NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid (NP0260863)

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Record Information

Version

2.0

Created at

2022-09-08 03:08:35 UTC

Updated at

2022-09-08 03:08:35 UTC

NP-MRD ID

NP0260863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

Description

3,4,5-Trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid is found in Scutellaria amabilis. 3,4,5-Trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004271515262D          

 33 36  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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 O   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
   -2.1434   -1.2375    0.0000 C   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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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  1  0  0  0  0
  6  7  1  0  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  5 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  3 26  1  0  0  0  0
 20 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.7248   -3.8975    1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5085   -3.2569    0.9946 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4933   -2.0114    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763   -1.3606    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966   -0.1310   -0.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9111    0.4676   -0.8712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1789   -0.0659   -0.5741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3605    0.2156    0.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5905    0.4822    1.2343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4959   -0.6763    1.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6848   -0.4423    1.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1750   -1.9943    1.2404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2115    1.6040    0.4389 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4582    1.9780    0.9417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4136    1.0752   -0.9576 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5808    0.2704   -0.8661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610    0.2572   -1.4728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8090    0.8421   -2.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5277    0.4793   -0.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -0.1147   -0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6854   -1.3686    0.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9489   -1.9130    0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -3.1590    0.5351 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809   -1.0339    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9883    0.2672    0.2311 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2767    0.9444    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285    1.6795    1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9618    2.4404    1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6418    2.5374   -0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1263    1.8281   -1.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852    1.0675   -1.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5094    0.3708   -2.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966    0.3985   -0.7251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424   -3.3503    1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3650   -3.8704    0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5523   -4.9510    1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5907   -1.8911    0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0580   -1.1958   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4563    0.9214    2.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6276   -2.5293    0.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    2.4185    0.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5418    2.9698    0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7195    1.9203   -1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3380    0.7908   -0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7552   -0.7150   -1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    1.7510   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    1.4272   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1234   -0.8966    2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0138   -1.6022    0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5027    0.9566    1.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3041    1.6250    2.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3477    2.9869    1.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5261    3.1388   -0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6986    1.8732   -2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0948    0.4422   -3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 33  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 21  3  1  0
 31 26  1  0
 17  7  1  0
 33 20  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  7 38  1  1
  9 39  1  1
 13 41  1  6
 14 42  1  0
 15 43  1  6
 16 44  1  0
 17 45  1  6
 18 46  1  0
 12 40  1  0
 19 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  1
 27 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
 32 55  1  0
M  END


  Mrv1533004271515262D          

 33 36  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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 O   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
   -2.1434   -1.2375    0.0000 C   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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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  1  0  0  0  0
  6  7  1  0  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  5 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  3 26  1  0  0  0  0
 20 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260863

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC2OC(C(O)C(O)C2O)C(O)=O)=CC2=C1C(=O)CC(O2)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-30-14-6-9(31-22-19(27)17(25)18(26)20(33-22)21(28)29)7-15-16(14)12(24)8-13(32-15)10-4-2-3-5-11(10)23/h2-7,13,17-20,22-23,25-27H,8H2,1H3,(H,28,29)

> <INCHI_KEY>
RYJWOWHMBGOYAT-UHFFFAOYSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.63388880104925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
0.38320855100000073

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.07817210114288

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.684012214780872

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868267780658686

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
107.78389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335  -3.080   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  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   0.000   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  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -0.770   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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14                                                            
CONECT   16    9   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    3   20                                                  
CONECT   27   22   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylate	Generator

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(OC2OC(C(O)C(O)C2O)C(O)=O)=CC2=C1C(=O)CC(O2)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C22H22O11/c1-30-14-6-9(31-22-19(27)17(25)18(26)20(33-22)21(28)29)7-15-16(14)12(24)8-13(32-15)10-4-2-3-5-11(10)23/h2-7,13,17-20,22-23,25-27H,8H2,1H3,(H,28,29)

InChI Key

RYJWOWHMBGOYAT-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
Scutellaria amabilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Pentacarboxylic acid or derivatives
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.52	ALOGPS
logP	0.38	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	2.68	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.78 m³·mol⁻¹	ChemAxon
Polarizability	44.63 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

73063356

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid (NP0260863)

MOL for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)

3D MOL for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)

3D SDF for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)

PDB for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)

3D PDB for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)

SMILES for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)

INCHI for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)

Structure for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)

3D Structure for NP0260863 (3,4,5-trihydroxy-6-{[2-(2-hydroxyphenyl)-5-methoxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid)