NP-MRD: Showing NP-Card for [2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate (NP0296811)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 06:38:00 UTC

Updated at

2022-09-10 06:38:00 UTC

NP-MRD ID

NP0296811

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate

Description

[2-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate belongs to the class of organic compounds known as coumarinolignans. These are lignans with a structure characterized by the presence of a 1,4-dioxane bridge substituted by a phenyl group, and fused to a coumarin. [2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate is found in Hyoscyamus niger. [2-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251515472D          

 31 34  0  0  0  0            999 V2000
    6.4895    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    2.5559    0.0000 O   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
    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    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   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
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    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
    3.6020   -1.7309    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
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  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
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   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  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  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
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 12 31  1  0  0  0  0
 25 31  2  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    2.6511   -3.1224    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520   -2.3994    0.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4460   -1.2593   -0.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243   -0.8688   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8197    0.2435   -1.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3926    0.6440   -1.8452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3987   -0.5017   -1.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -0.7375   -0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8870    0.3755   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8257    0.2358    0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484    1.3678    1.2576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3160    1.3078    2.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1841   -1.0454    1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6287   -2.1638    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9731   -3.4346    0.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3529   -4.4850    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072   -4.2781   -0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -5.2771   -1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -3.0386   -1.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885   -2.0194   -0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588    1.6289   -0.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0537    1.7968   -1.0454 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6416    1.9340    0.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462    3.0367    0.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1989    4.3550    0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3630    5.4716    1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    4.6355   -0.5333 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606    0.9622   -2.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1895    0.5823   -1.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4964   -0.5451   -1.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837   -0.9455   -1.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0072   -3.5748   -0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023   -2.4047    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325   -3.9012    1.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172   -1.4512   -0.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655    1.0037   -2.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9035    1.0713    3.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8583    2.2552    2.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0929    0.5297    2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9158   -1.1685    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7054   -3.5958    1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5919   -5.5058    0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0521    2.7328   -1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3287    1.0263    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372    1.8934    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4037    5.6795    1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1963    6.4191    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3936    5.2478    2.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425    1.8382   -2.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9962    1.1688   -2.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1776   -1.7195   -0.5698 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 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 20  2  0
 20 19  1  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  2  0
 30  3  1  0
 22  6  1  0
 15 14  1  0
 20  8  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
 28 49  1  0
 29 50  1  0
 31 51  1  0
  6 36  1  6
 22 43  1  6
 23 44  1  0
 23 45  1  0
 26 46  1  0
 26 47  1  0
 26 48  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 16 42  1  0
 15 41  1  0
M  END


  Mrv1533004251515472D          

 31 34  0  0  0  0            999 V2000
    6.4895    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    2.5559    0.0000 O   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
    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    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   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
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    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
    3.6020   -1.7309    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
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  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
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   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  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  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
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 12 31  1  0  0  0  0
 25 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0296811

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1OC2=C(OC1COC(C)=O)C(OC)=CC1=C2OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O9/c1-11(23)28-10-17-19(12-4-6-14(24)15(8-12)26-2)31-22-20-13(5-7-18(25)30-20)9-16(27-3)21(22)29-17/h4-9,17,19,24H,10H2,1-3H3

> <INCHI_KEY>
OPHOIUCADFRJAM-UHFFFAOYSA-N

> <FORMULA>
C22H20O9

> <MOLECULAR_WEIGHT>
428.393

> <EXACT_MASS>
428.110732224

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.103342725478974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.272614943333333

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908138133480637

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3588671095872416

> <JCHEM_POLAR_SURFACE_AREA>
109.75000000000001

> <JCHEM_REFRACTIVITY>
106.81009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2H,3H-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      12.114   6.105   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.344   4.771   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.034   6.105   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.804   7.438   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.804   2.104   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   13   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   12   25                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
[2-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-H]chromen-3-yl]methyl acetic acid	Generator

Chemical Formula

C₂₂H₂₀O₉

Average Mass

428.3930 Da

Monoisotopic Mass

428.11073 Da

IUPAC Name

[2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate

Traditional Name

[2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2H,3H-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1OC2=C(OC1COC(C)=O)C(OC)=CC1=C2OC(=O)C=C1

InChI Identifier

InChI=1S/C22H20O9/c1-11(23)28-10-17-19(12-4-6-14(24)15(8-12)26-2)31-22-20-13(5-7-18(25)30-20)9-16(27-3)21(22)29-17/h4-9,17,19,24H,10H2,1-3H3

InChI Key

OPHOIUCADFRJAM-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
Hyoscyamus niger	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarinolignans. These are lignans with a structure characterized by the presence of a 1,4-dioxane bridge substituted by a phenyl group, and fused to a coumarin.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Coumarinolignans

Sub Class

Not Available

Direct Parent

Coumarinolignans

Alternative Parents

Substituents

Angular-fused coumarolignan skeleton
2-phenylbenzo-1,4-dioxane
Phenylbenzodioxane
P-dioxolo[2,3-h]coumarin
Coumarin
Methoxyphenol
Benzopyran
1-benzopyran
Benzodioxane
Benzo-1,4-dioxane
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Pyran
Benzenoid
Para-dioxin
Heteroaromatic compound
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	3	ALOGPS
logP	2.27	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	109.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.81 m³·mol⁻¹	ChemAxon
Polarizability	43.1 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	Yes	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

73002293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate (NP0296811)

MOL for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)

3D MOL for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)

3D SDF for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)

3D-SDF for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)

PDB for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)

3D PDB for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)

SMILES for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)

INCHI for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)

Structure for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)

3D Structure for NP0296811 ([2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]methyl acetate)