NP-MRD: Showing NP-Card for (3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one (NP0309196)

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Record Information

Version

1.0

Created at

2022-09-11 03:37:41 UTC

Updated at

2022-09-11 03:37:42 UTC

NP-MRD ID

NP0309196

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one

Description

HYDRASTINE, also known as beta-hydrastine or isocoryne, belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide. (3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one is found in Hydrastis canadensis. It was first documented in 2020 (PMID: 32607087). Based on a literature review a significant number of articles have been published on HYDRASTINE (PMID: 35048143) (PMID: 34706137) (PMID: 32591416) (PMID: 35518292).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205372D          

 28 32  0  0  1  0            999 V2000
    3.4975    3.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525    3.1492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    2.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4554    1.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034    1.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3935    2.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385    3.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    4.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315    2.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -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
    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  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
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 18 28  1  0  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    4.8485    2.8998   -0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6645    1.7287    0.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561    1.1451    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018    1.7384   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0340    1.2147    0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    0.0589    0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0407   -0.5402    1.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3130   -0.0128    1.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300   -0.6422    1.5194 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1529   -1.6227    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7139   -1.7809    1.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5631   -2.5761    2.5268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590   -1.8956    1.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2448   -0.7716    1.3569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2694   -1.1272    0.3266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2909   -0.1219    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557    1.1103    0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776    1.9681    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3460    1.6294   -0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932    0.3980   -1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795   -0.4463   -0.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1561   -1.8097   -1.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7476   -2.1577   -1.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901   -1.7697   -0.8299 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -2.8141   -0.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2352    2.6726   -0.6859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9903    3.5310    0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6651    3.2581    0.8261 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5933    3.7614   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8741    3.0490   -1.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853    2.9910   -1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    2.6551   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667    1.7187   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3462   -2.5178    1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6725   -1.9302   -0.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1814   -1.2538    0.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7391   -0.2352    2.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787   -1.9696    0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5939    1.3800    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0422    0.0908   -1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098   -2.5272   -0.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7834   -1.9035   -2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198   -1.7325   -2.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7109   -3.2739   -1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458   -3.5358   -1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210   -2.4721   -0.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -3.4328    0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1156    4.5948    0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6441    3.2794    1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 14 15  1  0
 15 24  1  0
 24 25  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 18 28  1  0
 28 27  1  0
 27 26  1  0
 18 17  1  0
 17 16  2  0
  8  3  1  0
 16 15  1  0
  7  6  1  0
 16 21  1  0
 26 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
 14 37  1  1
 10 34  1  0
 10 35  1  0
 10 36  1  0
 15 38  1  1
 25 45  1  0
 25 46  1  0
 25 47  1  0
 23 43  1  0
 23 44  1  0
 22 41  1  0
 22 42  1  0
 20 40  1  0
 27 48  1  0
 27 49  1  0
 17 39  1  0
M  END


  Mrv1652309112205372D          

 28 32  0  0  1  0            999 V2000
    3.4975    3.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525    3.1492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    2.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4554    1.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034    1.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3935    2.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385    3.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    4.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315    2.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -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
    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  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
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 18 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309196

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2[C@H](OC(=O)C2=C1OC)C1N(C)CCC2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18?,19-/m0/s1

> <INCHI_KEY>
JZUTXVTYJDCMDU-GGYWPGCISA-N

> <FORMULA>
C21H21NO6

> <MOLECULAR_WEIGHT>
383.4

> <EXACT_MASS>
383.1368874

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.91628849705965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-6,7-dimethoxy-3-{6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-1,3-dihydro-2-benzofuran-1-one

> <JCHEM_LOGP>
2.738381303666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.048710218030013

> <JCHEM_PKA_STRONGEST_BASIC>
6.69851344740293

> <JCHEM_POLAR_SURFACE_AREA>
66.46000000000001

> <JCHEM_REFRACTIVITY>
100.6129

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-6,7-dimethoxy-3-{6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3H-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.529   7.343   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.005   5.879   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.974   4.734   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.450   3.269   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   2.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.913   2.445   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.437   3.910   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.468   5.054   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.992   6.519   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.022   7.663   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.897   3.910   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.992   5.156   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.421   2.445   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+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  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    6   15                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   15   25                                                  
CONECT   25   24                                                            
CONECT   26   19   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   18                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
Hydrastine hydrochloride, (S-(r,s))-isomer	MeSH
Hydrastine, (R-(r,s))-isomer	MeSH
beta-Hydrastine	MeSH
Hydrastine, (R-(r,r))-isomer	MeSH
Isocoryne	MeSH

Chemical Formula

C₂₁H₂₁NO₆

Average Mass

383.4000 Da

Monoisotopic Mass

383.13689 Da

IUPAC Name

(3S)-6,7-dimethoxy-3-{6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-1,3-dihydro-2-benzofuran-1-one

Traditional Name

(3S)-6,7-dimethoxy-3-{6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3H-2-benzofuran-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2[C@H](OC(=O)C2=C1OC)C1N(C)CCC2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18?,19-/m0/s1

InChI Key

JZUTXVTYJDCMDU-GGYWPGCISA-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
Hydrastis canadensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Phthalide isoquinolines

Sub Class

Not Available

Direct Parent

Phthalide isoquinolines

Alternative Parents

Substituents

Phthalide isoquinoline
Isobenzofuranone
Benzofuranone
Tetrahydroisoquinoline
Phthalide
Benzodioxole
Isocoumaran
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Acetal
Carboxylic acid derivative
Oxacycle
Ether
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
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	2.74	ChemAxon
pKa (Strongest Acidic)	13.05	ChemAxon
pKa (Strongest Basic)	6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.61 m³·mol⁻¹	ChemAxon
Polarizability	39.92 Å³	ChemAxon
Number of Rings	5	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

C00001867

Chemspider ID

330095

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

371942

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Adiwidjaja J, Boddy AV, McLachlan AJ: Physiologically based pharmacokinetic model predictions of natural product-drug interactions between goldenseal, berberine, imatinib and bosutinib. Eur J Clin Pharmacol. 2022 Apr;78(4):597-611. doi: 10.1007/s00228-021-03266-y. Epub 2022 Jan 20. [PubMed:35048143 ]
Serna AV, Kurti L, Siitonen JH: Synthesis of (+/-)-Setigerumine I: Biosynthetic Origins of the Elusive Racemic Papaveraceae Isoxazolidine Alkaloids*. Angew Chem Int Ed Engl. 2021 Dec 20;60(52):27236-27240. doi: 10.1002/anie.202111049. Epub 2021 Nov 18. [PubMed:34706137 ]
Khin M, Cech NB, Kellogg JJ, Caesar LK: Chemical Evaluation of the Effects of Storage Conditions on the Botanical Goldenseal using Marker-based and Metabolomics Approaches. Yale J Biol Med. 2020 Jun 29;93(2):265-275. eCollection 2020 Jun. [PubMed:32607087 ]
McDonald MG, Tian DD, Thummel KE, Paine MF, Rettie AE: Modulation of Major Human Liver Microsomal Cytochromes P450 by Component Alkaloids of Goldenseal: Time-Dependent Inhibition and Allosteric Effects. Drug Metab Dispos. 2020 Oct;48(10):1018-1027. doi: 10.1124/dmd.120.091041. Epub 2020 Jun 26. [PubMed:32591416 ]
Li J, Wu T, Song X, Zheng Y, Meng J, Qin Q, Liu Y, Zhao D, Cheng M: Studies on asymmetric total synthesis of (-)-beta-hydrastine via a chiral epoxide ring-opening cascade cyclization strategy. RSC Adv. 2020 May 19;10(32):18953-18958. doi: 10.1039/d0ra03038d. eCollection 2020 May 14. [PubMed:35518292 ]
LOTUS database [Link]

Showing NP-Card for (3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one (NP0309196)

MOL for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)

3D MOL for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)

3D SDF for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)

3D-SDF for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)

PDB for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)

3D PDB for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)

SMILES for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)

INCHI for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)

Structure for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)

3D Structure for NP0309196 ((3s)-6,7-dimethoxy-3-{6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-3h-2-benzofuran-1-one)