NP-MRD: Showing NP-Card for Sissotrin (NP0043983)

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Record Information

Version

1.0

Created at

2021-06-22 17:44:00 UTC

Updated at

2021-08-20 00:00:50 UTC

NP-MRD ID

NP0043983

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sissotrin

Description

Biochanin A 7-O-beta-D-glucoside, also known as sissotrin, 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. Biochanin A 7-O-beta-D-glucoside is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Sissotrin is found in Cicer flexuosum, Cicer songaricum, Dalbergia sissoo, Styphnolobium japonicum, Trifolium aureum, Trifolium diffusum and Trifolium subterraneum. It was first documented in 2006 (PMID: 16650770). Based on a literature review a significant number of articles have been published on biochanin A 7-O-beta-D-glucoside (PMID: 22926873) (PMID: 23030687) (PMID: 23397722) (PMID: 28552514).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119442D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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
   -1.4289   -1.6500    0.0000 C   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   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
    2.8579    0.0000    0.0000 C   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  2  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
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
 16 20  1  0  0  0  0
 14 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 25 30  1  6  0  0  0
 24 31  1  1  0  0  0
 23 32  1  6  0  0  0
M  END

NP0043983
     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    9.9106    0.6257   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9949   -0.3889   -1.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6796   -0.2658   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2289    0.8296   -0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8824    0.9305    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9859   -0.0619   -0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5780    0.0272    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2098    0.4232    1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9647    0.5202    1.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739    0.2374    1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276    0.3425    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776    0.0529    0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    0.1666    1.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494   -0.0683    0.4731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6010    1.1300    0.4274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5572    0.9784   -0.5450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3406    2.2937   -0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3197    2.1639   -1.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5354   -0.1292   -0.2834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1599   -0.4338   -1.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8716   -1.3954    0.2079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7986   -2.2531    0.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7357   -1.0727    1.1793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0801   -2.2386    1.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1044   -0.3488   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2180   -0.4596   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420   -0.8616   -2.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -0.1627   -0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5700   -0.2761   -0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398   -0.6454   -1.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -1.1532   -0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7902   -1.2574   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8110    0.8581    0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9199    0.2531   -1.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7219    1.5049   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8860    1.6230    0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5234    1.7783    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0019    0.6704    2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    0.6673    2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -0.4009   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0743    0.8069   -1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6689    3.1571   -0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8676    2.4387    0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0314    2.6791   -2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3506    0.2141    0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4909   -0.2850   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4102   -1.8995   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5823   -2.5766    1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2025   -0.5671    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4008   -2.4206    0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8852   -0.5808   -1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066   -1.0831   -2.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576   -1.9257   -1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0773   -2.1611   -1.7123 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
  6 31  1  0
 31 32  2  0
 32  3  1  0
 29  7  1  0
 28 10  1  0
 23 14  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  8 38  1  0
 11 39  1  0
 14 40  1  6
 16 41  1  6
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  1
 20 46  1  0
 21 47  1  6
 22 48  1  0
 23 49  1  1
 24 50  1  0
 25 51  1  0
 27 52  1  0
 31 53  1  0
 32 54  1  0
M  END


  Mrv1652306222119442D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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
   -1.4289   -1.6500    0.0000 C   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   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
    2.8579    0.0000    0.0000 C   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  2  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
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
 16 20  1  0  0  0  0
 14 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 25 30  1  6  0  0  0
 24 31  1  1  0  0  0
 23 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0043983

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)13-9-30-15-7-12(6-14(24)17(15)18(13)25)31-22-21(28)20(27)19(26)16(8-23)32-22/h2-7,9,16,19-24,26-28H,8H2,1H3/t16-,19-,20+,21-,22-/m1/s1

> <INCHI_KEY>
LFEUICHQZGNOHD-RECXWPGBSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.2971794661447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
0.9546983523333339

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200145466547728

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.282050987396348

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343758667

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
108.30959999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
biochanin A-β-D-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043983
     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    9.9106    0.6257   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9949   -0.3889   -1.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6796   -0.2658   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2289    0.8296   -0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8824    0.9305    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9859   -0.0619   -0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5780    0.0272    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2098    0.4232    1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9647    0.5202    1.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739    0.2374    1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276    0.3425    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776    0.0529    0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    0.1666    1.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494   -0.0683    0.4731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6010    1.1300    0.4274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5572    0.9784   -0.5450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3406    2.2937   -0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3197    2.1639   -1.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5354   -0.1292   -0.2834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1599   -0.4338   -1.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8716   -1.3954    0.2079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7986   -2.2531    0.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7357   -1.0727    1.1793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0801   -2.2386    1.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1044   -0.3488   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2180   -0.4596   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420   -0.8616   -2.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -0.1627   -0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5700   -0.2761   -0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398   -0.6454   -1.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -1.1532   -0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7902   -1.2574   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8110    0.8581    0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9199    0.2531   -1.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7219    1.5049   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8860    1.6230    0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5234    1.7783    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0019    0.6704    2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    0.6673    2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -0.4009   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0743    0.8069   -1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6689    3.1571   -0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8676    2.4387    0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0314    2.6791   -2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3506    0.2141    0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4909   -0.2850   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4102   -1.8995   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5823   -2.5766    1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2025   -0.5671    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4008   -2.4206    0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8852   -0.5808   -1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066   -1.0831   -2.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576   -1.9257   -1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0773   -2.1611   -1.7123 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
  6 31  1  0
 31 32  2  0
 32  3  1  0
 29  7  1  0
 28 10  1  0
 23 14  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  8 38  1  0
 11 39  1  0
 14 40  1  6
 16 41  1  6
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  1
 20 46  1  0
 21 47  1  6
 22 48  1  0
 23 49  1  1
 24 50  1  0
 25 51  1  0
 27 52  1  0
 31 53  1  0
 32 54  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17    9   19                                                  
CONECT   19   18                                                            
CONECT   20   16                                                            
CONECT   21   14   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   32                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25                                                            
CONECT   31   24                                                            
CONECT   32   23                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    NP0043983
HETATM    1  C1  UNL     1       9.911   0.626  -0.875  1.00  0.00           C  
HETATM    2  O1  UNL     1       8.995  -0.389  -1.207  1.00  0.00           O  
HETATM    3  C2  UNL     1       7.680  -0.266  -0.836  1.00  0.00           C  
HETATM    4  C3  UNL     1       7.229   0.830  -0.144  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.882   0.930   0.222  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.986  -0.062  -0.102  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.578   0.027   0.273  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.210   0.423   1.540  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.965   0.520   1.929  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.974   0.237   1.108  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.328   0.343   1.525  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.378   0.053   0.687  1.00  0.00           C  
HETATM   13  O3  UNL     1      -2.652   0.167   1.130  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.849  -0.068   0.473  1.00  0.00           C  
HETATM   15  O4  UNL     1      -4.601   1.130   0.427  1.00  0.00           O  
HETATM   16  C12 UNL     1      -5.557   0.978  -0.545  1.00  0.00           C  
HETATM   17  C13 UNL     1      -6.341   2.294  -0.609  1.00  0.00           C  
HETATM   18  O5  UNL     1      -7.320   2.164  -1.592  1.00  0.00           O  
HETATM   19  C14 UNL     1      -6.535  -0.129  -0.283  1.00  0.00           C  
HETATM   20  O6  UNL     1      -7.160  -0.434  -1.494  1.00  0.00           O  
HETATM   21  C15 UNL     1      -5.872  -1.395   0.208  1.00  0.00           C  
HETATM   22  O7  UNL     1      -6.799  -2.253   0.754  1.00  0.00           O  
HETATM   23  C16 UNL     1      -4.736  -1.073   1.179  1.00  0.00           C  
HETATM   24  O8  UNL     1      -4.080  -2.239   1.492  1.00  0.00           O  
HETATM   25  C17 UNL     1      -1.104  -0.349  -0.592  1.00  0.00           C  
HETATM   26  C18 UNL     1       0.218  -0.460  -1.029  1.00  0.00           C  
HETATM   27  O9  UNL     1       0.542  -0.862  -2.313  1.00  0.00           O  
HETATM   28  C19 UNL     1       1.268  -0.163  -0.168  1.00  0.00           C  
HETATM   29  C20 UNL     1       2.570  -0.276  -0.611  1.00  0.00           C  
HETATM   30  O10 UNL     1       2.840  -0.645  -1.789  1.00  0.00           O  
HETATM   31  C21 UNL     1       5.448  -1.153  -0.794  1.00  0.00           C  
HETATM   32  C22 UNL     1       6.790  -1.257  -1.161  1.00  0.00           C  
HETATM   33  H1  UNL     1       9.811   0.858   0.193  1.00  0.00           H  
HETATM   34  H2  UNL     1      10.920   0.253  -1.159  1.00  0.00           H  
HETATM   35  H3  UNL     1       9.722   1.505  -1.530  1.00  0.00           H  
HETATM   36  H4  UNL     1       7.886   1.623   0.129  1.00  0.00           H  
HETATM   37  H5  UNL     1       5.523   1.778   0.760  1.00  0.00           H  
HETATM   38  H6  UNL     1       4.002   0.670   2.263  1.00  0.00           H  
HETATM   39  H7  UNL     1      -0.523   0.667   2.558  1.00  0.00           H  
HETATM   40  H8  UNL     1      -3.777  -0.401  -0.576  1.00  0.00           H  
HETATM   41  H9  UNL     1      -5.074   0.807  -1.521  1.00  0.00           H  
HETATM   42  H10 UNL     1      -5.669   3.157  -0.780  1.00  0.00           H  
HETATM   43  H11 UNL     1      -6.868   2.439   0.361  1.00  0.00           H  
HETATM   44  H12 UNL     1      -7.031   2.679  -2.401  1.00  0.00           H  
HETATM   45  H13 UNL     1      -7.351   0.214   0.408  1.00  0.00           H  
HETATM   46  H14 UNL     1      -6.491  -0.285  -2.208  1.00  0.00           H  
HETATM   47  H15 UNL     1      -5.410  -1.899  -0.672  1.00  0.00           H  
HETATM   48  H16 UNL     1      -6.582  -2.577   1.644  1.00  0.00           H  
HETATM   49  H17 UNL     1      -5.203  -0.567   2.043  1.00  0.00           H  
HETATM   50  H18 UNL     1      -3.401  -2.421   0.771  1.00  0.00           H  
HETATM   51  H19 UNL     1      -1.885  -0.581  -1.268  1.00  0.00           H  
HETATM   52  H20 UNL     1      -0.207  -1.083  -2.958  1.00  0.00           H  
HETATM   53  H21 UNL     1       4.758  -1.926  -1.048  1.00  0.00           H  
HETATM   54  H22 UNL     1       7.077  -2.161  -1.712  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3
CONECT    3    4    4   32
CONECT    4    5   36
CONECT    5    6    6   37
CONECT    6    7   31
CONECT    7    8    8   29
CONECT    8    9   38
CONECT    9   10
CONECT   10   11   11   28
CONECT   11   12   39
CONECT   12   13   25   25
CONECT   13   14
CONECT   14   15   23   40
CONECT   15   16
CONECT   16   17   19   41
CONECT   17   18   42   43
CONECT   18   44
CONECT   19   20   21   45
CONECT   20   46
CONECT   21   22   23   47
CONECT   22   48
CONECT   23   24   49
CONECT   24   50
CONECT   25   26   51
CONECT   26   27   28   28
CONECT   27   52
CONECT   28   29
CONECT   29   30   30
CONECT   31   32   32   53
CONECT   32   54
END

NP0043983
     RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
    9.9106    0.6257   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9949   -0.3889   -1.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6796   -0.2658   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2289    0.8296   -0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8824    0.9305    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9859   -0.0619   -0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5780    0.0272    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2098    0.4232    1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9647    0.5202    1.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739    0.2374    1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276    0.3425    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776    0.0529    0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    0.1666    1.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494   -0.0683    0.4731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6010    1.1300    0.4274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5572    0.9784   -0.5450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3406    2.2937   -0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3197    2.1639   -1.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5354   -0.1292   -0.2834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1599   -0.4338   -1.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8716   -1.3954    0.2079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7986   -2.2531    0.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7357   -1.0727    1.1793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0801   -2.2386    1.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1044   -0.3488   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2180   -0.4596   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420   -0.8616   -2.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -0.1627   -0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5700   -0.2761   -0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398   -0.6454   -1.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -1.1532   -0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7902   -1.2574   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8110    0.8581    0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9199    0.2531   -1.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7219    1.5049   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8860    1.6230    0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5234    1.7783    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0019    0.6704    2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    0.6673    2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -0.4009   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0743    0.8069   -1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6689    3.1571   -0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8676    2.4387    0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0314    2.6791   -2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3506    0.2141    0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4909   -0.2850   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4102   -1.8995   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5823   -2.5766    1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2025   -0.5671    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4008   -2.4206    0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8852   -0.5808   -1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066   -1.0831   -2.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576   -1.9257   -1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0773   -2.1611   -1.7123 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
  6 31  1  0
 31 32  2  0
 32  3  1  0
 29  7  1  0
 28 10  1  0
 23 14  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  8 38  1  0
 11 39  1  0
 14 40  1  6
 16 41  1  6
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  1
 20 46  1  0
 21 47  1  6
 22 48  1  0
 23 49  1  1
 24 50  1  0
 25 51  1  0
 27 52  1  0
 31 53  1  0
 32 54  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Biochanin a-beta-D-glucoside	ChEBI
Sissotrin	ChEBI
Biochanin a-b-D-glucoside	Generator
Biochanin a-β-D-glucoside	Generator
Biochanin a 7-O-b-D-glucoside	Generator
Biochanin a 7-O-β-D-glucoside	Generator

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

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

Traditional Name

biochanin A-β-D-glucoside

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)13-9-30-15-7-12(6-14(24)17(15)18(13)25)31-22-21(28)20(27)19(26)16(8-23)32-22/h2-7,9,16,19-24,26-28H,8H2,1H3/t16-,19-,20+,21-,22-/m1/s1

InChI Key

LFEUICHQZGNOHD-RECXWPGBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, 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
Cicer arietinum	KNApSAcK Database	22123792
Cicer flexuosum	LOTUS Database	35616633
Cicer songaricum	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Medicago truncatula	KNApSAcK Database	22123792
Sophora japonica L.	KNApSAcK Database	22123792
Styphnolobium japonicum	LOTUS Database	35616633
Trifolium aureum	LOTUS Database	35616633
Trifolium diffusum	LOTUS Database	35616633
Trifolium pratense	KNApSAcK Database	22123792
Trifolium subterraneum	LOTUS Database	35616633

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:28751 )
hydroxyisoflavone (CHEBI:28751 )
methoxyisoflavone (CHEBI:28751 )
glycosyloxyisoflavone (CHEBI:28751 )
isoflavones (C05376 )
Isoflavonoids (C05376 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	754.90 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	383.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.970 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.71	ALOGPS
logP	0.95	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.28	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	44.3 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

C00010112

Chemspider ID

4444343

KEGG Compound ID

C05376

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Biochanin A

METLIN ID

Not Available

PubChem Compound

5280781

PDB ID

Not Available

ChEBI ID

28751

Good Scents ID

rw1698761

References

General References

Lapcik O, Honys D, Koblovska R, Mackova Z, Vitkova M, Klejdus B: Isoflavonoids are present in Arabidopsis thaliana despite the absence of any homologue to known isoflavonoid synthases. Plant Physiol Biochem. 2006 Feb-Mar;44(2-3):106-14. doi: 10.1016/j.plaphy.2005.11.006. Epub 2006 Mar 6. [PubMed:16650770 ]
Leuner O, Havlik J, Hummelova J, Prokudina E, Novy P, Kokoska L: Distribution of isoflavones and coumestrol in neglected tropical and subtropical legumes. J Sci Food Agric. 2013 Feb;93(3):575-9. doi: 10.1002/jsfa.5835. Epub 2012 Aug 28. [PubMed:22926873 ]
Shajib MT, Pedersen HA, Mortensen AG, Kudsk P, Fomsgaard IS: Phytotoxic effect, uptake, and transformation of biochanin A in selected weed species. J Agric Food Chem. 2012 Oct 31;60(43):10715-22. doi: 10.1021/jf3023589. Epub 2012 Oct 18. [PubMed:23030687 ]
Zhang YZ, Xu F, Liang J, Tang JS, Shang MY, Wang X, Cai SQ: [Isoflavonoids from roots of Astragalus membranaceus var. mongholicus]. Zhongguo Zhong Yao Za Zhi. 2012 Nov;37(21):3243-8. [PubMed:23397722 ]
Wahby MM, Mohammed DS, Newairy AA, Abdou HM, Zaky A: Aluminum-induced molecular neurodegeneration: The protective role of genistein and chickpea extract. Food Chem Toxicol. 2017 Sep;107(Pt A):57-67. doi: 10.1016/j.fct.2017.05.044. Epub 2017 May 24. [PubMed:28552514 ]
Philip Lewis, Seppo Kaltia and Kristiina Wähälä (1998). Philip Lewis, Seppo Kaltia and Kristiina Wähälä. The phase transfer catalysed synthesis of isoflavone-O-glucosides. J. Chem. Soc., Perkin Trans. 1, 1998, 2481-2484. DOI: 10.1039/A804406F. J. Chem. Soc., Perkin Trans..

Showing NP-Card for Sissotrin (NP0043983)

MOL for NP0043983 (Sissotrin)

3D MOL for NP0043983 (Sissotrin)

3D SDF for NP0043983 (Sissotrin)

3D-SDF for NP0043983 (Sissotrin)

PDB for NP0043983 (Sissotrin)

3D PDB for NP0043983 (Sissotrin)

SMILES for NP0043983 (Sissotrin)

INCHI for NP0043983 (Sissotrin)

Structure for NP0043983 (Sissotrin)

3D Structure for NP0043983 (Sissotrin)