NP-MRD: Showing NP-Card for 2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0255470)

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Record Information

Version

1.0

Created at

2022-09-07 19:59:08 UTC

Updated at

2022-09-07 19:59:09 UTC

NP-MRD ID

NP0255470

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Vinaginsenoside R6 belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Vinaginsenoside R6 is a constituent of Panax vietnamensis (Vietnamese gingseng). 2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Panax vietnamensis. It was first documented in 2000 (PMID: 11413487). Vinaginsenoside R6 is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241211202D          

 66 73  0  0  0  0            999 V2000
   -4.1106    1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1106    0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3966   -0.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6838    0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6838    1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3966    1.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9697   -0.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569    0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569    1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9697    1.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457    1.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457    2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569    2.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9697    2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346    1.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7148    1.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346    2.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8261   -0.1004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8093   -0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9837   -0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9697   -0.9259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6838    1.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736    0.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3324    0.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569    3.6064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4905    3.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739    2.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8087    3.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794    4.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8621    4.1403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3075    3.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2627    4.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0608    4.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494    5.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6755    5.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862   -1.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926   -2.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037   -2.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2098   -2.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048   -1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5938   -1.2934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3880   -2.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2101   -3.6862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790   -3.2445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7905   -1.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -2.2262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8008   -3.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6264   -3.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0378   -3.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6264   -4.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8008   -4.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3880   -3.9656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0378   -2.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8633   -3.9656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0378   -5.3938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -2.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3949   -3.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081   -3.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7598   -3.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5039   -2.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990   -2.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8431   -4.2489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640   -4.5889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661   -3.3642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0570   -1.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633   -1.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 21  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 23  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 13 25  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 26  1  0  0  0  0
 21 36  1  0  0  0  0
 26 27  1  0  0  0  0
 26 30  1  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
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 29 30  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 36 37  1  0  0  0  0
 36 41  1  0  0  0  0
 37 38  1  0  0  0  0
 37 42  1  0  0  0  0
 38 39  1  0  0  0  0
 38 43  1  0  0  0  0
 39 40  1  0  0  0  0
 39 44  1  0  0  0  0
 40 41  1  0  0  0  0
 40 45  1  0  0  0  0
 42 47  1  0  0  0  0
 45 46  1  0  0  0  0
 46 56  1  0  0  0  0
 47 48  1  0  0  0  0
 47 52  1  0  0  0  0
 48 49  1  0  0  0  0
 48 53  1  0  0  0  0
 49 50  1  0  0  0  0
 49 54  1  0  0  0  0
 50 51  1  0  0  0  0
 50 55  1  0  0  0  0
 51 52  1  0  0  0  0
 56 57  1  0  0  0  0
 56 61  1  0  0  0  0
 57 58  1  0  0  0  0
 57 62  1  0  0  0  0
 58 59  1  0  0  0  0
 58 63  1  0  0  0  0
 59 60  1  0  0  0  0
 59 64  1  0  0  0  0
 60 61  1  0  0  0  0
 60 65  1  0  0  0  0
 65 66  1  0  0  0  0
M  END

     RDKit          3D

146153  0  0  0  0  0  0  0  0999 V2000
    8.4885   -1.5502   -1.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4008   -0.1546   -2.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0664    0.8084   -1.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0525   -0.2127   -3.5184 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9558    0.1804   -2.5663 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8184    1.4249   -3.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4092    1.8129   -3.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3373    1.4190   -1.5811 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0019    2.5217   -0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9268    1.1435   -1.2865 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5176   -0.0352   -2.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -0.8955   -1.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2826    1.0810   -1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4732    0.7969    0.0736 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1125    1.9451    0.9739 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2863    2.3579    1.6681 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0661    0.4823    2.8146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3880    1.8900    3.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194   -0.0918    4.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2765    0.0947    5.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775   -0.5367    4.8827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7722   -1.5805    5.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2266   -1.2982    3.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1934   -2.5742    3.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045   -0.3535    2.4013 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9964   -1.1234    1.1298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8144   -0.7064    0.1016 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8537   -0.2219   -0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3769    1.0565   -1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1399    0.5451   -1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241211202D          

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> <DATABASE_ID>
NP0255470

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CCC(C)(O1)C1CCC2(C)C1C(O)CC1C3(C)CCC(O)C(C)(C)C3C(CC21C)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1OC1OCC(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C47H80O19/c1-42(2)27(51)10-12-44(5)26-15-21(49)29-20(47(8)14-11-28(66-47)43(3,4)59)9-13-45(29,6)46(26,7)16-23(38(42)44)62-41-37(65-40-35(57)30(52)22(50)18-60-40)34(56)32(54)25(64-41)19-61-39-36(58)33(55)31(53)24(17-48)63-39/h20-41,48-59H,9-19H2,1-8H3

> <INCHI_KEY>
MGROSLQKCJXSBT-UHFFFAOYSA-N

> <FORMULA>
C47H80O19

> <MOLECULAR_WEIGHT>
949.1267

> <EXACT_MASS>
948.529380378

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
100.57281133168193

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[6-({5,16-dihydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-1.4377342253333336

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.333188434021622

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.86176511955331

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806826167294

> <JCHEM_POLAR_SURFACE_AREA>
307.37

> <JCHEM_REFRACTIVITY>
228.94330000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[6-({5,16-dihydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <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  C   UNK     0      -7.673   2.124   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.673   0.583   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.340  -0.187   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.010   0.583   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.010   2.124   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.340   2.892   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.677  -0.187   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.346   0.583   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.346   2.124   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.677   2.892   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.019   2.892   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.019   4.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.346   5.191   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.677   4.425   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.438   2.419   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.660   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.438   4.896   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.009  -0.187   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -7.111  -1.523   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.570  -1.523   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.677  -1.728   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.010   3.660   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.257   1.035   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.620   1.402   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.346   6.732   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.916   6.360   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.005   5.271   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.376   5.969   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.135   7.490   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.609   7.729   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.574   6.758   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.224   8.579   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.713   8.181   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.826  10.068   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.994   9.914   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.588  -2.818   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.973  -4.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.874  -5.389   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.392  -4.978   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.009  -3.490   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.108  -2.414   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -4.458  -4.723   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -2.259  -6.881   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.707  -6.056   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.476  -3.077   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       2.575  -4.156   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -5.228  -6.056   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -6.769  -6.056   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -7.537  -7.402   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -6.769  -8.735   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -5.228  -8.735   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -4.458  -7.402   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -7.537  -4.723   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -9.078  -7.402   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      -7.537 -10.068   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       3.993  -5.322   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       4.470  -6.786   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       5.988  -7.102   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       7.018  -5.959   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       6.541  -4.495   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       5.038  -4.174   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       3.440  -7.931   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       6.466  -8.566   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       8.523  -6.280   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0       7.573  -3.352   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       9.078  -3.670   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   19   20                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    1    5                                                       
CONECT    7    4    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14   25                                                  
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   26                                                  
CONECT   18    2                                                            
CONECT   19    3                                                            
CONECT   20    3                                                            
CONECT   21    7   36                                                       
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25   13                                                            
CONECT   26   17   27   30   31                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   26   29                                                       
CONECT   31   26                                                            
CONECT   32   29   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   21   37   41                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37   39   43                                                  
CONECT   39   38   40   44                                                  
CONECT   40   39   41   45                                                  
CONECT   41   36   40                                                       
CONECT   42   37   47                                                       
CONECT   43   38                                                            
CONECT   44   39                                                            
CONECT   45   40   46                                                       
CONECT   46   45   56                                                       
CONECT   47   42   48   52                                                  
CONECT   48   47   49   53                                                  
CONECT   49   48   50   54                                                  
CONECT   50   49   51   55                                                  
CONECT   51   50   52                                                       
CONECT   52   47   51                                                       
CONECT   53   48                                                            
CONECT   54   49                                                            
CONECT   55   50                                                            
CONECT   56   46   57   61                                                  
CONECT   57   56   58   62                                                  
CONECT   58   57   59   63                                                  
CONECT   59   58   60   64                                                  
CONECT   60   59   61   65                                                  
CONECT   61   56   60                                                       
CONECT   62   57                                                            
CONECT   63   58                                                            
CONECT   64   59                                                            
CONECT   65   60   66                                                       
CONECT   66   65                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  146    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₈₀O₁₉

Average Mass

949.1267 Da

Monoisotopic Mass

948.52938 Da

IUPAC Name

2-{[6-({5,16-dihydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CCC(C)(O1)C1CCC2(C)C1C(O)CC1C3(C)CCC(O)C(C)(C)C3C(CC21C)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1OC1OCC(O)C(O)C1O

InChI Identifier

InChI=1S/C47H80O19/c1-42(2)27(51)10-12-44(5)26-15-21(49)29-20(47(8)14-11-28(66-47)43(3,4)59)9-13-45(29,6)46(26,7)16-23(38(42)44)62-41-37(65-40-35(57)30(52)22(50)18-60-40)34(56)32(54)25(64-41)19-61-39-36(58)33(55)31(53)24(17-48)63-39/h20-41,48-59H,9-19H2,1-8H3

InChI Key

MGROSLQKCJXSBT-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
Panax vietnamensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

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	-0.02	ALOGPS
logP	-1.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.86	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	307.37 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	228.94 m³·mol⁻¹	ChemAxon
Polarizability	100.57 Å³	ChemAxon
Number of Rings	8	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

HMDB0040420

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020152

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

75054976

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-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0255470)

MOL for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0255470 (2-{[6-({7,11-dihydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-yl}oxy)-3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)