NP-MRD: Showing NP-Card for 2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate (NP0319307)

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Record Information

Version

1.0

Created at

2022-09-11 20:16:04 UTC

Updated at

2022-09-11 20:16:04 UTC

NP-MRD ID

NP0319307

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate

Description

Physagulin G 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. Physagulin G is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, physagulin g has been detected, but not quantified in, fruits and herbs and spices. 2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate is found in Physalis angulata. It was first documented in 2000 (PMID: 11413487). This could make physagulin g a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241207442D          

 51 57  0  0  0  0            999 V2000
    2.3120   -1.0592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -0.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278    0.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3529    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3713    1.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822   -4.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822   -3.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -4.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8096   -3.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8096   -3.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -2.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -1.8409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8012   -3.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454   -2.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309   -2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454   -1.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0555    0.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0369   -0.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7405   -1.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6672   -4.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6672   -5.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2384   -1.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -1.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6672   -2.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0951    4.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8096    3.9036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2373    4.3161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373    2.6661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3669   -1.5002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6262   -3.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -4.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -2.9925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 20  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 27  1  0  0  0  0
  7 34  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 11 12  2  0  0  0  0
 11 34  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 24  1  0  0  0  0
 15 16  1  0  0  0  0
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 16 30  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 30  1  0  0  0  0
 25 26  1  0  0  0  0
 25 33  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 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
  5 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
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 37  1  0  0  0  0
 39 43  1  0  0  0  0
 43 44  1  0  0  0  0
 40 45  1  0  0  0  0
 41 46  1  0  0  0  0
 42 47  1  0  0  0  0
 15 48  1  0  0  0  0
 48 16  1  0  0  0  0
 13 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
M  END

     RDKit          3D

101107  0  0  0  0  0  0  0  0999 V2000
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  9 11  1  0
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 33 82  1  0
M  END


  Mrv0541 02241207442D          

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    1.6662    1.8411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6662    4.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9517    3.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6262   -3.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -4.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -2.9925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 20  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 27  1  0  0  0  0
  7 34  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 11 12  2  0  0  0  0
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 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
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 16 30  1  0  0  0  0
 17 18  1  0  0  0  0
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 24 30  1  0  0  0  0
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 29 30  1  0  0  0  0
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 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
  5 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
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 37  1  0  0  0  0
 39 43  1  0  0  0  0
 43 44  1  0  0  0  0
 40 45  1  0  0  0  0
 41 46  1  0  0  0  0
 42 47  1  0  0  0  0
 15 48  1  0  0  0  0
 48 16  1  0  0  0  0
 13 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0319307

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1CC(COC2OC(CO)C(O)C(O)C2O)=C(C)C(=O)O1)C12OC1C(OC(C)=O)C1(O)C3CC(O)C4(O)CC=CC(=O)C4(C)C3CCC21C

> <INCHI_IDENTIFIER>
InChI=1S/C36H50O15/c1-15-18(14-47-31-27(43)26(42)25(41)22(13-37)50-31)11-21(49-30(15)44)16(2)36-29(51-36)28(48-17(3)38)35(46)20-12-24(40)34(45)9-6-7-23(39)33(34,5)19(20)8-10-32(35,36)4/h6-7,16,19-22,24-29,31,37,40-43,45-46H,8-14H2,1-5H3

> <INCHI_KEY>
LBNOIKRBLYMNFW-UHFFFAOYSA-N

> <FORMULA>
C36H50O15

> <MOLECULAR_WEIGHT>
722.7732

> <EXACT_MASS>
722.31497093

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
74.08925545573163

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,6-dihydro-2H-pyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
-0.8658213410000021

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.743425750600572

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.114388186599882

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835523173056

> <JCHEM_POLAR_SURFACE_AREA>
242.26999999999998

> <JCHEM_REFRACTIVITY>
172.84740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.316  -1.977   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.002  -1.177   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.039   0.360   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.392   1.103   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.426   2.637   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.447  -8.829   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.447  -7.287   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.782  -8.057   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.111  -7.287   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.111  -5.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.782  -4.976   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.782  -3.436   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.496  -6.920   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.018  -5.454   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.924  -4.209   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.018  -2.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.496  -1.498   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.466  -0.353   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.056   1.036   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.704   0.300   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.669  -1.243   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.982  -2.043   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.286  -6.509   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.445  -4.976   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.780  -5.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.780  -7.287   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.112  -8.057   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.112  -9.597   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.286  -1.906   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.445  -3.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.780  -2.666   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.112  -3.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.112  -4.976   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.447  -5.746   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.447  -4.209   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.110   3.437   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.110   4.977   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.444   5.747   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.444   7.287   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.110   8.057   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.777   7.287   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.777   5.747   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.778   8.057   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       7.111   7.287   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       3.110   9.597   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.443   8.057   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.443   4.977   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       2.552  -2.800   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       3.036  -6.920   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       3.806  -8.253   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       3.806  -5.586   0.000  0.00  0.00           O+0
CONECT    1    2   21                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4   36                                                       
CONECT    6    7                                                            
CONECT    7    6    8   27   34                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   34                                                  
CONECT   12   11                                                            
CONECT   13   14   49                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16   48                                                  
CONECT   16   15   17   30   48                                             
CONECT   17    2   16   18                                                  
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20    4   19   21                                                  
CONECT   21    1   20   22                                                  
CONECT   22   21                                                            
CONECT   23   24                                                            
CONECT   24   14   23   25   30                                             
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27    7   26   28                                                  
CONECT   28   27                                                            
CONECT   29   30                                                            
CONECT   30   16   24   29   31                                             
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   25   32   34                                                  
CONECT   34    7   11   33   35                                             
CONECT   35   34                                                            
CONECT   36    5   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   43                                                  
CONECT   40   39   41   45                                                  
CONECT   41   40   42   46                                                  
CONECT   42   41   37   47                                                  
CONECT   43   39   44                                                       
CONECT   44   43                                                            
CONECT   45   40                                                            
CONECT   46   41                                                            
CONECT   47   42                                                            
CONECT   48   15   16                                                       
CONECT   49   13   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  114    0
END

View in JSmol

Synonyms

Value	Source
2,16,17-Trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,6-dihydro-2H-pyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetic acid	Generator

Chemical Formula

C₃₆H₅₀O₁₅

Average Mass

722.7732 Da

Monoisotopic Mass

722.31497 Da

IUPAC Name

2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,6-dihydro-2H-pyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C1CC(COC2OC(CO)C(O)C(O)C2O)=C(C)C(=O)O1)C12OC1C(OC(C)=O)C1(O)C3CC(O)C4(O)CC=CC(=O)C4(C)C3CCC21C

InChI Identifier

InChI=1S/C36H50O15/c1-15-18(14-47-31-27(43)26(42)25(41)22(13-37)50-31)11-21(49-30(15)44)16(2)36-29(51-36)28(48-17(3)38)35(46)20-12-24(40)34(45)9-6-7-23(39)33(34,5)19(20)8-10-32(35,36)4/h6-7,16,19-22,24-29,31,37,40-43,45-46H,8-14H2,1-5H3

InChI Key

LBNOIKRBLYMNFW-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
Physalis angulata	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

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	0.24	ALOGPS
logP	-0.87	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	242.27 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	172.85 m³·mol⁻¹	ChemAxon
Polarizability	74.09 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

HMDB0039694

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019323

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

131752708

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 2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate (NP0319307)

MOL for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)

3D MOL for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)

3D SDF for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)

3D-SDF for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)

PDB for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)

3D PDB for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)

SMILES for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)

INCHI for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)

Structure for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)

3D Structure for NP0319307 (2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate)