NP-MRD: Showing NP-Card for 2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0294143)

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Record Information

Version

2.0

Created at

2022-09-10 02:32:28 UTC

Updated at

2022-09-10 02:32:28 UTC

NP-MRD ID

NP0294143

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Astragaloside IV, also known as astramembrannin I or cyclosiversioside F, belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Astragalus caprinus, Astragalus ernestii, Astragalus lehmannianus, Astragalus melanophrurius, Astragalus membranaceus, Astragalus microcephalus and Astragalus oleifolius. 2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol was first documented in 2022 (PMID: 36115280). Based on a literature review a small amount of articles have been published on Astragaloside IV (PMID: 36113188) (PMID: 36103112) (PMID: 36092836) (PMID: 36076531).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102204322D          

 55 62  0  0  1  0            999 V2000
    4.4417    5.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9735    4.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3428    4.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042    5.2544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5053    4.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    4.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6390    3.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6032    2.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072    1.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123   -0.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002   -0.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562   -0.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.4384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -0.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077   -1.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -2.2296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1199   -1.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6517   -1.9392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392    1.8451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711    2.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    3.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3226    3.8824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    3.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983    4.1728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653    2.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3076    3.2909    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
  2  4  1  0  0  0  0
  2  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  1  0  0  0
  8 10  1  6  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 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
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 37 44  1  0  0  0  0
 44 45  1  0  0  0  0
 35 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 31 48  1  1  0  0  0
 48 49  1  1  0  0  0
 50 49  1  1  0  0  0
 16 50  1  0  0  0  0
 48 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
 10 53  1  0  0  0  0
 14 53  1  0  0  0  0
 53 54  1  1  0  0  0
  8 55  1  0  0  0  0
  5 55  1  0  0  0  0
M  END

     RDKit          3D

123130  0  0  0  0  0  0  0  0999 V2000
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   -7.9054    1.7094    1.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9940    0.4990   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8904   -0.4859   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6587    0.4448   -0.5446 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6888    1.2619   -1.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937   -0.4553   -0.5748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4295   -1.4811    0.5316 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9899   -2.7237    0.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9290   -1.7744    0.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4097   -0.3537    0.6485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9245    0.3358    1.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.2273    0.5778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1750   -1.4937    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073   -1.2257    0.2657 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.5099   -3.1799    0.1441 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8809   -3.3070    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630   -4.2380   -0.8618 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3020   -5.1578   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3910   -4.3641    0.1275 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7421   -6.2098   -1.9935 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5464    4.5977   -0.9832 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.6538    3.1535   -1.3325 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7485    2.5908   -0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4123    2.3462   -1.1742 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8189    1.0874   -0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533    2.7146    1.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606    2.5754    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8728    1.1792   -0.1827 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.6785   -3.0188   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102204322D          

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M  END
> <DATABASE_ID>
NP0294143

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CC[C@@](C)(O1)[C@@H]1C(O)C[C@@]2(C)[C@H]3CC(OC4OC(CO)C(O)C(O)C4O)[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(OC1OCC(O)C(O)C1O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C41H68O14/c1-35(2)24(54-33-29(48)26(45)20(44)17-51-33)9-11-41-18-40(41)13-12-37(5)31(39(7)10-8-25(55-39)36(3,4)50)19(43)15-38(37,6)23(40)14-21(32(35)41)52-34-30(49)28(47)27(46)22(16-42)53-34/h19-34,42-50H,8-18H2,1-7H3/t19?,20?,21?,22?,23-,24?,25?,26?,27?,28?,29?,30?,31-,32+,33?,34?,37-,38+,39-,40+,41-/m1/s1

> <INCHI_KEY>
QMNWISYXSJWHRY-ILRGXAOWSA-N

> <FORMULA>
C41H68O14

> <MOLECULAR_WEIGHT>
784.981

> <EXACT_MASS>
784.46090687

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
86.1818932882029

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(1S,3R,8R,11R,12S,15S,16R)-14-hydroxy-15-[(2R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-0.31154303033333286

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.455483801601325

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.92528420541649

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835427988813

> <JCHEM_POLAR_SURFACE_AREA>
228.21999999999994

> <JCHEM_REFRACTIVITY>
194.58010000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(1S,3R,8R,11R,12S,15S,16R)-14-hydroxy-15-[(2R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.291   9.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.284   8.815   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.107   7.823   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.461   9.808   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.277   7.638   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.813   7.749   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.393   6.323   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.326   4.263   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.147   2.112   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.130  -0.723   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.614  -0.994   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.621   0.183   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.105  -0.088   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.888   1.089   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.404   0.818   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.418  -1.536   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.934  -1.807   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.574  -2.714   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.051  -4.162   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.090  -2.442   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.083  -3.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.357   3.715   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.873   3.444   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -3.866   4.621   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -3.343   6.070   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.335   7.247   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -1.827   6.341   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -1.304   7.789   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.834   5.164   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       0.682   5.435   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       9.908   6.143   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   55                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   55                                             
CONECT    9    8                                                            
CONECT   10    8   11   53                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   53                                             
CONECT   15   14                                                            
CONECT   16   14   17   50                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
CONECT   31   18   32   48                                                  
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   36   46                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   44                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   37   45                                                  
CONECT   45   44                                                            
CONECT   46   35   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   31   49   50                                             
CONECT   49   48   50                                                       
CONECT   50   49   16   48   51                                             
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   10   14   54                                             
CONECT   54   53                                                            
CONECT   55    8    5                                                       
MASTER        0    0    0    0    0    0    0    0   55    0  124    0
END

View in JSmol

Synonyms

Value	Source
3beta,6alpha,16beta,20R,24S; astragaloside IV OF astragaloside a	MeSH
Astragaloside a	MeSH
Astragaloside-a	MeSH
Astramembrannin I	MeSH
Cyclosiversioside F	MeSH

Chemical Formula

C₄₁H₆₈O₁₄

Average Mass

784.9810 Da

Monoisotopic Mass

784.46091 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CC[C@@](C)(O1)[C@@H]1C(O)C[C@@]2(C)[C@H]3CC(OC4OC(CO)C(O)C(O)C4O)[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(OC1OCC(O)C(O)C1O)C4(C)C

InChI Identifier

InChI=1S/C41H68O14/c1-35(2)24(54-33-29(48)26(45)20(44)17-51-33)9-11-41-18-40(41)13-12-37(5)31(39(7)10-8-25(55-39)36(3,4)50)19(43)15-38(37,6)23(40)14-21(32(35)41)52-34-30(49)28(47)27(46)22(16-42)53-34/h19-34,42-50H,8-18H2,1-7H3/t19?,20?,21?,22?,23-,24?,25?,26?,27?,28?,29?,30?,31-,32+,33?,34?,37-,38+,39-,40+,41-/m1/s1

InChI Key

QMNWISYXSJWHRY-ILRGXAOWSA-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
Astragalus caprinus	LOTUS Database	35616633
Astragalus ernestii	LOTUS Database	35616633
Astragalus lehmannianus	LOTUS Database	35616633
Astragalus melanophrurius	LOTUS Database	35616633
Astragalus membranaceus	LOTUS Database	35616633
Astragalus microcephalus	LOTUS Database	35616633
Astragalus oleifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Triterpene saponin
Triterpene glycoside
Cycloartanol-skeleton
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
16-hydroxysteroid
Hydroxysteroid
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00035248

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

137706357

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang X, Wang Y, Huang D, Shi S, Pei C, Wu Y, Shen Z, Wang F, Wang Z: Astragaloside IV regulates the ferroptosis signaling pathway via the Nrf2/SLC7A11/GPX4 axis to inhibit PM2.5-mediated lung injury in mice. Int Immunopharmacol. 2022 Nov;112:109186. doi: 10.1016/j.intimp.2022.109186. Epub 2022 Sep 15. [PubMed:36115280 ]
Du Y, Li C, Xu S, Yang J, Wan H, He Y: LC-MS/MS combined with blood-brain dual channel microdialysis for simultaneous determination of active components of astragali radix-safflower combination and neurotransmitters in rats with cerebral ischemia reperfusion injury: Application in pharmacokinetic and pharmacodynamic study. Phytomedicine. 2022 Nov;106:154432. doi: 10.1016/j.phymed.2022.154432. Epub 2022 Sep 5. [PubMed:36113188 ]
Zhang Y, Xu G, Huang B, Chen D, Ye R: Astragaloside IV Regulates Insulin Resistance and Inflammatory Response of Adipocytes via Modulating CTRP3 and PI3K/AKT Signaling. Diabetes Ther. 2022 Dec;13(11-12):1823-1834. doi: 10.1007/s13300-022-01312-1. Epub 2022 Sep 14. [PubMed:36103112 ]
Su Y, Xu J, Chen S, Feng J, Li J, Lei Z, Qiao L, Wang Y, Zeng D: Astragaloside IV protects against ischemia/reperfusion (I/R)-induced kidney injury based on the Keap1-Nrf2/ARE signaling pathway. Transl Androl Urol. 2022 Aug;11(8):1177-1188. doi: 10.21037/tau-22-505. [PubMed:36092836 ]
Chen BY, Liou JC, Wu JL, Chen CH, Yang SL: Photoreceptor and vision protective effects of astragaloside IV in mice model with light-evoked retinal damage. Biomed Pharmacother. 2022 Sep;153:113404. doi: 10.1016/j.biopha.2022.113404. Epub 2022 Jul 12. [PubMed:36076531 ]
LOTUS database [Link]

Showing NP-Card for 2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0294143)

MOL for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0294143 (2-{[(1s,3r,8r,11r,12s,15s,16r)-14-hydroxy-15-[(2r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)