NP-MRD: Showing NP-Card for 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one (NP0223624)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 01:46:19 UTC

Updated at

2022-09-06 01:46:19 UTC

NP-MRD ID

NP0223624

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one

Description

5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3--4h-chromen-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3--4h-chromen-4-one. 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by Catechol O-methyltransferase (P21964) enzyme via a catechol-O-methylation-pattern2 reaction. 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one is found in Glycyrrhiza glabra, Sedum album, Senegalia pennata and Tocoyena formosa. This catechol-O-methylation-pattern2 occurs in humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308231908262D          

 33 36  0  0  0  0            999 V2000
    1.4289   -4.1250    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   -0.4125    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
    2.8579    0.8250    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    0.0000    0.0000 C   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
    2.8579    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
    4.2868    0.8250    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
    3.5724    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    3.5724   -3.7125    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
    2.1434   -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
    2.8579   -2.4750    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
    5.0013    1.2375    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
    2.8579   -4.9500    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
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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   -2.8875    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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  1  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  5  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  2  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  1  0  0  0  0
 21 17  1  0  0  0  0
 21 20  2  0  0  0  0
 22 19  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 25 12  1  0  0  0  0
 26 16  1  0  0  0  0
 27 17  2  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30  2  1  0  0  0  0
 30 13  1  0  0  0  0
 31  8  1  0  0  0  0
 31 22  1  0  0  0  0
 32 14  1  0  0  0  0
 32 20  1  0  0  0  0
 33 21  1  0  0  0  0
 33 22  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -1.9687   -3.3238    1.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4337   -2.3634    2.8698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569   -1.0369    2.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -0.5813    1.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    0.7386    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779    1.3038   -0.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5823    2.5739   -0.5185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214    3.1915   -1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5715    4.5165   -1.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116    5.1894   -2.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5661    6.5300   -3.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    4.5732   -3.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0880    3.2293   -3.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423    2.6639   -4.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727    2.5691   -2.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1220    1.2611   -2.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5525    0.5942   -3.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452    0.6586   -1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1532   -0.6667   -0.9872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1419   -0.8803   -0.3931 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1023   -1.7272    0.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2856   -1.5788    1.4069 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2242   -2.3641    2.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687   -2.0909    0.6076 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0171   -3.2169    1.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0475   -2.4949   -0.7886 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6198   -3.8195   -0.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -1.5301   -1.4040 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2548   -2.2694   -2.2625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2399    1.6219    1.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7549    1.2273    3.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8138   -0.1188    3.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3465   -0.5062    4.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984   -4.3241    2.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5197   -3.1438    0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8807   -3.2848    1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5113   -1.3136    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1540    5.0277   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4230    6.7440   -3.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754    5.1008   -4.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0035    1.7857   -4.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6279    0.0700   -0.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.5196    1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2492   -2.4096    3.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -3.3826    2.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5761   -1.8068    3.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619   -1.3224    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4011   -4.0014    1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745   -2.4350   -1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216   -3.9520   -0.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790   -0.7633   -2.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510   -2.7196   -1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    2.6731    1.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1295    1.9389    3.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816    0.1650    5.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 32  2  0
 32 33  1  0
 32 31  1  0
 31 30  2  0
 30  5  1  0
  5  4  2  0
  5  6  1  0
  6 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  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
 10  9  1  0
  9  8  2  0
  8  7  1  0
  4  3  1  0
  7  6  1  0
 28 20  1  0
  8 15  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 33 55  1  0
 31 54  1  0
 30 53  1  0
  4 37  1  0
 20 42  1  1
 22 43  1  1
 23 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  6
 25 48  1  0
 26 49  1  6
 27 50  1  0
 28 51  1  6
 29 52  1  0
 14 41  1  0
 12 40  1  0
 11 39  1  0
  9 38  1  0
M  END


  Mrv1652308231908262D          

 33 36  0  0  0  0            999 V2000
    1.4289   -4.1250    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   -0.4125    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
    2.8579    0.8250    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    0.0000    0.0000 C   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
    2.8579    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
    4.2868    0.8250    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
    3.5724    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    3.5724   -3.7125    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
    2.1434   -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
    2.8579   -2.4750    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
    5.0013    1.2375    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
    2.8579   -4.9500    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
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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   -2.8875    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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  1  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  5  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  2  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  1  0  0  0  0
 21 17  1  0  0  0  0
 21 20  2  0  0  0  0
 22 19  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 25 12  1  0  0  0  0
 26 16  1  0  0  0  0
 27 17  2  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30  2  1  0  0  0  0
 30 13  1  0  0  0  0
 31  8  1  0  0  0  0
 31 22  1  0  0  0  0
 32 14  1  0  0  0  0
 32 20  1  0  0  0  0
 33 21  1  0  0  0  0
 33 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223624

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=C(OC2OC(C)C(O)C(O)C2O)C(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-12(25)6-10(23)7-14(15)32-20(21)9-3-4-11(24)13(5-9)30-2/h3-8,16,18-19,22-26,28-29H,1-2H3

> <INCHI_KEY>
UXXAEVMOIUAYQT-UHFFFAOYSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.19097182000514

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.0479687266666664

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.934087097457554

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.3742892897535866

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612200408172593

> <JCHEM_POLAR_SURFACE_AREA>
175.36999999999998

> <JCHEM_REFRACTIVITY>
112.21409999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   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  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   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  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   30                                                            
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    9   13                                                       
CONECT    6   10   12                                                       
CONECT    7   10   14                                                       
CONECT    8    1   16   31                                                  
CONECT    9    3    5   20                                                  
CONECT   10    6    7   23                                                  
CONECT   11    4   13   24                                                  
CONECT   12    6   15   25                                                  
CONECT   13    5   11   30                                                  
CONECT   14    7   15   32                                                  
CONECT   15   12   14   17                                                  
CONECT   16    8   18   26                                                  
CONECT   17   15   21   27                                                  
CONECT   18   16   19   28                                                  
CONECT   19   18   22   29                                                  
CONECT   20    9   21   32                                                  
CONECT   21   17   20   33                                                  
CONECT   22   19   31   33                                                  
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30    2   13                                                       
CONECT   31    8   22                                                       
CONECT   32   14   20                                                       
CONECT   33   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C1=C(OC2OC(C)C(O)C(O)C2O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-12(25)6-10(23)7-14(15)32-20(21)9-3-4-11(24)13(5-9)30-2/h3-8,16,18-19,22-26,28-29H,1-2H3

InChI Key

UXXAEVMOIUAYQT-UHFFFAOYSA-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
Glycyrrhiza glabra	LOTUS Database	35616633
Sedum album	LOTUS Database	35616633
Senegalia pennata	LOTUS Database	35616633
Tocoyena formosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenol ether
Phenoxy compound
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	1.55	ALOGPS
logP	1.05	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.21 m³·mol⁻¹	ChemAxon
Polarizability	44.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0135156

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

13988312

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one (NP0223624)

MOL for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)

3D MOL for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)

3D SDF for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)

3D-SDF for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)

PDB for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)

3D PDB for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)

SMILES for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)

INCHI for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)

Structure for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)

3D Structure for NP0223624 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one)