NP-MRD: Showing NP-Card for Macranthoidin B (NP0140682)

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Record Information

Version

2.0

Created at

2022-06-29 21:46:35 UTC

Updated at

2022-06-29 21:46:35 UTC

NP-MRD ID

NP0140682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Macranthoidin B

Description

Macranthoidin B belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Macranthoidin B was first documented in 2017 (PMID: 29484987). Based on a literature review a small amount of articles have been published on Macranthoidin B (PMID: 34923253) (PMID: 35080709) (PMID: 31039532) (PMID: 29689551).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306292223462D          

 97107  0  0  1  0            999 V2000
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   11.0270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306292223462D          

 97107  0  0  1  0            999 V2000
   11.4395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2355    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0605    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4730    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0605    4.6993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2355    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7605    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4395    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0270    3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2020    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7895    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020    5.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7895    6.1283    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2020    6.8427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0270    6.8427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4395    6.1283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0270    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2645    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6770    6.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395    7.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895    7.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2645    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2645    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0140682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)CO[C@H]2O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C3[C@@H]5CC(C)(C)CC[C@@]5(CC[C@@]43C)C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)[C@]2(C)CO)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C65H106O32/c1-25-36(71)51(95-55-48(83)44(79)50(31(21-68)91-55)94-54-46(81)42(77)39(74)30(20-67)90-54)49(84)57(88-25)96-52-37(72)28(70)22-86-58(52)93-35-11-12-61(4)33(62(35,5)24-69)10-13-64(7)34(61)9-8-26-27-18-60(2,3)14-16-65(27,17-15-63(26,64)6)59(85)97-56-47(82)43(78)40(75)32(92-56)23-87-53-45(80)41(76)38(73)29(19-66)89-53/h8,25,27-58,66-84H,9-24H2,1-7H3/t25-,27-,28-,29+,30+,31+,32+,33+,34+,35-,36-,37-,38+,39+,40+,41-,42-,43-,44+,45+,46+,47+,48+,49+,50+,51+,52+,53+,54-,55-,56-,57-,58-,61-,62-,63+,64+,65-/m0/s1

> <INCHI_KEY>
RKINZCVTEPSBCI-ZBXZRPIVSA-N

> <FORMULA>
C65H106O32

> <MOLECULAR_WEIGHT>
1399.531

> <EXACT_MASS>
1398.666721253

> <JCHEM_ACCEPTOR_COUNT>
31

> <JCHEM_ATOM_COUNT>
203

> <JCHEM_AVERAGE_POLARIZABILITY>
145.70578906370986

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
19

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-{[(2S,3R,4S,5S)-3-{[(2S,3R,4R,5S,6S)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

> <ALOGPS_LOGP>
-0.22

> <JCHEM_LOGP>
-4.130939136333336

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.99726887720268

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.60826201343688

> <JCHEM_PKA_STRONGEST_BASIC>
-3.679025732357002

> <JCHEM_POLAR_SURFACE_AREA>
512.2000000000002

> <JCHEM_REFRACTIVITY>
322.3907

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-{[(2S,3R,4S,5S)-3-{[(2S,3R,4R,5S,6S)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      21.354  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.584  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.354   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.584   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.044   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.274   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.044  -0.564   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      16.734   0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.964  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.734  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.964  -3.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.424  -3.231   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.654  -1.897   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.424  -0.564   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.650   2.920   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.397   3.643   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.757   4.366   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.510  -2.103   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.742  -1.380   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -0.976   4.771   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -0.976   7.438   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -2.516   7.438   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -3.286   6.105   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -2.516   4.771   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -4.826   6.105   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -5.596   7.438   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -7.136   7.438   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -7.906   6.105   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -9.446   6.105   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -10.216   7.438   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -9.446   8.772   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -7.906   8.772   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0     -10.216  10.106   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0     -11.756  10.106   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0     -11.756   7.438   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0     -10.216   4.771   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      -7.136   4.771   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      -3.286   8.772   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      -0.206   8.772   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0       1.334   6.105   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       6.885   3.635   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      16.734  -4.565   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      18.274  -1.897   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      18.274   3.437   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      21.354   3.437   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      20.584   4.771   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      21.354   6.105   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      20.584   7.438   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      19.044   7.438   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      18.274   6.105   0.000  0.00  0.00           C+0
HETATM   80  O   UNK     0      19.044   4.771   0.000  0.00  0.00           O+0
HETATM   81  C   UNK     0      16.734   6.105   0.000  0.00  0.00           C+0
HETATM   82  O   UNK     0      15.964   4.771   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0      18.274   8.772   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0      19.044  10.106   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      18.274  11.439   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      19.044  12.773   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      20.584  12.773   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      21.354  11.439   0.000  0.00  0.00           C+0
HETATM   89  O   UNK     0      20.584  10.106   0.000  0.00  0.00           O+0
HETATM   90  C   UNK     0      22.894  11.439   0.000  0.00  0.00           C+0
HETATM   91  O   UNK     0      23.664  12.773   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0      21.354  14.107   0.000  0.00  0.00           O+0
HETATM   93  O   UNK     0      18.274  14.107   0.000  0.00  0.00           O+0
HETATM   94  O   UNK     0      16.734  11.439   0.000  0.00  0.00           O+0
HETATM   95  O   UNK     0      21.354   8.772   0.000  0.00  0.00           O+0
HETATM   96  O   UNK     0      22.894   6.105   0.000  0.00  0.00           O+0
HETATM   97  O   UNK     0      22.894   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   97                                                  
CONECT    4    3    5   74                                                  
CONECT    5    4    6   73                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   72                                                  
CONECT   11   10   12   71                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28   70                                             
CONECT   20   19   21   25                                                  
CONECT   21   20   16   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32   69                                             
CONECT   28   27   19   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   27   33   68                                             
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   40   43                                             
CONECT   36   35   31   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   41   42                                             
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   38                                                            
CONECT   42   38                                                            
CONECT   43   35   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   47   51                                                  
CONECT   47   46   48   67                                                  
CONECT   48   47   49   66                                                  
CONECT   49   48   50   65                                                  
CONECT   50   49   51   52                                                  
CONECT   51   50   46                                                       
CONECT   52   50   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   59                                                  
CONECT   55   54   56   64                                                  
CONECT   56   55   57   63                                                  
CONECT   57   56   58   62                                                  
CONECT   58   57   59   60                                                  
CONECT   59   58   54                                                       
CONECT   60   58   61                                                       
CONECT   61   60                                                            
CONECT   62   57                                                            
CONECT   63   56                                                            
CONECT   64   55                                                            
CONECT   65   49                                                            
CONECT   66   48                                                            
CONECT   67   47                                                            
CONECT   68   32                                                            
CONECT   69   27                                                            
CONECT   70   19                                                            
CONECT   71   11                                                            
CONECT   72   10                                                            
CONECT   73    5                                                            
CONECT   74    4   75                                                       
CONECT   75   74   76   80                                                  
CONECT   76   75   77   96                                                  
CONECT   77   76   78   95                                                  
CONECT   78   77   79   83                                                  
CONECT   79   78   80   81                                                  
CONECT   80   79   75                                                       
CONECT   81   79   82                                                       
CONECT   82   81                                                            
CONECT   83   78   84                                                       
CONECT   84   83   85   89                                                  
CONECT   85   84   86   94                                                  
CONECT   86   85   87   93                                                  
CONECT   87   86   88   92                                                  
CONECT   88   87   89   90                                                  
CONECT   89   88   84                                                       
CONECT   90   88   91                                                       
CONECT   91   90                                                            
CONECT   92   87                                                            
CONECT   93   86                                                            
CONECT   94   85                                                            
CONECT   95   77                                                            
CONECT   96   76                                                            
CONECT   97    3                                                            
MASTER        0    0    0    0    0    0    0    0   97    0  214    0
END

View in JSmol

Synonyms

Value	Source
3-O-beta-D-Glucopyranosyl-(1-4)-beta-D-glucopyranosyl-(1-3)-alpha-L-rhamnopyranosyl-(1-2)-alpha-L-arabinopyranosyl-3,23-dihydroxyolean-12-en-28-O-D-glucopyranosyl-(1-6)glucopyranoside	MeSH

Chemical Formula

C₆₅H₁₀₆O₃₂

Average Mass

1399.5310 Da

Monoisotopic Mass

1398.66672 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-{[(2S,3R,4S,5S)-3-{[(2S,3R,4R,5S,6S)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-{[(2S,3R,4S,5S)-3-{[(2S,3R,4R,5S,6S)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)CO[C@H]2O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C3[C@@H]5CC(C)(C)CC[C@@]5(CC[C@@]43C)C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)[C@]2(C)CO)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H]1O

InChI Identifier

InChI=1S/C65H106O32/c1-25-36(71)51(95-55-48(83)44(79)50(31(21-68)91-55)94-54-46(81)42(77)39(74)30(20-67)90-54)49(84)57(88-25)96-52-37(72)28(70)22-86-58(52)93-35-11-12-61(4)33(62(35,5)24-69)10-13-64(7)34(61)9-8-26-27-18-60(2,3)14-16-65(27,17-15-63(26,64)6)59(85)97-56-47(82)43(78)40(75)32(92-56)23-87-53-45(80)41(76)38(73)29(19-66)89-53/h8,25,27-58,66-84H,9-24H2,1-7H3/t25-,27-,28-,29+,30+,31+,32+,33+,34+,35-,36-,37-,38+,39+,40+,41-,42-,43-,44+,45+,46+,47+,48+,49+,50+,51+,52+,53+,54-,55-,56-,57-,58-,61-,62-,63+,64+,65-/m0/s1

InChI Key

RKINZCVTEPSBCI-ZBXZRPIVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Oligosaccharide
Steroid
Glycosyl compound
O-glycosyl compound
Oxane
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	-0.22	ALOGPS
logP	-4.1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.61	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	31	ChemAxon
Hydrogen Donor Count	19	ChemAxon
Polar Surface Area	512.2 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	322.39 m³·mol⁻¹	ChemAxon
Polarizability	145.71 Å³	ChemAxon
Number of Rings	11	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

C00051394

Chemspider ID

28420755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71307567

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang R, Min K, Wang Y, Chen S, Ma M, Li M, Yan J, Chen B, Yao S: Rapid semi-quantitative analysis of hemolytic triterpenoid saponins in Lonicerae Flos crude drugs and preparations by paper spray mass spectrometry. Talanta. 2022 Mar 1;239:123148. doi: 10.1016/j.talanta.2021.123148. Epub 2021 Dec 13. [PubMed:34923253 ]
Liu X, Zhou R, Shen B, Chen L, Zhou Q, Wan D, Huang L, Zhang S: Determination and Isolation of Four Anti-tumour Saponins from Lonicera macranthoides by HPLC-ESI-QTOF/MS and HSCCC. Curr Pharm Biotechnol. 2017;18(13):1106-1114. doi: 10.2174/1389201019666180226145427. [PubMed:29484987 ]
Tan S, Liu Q, Yang J, Cai J, Yu M, Ji Y: Macranthoidin B (MB) Promotes Oxidative Stress-Induced Inhibiting of Hepa1-6 Cell Proliferation via Selenoprotein. Biol Trace Elem Res. 2022 Jan 26. doi: 10.1007/s12011-022-03120-x. [PubMed:35080709 ]
Gao W, Liu K, Wang R, Liu XG, Li XS, Li P, Yang H: Integration of targeted metabolite profiling and sequential optimization method for discovery of chemical marker combination to identify the closely-related plant species. Phytomedicine. 2019 Aug;61:152829. doi: 10.1016/j.phymed.2019.152829. Epub 2019 Jan 22. [PubMed:31039532 ]
Fan X, Rao J, Zhang Z, Li D, Cui W, Zhang J, Wang H, Tou F, Zheng Z, Shen Q: Macranthoidin B Modulates Key Metabolic Pathways to Enhance ROS Generation and Induce Cytotoxicity and Apoptosis in Colorectal Cancer. Cell Physiol Biochem. 2018;46(4):1317-1330. doi: 10.1159/000489147. Epub 2018 Apr 18. [PubMed:29689551 ]

Showing NP-Card for Macranthoidin B (NP0140682)

MOL for NP0140682 (Macranthoidin B)

3D MOL for NP0140682 (Macranthoidin B)

3D SDF for NP0140682 (Macranthoidin B)

3D-SDF for NP0140682 (Macranthoidin B)

PDB for NP0140682 (Macranthoidin B)

3D PDB for NP0140682 (Macranthoidin B)

SMILES for NP0140682 (Macranthoidin B)

INCHI for NP0140682 (Macranthoidin B)

Structure for NP0140682 (Macranthoidin B)

3D Structure for NP0140682 (Macranthoidin B)