NP-MRD: Showing NP-Card for [2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol (NP0059689)

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Record Information

Version

2.0

Created at

2022-04-28 04:54:23 UTC

Updated at

2022-04-28 04:54:23 UTC

NP-MRD ID

NP0059689

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol

Description

Pyranochromene belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. Thus, pyranochromene is considered to be a flavonoid. [2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol is found in Lupinus angustifolius . [2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol was first documented in 2009 (PMID: 19725504). Based on a literature review a significant number of articles have been published on Pyranochromene (PMID: 34205355) (PMID: 29692239) (PMID: 26396757) (PMID: 25795609) (PMID: 24780121) (PMID: 24623606).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206542D          

 26 29  0  0  1  0            999 V2000
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  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
  3 11  1  0  0  0  0
 11 12  1  6  0  0  0
  9 13  1  1  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 16 18  1  6  0  0  0
 15 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 21 26  1  0  0  0  0
M  END

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
   -2.2292    2.1242   -1.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0540    1.3893    0.1227 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2231    1.7450    1.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5055    1.2994    0.3861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5301    1.3315    1.3352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4510   -0.0012   -0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2955   -0.7244   -0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2365   -2.0722   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393   -2.7768   -0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0877   -4.1247   -0.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8418   -2.0902   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8665   -0.7321   -0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792   -0.0651   -0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3480   -0.0342   -0.1110 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -0.8465    0.3082 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6144    0.0298    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4486    1.2289    1.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207    2.1075    1.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7607    1.8028    0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8164    2.6676    1.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9462    0.6095    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2165    0.3168   -0.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8838   -0.2495    0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6185   -1.9182   -0.7088 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6211   -1.3961   -2.0224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4367   -2.8611   -0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5860    3.1603   -1.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270    2.1082   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8997    1.5431   -1.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041    1.7123    0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0887    1.3033    2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396    2.8482    1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7940    1.9941   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2808    0.7646    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563   -2.6284   -0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290   -4.6391   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850   -1.3431    1.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5025    1.5580    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3830    3.0531    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6585    3.5332    1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9914    0.9443   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0679   -1.1680   -0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5293   -2.5297   -0.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0934   -1.9863   -2.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3963   -3.5470   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -3.4412    0.3288 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
  4  6  1  0
  6  7  1  0
  7 13  2  0
 13 12  1  0
 12 11  2  0
 11 26  1  0
 26 24  1  0
 24 25  1  0
 24 15  1  0
 15 14  1  0
 15 16  1  0
 16 23  2  0
 23 21  1  0
 21 22  1  0
 21 19  2  0
 19 20  1  0
 19 18  1  0
 18 17  2  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
 13  2  1  0
 14 12  1  0
 17 16  1  0
  8  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  3 31  1  0
  3 32  1  0
  4 33  1  6
  5 34  1  0
 26 45  1  0
 26 46  1  0
 24 43  1  1
 25 44  1  0
 15 37  1  1
 23 42  1  0
 22 41  1  0
 20 40  1  0
 18 39  1  0
 17 38  1  0
 10 36  1  0
  8 35  1  0
M  END


  Mrv1652304282206542D          

 26 29  0  0  1  0            999 V2000
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  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
  3 11  1  0  0  0  0
 11 12  1  6  0  0  0
  9 13  1  1  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 16 18  1  6  0  0  0
 15 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 21 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059689

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@H](O)OC2=C1C1=C(C[C@@H](O)[C@H](O1)C1=CC(O)=C(O)C=C1)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O7/c1-8-4-16(24)25-15-7-12(21)10-6-14(23)18(26-19(10)17(8)15)9-2-3-11(20)13(22)5-9/h2-3,5,7-8,14,16,18,20-24H,4,6H2,1H3/t8-,14+,16+,18+/m0/s1

> <INCHI_KEY>
KLFQXCVGEVYPOF-PCPPRTPOSA-N

> <FORMULA>
C19H20O7

> <MOLECULAR_WEIGHT>
360.362

> <EXACT_MASS>
360.120902984

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.67489551134311

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,5R,12R,14S)-4-(3,4-dihydroxyphenyl)-14-methyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-triene-5,8,12-triol

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
2.1195519313333326

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.998366559301173

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.131039346433841

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2911422766400014

> <JCHEM_POLAR_SURFACE_AREA>
119.61000000000001

> <JCHEM_REFRACTIVITY>
92.08149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5R,12R,14S)-4-(3,4-dihydroxyphenyl)-14-methyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-triene-5,8,12-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.494   6.105   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.034   6.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.804   7.438   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.724   7.438   0.000  0.00  0.00           O+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11                                                            
CONECT   13    9                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16    1                                                       
CONECT   18   16                                                            
CONECT   19   15   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   22                                                            
CONECT   26   21                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₇

Average Mass

360.3620 Da

Monoisotopic Mass

360.12090 Da

IUPAC Name

(4R,5R,12R,14S)-4-(3,4-dihydroxyphenyl)-14-methyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-triene-5,8,12-triol

Traditional Name

(4R,5R,12R,14S)-4-(3,4-dihydroxyphenyl)-14-methyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-triene-5,8,12-triol

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@H](O)OC2=C1C1=C(C[C@@H](O)[C@H](O1)C1=CC(O)=C(O)C=C1)C(O)=C2

InChI Identifier

InChI=1S/C19H20O7/c1-8-4-16(24)25-15-7-12(21)10-6-14(23)18(26-19(10)17(8)15)9-2-3-11(20)13(22)5-9/h2-3,5,7-8,14,16,18,20-24H,4,6H2,1H3/t8-,14+,16+,18+/m0/s1

InChI Key

KLFQXCVGEVYPOF-PCPPRTPOSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lupinus angustifolius	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
Pyranoflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Pyranochromene
1-benzopyran
Chromane
Benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Hemiacetal
Polyol
Organoheterocyclic compound
Ether
Oxacycle
Alcohol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020088 )

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	1.43	ALOGPS
logP	2.12	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.08 m³·mol⁻¹	ChemAxon
Polarizability	35.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00013262

Chemspider ID

24842555

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257104

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cakir SP, Stokes S, Sygula A, Mead KT: Evidence for pi-stacking as a source of stereocontrol in the synthesis of the core pyranochromene ring system common to calyxin I, calyxin J, and epicalyxin J. J Org Chem. 2009 Oct 2;74(19):7529-32. doi: 10.1021/jo901436u. [PubMed:19725504 ]
Suresh D, Sabir S, Yu TT, Wenholz D, Das T, Black DS, Kumar N: Natural Product Rottlerin Derivatives Targeting Quorum Sensing. Molecules. 2021 Jun 19;26(12). pii: molecules26123745. doi: 10.3390/molecules26123745. [PubMed:34205355 ]
Gomha SM, Abdelhamid AO, Kandil OM, Kandeel SM, Abdelrehem NA: Synthesis and Molecular Docking of Some Novel Thiazoles and Thiadiazoles Incorporating Pyranochromene Moiety as Potent Anticancer Agents. Mini Rev Med Chem. 2018;18(19):1670-1682. doi: 10.2174/1389557518666180424113819. [PubMed:29692239 ]
Swaminathan K, Sethusankar K, Kumar GS, Bakthadoss M: Crystal structures and conformational analyses of three pyranochromene derivatives. Acta Crystallogr E Crystallogr Commun. 2015 Jul 15;71(Pt 8):926-30. doi: 10.1107/S2056989015012967. eCollection 2015 Aug 1. [PubMed:26396757 ]
Dehkordi MF, Dehghan G, Mahdavi M, Hosseinpour Feizi MA: Multispectral studies of DNA binding, antioxidant and cytotoxic activities of a new pyranochromene derivative. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jun 15;145:353-359. doi: 10.1016/j.saa.2015.03.026. Epub 2015 Mar 9. [PubMed:25795609 ]
Volgraf M, Chan L, Huestis MP, Purkey HE, Burkard M, Geck Do M, Harris J, Hunt KW, Liu X, Lyssikatos JP, Rana S, Thomas AA, Vigers GP, Siu M: Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors. Bioorg Med Chem Lett. 2014 Jun 1;24(11):2477-80. doi: 10.1016/j.bmcl.2014.04.012. Epub 2014 Apr 13. [PubMed:24780121 ]
Pawar SS, Koorbanally NA: Synthesis and structure elucidation of a series of pyranochromene chalcones and flavanones using 1D and 2D NMR spectroscopy and X-ray crystallography. Magn Reson Chem. 2014 Jun;52(6):279-88. doi: 10.1002/mrc.4062. Epub 2014 Mar 13. [PubMed:24623606 ]
Kanakaraju S, Sagar Vijay Kumar P, Prasanna B, Chandramouli GV: Design, Synthesis, and In Vitro Antimicrobial Evaluation of Fused Pyrano[3,2-e]tetrazolo[1,5-c]pyrimidines and Diazepines. ISRN Org Chem. 2013 Aug 21;2013:635384. doi: 10.1155/2013/635384. eCollection 2013. [PubMed:24052866 ]
Vijaya Laxmi S, Thirupathi Reddy Y, Suresh Kuarm B, Narsimha Reddy P, Crooks PA, Rajitha B: Synthesis and evaluation of chromenyl barbiturates and thiobarbiturates as potential antitubercular agents. Bioorg Med Chem Lett. 2011 Jul 15;21(14):4329-31. doi: 10.1016/j.bmcl.2011.05.055. Epub 2011 May 25. [PubMed:21684158 ]

Showing NP-Card for [2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol (NP0059689)

MOL for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)

3D MOL for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)

3D SDF for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)

3D-SDF for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)

PDB for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)

3D PDB for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)

SMILES for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)

INCHI for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)

Structure for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)

3D Structure for NP0059689 ([2R-(2alpha,3alpha,8beta,10alpha)]-2-(3,4-Dihydroxyphenyl)-3,4,9,10-tetrahydro-10-methyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3,5,8-triol)