NP-MRD: Showing NP-Card for Aquilegioside A (NP0070873)

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Record Information

Version

2.0

Created at

2022-04-28 16:17:34 UTC

Updated at

2022-04-28 16:17:35 UTC

NP-MRD ID

NP0070873

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aquilegioside A

Description

(6S)-6-[(1S)-1-[(1S,3R,6S,7R,8R,11S,12S,14R,15R,16R)-6-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2R,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]oxy}oxan-2-yl]oxy}-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-15-yl]ethyl]-3-methyl-5,6-dihydro-2H-pyran-2-one belongs to the class of organic compounds known as withanolide glycosides and derivatives. These are withanolides in which at least one hydroxyl group is glycosylated. Aquilegioside A is found in Aquilegia flabellata, Aquilegia flabellate SIEB.et ZUCC.var.flabellata and Aquilegia vulgaris . Based on a literature review very few articles have been published on (6S)-6-[(1S)-1-[(1S,3R,6S,7R,8R,11S,12S,14R,15R,16R)-6-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2R,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]oxy}oxan-2-yl]oxy}-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-15-yl]ethyl]-3-methyl-5,6-dihydro-2H-pyran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218172D          

 66 74  0  0  1  0            999 V2000
   -0.5318   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.5318   -1.4557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8121   -0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2803   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -0.5346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1561   -1.1653    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8758   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -1.0201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2485   -0.2441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7167    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9045    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730   -0.2709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3024   -1.0634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6195   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783   -1.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794    0.3804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3966    0.2675    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9030    0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7202    0.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0311    0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5248   -0.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8357   -1.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7075   -0.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8484   -0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    1.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0924    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921   -2.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7186   -2.9610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1635   -2.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045   -1.8914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3727   -2.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6530   -3.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4651   -3.4432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9970   -2.8125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7167   -2.0366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2485   -1.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0606   -1.5511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5924   -0.9204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4045   -1.0656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6848   -1.8415    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1530   -2.4722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3409   -2.3270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4333   -3.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9015   -3.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1818   -4.6548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6500   -5.2855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9303   -6.0614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7424   -6.2066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2742   -5.5759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -7.0863   -5.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0227   -6.9825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3985   -6.6921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8379   -5.1403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4970   -1.9867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9364   -0.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3121   -0.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8091   -2.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454   -4.2191    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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  6  0  0  0
 15 19  1  1  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 20 26  1  0  0  0  0
 23 27  1  0  0  0  0
 19 28  1  6  0  0  0
 12 29  1  1  0  0  0
 11 30  1  6  0  0  0
  7 31  1  1  0  0  0
  5 31  1  1  0  0  0
  3 32  1  6  0  0  0
 32 33  1  0  0  0  0
  3 34  1  1  0  0  0
  2 35  1  1  0  0  0
 36 35  1  6  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
 36 41  1  0  0  0  0
 41 42  1  1  0  0  0
 43 42  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 43 48  1  0  0  0  0
 47 49  1  6  0  0  0
 49 50  1  0  0  0  0
 51 50  1  1  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 51 56  1  0  0  0  0
 55 57  1  1  0  0  0
 57 58  1  0  0  0  0
 54 59  1  6  0  0  0
 53 60  1  1  0  0  0
 52 61  1  6  0  0  0
 46 62  1  1  0  0  0
 45 63  1  6  0  0  0
 44 64  1  1  0  0  0
 40 65  1  6  0  0  0
 39 66  1  6  0  0  0
M  END

     RDKit          3D

140148  0  0  0  0  0  0  0  0999 V2000
   12.0993   -2.0958    2.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1495   -1.4073    1.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9120   -1.7823    1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9526   -1.1418    0.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3880    0.0901    0.2425 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7550    1.3439    0.7879 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3615    2.4698   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3320    1.3037    0.9425 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7765    2.5976    1.6385 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2162    2.6200    2.9562 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2798    2.3979    1.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0434    0.0101    1.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7858    1.1980   -0.0112 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.0577   -1.7712   -1.4342 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6020   -0.7844   -2.2240 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9659    1.0229   -4.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1219    2.0651   -2.9699 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0994   -0.8669   -2.6803 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4598   -0.7345   -0.9803 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5329    0.3156   -2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7975    0.3371    0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4813   -2.6615    3.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5741   -2.6126    2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0117   -1.0217    1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2012    1.4674    1.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4253    2.5756    0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5230    2.2567   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282218172D          

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M  END
> <DATABASE_ID>
NP0070873

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)[C@@]4(C)CO)[C@@H]1CC=C(C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C47H74O19/c1-20-6-7-24(62-39(20)59)21(2)30-22(50)14-45(5)28-9-8-27-43(3,19-49)29(10-11-46(27)18-47(28,46)13-12-44(30,45)4)65-42-38(31(52)23(51)16-60-42)66-41-37(58)35(56)33(54)26(64-41)17-61-40-36(57)34(55)32(53)25(15-48)63-40/h6,21-38,40-42,48-58H,7-19H2,1-5H3/t21-,22-,23+,24+,25-,26-,27+,28+,29+,30+,31+,32-,33-,34+,35+,36-,37-,38-,40-,41-,42+,43+,44-,45+,46-,47+/m1/s1

> <INCHI_KEY>
YUCORSXPQUBWMI-PRNIWAPBSA-N

> <FORMULA>
C47H74O19

> <MOLECULAR_WEIGHT>
943.09

> <EXACT_MASS>
942.482430163

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
140

> <JCHEM_AVERAGE_POLARIZABILITY>
101.61378908940647

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S)-6-[(1S)-1-[(1S,3R,6S,7R,8R,11S,12S,14R,15R,16R)-6-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2R,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]oxy}oxan-2-yl]oxy}-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]ethyl]-3-methyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
-0.83

> <JCHEM_LOGP>
-0.9433133093333307

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.336045516546317

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.861379146306822

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5268774589064034

> <JCHEM_POLAR_SURFACE_AREA>
304.21000000000004

> <JCHEM_REFRACTIVITY>
226.49530000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-6-[(1S)-1-[(1S,3R,6S,7R,8R,11S,12S,14R,15R,16R)-6-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2R,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]oxy}oxan-2-yl]oxy}-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]ethyl]-3-methyl-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.993  -0.363   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.516  -1.811   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.523  -2.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.993  -2.717   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.516  -1.269   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.523  -0.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.032  -0.998   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.025  -2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.501  -3.624   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.985  -3.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.541  -1.904   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.064  -0.456   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.071   0.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.555   0.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.603  -0.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.031  -1.985   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.756  -2.849   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.479  -2.508   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.548   0.710   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.074   0.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.019   1.715   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.544   1.505   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.125   0.078   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.180  -1.138   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.760  -2.564   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.654  -0.927   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.650  -0.133   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.968   2.137   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.736   0.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.172  -3.399   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.039   0.179   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.665  -4.022   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.341  -5.527   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.305  -4.513   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.032  -2.082   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -3.555  -3.531   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.562  -4.708   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -3.086  -6.156   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.602  -6.427   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.594  -5.250   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.071  -3.802   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.064  -2.624   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -7.580  -2.895   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -8.573  -1.718   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -10.088  -1.989   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -10.612  -3.437   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -9.619  -4.615   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -8.103  -4.344   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0     -10.142  -6.063   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -9.149  -7.241   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -9.673  -8.689   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -8.680  -9.866   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -9.203 -11.315   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -10.719 -11.586   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -11.712 -10.408   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0     -11.189  -8.960   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0     -13.228 -10.679   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0     -13.751 -12.128   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0     -11.242 -13.034   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -8.210 -12.492   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      -7.164  -9.595   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0     -12.128  -3.709   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0     -11.081  -0.812   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      -8.049  -0.270   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      -7.110  -5.521   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      -5.125  -7.876   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   35                                                  
CONECT    3    2    4   32   34                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   31                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14   31                                             
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   17   30                                             
CONECT   12   11   13   15   29                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16                                                            
CONECT   19   15   20   28                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20                                                       
CONECT   27   23                                                            
CONECT   28   19                                                            
CONECT   29   12                                                            
CONECT   30   11                                                            
CONECT   31    7    5                                                       
CONECT   32    3   33                                                       
CONECT   33   32                                                            
CONECT   34    3                                                            
CONECT   35    2   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   66                                                  
CONECT   40   39   41   65                                                  
CONECT   41   40   36   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45   64                                                  
CONECT   45   44   46   63                                                  
CONECT   46   45   47   62                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47   43                                                       
CONECT   49   47   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   56                                                  
CONECT   52   51   53   61                                                  
CONECT   53   52   54   60                                                  
CONECT   54   53   55   59                                                  
CONECT   55   54   56   57                                                  
CONECT   56   55   51                                                       
CONECT   57   55   58                                                       
CONECT   58   57                                                            
CONECT   59   54                                                            
CONECT   60   53                                                            
CONECT   61   52                                                            
CONECT   62   46                                                            
CONECT   63   45                                                            
CONECT   64   44                                                            
CONECT   65   40                                                            
CONECT   66   39                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  148    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₇₄O₁₉

Average Mass

943.0900 Da

Monoisotopic Mass

942.48243 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)[C@@]4(C)CO)[C@@H]1CC=C(C)C(=O)O1

InChI Identifier

InChI=1S/C47H74O19/c1-20-6-7-24(62-39(20)59)21(2)30-22(50)14-45(5)28-9-8-27-43(3,19-49)29(10-11-46(27)18-47(28,46)13-12-44(30,45)4)65-42-38(31(52)23(51)16-60-42)66-41-37(58)35(56)33(54)26(64-41)17-61-40-36(57)34(55)32(53)25(15-48)63-40/h6,21-38,40-42,48-58H,7-19H2,1-5H3/t21-,22-,23+,24+,25-,26-,27+,28+,29+,30+,31+,32-,33-,34+,35+,36-,37-,38-,40-,41-,42+,43+,44-,45+,46-,47+/m1/s1

InChI Key

YUCORSXPQUBWMI-PRNIWAPBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aquilegia flabellata	LOTUS Database	35616633
Aquilegia flabellate SIEB.et ZUCC.var.flabellata	Plant	KNApSAcK
Aquilegia vulgaris	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolide glycosides and derivatives. These are withanolides in which at least one hydroxyl group is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolide glycosides and derivatives

Alternative Parents

Substituents

Withanolide-glycoside
Cycloartanol-skeleton
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
Oligosaccharide
16-hydroxysteroid
16-alpha-hydroxysteroid
Hydroxysteroid
O-glycosyl compound
Glycosyl compound
Dihydropyranone
Pyran
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen 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	-0.83	ALOGPS
logP	-0.94	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.86	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	304.21 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	226.5 m³·mol⁻¹	ChemAxon
Polarizability	101.61 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

162973317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Aquilegioside A (NP0070873)

MOL for NP0070873 (Aquilegioside A)

3D MOL for NP0070873 (Aquilegioside A)

3D SDF for NP0070873 (Aquilegioside A)

3D-SDF for NP0070873 (Aquilegioside A)

PDB for NP0070873 (Aquilegioside A)

3D PDB for NP0070873 (Aquilegioside A)

SMILES for NP0070873 (Aquilegioside A)

INCHI for NP0070873 (Aquilegioside A)

Structure for NP0070873 (Aquilegioside A)

3D Structure for NP0070873 (Aquilegioside A)