NP-MRD: Showing NP-Card for calycosin-7-O-beta-D-glucopyranoside (NP0029696)

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Record Information

Version

2.0

Created at

2021-06-19 21:15:22 UTC

Updated at

2021-06-29 23:57:14 UTC

NP-MRD ID

NP0029696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

calycosin-7-O-beta-D-glucopyranoside

Provided By

JEOL Database JEOL Logo

Description

Calycosin-7-O-beta-D-glucoside belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. calycosin-7-O-beta-D-glucopyranoside is found in Amorpha fruticosa, Astragalus complanatus, Astragalus membranaceus, Astragalus membranaceus var. mongholicus, Baptisia spp., Glycyrrhiza glabra , Glycyrrhiza pallidiflora, Maackia amurensis, Styphnolobium japonicum, Thermopsis spp. and Trifolium pratense . calycosin-7-O-beta-D-glucopyranoside was first documented in 2008 (PMID: 18346946). Based on a literature review a small amount of articles have been published on calycosin-7-O-beta-D-glucoside (PMID: 24417088) (PMID: 34296565) (PMID: 34296563).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306192123153D          

 54 57  0  0  0  0            999 V2000
    0.1018    7.8498    3.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6972    6.6437    4.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0032    5.5241    2.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    4.3310    1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503    3.1529    2.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350    1.9060    1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    1.8660    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6264   -0.4098   -0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 33  1  0  0  0  0
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  1 35  1  0  0  0  0
M  END

     RDKit          3D

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M  END

  Mrv1652306192123153D          

 54 57  0  0  0  0            999 V2000
    0.1018    7.8498    3.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6972    6.6437    4.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4997    4.3297    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    2.7177   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1677   -1.3618   -2.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8862   -3.4832   -2.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7636   -2.6480   -4.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080   -2.0331   -6.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0749   -2.5412   -6.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5142   -1.0475   -4.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1461   -4.9059   -5.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107   -5.4448   -7.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6536   -5.1526   -4.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970   -7.3206   -4.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0411   -5.8087   -3.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3606   -6.0245   -1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005   -3.8267    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423   -1.8786    2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5808    2.2936    3.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457    5.2839    5.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 10 27  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 10  9  1  0  0  0  0
 27 28  1  0  0  0  0
 28  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  6  5  2  0  0  0  0
 17 18  1  0  0  0  0
  5  4  1  0  0  0  0
 14 23  1  0  0  0  0
  4  3  2  0  0  0  0
 23 21  1  0  0  0  0
  3 31  1  0  0  0  0
 12 25  2  0  0  0  0
 31 30  2  0  0  0  0
 30  6  1  0  0  0  0
  7  6  1  0  0  0  0
 12 13  1  0  0  0  0
 21 19  1  0  0  0  0
 28 29  2  0  0  0  0
 25 26  1  0  0  0  0
  3  2  1  0  0  0  0
 26 27  2  0  0  0  0
 31 32  1  0  0  0  0
 19 16  1  0  0  0  0
  2  1  1  0  0  0  0
 16 17  1  0  0  0  0
 14 13  1  0  0  0  0
 14 40  1  1  0  0  0
 19 45  1  6  0  0  0
 20 46  1  0  0  0  0
 21 47  1  1  0  0  0
 22 48  1  0  0  0  0
 23 49  1  6  0  0  0
 24 50  1  0  0  0  0
 17 42  1  0  0  0  0
 17 43  1  0  0  0  0
 16 41  1  1  0  0  0
 18 44  1  0  0  0  0
 25 51  1  0  0  0  0
 26 52  1  0  0  0  0
 11 39  1  0  0  0  0
  8 38  1  0  0  0  0
  5 37  1  0  0  0  0
  4 36  1  0  0  0  0
 30 53  1  0  0  0  0
 32 54  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C1=C([H])OC2=C([H])C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])=C([H])C([H])=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c1-29-15-5-2-10(6-14(15)24)13-9-30-16-7-11(3-4-12(16)18(13)25)31-22-21(28)20(27)19(26)17(8-23)32-22/h2-7,9,17,19-24,26-28H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1

> <INCHI_KEY>
WACBUPFEGWUGPB-MIUGBVLSSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.37016468868673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
0.30469835233333387

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200536758050106

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.206878162581587

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343722586

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
108.3096

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    0.1018    7.8498    3.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6972    6.6437    4.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5989    5.5538    3.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032    5.5241    2.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    4.3310    1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503    3.1529    2.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350    1.9060    1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    1.8660    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451    0.7758   -0.7545 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264   -0.4098   -0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7101   -1.5102   -1.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2008   -2.7474   -0.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2116   -3.9011   -1.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705   -3.8845   -2.7666 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1280   -3.1198   -3.7202 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -3.0912   -5.0119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0566   -2.1624   -5.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616   -0.8769   -5.2914 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8576   -4.5043   -5.5979 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5542   -4.5014   -6.8440 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904   -5.4201   -4.6153 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5541   -6.7659   -5.1156 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569   -5.3534   -3.2270 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7474   -6.1515   -2.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3939   -2.8691    0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4768   -1.7711    1.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374   -0.5386    0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0393    0.6392    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5591    0.5573    2.9454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405    3.1861    3.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1629    4.3765    4.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601    4.3744    5.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9768    7.7278    3.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2504    8.6133    4.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873    8.2015    3.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    6.4036    1.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    4.3297    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    2.7177   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1677   -1.3618   -2.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8862   -3.4832   -2.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7636   -2.6480   -4.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080   -2.0331   -6.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0749   -2.5412   -6.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5142   -1.0475   -4.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1461   -4.9059   -5.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107   -5.4448   -7.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6536   -5.1526   -4.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970   -7.3206   -4.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0411   -5.8087   -3.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3606   -6.0245   -1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005   -3.8267    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423   -1.8786    2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5808    2.2936    3.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457    5.2839    5.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11 12  1  0
 10 27  1  0
 16 15  1  0
 15 14  1  0
 19 20  1  0
 21 22  1  0
 23 24  1  0
 10  9  1  0
 27 28  1  0
 28  7  1  0
  7  8  2  0
  8  9  1  0
  6  5  2  0
 17 18  1  0
  5  4  1  0
 14 23  1  0
  4  3  2  0
 23 21  1  0
  3 31  1  0
 12 25  2  0
 31 30  2  0
 30  6  1  0
  7  6  1  0
 12 13  1  0
 21 19  1  0
 28 29  2  0
 25 26  1  0
  3  2  1  0
 26 27  2  0
 31 32  1  0
 19 16  1  0
  2  1  1  0
 16 17  1  0
 14 13  1  0
 14 40  1  1
 19 45  1  6
 20 46  1  0
 21 47  1  1
 22 48  1  0
 23 49  1  6
 24 50  1  0
 17 42  1  0
 17 43  1  0
 16 41  1  1
 18 44  1  0
 25 51  1  0
 26 52  1  0
 11 39  1  0
  8 38  1  0
  5 37  1  0
  4 36  1  0
 30 53  1  0
 32 54  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.102   7.850   3.934  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.697   6.644   4.399  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.599   5.554   3.573  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.003   5.524   2.314  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.019   4.331   1.578  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.550   3.153   2.090  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.535   1.906   1.307  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.075   1.866   0.079  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.145   0.776  -0.755  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.626  -0.410  -0.298  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.710  -1.510  -1.157  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.201  -2.747  -0.758  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.212  -3.901  -1.492  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.871  -3.885  -2.767  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.128  -3.120  -3.720  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.766  -3.091  -5.012  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.057  -2.162  -5.910  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.162  -0.877  -5.291  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.858  -4.504  -5.598  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.554  -4.501  -6.844  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.590  -5.420  -4.615  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.554  -6.766  -5.116  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.957  -5.353  -3.227  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.747  -6.152  -2.331  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.394  -2.869   0.503  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.477  -1.771   1.363  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.037  -0.539   0.956  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.039   0.639   1.839  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.559   0.557   2.945  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.141   3.186   3.357  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.163   4.377   4.077  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.760   4.374   5.309  0.00  0.00           O+0
HETATM   33  H   UNK     0      -0.977   7.728   3.790  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.250   8.613   4.704  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.587   8.201   3.018  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.454   6.404   1.874  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.500   4.330   0.601  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.539   2.718  -0.405  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.168  -1.362  -2.130  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.886  -3.483  -2.643  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.764  -2.648  -4.892  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.408  -2.033  -6.892  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.075  -2.541  -6.046  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.514  -1.048  -4.397  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.146  -4.906  -5.786  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.711  -5.445  -7.056  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.654  -5.153  -4.567  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.897  -7.321  -4.385  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.041  -5.809  -3.251  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.361  -6.024  -1.442  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.801  -3.827   0.822  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.942  -1.879   2.340  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.581   2.294   3.794  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.646   5.284   5.646  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    3    1                                                       
CONECT    3    4   31    2                                                  
CONECT    4    5    3   36                                                  
CONECT    5    6    4   37                                                  
CONECT    6    5   30    7                                                  
CONECT    7   28    8    6                                                  
CONECT    8    7    9   38                                                  
CONECT    9   10    8                                                       
CONECT   10   11   27    9                                                  
CONECT   11   10   12   39                                                  
CONECT   12   11   25   13                                                  
CONECT   13   12   14                                                       
CONECT   14   15   23   13   40                                             
CONECT   15   16   14                                                       
CONECT   16   15   19   17   41                                             
CONECT   17   18   16   42   43                                             
CONECT   18   17   44                                                       
CONECT   19   20   21   16   45                                             
CONECT   20   19   46                                                       
CONECT   21   22   23   19   47                                             
CONECT   22   21   48                                                       
CONECT   23   24   14   21   49                                             
CONECT   24   23   50                                                       
CONECT   25   12   26   51                                                  
CONECT   26   25   27   52                                                  
CONECT   27   10   28   26                                                  
CONECT   28   27    7   29                                                  
CONECT   29   28                                                            
CONECT   30   31    6   53                                                  
CONECT   31    3   30   32                                                  
CONECT   32   31   54                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    8                                                            
CONECT   39   11                                                            
CONECT   40   14                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   17                                                            
CONECT   44   18                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   26                                                            
CONECT   53   30                                                            
CONECT   54   32                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
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    1.7474   -6.1515   -2.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0374   -0.5386    0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7107   -5.4448   -7.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6536   -5.1526   -4.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970   -7.3206   -4.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8005   -3.8267    0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423   -1.8786    2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol

Synonyms

Value	Source
Calycosin-7-O-b-D-glucoside	Generator
Calycosin-7-O-β-D-glucoside	Generator
Ononin	MeSH

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

3-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

3-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C1=C([H])OC2=C([H])C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])=C([H])C([H])=C2C1=O

InChI Identifier

InChI=1S/C22H22O10/c1-29-15-5-2-10(6-14(15)24)13-9-30-16-7-11(3-4-12(16)18(13)25)31-22-21(28)20(27)19(26)17(8-23)32-22/h2-7,9,17,19-24,26-28H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1

InChI Key

WACBUPFEGWUGPB-MIUGBVLSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amorpha fruticosa	LOTUS Database	35616633
Astragalus complanatus	LOTUS Database	35616633
Astragalus membranaceus	LOTUS Database	35616633
Astragalus mongholicus	JEOL database	Du, X., et al, Magn. Reson. Chem. 44, 708(2006)
Baptisia spp.	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza pallidiflora	Plant	KNApSAcK
Maackia amurensis	LOTUS Database	35616633
Styphnolobium japonicum	LOTUS Database	35616633
Thermopsis spp.	Plant	KNApSAcK
Trifolium pratense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid O-glycosides

Direct Parent

Isoflavonoid O-glycosides

Alternative Parents

Substituents

Isoflavonoid o-glycoside
Isoflavonoid-7-o-glycoside
4p-o-methylisoflavone
3'-hydroxy,4'-methoxyisoflavonoid
Hydroxyisoflavonoid
Isoflavone
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Pyranone
Benzenoid
Monocyclic benzene moiety
Oxane
Pyran
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Ether
Oxacycle
Polyol
Acetal
Organoheterocyclic compound
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:86512 )
monosaccharide derivative (CHEBI:86512 )
hydroxyisoflavone (CHEBI:86512 )
methoxyisoflavone (CHEBI:86512 )
glycosyloxyisoflavone (CHEBI:86512 )

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	0.8	ALOGPS
logP	0.3	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.31 m³·mol⁻¹	ChemAxon
Polarizability	45.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

4476876

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ononin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

86512

Good Scents ID

Not Available

References

General References

Wen XD, Qi LW, Li P, Bao KD, Yan XW, Yi L, Li CY: Simultaneous determination of calycosin-7-O-beta-D-glucoside, ononin, astragaloside IV, astragaloside I and ferulic acid in rat plasma after oral administration of Danggui Buxue Tang extract for their pharmacokinetic studies by liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Apr 1;865(1-2):99-105. doi: 10.1016/j.jchromb.2008.02.024. Epub 2008 Mar 4. [PubMed:18346946 ]
He P, Li ZY, Fan SC, Zhang FS, Qin XM, Du GJ: [Between Hengshanhuangqi and Chuanhuangqi based on metabolomics and ITS2 sequences]. Yao Xue Xue Bao. 2013 Oct;48(10):1595-601. [PubMed:24417088 ]
Zhang SJ, Zhang YG, Li DH, Wu HW, Niu JT, Si XL, Li YF: [Prediction of Q-markers of Astragali Radix based on network pharmacology and fingerprint]. Zhongguo Zhong Yao Za Zhi. 2021 Jun;46(11):2691-2698. doi: 10.19540/j.cnki.cjcmm.20200925.201. [PubMed:34296565 ]
Yang FX, Wang Y, Xia PF, Yang RJ, Wang YX, Zhang J, Fan Q, Zhao L: [Review of chemical constituents,pharmacological effects and clinical applications of Danggui Buxue Decoction and prediction and analysis of its Q-markers]. Zhongguo Zhong Yao Za Zhi. 2021 Jun;46(11):2677-2685. doi: 10.19540/j.cnki.cjcmm.20200828.201. [PubMed:34296563 ]
Du, X., et al. (2006). Du, X., et al, Magn. Reson. Chem. 44, 708(2006). Mag. Reson. Chem..

Showing NP-Card for calycosin-7-O-beta-D-glucopyranoside (NP0029696)

MOL for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)

3D MOL for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)

3D SDF for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)

3D-SDF for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)

PDB for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)

3D PDB for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)

SMILES for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)

INCHI for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)

Structure for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)

3D Structure for NP0029696 (calycosin-7-O-beta-D-glucopyranoside)