NP-MRD: Showing NP-Card for (9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate (NP0296518)

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Record Information

Version

2.0

Created at

2022-09-10 06:08:37 UTC

Updated at

2022-09-10 06:08:37 UTC

NP-MRD ID

NP0296518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate

Description

Hyuganin C belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. (9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate was first documented in 2016 (PMID: 27286335). Based on a literature review a small amount of articles have been published on Hyuganin C (PMID: 34768849) (PMID: 30891904) (PMID: 26177661).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102208082D          

 28 30  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   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
    2.1434    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  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
    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
    4.2868    2.4750    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
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    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
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    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
    1.0416   -0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  2  0  0  0  0
 18 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    0.5107   -1.7862    3.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2193   -2.0594    2.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869   -3.0747    1.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5945   -1.1979    1.6757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9009   -1.4228    0.3166 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4894   -0.2373   -0.5220 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8635   -0.0526   -0.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3488   -0.1684   -1.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369    0.0251   -1.9744 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1865   -0.1368   -3.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6275   -0.9253   -1.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344   -1.0312    0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4040   -1.6733   -1.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254    0.9480   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318    0.7822    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840    1.8493    0.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7231    3.1065    0.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4171    3.2698    0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8815    4.5526    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182    4.6880    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1223    3.5764   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3236    3.7816   -0.7033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931    2.3751   -0.3887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6567    2.2142    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1376   -0.4804    0.3231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786   -1.6655    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517   -2.6269    1.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7567   -2.2966   -1.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338   -1.3612    3.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933   -2.7261    4.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844   -1.0222    4.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -2.3556    0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8534   -0.4402   -1.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8786    0.5576   -2.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1112   -1.1809   -2.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1119    1.0662   -1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    0.7747   -4.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2633   -0.2538   -3.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6537   -0.9782   -3.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2877   -2.0603    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329   -0.2636    0.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5224   -0.7667    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070    1.6704    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    3.9459    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4928    5.3725    0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536    5.6738    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9275   -2.5280    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197   -2.4530    2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6820   -3.6904    0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824   -3.3412   -1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -2.3100   -1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4304   -1.6632   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 26  1  0
 26 27  1  0
 26 28  1  0
 26 25  1  0
 25 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 14  2  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 14  6  1  0
 14 15  1  0
 24 18  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
  9 36  1  1
  8 34  1  0
  8 35  1  0
  6 33  1  6
  5 32  1  6
  1 29  1  0
  1 30  1  0
  1 31  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 28 50  1  0
 28 51  1  0
 28 52  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
M  END


  Mrv1652309102208082D          

 28 30  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   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
    2.1434    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  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
    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
    4.2868    2.4750    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
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    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
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    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
    1.0416   -0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  2  0  0  0  0
 18 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO[C@H]1[C@@H](OC(C)=O)C(C)(C)OC2=CC=C3C=CC(=O)OC3=C12)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O7/c1-11(12(2)22)10-25-19-17-15(28-21(4,5)20(19)26-13(3)23)8-6-14-7-9-16(24)27-18(14)17/h6-9,11,19-20H,10H2,1-5H3/t11?,19-,20-/m1/s1

> <INCHI_KEY>
GMHDTFBUYSRCCK-JWOXJJEYSA-N

> <FORMULA>
C21H24O7

> <MOLECULAR_WEIGHT>
388.416

> <EXACT_MASS>
388.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.50308209317247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(13R,14R)-12,12-dimethyl-14-(2-methyl-3-oxobutoxy)-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-13-yl acetate

> <JCHEM_LOGP>
2.4852572196666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.039962426032165

> <JCHEM_PKA_STRONGEST_BASIC>
-4.122944163728994

> <JCHEM_POLAR_SURFACE_AREA>
88.13000000000001

> <JCHEM_REFRACTIVITY>
100.36070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(13R,14R)-12,12-dimethyl-14-(2-methyl-3-oxobutoxy)-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.944  -1.360   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.390  -1.360   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6   15   24                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   14   18                                                  
CONECT   25   15   26                                                       
CONECT   26   25    5   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₇

Average Mass

388.4160 Da

Monoisotopic Mass

388.15220 Da

IUPAC Name

(13R,14R)-12,12-dimethyl-14-(2-methyl-3-oxobutoxy)-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-13-yl acetate

Traditional Name

(13R,14R)-12,12-dimethyl-14-(2-methyl-3-oxobutoxy)-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-13-yl acetate

CAS Registry Number

Not Available

SMILES

CC(CO[C@H]1[C@@H](OC(C)=O)C(C)(C)OC2=CC=C3C=CC(=O)OC3=C12)C(C)=O

InChI Identifier

InChI=1S/C21H24O7/c1-11(12(2)22)10-25-19-17-15(28-21(4,5)20(19)26-13(3)23)8-6-14-7-9-16(24)27-18(14)17/h6-9,11,19-20H,10H2,1-5H3/t11?,19-,20-/m1/s1

InChI Key

GMHDTFBUYSRCCK-JWOXJJEYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
1-benzopyran
Benzopyran
Chromane
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.49	ChemAxon
pKa (Strongest Acidic)	19.04	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	100.36 m³·mol⁻¹	ChemAxon
Polarizability	39.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031868

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

100946026

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Koziol E, Jozwiak K, Budzynska B, de Witte PAM, Copmans D, Skalicka-Wozniak K: Comparative Antiseizure Analysis of Diverse Natural Coumarin Derivatives in Zebrafish. Int J Mol Sci. 2021 Oct 22;22(21). pii: ijms222111420. doi: 10.3390/ijms222111420. [PubMed:34768849 ]
Skalicka-Wozniak K, Mroczek T, Walasek M, Glowniak K: Efficient Isolation of Dihydropyranocoumarins and Simple Coumarins from Mutellina purpurea Fruits. Planta Med. 2016 Jul;82(11-12):1105-9. doi: 10.1055/s-0042-108738. Epub 2016 Jun 10. [PubMed:27286335 ]
Orhan IE, Senol Deniz FS, Traedal-Henden S, Ceron-Carrasco JP, den Haan H, Pena-Garcia J, Perez-Sanchez H, Emerce E, Skalicka-Wozniak K: Profiling Auspicious Butyrylcholinesterase Inhibitory Activity of Two Herbal Molecules: Hyperforin and Hyuganin C. Chem Biodivers. 2019 May;16(5):e1900017. doi: 10.1002/cbdv.201900017. Epub 2019 Apr 10. [PubMed:30891904 ]
Mira A, Alkhiary W, Shimizu K: Antiplatelet and Anticoagulant Activities of Angelica shikokiana Extract and Its Isolated Compounds. Clin Appl Thromb Hemost. 2017 Jan;23(1):91-99. doi: 10.1177/1076029615595879. Epub 2015 Jul 15. [PubMed:26177661 ]
LOTUS database [Link]

Showing NP-Card for (9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate (NP0296518)

MOL for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)

3D MOL for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)

3D SDF for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)

3D-SDF for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)

PDB for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)

3D PDB for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)

SMILES for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)

INCHI for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)

Structure for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)

3D Structure for NP0296518 ((9r,10r)-8,8-dimethyl-10-(2-methyl-3-oxobutoxy)-2-oxo-9h,10h-pyrano[2,3-h]chromen-9-yl acetate)