NP-MRD: Showing NP-Card for (1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one (NP0157840)

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Record Information

Version

2.0

Created at

2022-09-02 15:19:40 UTC

Updated at

2022-09-02 15:19:40 UTC

NP-MRD ID

NP0157840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one

Description

3Beta-[2-O,4-O-Bis(beta-D-glucopyranosyl)-alpha-L-arabinopyranosyloxy]-13,28-epoxyoleanane-16-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one is found in Lysimachia davurica. Based on a literature review very few articles have been published on 3beta-[2-O,4-O-Bis(beta-D-glucopyranosyl)-alpha-L-arabinopyranosyloxy]-13,28-epoxyoleanane-16-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217192D          

 64 72  0  0  1  0            999 V2000
    1.1943   -1.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485   -1.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541   -1.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505   -0.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822    0.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8120    0.4239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5456   -0.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1663   -0.9886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0072   -0.4206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4910   -1.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3251   -1.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7337   -0.3980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5587   -0.3992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1451   -1.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9701   -1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7951   -1.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2087   -0.4017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0337   -0.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4451   -1.1180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2701   -1.1193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6815   -1.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2679   -2.5482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6794   -3.2633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5044   -3.2646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9179   -2.5507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7429   -2.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1565   -1.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7451   -1.1230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1544   -3.2671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9794   -3.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7408   -3.9809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1522   -4.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9158   -3.9797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5022   -4.6935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4429   -2.5470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    7.2065   -1.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7929   -2.5445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2044   -3.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2022   -4.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0272   -4.6898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5544   -3.2571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7294   -3.2558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9679   -2.5432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.7973    0.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6552    1.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9723    0.3146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.7358    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3223    0.3171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9114    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4866    0.3197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4476    1.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1386    1.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    1.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054    1.8847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -0.0158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4784   -0.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  6  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  6  0  0  0
 24 23  1  6  0  0  0
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 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
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 31 33  1  0  0  0  0
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 35 36  1  6  0  0  0
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 17 50  1  0  0  0  0
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 50 52  1  0  0  0  0
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 13 53  1  0  0  0  0
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 54 55  1  0  0  0  0
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 12 56  1  0  0  0  0
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 56 58  1  0  0  0  0
  9 58  1  0  0  0  0
 58 59  1  6  0  0  0
 58 60  1  0  0  0  0
 60 61  1  0  0  0  0
  6 61  1  0  0  0  0
 61 62  2  0  0  0  0
  9 63  1  0  0  0  0
  6 63  1  0  0  0  0
 63 64  1  1  0  0  0
  2 64  1  0  0  0  0
M  END

     RDKit          3D

140148  0  0  0  0  0  0  0  0999 V2000
    9.1538   -1.0745    1.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5959   -0.8517    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7068   -2.1654   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3283    0.1999   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8066    1.6012    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3609    1.7230   -0.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8981    2.3598   -1.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391    1.8940   -1.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4273    0.7255   -0.8335 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7698   -0.2057   -1.8434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513    0.4040   -2.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7768    2.1143   -2.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6756   -0.2633   -2.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8285   -0.4087   -2.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7224    2.0110    1.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022217192D          

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M  END
> <DATABASE_ID>
NP0157840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@]23CO[C@@]4(CC[C@@H]5[C@@]6(C)CC[C@H](O[C@@H]7OC[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)CC2=O)[C@@H]3C1

> <INCHI_IDENTIFIER>
InChI=1S/C47H76O17/c1-41(2)14-15-46-21-59-47(27(46)16-41)13-9-26-43(5)11-10-29(42(3,4)25(43)8-12-44(26,6)45(47,7)17-28(46)50)63-40-37(64-39-36(57)34(55)31(52)23(19-49)61-39)32(53)24(20-58-40)62-38-35(56)33(54)30(51)22(18-48)60-38/h22-27,29-40,48-49,51-57H,8-21H2,1-7H3/t22-,23-,24+,25+,26-,27-,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39+,40+,43+,44-,45+,46-,47+/m1/s1

> <INCHI_KEY>
XTYJROYNRUEJHM-OYBQSHDESA-N

> <FORMULA>
C47H76O17

> <MOLECULAR_WEIGHT>
913.108

> <EXACT_MASS>
912.508250987

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
140

> <JCHEM_AVERAGE_POLARIZABILITY>
98.63556747167065

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,5R,8R,10S,13R,14R,17S,18R)-10-{[(2S,3R,4S,5S)-4-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-2-one

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.258851340000004

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.3582754835701

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.873923173185982

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835766873387

> <JCHEM_POLAR_SURFACE_AREA>
263.74999999999994

> <JCHEM_REFRACTIVITY>
222.74360000000013

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,8R,10S,13R,14R,17S,18R)-10-{[(2S,3R,4S,5S)-4-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.229  -3.427   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.264  -2.286   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.208  -3.503   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.961  -1.466   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.020   0.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.382   0.791   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.885  -0.746   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.044  -1.845   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.613  -0.785   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.516  -2.096   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.074  -2.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.836  -0.743   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.376  -0.745   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.604  -2.078   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.144  -2.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.684  -2.082   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.456  -0.750   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.996  -0.752   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      15.764  -2.087   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.304  -2.089   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      18.072  -3.424   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.300  -4.757   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      18.068  -6.092   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      19.608  -6.094   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      20.380  -4.761   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      21.920  -4.764   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.692  -3.431   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      21.924  -2.096   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      22.688  -6.099   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      24.228  -6.101   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      21.916  -7.431   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      22.684  -8.766   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      20.376  -7.429   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      19.604  -8.761   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      15.760  -4.754   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.988  -6.087   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      14.992  -3.420   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.452  -3.417   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.680  -4.750   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.448  -6.085   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      12.676  -7.417   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.444  -8.752   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      14.984  -8.754   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      11.136  -7.415   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      10.364  -8.747   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      10.368  -6.080   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       8.828  -6.078   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      11.140  -4.747   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      10.372  -3.413   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      12.688   0.585   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      14.136   1.110   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      12.423   2.102   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      11.148   0.587   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      10.380   1.922   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       8.840   1.925   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.068   0.592   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       7.301   1.927   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       6.508   0.597   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       6.435   2.135   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       5.859   2.083   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       4.264   2.150   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       3.557   3.518   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       4.686  -0.029   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       4.626  -1.568   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   64                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   61   63                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   58   63                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   56                                                  
CONECT   13   12   14   15   53                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   50                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   37                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   24   34                                                  
CONECT   34   33                                                            
CONECT   35   22   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   19   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   48                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   44                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   41   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   39   49                                                  
CONECT   49   48                                                            
CONECT   50   17   51   52   53                                             
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   50   13   54                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   12   57   58                                             
CONECT   57   56                                                            
CONECT   58   56    9   59   60                                             
CONECT   59   58                                                            
CONECT   60   58   61                                                       
CONECT   61   60    6   62                                                  
CONECT   62   61                                                            
CONECT   63    9    6   64                                                  
CONECT   64   63    2                                                       
MASTER        0    0    0    0    0    0    0    0   64    0  144    0
END

View in JSmol

Synonyms

Value	Source
3b-[2-O,4-O-Bis(b-D-glucopyranosyl)-a-L-arabinopyranosyloxy]-13,28-epoxyoleanane-16-one	Generator
3Β-[2-O,4-O-bis(β-D-glucopyranosyl)-α-L-arabinopyranosyloxy]-13,28-epoxyoleanane-16-one	Generator

Chemical Formula

C₄₇H₇₆O₁₇

Average Mass

913.1080 Da

Monoisotopic Mass

912.50825 Da

IUPAC Name

(1S,4S,5R,8R,10S,13R,14R,17S,18R)-10-{[(2S,3R,4S,5S)-4-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@]23CO[C@@]4(CC[C@@H]5[C@@]6(C)CC[C@H](O[C@@H]7OC[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)CC2=O)[C@@H]3C1

InChI Identifier

InChI=1S/C47H76O17/c1-41(2)14-15-46-21-59-47(27(46)16-41)13-9-26-43(5)11-10-29(42(3,4)25(43)8-12-44(26,6)45(47,7)17-28(46)50)63-40-37(64-39-36(57)34(55)31(52)23(19-49)61-39)32(53)24(20-58-40)62-38-35(56)33(54)30(51)22(18-48)60-38/h22-27,29-40,48-49,51-57H,8-21H2,1-7H3/t22-,23-,24+,25+,26-,27-,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39+,40+,43+,44-,45+,46-,47+/m1/s1

InChI Key

XTYJROYNRUEJHM-OYBQSHDESA-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
Lysimachia davurica	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
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxepane
Oxane
Tetrahydrofuran
Secondary alcohol
Ketone
Organoheterocyclic compound
Dialkyl ether
Ether
Acetal
Oxacycle
Polyol
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen 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	1.83	ALOGPS
logP	1.26	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	263.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	222.74 m³·mol⁻¹	ChemAxon
Polarizability	98.64 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

101412172

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one (NP0157840)

MOL for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)

3D MOL for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)

3D SDF for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)

3D-SDF for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)

PDB for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)

3D PDB for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)

SMILES for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)

INCHI for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)

Structure for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)

3D Structure for NP0157840 ((1s,4s,5r,8r,10s,13r,14r,17s,18r)-10-{[(2s,3r,4s,5s)-4-hydroxy-3,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-2-one)