NP-MRD: Showing NP-Card for 2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol (NP0322483)

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Record Information

Version

2.0

Created at

2022-09-12 01:16:46 UTC

Updated at

2022-09-12 01:16:46 UTC

NP-MRD ID

NP0322483

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol

Description

2-[(4,16-Dihydroxy-2,6,6,10,11-pentamethyl-14-{6-methyl-2-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]hept-5-en-2-yl}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol is found in Gynostemma pentaphyllum. 2-[(4,16-Dihydroxy-2,6,6,10,11-pentamethyl-14-{6-methyl-2-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]hept-5-en-2-yl}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251508152D          

 65 71  0  0  0  0            999 V2000
    2.1684    0.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512    0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0403   -0.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -1.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -1.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2328   -2.4739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9970   -2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1099   -1.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9869   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511    0.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8639    0.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    1.4169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3254    2.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    2.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2025    3.3622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7410    2.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5051    2.3495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6281    1.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2794    0.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254   -1.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896   -1.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125   -2.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0638   -2.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483   -2.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5355   -3.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274   -4.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -1.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0615   -1.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1540   -2.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8737   -2.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4055   -1.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1252   -0.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3131   -0.5049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2176   -1.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7494   -0.9405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4979   -2.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9661   -2.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2464   -3.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -4.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448    0.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 29 34  1  0  0  0  0
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 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
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 42 44  1  0  0  0  0
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 49 50  1  0  0  0  0
 48 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 46 55  1  0  0  0  0
 55 56  1  0  0  0  0
 44 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  1  0  0  0  0
 57 60  1  0  0  0  0
 39 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 32 63  1  0  0  0  0
 38 63  1  0  0  0  0
 63 64  1  0  0  0  0
  2 65  1  0  0  0  0
M  END

     RDKit          3D

145151  0  0  0  0  0  0  0  0999 V2000
    3.4208    5.7657    1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650    4.3446    2.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1888    4.0673    2.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7721    3.4935    2.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7508    2.0793    2.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318    1.1482    1.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5452    0.9064    0.2821 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6304    2.2390   -0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178    0.4708    0.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944    0.0914   -0.4041 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8850    0.8611   -0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6773    0.8181    0.6390 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1133    1.1004    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7409    0.4437   -0.6600 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9750   -0.8674   -0.6771 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5612   -1.4853   -1.8767 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5991   -2.8535   -1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0143   -3.3768   -1.5482 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9643   -4.7324   -1.3346 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6129   -2.6522   -0.3427 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9454   -3.0313   -0.1667 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4890   -1.1773   -0.6293 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0300   -0.9093   -1.8672 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5703   -0.7229   -2.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322    0.3253   -1.8538 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0156    1.6274   -2.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    0.1689   -0.4528 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4350   -1.0847    0.1301 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -7.2040   -0.7109   -0.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1428    1.7164    0.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4300    0.7261    1.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4206    1.4674   -1.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6276    4.8616    3.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7590    4.1118    1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610    3.9083    1.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    1.7335    2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6558    2.1574   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004251508152D          

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M  END
> <DATABASE_ID>
NP0322483

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)(OC1OC(COC2OCC(O)C(O)C2O)C(O)C(O)C1O)C1CCC2(C)C1C(O)CC1C3(C)CC(O)C(OC4OC(CO)C(O)C(O)C4O)C(C)(C)C3CCC21C

> <INCHI_IDENTIFIER>
InChI=1S/C47H80O18/c1-21(2)10-9-13-47(8,65-42-38(59)35(56)33(54)27(63-42)20-61-40-36(57)31(52)25(51)19-60-40)22-11-14-46(7)30(22)23(49)16-29-44(5)17-24(50)39(43(3,4)28(44)12-15-45(29,46)6)64-41-37(58)34(55)32(53)26(18-48)62-41/h10,22-42,48-59H,9,11-20H2,1-8H3

> <INCHI_KEY>
GELOPBLVWSJPGZ-UHFFFAOYSA-N

> <FORMULA>
C47H80O18

> <MOLECULAR_WEIGHT>
933.139

> <EXACT_MASS>
932.534465736

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
145

> <JCHEM_AVERAGE_POLARIZABILITY>
101.181819928349

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[2-(4,16-dihydroxy-2,6,6,10,11-pentamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.22

> <JCHEM_LOGP>
-0.2251377969999974

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.202503123426332

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.757477306617746

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648377558164718

> <JCHEM_POLAR_SURFACE_AREA>
298.14

> <JCHEM_REFRACTIVITY>
229.87480000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[2-(4,16-dihydroxy-2,6,6,10,11-pentamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       4.048   0.817   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.522   0.607   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.942  -0.820   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.416  -1.030   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.164  -2.457   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.997  -2.728   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.435  -4.618   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.861  -4.038   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.072  -2.512   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.498  -1.932   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.709  -0.406   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.135   0.174   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.346   1.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.130   2.645   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.341   4.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.767   4.751   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.978   6.276   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.983   3.805   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.410   4.386   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.772   2.280   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.988   1.335   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.714  -2.877   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.140  -2.297   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.503  -4.403   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.719  -5.348   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.077  -4.983   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.866  -6.508   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.158  -7.782   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.735  -2.213   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      11.315  -3.568   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      13.354  -5.288   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      12.831  -3.839   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      13.824  -2.662   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      13.300  -1.214   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      11.784  -0.942   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      15.340  -2.933   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      16.332  -1.756   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      15.863  -4.381   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      17.379  -4.652   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      14.870  -5.559   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      15.393  -7.007   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       4.724  -7.984   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       1.577   1.822   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   65                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   29                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21                                                            
CONECT   23   11   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    9   28                                                  
CONECT   28   27                                                            
CONECT   29    6   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   63                                             
CONECT   33   32                                                            
CONECT   34   32   29   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   63                                                  
CONECT   39   38   40   41   60                                             
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   57                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   55                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   51                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51   48   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   46   56                                                  
CONECT   56   55                                                            
CONECT   57   44   58   59   60                                             
CONECT   58   57                                                            
CONECT   59   57                                                            
CONECT   60   57   39   61                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   32   38   64                                             
CONECT   64   63                                                            
CONECT   65    2                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  142    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₈₀O₁₈

Average Mass

933.1390 Da

Monoisotopic Mass

932.53447 Da

IUPAC Name

2-{[2-(4,16-dihydroxy-2,6,6,10,11-pentamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)(OC1OC(COC2OCC(O)C(O)C2O)C(O)C(O)C1O)C1CCC2(C)C1C(O)CC1C3(C)CC(O)C(OC4OC(CO)C(O)C(O)C4O)C(C)(C)C3CCC21C

InChI Identifier

InChI=1S/C47H80O18/c1-21(2)10-9-13-47(8,65-42-38(59)35(56)33(54)27(63-42)20-61-40-36(57)31(52)25(51)19-60-40)22-11-14-46(7)30(22)23(49)16-29-44(5)17-24(50)39(43(3,4)28(44)12-15-45(29,46)6)64-41-37(58)34(55)32(53)26(18-48)62-41/h10,22-42,48-59H,9,11-20H2,1-8H3

InChI Key

GELOPBLVWSJPGZ-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
Gynostemma pentaphyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroidal glycoside
12-hydroxysteroid
2-hydroxysteroid
Hydroxysteroid
Steroid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Oxane
Fatty acyl
Cyclic alcohol
Secondary alcohol
Organoheterocyclic compound
Polyol
Oxacycle
Acetal
Primary alcohol
Alcohol
Organic oxygen compound
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	0.22	ALOGPS
logP	-0.23	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.76	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	298.14 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	229.87 m³·mol⁻¹	ChemAxon
Polarizability	101.18 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol (NP0322483)

MOL for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)

3D MOL for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)

3D SDF for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)

3D-SDF for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)

PDB for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)

3D PDB for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)

SMILES for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)

INCHI for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)

Structure for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)

3D Structure for NP0322483 (2-{[2-(8,11-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl)-6-methylhept-5-en-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol)