NP-MRD: Showing NP-Card for 2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0203155)

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Record Information

Version

2.0

Created at

2022-09-04 22:32:43 UTC

Updated at

2022-09-04 22:32:43 UTC

NP-MRD ID

NP0203155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201505122D          

 65 72  0  0  0  0            999 V2000
   11.0723    2.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7920    2.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9799    1.9145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6996    1.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875    0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511    1.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6113    1.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7603   -1.2284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4648   -0.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627   -0.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175   -1.4224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997   -1.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888   -2.2628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0051   -0.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6879   -0.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284   -1.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303   -0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1131   -0.8165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025    2.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5311    1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4829   -0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2026   -1.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7345   -2.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4542   -3.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6420   -3.2265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5466   -2.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0784   -2.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8269   -1.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6390   -1.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2951   -0.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5754    0.0224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2314    0.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4607   -0.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0435    0.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8445    0.4554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3238    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1360    1.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 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
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 22 26  1  0  0  0  0
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 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
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 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 31  1  4  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 14 40  1  0  0  0  0
  9 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
  7 43  1  0  0  0  0
 43 44  1  0  0  0  0
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 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
  6 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 51 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
 49 58  1  0  0  0  0
 58 59  1  0  0  0  0
  4 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
  2 64  1  0  0  0  0
 64 65  1  0  0  0  0
M  END

     RDKit          3D

143150  0  0  0  0  0  0  0  0999 V2000
   11.2577    3.6558   -3.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8734    2.6276   -2.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6415    2.4568   -1.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2623    1.4406   -0.7514 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7751    1.4583   -0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7340    0.9211    0.9800 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3626    1.8511    1.9525 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9208   -0.3502    1.0723 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1111   -0.9880    2.4113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7107   -1.3077    2.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9200   -1.3274    1.6723 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3314   -2.5978    1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706   -0.0685    1.0514 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8104    0.4199   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030    0.5358    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8054   -0.8217    0.6096 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3501   -1.0329    0.4332 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1451   -1.4767   -1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    0.2777    0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8965    0.0473    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5603   -1.1609    0.7166 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6366   -1.4793   -0.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8354   -0.4742   -1.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6616    0.3282   -0.3591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6379   -0.2059    0.4953 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.2401    0.8542    1.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1978    0.1801    2.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1886    0.5232   -1.0687 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2894    2.5534   -0.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749    3.6771    0.2583 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.6859   -1.8789    1.4494 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4952   -2.9043    2.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -2.7107    2.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4137   -1.2656    1.9121 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1586   -0.4169    3.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2332    0.5686    1.1996 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4726   -0.5951    0.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.9931    1.7952   -1.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9524    2.5986   -1.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004201505122D          

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M  END
> <DATABASE_ID>
NP0203155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(OC3CCC4(C)C(CCC5(C)C4CCC4C(CCC54C)C4(O)CC(OC4O)C=C(C)CO)C3(C)C)OCC(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C47H78O18/c1-21(18-48)16-23-17-47(58,42(57)61-23)25-10-14-45(6)24(25)8-9-29-44(5)13-12-30(43(3,4)28(44)11-15-46(29,45)7)63-41-38(65-39-35(55)33(53)31(51)22(2)60-39)37(26(50)20-59-41)64-40-36(56)34(54)32(52)27(19-49)62-40/h16,22-42,48-58H,8-15,17-20H2,1-7H3

> <INCHI_KEY>
CSOQQFFLTNOHSQ-UHFFFAOYSA-N

> <FORMULA>
C47H78O18

> <MOLECULAR_WEIGHT>
931.123

> <EXACT_MASS>
930.518815672

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
143

> <JCHEM_AVERAGE_POLARIZABILITY>
101.08606133820054

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[2-({14-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)-5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
0.37163400800000035

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.964052011953063

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.14602386952995

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826294462256

> <JCHEM_POLAR_SURFACE_AREA>
287.14

> <JCHEM_REFRACTIVITY>
227.68720000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[2-({14-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)-5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      20.668   5.293   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.145   3.845   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      18.629   3.574   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      18.106   2.125   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      16.590   1.854   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.509   2.583   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.874   2.670   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.286  -2.293   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.868  -0.413   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.490  -1.139   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.219  -2.655   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.306  -2.866   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.032  -4.224   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.876  -0.467   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.151  -1.332   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.040  -2.868   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.537  -0.660   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.811  -1.524   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.831   3.743   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.191   3.252   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      14.028  -1.314   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      19.568  -1.678   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      19.045  -3.126   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      20.038  -4.303   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      19.514  -5.752   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      17.998  -6.023   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      21.554  -4.032   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      22.546  -5.210   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      22.077  -2.584   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      23.593  -2.313   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      21.084  -1.407   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      21.607   0.042   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      19.099   0.948   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      19.527  -0.531   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      20.615   1.219   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      22.110   0.850   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      21.138   2.667   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      22.654   2.939   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   64                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   60                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   47                                                  
CONECT    7    6    8   43                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   40                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   19                                             
CONECT   13   12                                                            
CONECT   14   12   15   40                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   26                                             
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   17   22   27                                             
CONECT   27   26                                                            
CONECT   28   23   29   30   33                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   31   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   14    9   41   42                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43    7   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45    6   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   58                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   54                                                  
CONECT   52   51   53                                                       
CONECT   53   52                                                            
CONECT   54   51   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   49   59                                                  
CONECT   59   58                                                            
CONECT   60    4   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62    2   65                                                  
CONECT   65   64                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  144    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₇₈O₁₈

Average Mass

931.1230 Da

Monoisotopic Mass

930.51882 Da

IUPAC Name

2-{[2-({14-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)-5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(OC3CCC4(C)C(CCC5(C)C4CCC4C(CCC54C)C4(O)CC(OC4O)C=C(C)CO)C3(C)C)OCC(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C47H78O18/c1-21(18-48)16-23-17-47(58,42(57)61-23)25-10-14-45(6)24(25)8-9-29-44(5)13-12-30(43(3,4)28(44)11-15-46(29,45)7)63-41-38(65-39-35(55)33(53)31(51)22(2)60-39)37(26(50)20-59-41)64-40-36(56)34(54)32(52)27(19-49)62-40/h16,22-42,48-58H,8-15,17-20H2,1-7H3

InChI Key

CSOQQFFLTNOHSQ-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
20-hydroxysteroid
Hydroxysteroid
Steroid
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Tetrahydrofuran
Tertiary alcohol
Hemiacetal
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
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	0.57	ALOGPS
logP	0.37	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.15	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	287.14 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	227.69 m³·mol⁻¹	ChemAxon
Polarizability	101.09 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

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

75231958

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-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0203155)

MOL for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0203155 (2-{[2-({1-[2,3-dihydroxy-5-(3-hydroxy-2-methylprop-1-en-1-yl)oxolan-3-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl}oxy)-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)