NP-MRD: Showing NP-Card for (6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid (NP0148152)

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Record Information

Version

2.0

Created at

2022-09-02 03:51:52 UTC

Updated at

2022-09-02 03:51:52 UTC

NP-MRD ID

NP0148152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid

Description

(2R)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. (6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid is found in Streptomyces rimosus. Based on a literature review very few articles have been published on (2R)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205512D          

 33 36  0  0  1  0            999 V2000
   -3.5724   -1.2375    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
   -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
   -2.1434   -0.4125    0.0000 C   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
   -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   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    4.2868   -0.0000    0.0000 O   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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  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
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 22 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  2  0  0  0  0
 12 32  1  0  0  0  0
 10 33  1  0  0  0  0
  4 33  1  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -4.2075    1.6118    3.9255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1336    0.9361    3.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1295    0.4668    4.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1987    0.6306    1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1965   -0.0843    1.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1785   -0.3477    0.0250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5479    0.8271   -0.6191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7593   -0.7343   -0.3948 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7773   -0.8331   -1.7900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866    0.3826   -0.0400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5127   -0.0823    0.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3759    0.3558   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3110    1.3069   -1.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1538    1.7216   -1.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1337    2.6912   -2.9753 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0425    1.1540   -1.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312    1.5175   -2.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456    2.3999   -3.0691 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4011    0.8982   -1.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    1.3034   -2.3371 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3430   -0.0556   -0.7638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5386   -0.7467   -0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3757   -1.7275    0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4404   -2.3992    1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7312   -2.1749    0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7949   -2.8951    1.3714 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9228   -1.2176   -0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1856   -0.9288   -0.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8172   -0.5201   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1670   -0.3587   -0.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328    0.1775   -0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1522   -0.2219   -0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2340    1.0768    1.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1012    0.6220    4.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9705   -0.4529    2.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8552   -1.1675   -0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9070    1.0564   -1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4654   -1.7043    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8484   -0.8737   -2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7678    1.1466   -0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2232    1.7855   -1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0199    3.0997   -3.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6170    1.9961   -3.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -1.9080    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2675   -3.1531    1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5985   -3.5860    2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3545   -0.2289   -1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0370    0.2195   -1.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097   -0.9813    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4 33  1  0
 33 10  1  0
 10 11  1  0
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 12 13  2  0
 13 14  1  0
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 14 16  2  0
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 31 30  1  0
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 31 32  2  0
 10  8  1  0
  8  9  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  8  6  1  0
 32 12  1  0
 17 16  1  0
 29 22  1  0
  7 37  1  0
  6 36  1  1
  5 35  1  0
 10 40  1  6
 13 41  1  0
 15 42  1  0
 20 43  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
 28 47  1  0
 29 48  1  0
 32 49  1  0
  8 38  1  1
  9 39  1  0
  3 34  1  0
M  END


  Mrv1652309022205512D          

 33 36  0  0  1  0            999 V2000
   -3.5724   -1.2375    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
   -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
   -2.1434   -0.4125    0.0000 C   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
   -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   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    4.2868   -0.0000    0.0000 O   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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
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 12 13  2  0  0  0  0
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 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
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 19 20  1  0  0  0  0
 19 21  2  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
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 22 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  2  0  0  0  0
 12 32  1  0  0  0  0
 10 33  1  0  0  0  0
  4 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0148152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C=C(O[C@@H](OC2=CC(O)=C3C(OC(=C(O)C3=O)C3=CC=C(O)C(O)=C3)=C2)C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H16O12/c22-9-2-1-7(3-10(9)23)19-18(28)17(27)15-11(24)4-8(5-13(15)32-19)31-21-16(26)12(25)6-14(33-21)20(29)30/h1-6,12,16,21-26,28H,(H,29,30)/t12?,16?,21-/m1/s1

> <INCHI_KEY>
PVARKDPFQOSDCZ-NAQHUMPESA-N

> <FORMULA>
C21H16O12

> <MOLECULAR_WEIGHT>
460.347

> <EXACT_MASS>
460.064175955

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
42.5863147241988

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
0.9474346703333327

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.078082905001904

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.686090227683757

> <JCHEM_PKA_STRONGEST_BASIC>
-3.454819996155253

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
109.235

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   31                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   30                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22                                                       
CONECT   30   21   31                                                       
CONECT   31   30   16   32                                                  
CONECT   32   31   12                                                       
CONECT   33   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylate	Generator

Chemical Formula

C₂₁H₁₆O₁₂

Average Mass

460.3470 Da

Monoisotopic Mass

460.06418 Da

IUPAC Name

(2R)-2-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid

Traditional Name

(6R)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1C=C(O[C@@H](OC2=CC(O)=C3C(OC(=C(O)C3=O)C3=CC=C(O)C(O)=C3)=C2)C1O)C(O)=O

InChI Identifier

InChI=1S/C21H16O12/c22-9-2-1-7(3-10(9)23)19-18(28)17(27)15-11(24)4-8(5-13(15)32-19)31-21-16(26)12(25)6-14(33-21)20(29)30/h1-6,12,16,21-26,28H,(H,29,30)/t12?,16?,21-/m1/s1

InChI Key

PVARKDPFQOSDCZ-NAQHUMPESA-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
Streptomyces rimosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
Hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
3'-hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
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	1.53	ALOGPS
logP	0.95	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	2.69	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.24 m³·mol⁻¹	ChemAxon
Polarizability	42.59 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

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

162843904

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid (NP0148152)

MOL for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)

3D MOL for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)

3D SDF for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)

3D-SDF for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)

PDB for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)

3D PDB for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)

SMILES for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)

INCHI for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)

Structure for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)

3D Structure for NP0148152 ((6r)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4h-pyran-2-carboxylic acid)