NP-MRD: Showing NP-Card for (1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol (NP0251972)

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Record Information

Version

2.0

Created at

2022-09-07 15:20:06 UTC

Updated at

2022-09-07 15:20:06 UTC

NP-MRD ID

NP0251972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol

Description

MONILOSIDE C belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. (1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol is found in Fromia monilis. Based on a literature review very few articles have been published on MONILOSIDE C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217202D          

 42 46  0  0  1  0            999 V2000
    6.4223   -1.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  2  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  1  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  1  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  1  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8557    2.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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  2  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  2  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  1  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
    2.6708    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0463    1.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3705   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -1.2185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3921   -0.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1996    1.9643    0.0000 O   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
    8.8587   -1.1892    0.0000 C   0  0  1  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
    8.0466   -1.3344    0.0000 C   0  0  2  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
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 21 19  1  1  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 11 35  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  1  1  0  0  0
  4 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  END

     RDKit          3D

100104  0  0  0  0  0  0  0  0999 V2000
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   -7.2752    1.2653   -0.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5988    0.1511    0.5221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4344   -0.3633    1.3508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3280   -0.6412    0.5869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1548   -0.0329    1.0756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2222   -1.1101    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7664   -0.6731    1.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4034   -0.2088    0.1504 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7941   -1.2930   -0.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    1.0769   -0.0085 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.0006    1.7189   -1.8187 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6629    0.8921    0.0201 C   0  0  1  0  0  0  0  0  0  0  0  0
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 27 79  1  0
 28 80  1  0
 28 81  1  0
 29 82  1  0
 29 83  1  0
 30 84  1  6
 31 85  1  0
 32 86  1  0
 33 87  1  0
 33 88  1  0
 33 89  1  0
 34 90  1  0
 34 91  1  0
 34 92  1  0
M  END


  Mrv1652309072217202D          

 42 46  0  0  1  0            999 V2000
    6.4223   -1.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  2  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  1  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  1  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  1  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8557    2.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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  2  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  2  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  1  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
    2.6708    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0463    1.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3705   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -1.2185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3921   -0.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1996    1.9643    0.0000 O   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
    8.8587   -1.1892    0.0000 C   0  0  1  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
    8.0466   -1.3344    0.0000 C   0  0  2  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
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 21 19  1  1  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 11 35  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  1  1  0  0  0
  4 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0251972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](C[C@@H](O)[C@H]4[C@@H]3C[C@@H](O)[C@H]2[C@H]1O)[C@H](C)CC[C@H](O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H58O9/c1-16(2)21(34)8-7-17(3)20-14-23(36)26-18-13-22(35)27-29(39)25(42-31-30(40-6)28(38)24(37)15-41-31)10-12-32(27,4)19(18)9-11-33(20,26)5/h16-31,34-39H,7-15H2,1-6H3/t17-,18-,19+,20-,21+,22-,23-,24-,25+,26-,27+,28+,29+,30-,31+,32-,33-/m1/s1

> <INCHI_KEY>
LZBNPNPCWANRFX-XXLHBMOLSA-N

> <FORMULA>
C33H58O9

> <MOLECULAR_WEIGHT>
598.818

> <EXACT_MASS>
598.408083448

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
69.90106023959477

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,6R,7S,8R,10R,11S,12R,14R,15R)-5-{[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-6,8,12-triol

> <JCHEM_LOGP>
2.0614530410000005

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.736269679808732

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.786992486520774

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5478694574664872

> <JCHEM_POLAR_SURFACE_AREA>
149.07

> <JCHEM_REFRACTIVITY>
157.0087

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6R,7S,8R,10R,11S,12R,14R,15R)-5-{[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-6,8,12-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      11.988  -3.033   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.512  -1.585   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.064   4.573   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.820   3.618   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.558  -2.907   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.018  -2.275   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.599  -0.848   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.963  -3.490   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.489  -3.280   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.383  -4.917   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.573   3.667   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      16.067   0.406   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      14.497  -3.939   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5   37                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12   35                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   25                                             
CONECT   20   19                                                            
CONECT   21   19   15   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   11    6   36                                                  
CONECT   36   35                                                            
CONECT   37    4   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39    3   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₅₈O₉

Average Mass

598.8180 Da

Monoisotopic Mass

598.40808 Da

IUPAC Name

(1S,2R,5S,6R,7S,8R,10R,11S,12R,14R,15R)-5-{[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-6,8,12-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](C[C@@H](O)[C@H]4[C@@H]3C[C@@H](O)[C@H]2[C@H]1O)[C@H](C)CC[C@H](O)C(C)C

InChI Identifier

InChI=1S/C33H58O9/c1-16(2)21(34)8-7-17(3)20-14-23(36)26-18-13-22(35)27-29(39)25(42-31-30(40-6)28(38)24(37)15-41-31)10-12-32(27,4)19(18)9-11-33(20,26)5/h16-31,34-39H,7-15H2,1-6H3/t17-,18-,19+,20-,21+,22-,23-,24-,25+,26-,27+,28+,29+,30-,31+,32-,33-/m1/s1

InChI Key

LZBNPNPCWANRFX-XXLHBMOLSA-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
Fromia monilis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Tetrahydroxy bile acid, alcohol, or derivatives
Steroidal glycoside
24-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
4-hydroxysteroid
6-hydroxysteroid
Hydroxysteroid
15-hydroxysteroid
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Cyclic alcohol
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Hydrocarbon derivative
Organic oxygen compound
Alcohol
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	2.06	ChemAxon
pKa (Strongest Acidic)	12.79	ChemAxon
pKa (Strongest Basic)	-0.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	157.01 m³·mol⁻¹	ChemAxon
Polarizability	69.9 Å³	ChemAxon
Number of Rings	5	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

24713724

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44575902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol (NP0251972)

MOL for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)

3D MOL for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)

3D SDF for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)

3D-SDF for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)

PDB for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)

3D PDB for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)

SMILES for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)

INCHI for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)

Structure for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)

3D Structure for NP0251972 ((1r,3r,3as,3br,5r,5as,6r,7s,9ar,9bs,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,6-triol)