NP-MRD: Showing NP-Card for (3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol (NP0243657)

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Record Information

Version

2.0

Created at

2022-09-07 04:15:24 UTC

Updated at

2022-09-07 04:15:24 UTC

NP-MRD ID

NP0243657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol

Description

(-)-Noscapine hemiacetal, also known as narcotine hemiacetal, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. (3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol is found in Papaver orientale. (3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol was first documented in 2018 (PMID: 29723437). Based on a literature review a small amount of articles have been published on (-)-noscapine hemiacetal.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206152D          

 30 34  0  0  1  0            999 V2000
    6.1354    6.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3903    5.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8383    4.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0932    4.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412    3.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0313    5.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763    5.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3284    6.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6543    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693    5.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993    3.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    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
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  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
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 29  1  6  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    5.2609    2.1345   -1.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4094    1.0438   -2.0347 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778    0.6662   -1.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3587    1.3223    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4369    0.9525    1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903   -0.1210    0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297   -0.7553   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.4073   -1.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7709   -1.0560   -2.6074 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697   -2.1483   -2.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121   -1.8384   -0.3967 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1749   -2.9828   -1.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -2.0616    0.9617 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5137   -0.8150    1.5028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7254   -0.1170    1.8217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7419    0.1149    0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6165   -0.9279    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6474   -0.7494   -0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8232    0.4442   -1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    1.4797   -0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9384    1.2800    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1414    2.3743    0.3852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0526    2.6088   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3820    2.5464   -1.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6472    2.2590   -2.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7600    0.8713   -1.9876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5419   -2.2543    1.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8543   -2.1839    2.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -0.9337    2.8718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2755   -0.1363    3.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7491    2.0147   -0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6586    3.0812   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0870    2.2322   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0088    2.1615    0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3084    1.4288    2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813   -3.0672   -3.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383   -1.9524   -3.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0785   -2.4137   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979   -1.4976   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5791   -3.2521   -1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267   -1.0187    2.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4634    0.8357    2.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3225   -1.5846   -0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143    3.0457    0.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2160    1.6522   -0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3731    3.2707   -1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7281    2.6234   -3.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4077    2.7349   -1.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891   -2.9520    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850   -2.6518    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922   -2.9127    2.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4990   -2.5834    3.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5274    0.8305    3.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7559    0.1127    4.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509   -0.7479    3.9140 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  1  0
 11  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 14 15  1  0
 15 29  1  0
 29 30  1  0
 29 28  1  0
 28 27  1  0
 27 17  1  0
 17 16  2  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 21 20  2  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 26 19  1  0
 19 18  2  0
  8  3  1  0
 16 15  1  0
 19 20  1  0
  7  6  1  0
 18 17  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
 14 41  1  1
 11 39  1  6
 12 40  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 15 42  1  1
 30 53  1  0
 30 54  1  0
 30 55  1  0
 28 51  1  0
 28 52  1  0
 27 49  1  0
 27 50  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
 25 47  1  0
 25 48  1  0
 18 43  1  0
M  END


  Mrv1652309072206152D          

 30 34  0  0  1  0            999 V2000
    6.1354    6.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3903    5.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8383    4.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0932    4.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412    3.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0313    5.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763    5.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3284    6.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6543    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693    5.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993    3.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    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
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  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
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 29  1  6  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2[C@H](OC(O)C2=C1OC)[C@@H]1N(C)CCC2=C1C(OC)=C1OCOC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18,22,24H,7-8,10H2,1-4H3/t17-,18+,22?/m1/s1

> <INCHI_KEY>
TZNFGVJRQISOHK-HVHHGIHYSA-N

> <FORMULA>
C22H25NO7

> <MOLECULAR_WEIGHT>
415.442

> <EXACT_MASS>
415.163102149

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.53283829304671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.2887858686666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.266126636352316

> <JCHEM_PKA_STRONGEST_BASIC>
6.478756694198284

> <JCHEM_POLAR_SURFACE_AREA>
78.85000000000001

> <JCHEM_REFRACTIVITY>
107.64779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      11.453  11.726   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.929  10.261   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.898   9.117   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.374   7.652   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.344   6.508   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.837   6.828   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.361   8.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.392   9.437   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.916  10.902   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.946  12.046   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.821   8.293   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.916   9.539   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.345   6.828   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       8.925   3.613   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      10.259   4.383   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                                                       
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   29                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   19                                                       
CONECT   27   17   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   15   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
(-)-alpha-Narcotine hemiacetal	ChEBI
(-)-Narcotine hemiacetal	ChEBI
Narcotine hemiacetal	ChEBI
Noscapine hemiacetal	ChEBI
(-)-a-Narcotine hemiacetal	Generator
(-)-Α-narcotine hemiacetal	Generator

Chemical Formula

C₂₂H₂₅NO₇

Average Mass

415.4420 Da

Monoisotopic Mass

415.16310 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=C2[C@H](OC(O)C2=C1OC)[C@@H]1N(C)CCC2=C1C(OC)=C1OCOC1=C2

InChI Identifier

InChI=1S/C22H25NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18,22,24H,7-8,10H2,1-4H3/t17-,18+,22?/m1/s1

InChI Key

TZNFGVJRQISOHK-HVHHGIHYSA-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
Papaver orientale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
Benzodioxole
Isocoumaran
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Hemiacetal
Oxacycle
Azacycle
Acetal
Ether
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organopnictogen compound
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	2.29	ChemAxon
pKa (Strongest Acidic)	11.27	ChemAxon
pKa (Strongest Basic)	6.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.85 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.65 m³·mol⁻¹	ChemAxon
Polarizability	41.53 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

Not Available

Chemspider ID

58829923

KEGG Compound ID

Not Available

BioCyc ID

CPD-14833

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90657121

PDB ID

Not Available

ChEBI ID

141667

Good Scents ID

Not Available

References

General References

Park MR, Chen X, Lang DE, Ng KKS, Facchini PJ: Heterodimeric O-methyltransferases involved in the biosynthesis of noscapine in opium poppy. Plant J. 2018 Jul;95(2):252-267. doi: 10.1111/tpj.13947. Epub 2018 Jun 8. [PubMed:29723437 ]
LOTUS database [Link]

Showing NP-Card for (3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol (NP0243657)

MOL for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)

3D MOL for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)

3D SDF for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)

3D-SDF for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)

PDB for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)

3D PDB for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)

SMILES for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)

INCHI for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)

Structure for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)

3D Structure for NP0243657 ((3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol)