NP-MRD: Showing NP-Card for (+)-Hoodigoside J (NP0074441)

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Record Information

Version

2.0

Created at

2022-04-28 19:41:29 UTC

Updated at

2022-04-28 19:41:29 UTC

NP-MRD ID

NP0074441

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Hoodigoside J

Description

(1S,2R,5S,10R,11S,14S,15S,16R)-14-acetyl-11-hydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4S,5S,6R)-4-hydroxy-5-{[(2S,4R,5R,6R)-4-methoxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate 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. (+)-Hoodigoside J is found in Hoodia gordonii . Based on a literature review very few articles have been published on (1S,2R,5S,10R,11S,14S,15S,16R)-14-acetyl-11-hydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4S,5S,6R)-4-hydroxy-5-{[(2S,4R,5R,6R)-4-methoxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221412D          

 81 89  0  0  1  0            999 V2000
    6.1708   -0.2182    0.0000 C   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
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    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  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
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  2  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
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    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2890    4.8730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   13.1708   -1.8697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9829   -1.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5148   -2.3552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2345   -3.1312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4223   -3.2764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  8 12  1  1  0  0  0
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  7 15  1  0  0  0  0
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 14 18  1  0  0  0  0
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  2 31  1  1  0  0  0
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M  END

     RDKit          3D

175183  0  0  0  0  0  0  0  0999 V2000
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   11.8888    0.6420    0.5355 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221412D          

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    9.4769    4.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2890    4.8730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8208    4.2423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5405    3.4663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7284    3.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0723    2.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6329    4.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1647    3.7568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9769    3.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5087    3.2713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2284    2.4954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4163    2.3501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8844    2.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1360    1.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7602    1.8647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4799    1.0887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0117    0.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7314   -0.3179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9193   -0.4631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3875    0.1676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6678    0.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5754    0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6390   -1.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1708   -1.8697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9829   -1.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5148   -2.3552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2345   -3.1312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4223   -3.2764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8905   -2.6457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0784   -2.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1420   -4.0523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7663   -3.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3269   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8587   -2.8407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2632   -0.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0754   -0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3208    3.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5693    5.6489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3814    5.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4481    2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  1  0  0  0
 14 23  1  1  0  0  0
 13 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
  2 31  1  1  0  0  0
 32 31  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 36 38  1  6  0  0  0
 38 39  1  0  0  0  0
 35 40  1  6  0  0  0
 41 40  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 41 46  1  0  0  0  0
 45 47  1  1  0  0  0
 44 48  1  6  0  0  0
 49 48  1  6  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 49 54  1  0  0  0  0
 53 55  1  1  0  0  0
 52 56  1  1  0  0  0
 57 56  1  1  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 57 62  1  0  0  0  0
 61 63  1  1  0  0  0
 60 64  1  6  0  0  0
 65 64  1  6  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 65 70  1  0  0  0  0
 70 71  1  1  0  0  0
 69 72  1  6  0  0  0
 68 73  1  1  0  0  0
 67 74  1  6  0  0  0
 74 75  1  0  0  0  0
 59 76  1  1  0  0  0
 76 77  1  0  0  0  0
 51 78  1  6  0  0  0
 43 79  1  6  0  0  0
 79 80  1  0  0  0  0
 34 81  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074441

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C(\C)=C\C)[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC=C3C2)C(C)=O)O[C@H](C)[C@H]1O[C@H]1C[C@H](OC)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]3C[C@@H](OC)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C59H94O22/c1-13-27(2)55(66)77-43-21-37-36(59(67)19-17-35(28(3)61)58(43,59)9)15-14-33-20-34(16-18-57(33,37)8)75-45-23-39(68-10)53(30(5)72-45)80-47-24-40(69-11)52(31(6)73-47)79-44-22-38(62)51(29(4)71-44)78-46-25-41(70-12)54(32(7)74-46)81-56-50(65)49(64)48(63)42(26-60)76-56/h13-14,29-32,34-54,56,60,62-65,67H,15-26H2,1-12H3/b27-13+/t29-,30-,31-,32-,34+,35-,36-,37+,38+,39+,40+,41-,42-,43-,44+,45+,46+,47+,48-,49+,50-,51-,52-,53-,54-,56+,57+,58+,59+/m1/s1

> <INCHI_KEY>
AFMABPRBXOCKJG-DHYBIPOFSA-N

> <FORMULA>
C59H94O22

> <MOLECULAR_WEIGHT>
1155.379

> <EXACT_MASS>
1154.623674667

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
175

> <JCHEM_AVERAGE_POLARIZABILITY>
126.64138322072053

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10R,11S,14S,15S,16R)-14-acetyl-11-hydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4S,5S,6R)-4-hydroxy-5-{[(2S,4R,5R,6R)-4-methoxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
4.347531986666672

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.09410569619559

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.196539496307432

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083565219918

> <JCHEM_POLAR_SURFACE_AREA>
284.73999999999995

> <JCHEM_REFRACTIVITY>
284.65559999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10R,11S,14S,15S,16R)-14-acetyl-11-hydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4S,5S,6R)-4-hydroxy-5-{[(2S,4R,5R,6R)-4-methoxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   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      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.558  -2.907   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.932  -2.940   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.925  -4.117   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.441  -3.846   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.401  -5.566   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.394  -6.743   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.871  -8.191   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.885  -5.837   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.597   3.032   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.128   5.657   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.612   5.386   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.089   3.938   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.619   6.564   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.142   8.012   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      15.651   7.106   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      17.167   7.377   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.690   8.825   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      19.206   9.096   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      20.199   7.919   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      19.676   6.471   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      18.160   6.199   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      20.668   5.293   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      21.715   8.190   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      22.708   7.013   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      24.223   7.284   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      25.216   6.106   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      24.693   4.658   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      23.177   4.387   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      22.184   5.564   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      22.654   2.939   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      25.686   3.481   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      25.162   2.032   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      26.155   0.855   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      25.632  -0.593   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      24.116  -0.864   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      23.123   0.313   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      23.647   1.761   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      21.607   0.042   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      23.593  -2.313   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      24.586  -3.490   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      26.101  -3.219   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      27.094  -4.396   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      26.571  -5.845   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      25.055  -6.116   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      24.062  -4.939   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      22.546  -5.210   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      24.532  -7.564   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      27.564  -7.022   0.000  0.00  0.00           O+0
HETATM   74  C   UNK     0      28.610  -4.125   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0      29.603  -5.303   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      26.625  -1.771   0.000  0.00  0.00           O+0
HETATM   77  C   UNK     0      28.141  -1.500   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      26.732   6.377   0.000  0.00  0.00           C+0
HETATM   79  O   UNK     0      19.729  10.545   0.000  0.00  0.00           O+0
HETATM   80  C   UNK     0      21.245  10.816   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      17.636   4.751   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   18   23                                             
CONECT   15   14    7   16   22                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24   13   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27                                                            
CONECT   31    2   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   81                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36   32                                                       
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   35   41                                                       
CONECT   41   40   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   79                                                  
CONECT   44   43   45   48                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45   41                                                       
CONECT   47   45                                                            
CONECT   48   44   49                                                       
CONECT   49   48   50   54                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   78                                                  
CONECT   52   51   53   56                                                  
CONECT   53   52   54   55                                                  
CONECT   54   53   49                                                       
CONECT   55   53                                                            
CONECT   56   52   57                                                       
CONECT   57   56   58   62                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60   76                                                  
CONECT   60   59   61   64                                                  
CONECT   61   60   62   63                                                  
CONECT   62   61   57                                                       
CONECT   63   61                                                            
CONECT   64   60   65                                                       
CONECT   65   64   66   70                                                  
CONECT   66   65   67                                                       
CONECT   67   66   68   74                                                  
CONECT   68   67   69   73                                                  
CONECT   69   68   70   72                                                  
CONECT   70   69   65   71                                                  
CONECT   71   70                                                            
CONECT   72   69                                                            
CONECT   73   68                                                            
CONECT   74   67   75                                                       
CONECT   75   74                                                            
CONECT   76   59   77                                                       
CONECT   77   76                                                            
CONECT   78   51                                                            
CONECT   79   43   80                                                       
CONECT   80   79                                                            
CONECT   81   34                                                            
MASTER        0    0    0    0    0    0    0    0   81    0  178    0
END

View in JSmol

Synonyms

Value

Source

(1S,2R,5S,10R,11S,14S,15S,16R)-14-Acetyl-11-hydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4S,5S,6R)-4-hydroxy-5-{[(2S,4R,5R,6R)-4-methoxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-16-yl (2E)-2-methylbut-2-enoic acid

Generator

Chemical Formula

C₅₉H₉₄O₂₂

Average Mass

1155.3790 Da

Monoisotopic Mass

1154.62367 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C(\C)=C\C)[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC=C3C2)C(C)=O)O[C@H](C)[C@H]1O[C@H]1C[C@H](OC)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]3C[C@@H](OC)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1

InChI Identifier

InChI=1S/C59H94O22/c1-13-27(2)55(66)77-43-21-37-36(59(67)19-17-35(28(3)61)58(43,59)9)15-14-33-20-34(16-18-57(33,37)8)75-45-23-39(68-10)53(30(5)72-45)80-47-24-40(69-11)52(31(6)73-47)79-44-22-38(62)51(29(4)71-44)78-46-25-41(70-12)54(32(7)74-46)81-56-50(65)49(64)48(63)42(26-60)76-56/h13-14,29-32,34-54,56,60,62-65,67H,15-26H2,1-12H3/b27-13+/t29-,30-,31-,32-,34+,35-,36-,37+,38+,39+,40+,41-,42-,43-,44+,45+,46+,47+,48-,49+,50-,51-,52-,53-,54-,56+,57+,58+,59+/m1/s1

InChI Key

AFMABPRBXOCKJG-DHYBIPOFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Hoodia gordonii	Plant	KNApSAcK

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

Steroidal glycoside
Oligosaccharide
20-oxosteroid
Steroid ester
Pregnane-skeleton
Oxosteroid
Hydroxysteroid
14-hydroxysteroid
Delta-5-steroid
Glycosyl compound
O-glycosyl compound
Oxane
Tertiary alcohol
Cyclic alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Ketone
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Organic oxygen compound
Primary alcohol
Organic oxide
Hydrocarbon derivative
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	2.78	ALOGPS
logP	4.35	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	284.74 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	284.66 m³·mol⁻¹	ChemAxon
Polarizability	126.64 Å³	ChemAxon
Number of Rings	9	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

20564762

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16733244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Hoodigoside J (NP0074441)

MOL for NP0074441 ((+)-Hoodigoside J)

3D MOL for NP0074441 ((+)-Hoodigoside J)

3D SDF for NP0074441 ((+)-Hoodigoside J)

3D-SDF for NP0074441 ((+)-Hoodigoside J)

PDB for NP0074441 ((+)-Hoodigoside J)

3D PDB for NP0074441 ((+)-Hoodigoside J)

SMILES for NP0074441 ((+)-Hoodigoside J)

INCHI for NP0074441 ((+)-Hoodigoside J)

Structure for NP0074441 ((+)-Hoodigoside J)

3D Structure for NP0074441 ((+)-Hoodigoside J)