NP-MRD: Showing NP-Card for 1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone (NP0308963)

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Record Information

Version

2.0

Created at

2022-09-11 03:10:25 UTC

Updated at

2022-09-11 03:10:25 UTC

NP-MRD ID

NP0308963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone

Description

1-(5-{[5-({5-[(3,5-Dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-14-yl)ethan-1-one 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. 1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone is found in Hoodia gordonii. 1-(5-{[5-({5-[(3,5-Dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-14-yl)ethan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171520402D          

 56 62  0  0  0  0            999 V2000
   -3.6264   -3.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946   -4.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0022   -3.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.9700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -0.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -3.7596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385   -4.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067   -5.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7507   -4.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0310   -5.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431   -5.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -4.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870   -5.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7188   -4.4856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5310   -4.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673   -5.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794   -6.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5597   -6.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0279   -7.4441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082   -8.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7764   -8.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203   -8.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4006   -9.1412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6522   -7.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4643   -7.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9961   -7.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3719   -6.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9037   -6.3279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9355   -6.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2158   -7.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1234   -6.3778    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
 10 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
 14 16  1  0  0  0  0
 16 17  1  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
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 12 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
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  3 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
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  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
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 49 52  1  0  0  0  0
 43 52  1  0  0  0  0
 52 53  1  0  0  0  0
 41 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 36 56  1  0  0  0  0
M  END

     RDKit          3D

124130  0  0  0  0  0  0  0  0999 V2000
   -2.5676   -3.0325   -1.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8925   -2.1299   -0.8097 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2039   -0.6549   -0.2229 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.5004   -0.6307   -0.1291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2667   -0.2985    1.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5665   -1.0349    1.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4282   -1.0029    0.0150 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4249   -2.4506   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7865   -0.0945   -0.9264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3935    0.9502   -1.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7850    1.3506   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1595    0.8283    0.2376 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8386   -0.6353    0.3034 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7470   -1.3648   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2240   -1.0913   -0.3975 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8527   -2.3004    0.0003 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4717   -0.1151    0.6807 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4114   -0.7401    2.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8324    0.5128    0.5678 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9852   -0.3470    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4436   -1.2695   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6340    1.4196   -0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2967    2.0397   -0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6661    1.4511   -3.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.4828    1.3833    0.3012 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.3372    0.5333   -0.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0063   -0.7931   -0.3454 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.2946   -1.5782   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4709   -1.0982    1.0149 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.4903    0.7201   -1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -1.7039   -0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2366   -1.7079   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140   -0.5666    1.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    0.8014    1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0931   -0.5737    2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3396   -2.0723    1.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3585   -2.8374   -0.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8401   -2.5206   -1.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9434   -3.1199    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8485    1.5981   -2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4105    0.9656   -1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0308963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(OC2CCC3(C)C4CC(O)C5(C)C(CCC5(O)C4CC=C3C2)C(C)=O)OC(C)C1OC1CC(OC)C(OC2OC(C)C(O)C(OC)C2O)C(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C42H68O14/c1-20(43)26-13-15-42(47)27-11-10-24-16-25(12-14-40(24,5)28(27)17-31(44)41(26,42)6)54-32-18-29(48-7)36(22(3)51-32)55-33-19-30(49-8)37(23(4)52-33)56-39-35(46)38(50-9)34(45)21(2)53-39/h10,21-23,25-39,44-47H,11-19H2,1-9H3

> <INCHI_KEY>
YYCTZBHRECJQGA-UHFFFAOYSA-N

> <FORMULA>
C42H68O14

> <MOLECULAR_WEIGHT>
796.992

> <EXACT_MASS>
796.46090687

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
124

> <JCHEM_AVERAGE_POLARIZABILITY>
87.77452930588461

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(5-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)ethan-1-one

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
2.8280799506666687

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.222123239193891

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.28671693525321

> <JCHEM_PKA_STRONGEST_BASIC>
-2.978746438864352

> <JCHEM_POLAR_SURFACE_AREA>
181.06

> <JCHEM_REFRACTIVITY>
200.5643

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(5-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -6.769  -6.654   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.777  -7.831   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.261  -7.560   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.737  -6.112   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.221  -5.841   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.928  -0.140   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.407  -1.811   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.302  -0.173   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.229  -7.018   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.752  -8.466   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.759  -9.644   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.268  -8.737   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.791 -10.186   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -5.307 -10.457   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.300  -9.279   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.816  -9.551   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -8.809  -8.373   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0     -10.324  -8.644   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -8.339 -10.999   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -9.855 -11.270   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0     -10.378 -12.718   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -9.385 -13.896   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -9.909 -15.344   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -8.916 -16.521   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -11.425 -15.615   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0     -11.948 -17.064   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0     -12.417 -14.438   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0     -13.933 -14.709   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0     -14.926 -13.532   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -11.894 -12.989   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0     -12.887 -11.812   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -7.346 -12.176   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -7.869 -13.625   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -5.830 -11.905   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   26                                             
CONECT   11   10                                                            
CONECT   12   10   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   10   27                                                  
CONECT   27   26    7                                                       
CONECT   28   18   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    5   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    3   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   56                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   54                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   52                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   52                                                  
CONECT   50   49   51                                                       
CONECT   51   50                                                            
CONECT   52   49   43   53                                                  
CONECT   53   52                                                            
CONECT   54   41   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   36                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₆₈O₁₄

Average Mass

796.9920 Da

Monoisotopic Mass

796.46091 Da

IUPAC Name

1-(5-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)ethan-1-one

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1CC(OC2CCC3(C)C4CC(O)C5(C)C(CCC5(O)C4CC=C3C2)C(C)=O)OC(C)C1OC1CC(OC)C(OC2OC(C)C(O)C(OC)C2O)C(C)O1

InChI Identifier

InChI=1S/C42H68O14/c1-20(43)26-13-15-42(47)27-11-10-24-16-25(12-14-40(24,5)28(27)17-31(44)41(26,42)6)54-32-18-29(48-7)36(22(3)51-32)55-33-19-30(49-8)37(23(4)52-33)56-39-35(46)38(50-9)34(45)21(2)53-39/h10,21-23,25-39,44-47H,11-19H2,1-9H3

InChI Key

YYCTZBHRECJQGA-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
Hoodia gordonii	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

Steroidal glycoside
Oligosaccharide
Pregnane-skeleton
20-oxosteroid
12-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-5-steroid
Glycosyl compound
O-glycosyl compound
Oxane
Cyclic alcohol
Tertiary alcohol
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Acetal
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.52	ALOGPS
logP	2.83	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	181.06 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	200.56 m³·mol⁻¹	ChemAxon
Polarizability	87.77 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

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

85067527

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone (NP0308963)

MOL for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)

3D MOL for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)

3D SDF for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)

3D-SDF for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)

PDB for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)

3D PDB for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)

SMILES for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)

INCHI for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)

Structure for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)

3D Structure for NP0308963 (1-(7-{[5-({5-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl)ethanone)