NP-MRD: Showing NP-Card for Orobol 8-C-(6''-acetylglucoside) (NP0054082)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 00:33:04 UTC

Updated at

2022-04-28 00:33:04 UTC

NP-MRD ID

NP0054082

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Orobol 8-C-(6''-acetylglucoside)

Description

[(2S,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetate belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Orobol 8-C-(6''-acetylglucoside) is found in Dalbergia monetaria . Based on a literature review very few articles have been published on [(2S,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202332D          

 35 38  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.7145   -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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   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
   -1.4289    0.8250    0.0000 O   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
    2.1434   -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   -1.6500    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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
  1  2  2  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
  1  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  6  0  0  0
  9 19  1  1  0  0  0
  8 20  1  6  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
  3 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.7946    3.0401    1.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1093    1.8585    1.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577    1.9402    0.7103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7371    0.6810    1.1870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4781   -0.5782    0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2485   -1.2638    1.2751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1140   -0.6706    0.7362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7274   -1.2102   -0.4422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9395   -0.3995   -1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3975    0.0384   -2.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6254   -0.2892   -3.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6176    0.8714   -3.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251    1.2524   -2.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4404    2.0724   -3.7333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1310    0.8443   -1.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3921    1.1871   -1.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041    1.9131   -1.9759 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437    0.7106   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1927    1.0423    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2446    1.0023   -0.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5574    1.2732   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8150    1.5953    1.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1169    1.8604    1.5616 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7764    1.6349    2.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0101    1.9541    3.4076 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667    1.3610    1.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9767   -0.0886    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7745   -0.3861    0.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564    0.0583   -0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -2.6781   -0.4343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6922   -3.2938   -1.5940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -3.3276    0.7194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2745   -3.2412    1.9167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3572   -2.6993    1.0003 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1454   -2.9799   -0.1376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7997    2.7582    2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477    3.8837    1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2057    3.3940    2.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4046   -1.1962    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4332   -0.5175   -0.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2606   -1.0976    2.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648   -1.3104   -0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3572   -0.8314   -2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9817    1.1976   -4.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667    2.3603   -4.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0852    0.7489   -1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3961    1.2440   -0.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4110    2.0966    2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9064    2.1390    3.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318    1.4190    2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3411   -0.4468    1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327   -2.7819   -0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -3.9134   -1.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1918   -4.4141    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8016   -3.4327    2.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8645   -3.2624    1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1042   -3.1226    0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  8  9  1  0
  9 29  2  0
 29 28  1  0
 28 27  1  0
 27 18  2  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 34  6  1  0
 10  9  1  0
 26 19  1  0
 15 29  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  8 42  1  6
 30 52  1  1
 31 53  1  0
 32 54  1  6
 33 55  1  0
 34 56  1  1
 35 57  1  0
 27 51  1  0
 14 45  1  0
 12 44  1  0
 11 43  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
 25 49  1  0
 26 50  1  0
M  END


  Mrv1652304282202332D          

 35 38  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.7145   -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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   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
   -1.4289    0.8250    0.0000 O   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
    2.1434   -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   -1.6500    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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
  1  2  2  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
  1  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  6  0  0  0
  9 19  1  1  0  0  0
  8 20  1  6  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
  3 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O12/c1-8(24)33-7-15-19(30)20(31)21(32)23(35-15)17-14(28)5-13(27)16-18(29)10(6-34-22(16)17)9-2-3-11(25)12(26)4-9/h2-6,15,19-21,23,25-28,30-32H,7H2,1H3/t15-,19+,20-,21+,23-/m0/s1

> <INCHI_KEY>
PPCJHDPUVJLYLC-BIPHFIHCSA-N

> <FORMULA>
C23H22O12

> <MOLECULAR_WEIGHT>
490.417

> <EXACT_MASS>
490.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
47.068367396327474

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
0.45711157333333374

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.964916589988428

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.1432979163130526

> <JCHEM_PKA_STRONGEST_BASIC>
-3.645438207004494

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
115.93359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10                                                            
CONECT   19    9                                                            
CONECT   20    8                                                            
CONECT   21    5   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23    4   25                                                  
CONECT   25   24                                                            
CONECT   26   23   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30                                                            
CONECT   33   29                                                            
CONECT   34    3                                                            
CONECT   35    1                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
[(2S,3S,4R,5R,6S)-6-[3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₃H₂₂O₁₂

Average Mass

490.4170 Da

Monoisotopic Mass

490.11113 Da

IUPAC Name

[(2S,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2S,3S,4R,5R,6S)-6-[3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C23H22O12/c1-8(24)33-7-15-19(30)20(31)21(32)23(35-15)17-14(28)5-13(27)16-18(29)10(6-34-22(16)17)9-2-3-11(25)12(26)4-9/h2-6,15,19-21,23,25-28,30-32H,7H2,1H3/t15-,19+,20-,21+,23-/m0/s1

InChI Key

PPCJHDPUVJLYLC-BIPHFIHCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dalbergia monetaria	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-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 C-glycosides

Direct Parent

Isoflavonoid C-glycosides

Alternative Parents

Substituents

Isoflavonoid-8-c-glycoside
Isoflavonoid c-glycoside
Hydroxyisoflavonoid
Isoflavone
Phenolic glycoside
Glycosyl compound
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.16	ALOGPS
logP	0.46	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.14	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.93 m³·mol⁻¹	ChemAxon
Polarizability	47.07 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163082481

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Orobol 8-C-(6''-acetylglucoside) (NP0054082)

MOL for NP0054082 (Orobol 8-C-(6''-acetylglucoside))

3D MOL for NP0054082 (Orobol 8-C-(6''-acetylglucoside))

3D SDF for NP0054082 (Orobol 8-C-(6''-acetylglucoside))

3D-SDF for NP0054082 (Orobol 8-C-(6''-acetylglucoside))

PDB for NP0054082 (Orobol 8-C-(6''-acetylglucoside))

3D PDB for NP0054082 (Orobol 8-C-(6''-acetylglucoside))

SMILES for NP0054082 (Orobol 8-C-(6''-acetylglucoside))

INCHI for NP0054082 (Orobol 8-C-(6''-acetylglucoside))

Structure for NP0054082 (Orobol 8-C-(6''-acetylglucoside))

3D Structure for NP0054082 (Orobol 8-C-(6''-acetylglucoside))