI Key

DGPZFZCNZRLKLF-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
Convallaria majalis	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

Not Available

Substituents

Not Available

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	-1.5	ALOGPS
logP	-1.9	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	245.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	170.18 m³·mol⁻¹	ChemAxon
Polarizability	75.02 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

HMDB0030566

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002452

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

131751050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
LOTUS database [Link]

Showing NP-Card for 4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one (NP0217834)

MOL for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D MOL for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D SDF for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D-SDF for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

PDB for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D PDB for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

SMILES for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

INCHI for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

Structure for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)

3D Structure for NP0217834 (4-{7-[(4,5-dihydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a,5a-dihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}-5h-furan-2-one)