NP-MRD: Showing NP-Card for aurantio-obtusin β-d-glucoside (NP0309190)

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Record Information

Version

1.0

Created at

2022-09-11 03:37:01 UTC

Updated at

2022-09-11 03:37:01 UTC

NP-MRD ID

NP0309190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aurantio-obtusin β-d-glucoside

Description

Aurantio-obtusin beta-D-glucoside belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. aurantio-obtusin β-d-glucoside is found in Senna obtusifolia and Senna tora. It was first documented in 2022 (PMID: 34731817). Based on a literature review very few articles have been published on aurantio-obtusin beta-D-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205372D          

 35 38  0  0  1  0            999 V2000
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  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
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 34  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -1.6687    4.1123    0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852    3.2972   -0.3272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4524    2.2135   -0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806    0.9436   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3506    0.8464    0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720   -0.3108    0.3926 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9196   -0.4968   -0.7336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577   -1.3213   -0.3523 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5576   -2.0691   -1.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5950   -2.8633   -0.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0166   -0.4357    0.2935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0167   -1.1789    0.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2902    0.4649    1.2669 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0845    1.6992    0.6288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9286   -0.0677    1.6299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0002   -1.2070    2.4343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844   -0.1697    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789   -0.0402   -0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431    1.2031   -0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9301    2.3135   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586    3.5475   -0.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1883    1.2266   -0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667    2.3066   -0.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0056    0.0097   -0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205   -1.2032   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574   -2.3762   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215   -2.3283   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2838   -3.5973   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1137   -1.1141   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4971   -1.1003   -0.6154 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3805    0.0553   -0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768    1.2721   -0.8020 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4261    2.1054    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -1.2565   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580   -2.3905    0.2163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0776    5.0363    0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5989    3.5627    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7656    4.3267    0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131   -1.2510    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5789   -2.0904    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9977   -1.4128   -2.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7982   -2.7561   -1.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3612   -3.1931   -0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4683    0.1513   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1531   -0.7878    1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8488    0.6317    2.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    2.3938    1.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4361    0.7144    2.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -1.7739    2.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5919   -1.1797    0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472    3.8970   -0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6573   -3.3099    0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4052   -4.0736   -1.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7305   -4.3259    0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2566   -3.4323    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0226   -0.2552   -0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3511    3.1539   -0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4782    1.9153    0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8064    1.9686    1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  2  0
 18 34  1  0
 34 35  2  0
 34 25  1  0
 25 24  2  0
 24 22  1  0
 22 23  2  0
 22 19  1  0
 19 20  2  0
 20 21  1  0
 24 31  1  0
 31 32  1  0
 32 33  1  0
 31 29  2  0
 29 30  1  0
 29 27  1  0
 27 28  1  0
 27 26  2  0
 20  3  1  0
 15  6  1  0
 19 18  1  0
 26 25  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  6 39  1  1
  8 40  1  1
  9 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  0
 13 46  1  1
 14 47  1  0
 15 48  1  1
 16 49  1  0
 17 50  1  0
 21 51  1  0
 33 57  1  0
 33 58  1  0
 33 59  1  0
 30 56  1  0
 28 53  1  0
 28 54  1  0
 28 55  1  0
 26 52  1  0
M  END


  Mrv1652309112205372D          

 35 38  0  0  1  0            999 V2000
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  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
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 34  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0309190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C2C(=O)C3=C(C(=O)C2=C1O)C(OC)=C(O)C(C)=C3

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O12/c1-7-4-8-13(22(33-3)14(7)25)17(28)12-9(15(8)26)5-10(21(32-2)18(12)29)34-23-20(31)19(30)16(27)11(6-24)35-23/h4-5,11,16,19-20,23-25,27,29-31H,6H2,1-3H3/t11-,16-,19+,20-,23-/m1/s1

> <INCHI_KEY>
LQYQYAJWKXDTHR-PHVGODQESA-N

> <FORMULA>
C23H24O12

> <MOLECULAR_WEIGHT>
492.433

> <EXACT_MASS>
492.126776213

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
47.9689991045199

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,7-dihydroxy-2,8-dimethoxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

> <JCHEM_LOGP>
0.588020874333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.842854289713824

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.142669519578526

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549535424

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
117.20569999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
aurantio-obtusin β-D-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   25   18   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Aurantio-obtusin b-D-glucoside	Generator
Aurantio-obtusin β-D-glucoside	Generator

Chemical Formula

C₂₃H₂₄O₁₂

Average Mass

492.4330 Da

Monoisotopic Mass

492.12678 Da

IUPAC Name

1,7-dihydroxy-2,8-dimethoxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

Traditional Name

aurantio-obtusin β-D-glucoside

CAS Registry Number

Not Available

SMILES

COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C2C(=O)C3=C(C(=O)C2=C1O)C(OC)=C(O)C(C)=C3

InChI Identifier

InChI=1S/C23H24O12/c1-7-4-8-13(22(33-3)14(7)25)17(28)12-9(15(8)26)5-10(21(32-2)18(12)29)34-23-20(31)19(30)16(27)11(6-24)35-23/h4-5,11,16,19-20,23-25,27,29-31H,6H2,1-3H3/t11-,16-,19+,20-,23-/m1/s1

InChI Key

LQYQYAJWKXDTHR-PHVGODQESA-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
Senna obtusifolia	LOTUS Database	35616633
Senna tora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Anisole
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monosaccharide
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:28268 )
Anthraquinone type (C10303 )

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	0.59	ChemAxon
pKa (Strongest Acidic)	8.14	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.21 m³·mol⁻¹	ChemAxon
Polarizability	47.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00002796

Chemspider ID

391073

KEGG Compound ID

C10303

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442725

PDB ID

Not Available

ChEBI ID

28268

Good Scents ID

Not Available

References

General References

Duan H, Wang W, Li Y, Jilany Khan G, Chen Y, Shen T, Bao N, Hua J, Xue Z, Zhai K, Wei Z: Identification of phytochemicals and antioxidant activity of Premna microphylla Turcz. stem through UPLC-LTQ-Orbitrap-MS. Food Chem. 2022 Mar 30;373(Pt B):131482. doi: 10.1016/j.foodchem.2021.131482. Epub 2021 Oct 27. [PubMed:34731817 ]
LOTUS database [Link]

Showing NP-Card for aurantio-obtusin β-d-glucoside (NP0309190)

MOL for NP0309190 (aurantio-obtusin β-d-glucoside)

3D MOL for NP0309190 (aurantio-obtusin β-d-glucoside)

3D SDF for NP0309190 (aurantio-obtusin β-d-glucoside)

3D-SDF for NP0309190 (aurantio-obtusin β-d-glucoside)

PDB for NP0309190 (aurantio-obtusin β-d-glucoside)

3D PDB for NP0309190 (aurantio-obtusin β-d-glucoside)

SMILES for NP0309190 (aurantio-obtusin β-d-glucoside)

INCHI for NP0309190 (aurantio-obtusin β-d-glucoside)

Structure for NP0309190 (aurantio-obtusin β-d-glucoside)

3D Structure for NP0309190 (aurantio-obtusin β-d-glucoside)