NP-MRD: Showing NP-Card for (3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate (NP0159171)

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Record Information

Version

2.0

Created at

2022-09-02 16:52:55 UTC

Updated at

2022-09-02 16:52:55 UTC

NP-MRD ID

NP0159171

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate

Description

4-Hydroxy-1,26-dioxo-5,6:22,26-Diepoxyergosta-2,24-dien-27-yl 6-o-hexadecanoylhexopyranoside, also known as sitoindoside X, belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. (3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate is found in Withania somnifera. Based on a literature review very few articles have been published on 4-hydroxy-1,26-dioxo-5,6:22,26-Diepoxyergosta-2,24-dien-27-yl 6-o-hexadecanoylhexopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022218522D          

 62 68  0  0  0  0            999 V2000
   -9.9919  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2774  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5629  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8484  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1340  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4195  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7050  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9906  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2761  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8471  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7037  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0107  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7252  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7252  -15.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4397  -16.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542  -16.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8686  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5831  -16.3831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976  -16.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0120  -16.3831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7265  -14.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0120  -13.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4410  -13.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8699  -13.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5795  -10.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1315   -9.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6836   -9.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9385   -9.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2356   -8.5766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975   -9.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5525  -10.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0004  -10.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2554  -11.7151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2976  -17.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0120  -18.0331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5831  -18.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8686  -17.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542  -18.0331    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
  9 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  2  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  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  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 35 52  1  0  0  0  0
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 22 57  1  0  0  0  0
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 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
 20 61  1  0  0  0  0
 61 62  1  0  0  0  0
M  END

     RDKit          3D

140146  0  0  0  0  0  0  0  0999 V2000
   17.2250    0.0836    0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8640   -0.5033   -0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8051    0.1238    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4360   -0.4191    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4087    0.2204    1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0105   -0.3236    0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0685    0.3740    1.8459 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6340   -0.0093    1.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0957    0.2808    0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292    1.7222   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7031    2.0112   -1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1936    1.6594   -1.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6241    1.9694   -2.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022218522D          

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M  END
> <DATABASE_ID>
NP0159171

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OCC1OC(OCC2=C(C)CC(OC2=O)C(C)C2CCC3C4CC5OC55C(O)C=CC(=O)C5(C)C4CCC23C)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C50H78O12/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-42(53)58-29-38-43(54)44(55)45(56)47(61-38)59-28-33-30(2)26-37(60-46(33)57)31(3)34-20-21-35-32-27-41-50(62-41)40(52)23-22-39(51)49(50,5)36(32)24-25-48(34,35)4/h22-23,31-32,34-38,40-41,43-45,47,52,54-56H,6-21,24-29H2,1-5H3

> <INCHI_KEY>
AGNOSYRBHQJIEE-UHFFFAOYSA-N

> <FORMULA>
C50H78O12

> <MOLECULAR_WEIGHT>
871.162

> <EXACT_MASS>
870.549327952

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
140

> <JCHEM_AVERAGE_POLARIZABILITY>
102.66405268710368

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydro-2H-pyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate

> <ALOGPS_LOGP>
6.34

> <JCHEM_LOGP>
8.732192371000002

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.038122264363299

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.187348587735832

> <JCHEM_PKA_STRONGEST_BASIC>
-3.473588445945432

> <JCHEM_POLAR_SURFACE_AREA>
181.57999999999998

> <JCHEM_REFRACTIVITY>
233.19940000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0     -18.651 -31.352   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.318 -30.582   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -15.984 -31.352   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.650 -30.582   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.317 -31.352   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.983 -30.582   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.649 -31.352   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.316 -30.582   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.982 -31.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.648 -30.582   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.315 -31.352   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.981 -30.582   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.647 -31.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.314 -30.582   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.020 -31.352   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.354 -30.582   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.354 -29.042   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.687 -31.352   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.021 -30.582   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.355 -31.352   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.688 -30.582   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.022 -31.352   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.356 -30.582   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.356 -29.042   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.689 -28.272   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.689 -26.732   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.356 -25.962   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.023 -25.962   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.357 -26.732   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.691 -25.962   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.024 -26.732   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.691 -24.422   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.445 -23.517   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.921 -22.052   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.461 -22.052   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.491 -20.908   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.015 -19.443   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.046 -18.299   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      18.076 -17.154   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      18.552 -18.619   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      19.582 -17.474   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      19.106 -16.010   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      21.089 -17.794   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      21.565 -19.259   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      20.534 -20.404   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      21.010 -21.868   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      19.028 -20.083   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      19.504 -21.548   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      17.997 -21.228   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      18.473 -22.692   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      17.443 -23.837   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      15.936 -23.517   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      16.257 -25.023   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      13.357 -28.272   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      12.023 -29.042   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      12.023 -30.582   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       8.022 -32.892   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       9.356 -33.662   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       6.688 -33.662   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       6.688 -35.202   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0       5.355 -32.892   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       4.021 -33.662   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   61                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   57                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   55                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   54                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   52                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   52                                                  
CONECT   36   35   37   49                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38   40                                                       
CONECT   40   39   38   41   47                                             
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   40   48   49                                             
CONECT   48   47                                                            
CONECT   49   47   36   50                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   32   35   53                                             
CONECT   53   52                                                            
CONECT   54   29   55                                                       
CONECT   55   54   25   56                                                  
CONECT   56   55                                                            
CONECT   57   22   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59   20   62                                                  
CONECT   62   61                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  136    0
END

View in JSmol

Synonyms

Value	Source
Sitoindoside X	MeSH

Chemical Formula

C₅₀H₇₈O₁₂

Average Mass

871.1620 Da

Monoisotopic Mass

870.54933 Da

IUPAC Name

(3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydro-2H-pyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OCC1OC(OCC2=C(C)CC(OC2=O)C(C)C2CCC3C4CC5OC55C(O)C=CC(=O)C5(C)C4CCC23C)C(O)C(O)C1O

InChI Identifier

InChI=1S/C50H78O12/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-42(53)58-29-38-43(54)44(55)45(56)47(61-38)59-28-33-30(2)26-37(60-46(33)57)31(3)34-20-21-35-32-27-41-50(62-41)40(52)23-22-39(51)49(50,5)36(32)24-25-48(34,35)4/h22-23,31-32,34-38,40-41,43-45,47,52,54-56H,6-21,24-29H2,1-5H3

InChI Key

AGNOSYRBHQJIEE-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
Withania somnifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
Steroidal glycoside
Saccharolipid
5,6-epoxysteroid
Glycosyl compound
O-glycosyl compound
Dihydropyranone
Cyclohexenone
Oxepane
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Acetal
Oxirane
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Alcohol
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	6.34	ALOGPS
logP	8.73	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	181.58 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	233.2 m³·mol⁻¹	ChemAxon
Polarizability	102.66 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

164765

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

189702

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate (NP0159171)

MOL for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)

3D MOL for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)

3D SDF for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)

3D-SDF for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)

PDB for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)

3D PDB for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)

SMILES for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)

INCHI for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)

Structure for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)

3D Structure for NP0159171 ((3,4,5-trihydroxy-6-{[6-(1-{6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-15-yl}ethyl)-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}oxan-2-yl)methyl hexadecanoate)