NP-MRD: Showing NP-Card for (3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0211098)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 09:12:51 UTC

Updated at

2022-09-05 09:12:52 UTC

NP-MRD ID

NP0211098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

Description

(3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as flavonoid-3-o-glycosides. (3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one is found in Artocarpus dadah, Flindersia australis, Hymenaea martiana, Iryanthera sagotiana, Kandelia candel, Petiveria alliacea, Smilax glabra, Stelechocarpus cauliflorus and Vitis vinifera. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position (3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

5317046
  Mrv0541 02271201592D          

 31 34  0  0  1  0            999 V2000
    4.5079   -1.1591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -2.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -3.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6648   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347    1.7483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.9841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0789   -1.1591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7934   -2.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.7466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5079   -1.9841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5079    0.4909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5079    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -2.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    0.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    1.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
 14  2  1  6  0  0  0
 16  2  1  6  0  0  0
 11  3  1  1  0  0  0
 12  4  1  1  0  0  0
  5 13  1  0  0  0  0
  6 17  1  0  0  0  0
  6 22  1  0  0  0  0
  7 19  2  0  0  0  0
  8 23  1  0  0  0  0
  9 28  1  0  0  0  0
 10 31  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 18  1  1  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 24  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 29  1  0  0  0  0
 25 30  2  0  0  0  0
 26 28  1  0  0  0  0
 27 28  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    3.7814   -0.0894    2.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5247    0.3793    2.9538 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3738   -0.0786    2.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9235    0.5033    1.2451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4398    0.2069    1.2182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8231   -0.6875    0.2742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3874   -1.9470    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -2.2217    2.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1323   -2.8238   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2547   -4.1680    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6802   -4.7637    1.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -4.9291   -0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5959   -4.4070   -1.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -5.2296   -2.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4655   -3.0628   -2.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7472   -2.2773   -1.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896   -0.9239   -1.3727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8688   -0.0260   -0.6094 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3105    1.0051   -1.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321    0.6630   -2.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1157    1.6021   -3.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695    2.9329   -3.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2554    3.8979   -4.1149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489    3.3214   -2.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4648    2.3424   -1.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1930    1.9325    1.0291 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6060    2.2254   -0.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    2.6263    1.9439 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3351    2.8846    1.2495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5062    1.8746    3.1775 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7577    2.2354    3.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981   -0.3386    2.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6063   -1.0222    1.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570    0.7363    1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -0.0688    3.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392   -0.0827    0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0009   -1.0256   -0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1384   -4.3352    1.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0652   -5.9883   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7686   -5.6322   -3.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301   -2.6314   -2.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877    0.4452    0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5242   -0.4032   -2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042    1.2959   -4.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1938    4.2657   -4.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519    4.3709   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9830    2.7046   -0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001    2.4717    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843    1.4175   -0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    3.6656    2.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1683    3.4769    0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658    2.1130    3.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867    1.5669    4.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 10  1  0
 10 11  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  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  2  0
  4 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30  2  1  0
  7  6  1  0
 25 19  1  0
  9 16  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  1
  4 36  1  6
  6 37  1  6
 18 42  1  1
 15 41  1  0
 14 40  1  0
 12 39  1  0
 11 38  1  0
 20 43  1  0
 21 44  1  0
 23 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  6
 27 49  1  0
 28 50  1  1
 29 51  1  0
 30 52  1  1
 31 53  1  0
M  END

5317046
  Mrv0541 02271201592D          

 31 34  0  0  1  0            999 V2000
    4.5079   -1.1591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -2.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -3.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6648   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347    1.7483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.9841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0789   -1.1591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7934   -2.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.7466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5079   -1.9841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5079    0.4909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5079    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -2.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    0.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    1.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
 14  2  1  6  0  0  0
 16  2  1  6  0  0  0
 11  3  1  1  0  0  0
 12  4  1  1  0  0  0
  5 13  1  0  0  0  0
  6 17  1  0  0  0  0
  6 22  1  0  0  0  0
  7 19  2  0  0  0  0
  8 23  1  0  0  0  0
  9 28  1  0  0  0  0
 10 31  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 18  1  1  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 24  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 29  1  0  0  0  0
 25 30  2  0  0  0  0
 26 28  1  0  0  0  0
 27 28  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-25,27-28H,1H3/t8-,15?,17+,18+,19?,20-,21-/m0/s1

> <INCHI_KEY>
VQUPQWGKORWZII-UXTZWZSCSA-N

> <FORMULA>
C21H22O10

> <MOLECULAR_WEIGHT>
434.3934

> <EXACT_MASS>
434.121296924

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
41.72958563789747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
1.3960239106666659

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.441876459906222

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.804241945445436

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612182875000423

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
103.4976

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5317046                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415  -2.164   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081   0.146   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.414  -4.474   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414  -1.394   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.081  -6.014   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.748   3.226   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.748  -1.394   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      12.441  -1.447   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      15.185   3.263   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.080   5.536   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.747  -3.704   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -4.474   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -1.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415  -3.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   0.916   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   2.456   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748  -4.474   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748   0.146   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081   3.226   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082   0.916   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.082   2.456   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.459   0.093   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.081   4.766   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.747   2.456   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.459   3.280   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.854   0.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.854   2.488   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.747   5.536   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.414   3.226   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.414   4.766   0.000  0.00  0.00           C+0
CONECT    1   14   15                                                       
CONECT    2   14   16                                                       
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6   17   22                                                       
CONECT    7   19                                                            
CONECT    8   23                                                            
CONECT    9   28                                                            
CONECT   10   31                                                            
CONECT   11    3   12   13                                                  
CONECT   12    4   11   14                                                  
CONECT   13    5   11   15                                                  
CONECT   14    1    2   12                                                  
CONECT   15    1   13   18                                                  
CONECT   16    2   17   19                                                  
CONECT   17    6   16   20                                                  
CONECT   18   15                                                            
CONECT   19    7   16   21                                                  
CONECT   20   17   24   25                                                  
CONECT   21   19   22   23                                                  
CONECT   22    6   21   26                                                  
CONECT   23    8   21   27                                                  
CONECT   24   20   29                                                       
CONECT   25   20   30                                                       
CONECT   26   22   28                                                       
CONECT   27   23   28                                                       
CONECT   28    9   26   27                                                  
CONECT   29   24   31                                                       
CONECT   30   25   31                                                       
CONECT   31   10   29   30                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₁₀

Average Mass

434.3934 Da

Monoisotopic Mass

434.12130 Da

IUPAC Name

(3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)C1O

InChI Identifier

InChI=1S/C21H22O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-25,27-28H,1H3/t8-,15?,17+,18+,19?,20-,21-/m0/s1

InChI Key

VQUPQWGKORWZII-UXTZWZSCSA-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
Artocarpus dadah	LOTUS Database	35616633
Flindersia australis	LOTUS Database	35616633
Hymenaea martiana	LOTUS Database	35616633
Iryanthera sagotiana	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Petiveria alliacea	LOTUS Database	35616633
Smilax glabra	LOTUS Database	35616633
Stelechocarpus cauliflorus	LOTUS Database	35616633
Vitis vinifera	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
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Flavanonol
Hydroxyflavonoid
Flavan
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Aldehyde
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	0.77	ALOGPS
logP	1.4	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.5 m³·mol⁻¹	ChemAxon
Polarizability	41.73 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

5317046

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0211098)

MOL for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0211098 ((3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)