NP-MRD: Showing NP-Card for (3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol (NP0043784)

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Record Information

Version

2.0

Created at

2021-06-22 17:17:26 UTC

Updated at

2021-06-22 17:17:26 UTC

NP-MRD ID

NP0043784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol

Description

(3S,4R)-6-hydroxy-8-methoxy-3,5-dimethyl-4-isochromanol belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. (3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol is found in Penicillium sp. WN-11-1-3-1-2. (3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol was first documented in 2015 (SOrfali, et al.). Based on a literature review very few articles have been published on (3S,4R)-6-hydroxy-8-methoxy-3,5-dimethyl-4-isochromanol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043784
     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    3.7314   -1.9012   -1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550   -1.9410   -0.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7337   -0.7543   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3820    0.4582   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    1.6142    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3483    2.8284    0.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3506    1.5799    0.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155    2.7938    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    0.3544    0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843   -0.8118   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040   -2.0482   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6774   -1.9281   -0.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608   -0.7090   -0.4730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7484   -0.8831   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    0.1728    0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4217    1.3254    0.7951 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518   -2.8199   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2714   -1.7420   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -1.0582   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    0.5130   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135    2.9460   -0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    3.1167    0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370    3.6247    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492    2.7184    1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414   -2.7600   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720   -2.5310    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1522   -0.1512   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892    0.1103    0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517   -1.5159    0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027   -1.3400   -1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489   -0.4726    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0337    1.2115    1.5874 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  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 10  3  1  0
 15  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  6
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  1
 16 32  1  0
M  END


  Mrv1652306222119172D          

 16 17  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 O   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 C   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
    1.4289    0.8250    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  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
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -2.4750    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2CO[C@@H](C)[C@H](O)C2=C(C)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O4/c1-6-9(13)4-10(15-3)8-5-16-7(2)12(14)11(6)8/h4,7,12-14H,5H2,1-3H3/t7-,12-/m0/s1

> <INCHI_KEY>
FWQJAZKWNXACKB-MADCSZMMSA-N

> <FORMULA>
C12H16O4

> <MOLECULAR_WEIGHT>
224.256

> <EXACT_MASS>
224.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.61826860483808

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R)-8-methoxy-3,5-dimethyl-3,4-dihydro-1H-2-benzopyran-4,6-diol

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
1.4386747383333334

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.485997519897833

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.587546913937961

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5289628183970736

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
60.04630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R)-8-methoxy-3,5-dimethyl-3,4-dihydro-1H-2-benzopyran-4,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043784
     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    3.7314   -1.9012   -1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550   -1.9410   -0.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7337   -0.7543   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3820    0.4582   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    1.6142    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3483    2.8284    0.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3506    1.5799    0.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155    2.7938    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    0.3544    0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843   -0.8118   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040   -2.0482   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6774   -1.9281   -0.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608   -0.7090   -0.4730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7484   -0.8831   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    0.1728    0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4217    1.3254    0.7951 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518   -2.8199   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2714   -1.7420   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -1.0582   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    0.5130   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135    2.9460   -0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    3.1167    0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370    3.6247    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492    2.7184    1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414   -2.7600   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720   -2.5310    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1522   -0.1512   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892    0.1103    0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517   -1.5159    0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027   -1.3400   -1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489   -0.4726    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0337    1.2115    1.5874 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  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 10  3  1  0
 15  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  6
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  1
 16 32  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    NP0043784
HETATM    1  C1  UNL     1       3.731  -1.901  -1.017  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.355  -1.941  -0.701  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.734  -0.754  -0.340  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.382   0.458  -0.273  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.699   1.614   0.097  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.348   2.828   0.164  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.351   1.580   0.407  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.415   2.794   0.807  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.278   0.354   0.332  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.384  -0.812  -0.034  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.404  -2.048  -0.073  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.677  -1.928  -0.540  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.261  -0.709  -0.473  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.748  -0.883  -0.202  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.722   0.173   0.638  1.00  0.00           C  
HETATM   16  O4  UNL     1      -2.422   1.325   0.795  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.052  -2.820  -1.550  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.271  -1.742  -0.063  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.930  -1.058  -1.711  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.433   0.513  -0.510  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.314   2.946  -0.041  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.136   3.117   0.026  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.337   3.625   0.865  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.849   2.718   1.814  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.141  -2.760  -0.755  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.372  -2.531   0.936  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.152  -0.151  -1.422  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.189   0.110   0.057  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.852  -1.516   0.702  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.203  -1.340  -1.089  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.749  -0.473   1.565  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.034   1.211   1.587  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   20
CONECT    5    6    7    7
CONECT    6   21
CONECT    7    8    9
CONECT    8   22   23   24
CONECT    9   10   10   15
CONECT   10   11
CONECT   11   12   25   26
CONECT   12   13
CONECT   13   14   15   27
CONECT   14   28   29   30
CONECT   15   16   31
CONECT   16   32
END

NP0043784
     RDKit          3D

32 33  0  0  0  0  0  0  0  0999 V2000
    3.7314   -1.9012   -1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550   -1.9410   -0.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7337   -0.7543   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3820    0.4582   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    1.6142    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3483    2.8284    0.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3506    1.5799    0.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155    2.7938    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    0.3544    0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843   -0.8118   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040   -2.0482   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6774   -1.9281   -0.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608   -0.7090   -0.4730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7484   -0.8831   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    0.1728    0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4217    1.3254    0.7951 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518   -2.8199   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2714   -1.7420   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -1.0582   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    0.5130   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135    2.9460   -0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    3.1167    0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370    3.6247    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492    2.7184    1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414   -2.7600   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720   -2.5310    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1522   -0.1512   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892    0.1103    0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517   -1.5159    0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027   -1.3400   -1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489   -0.4726    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0337    1.2115    1.5874 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  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 10  3  1  0
 15  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  6
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  1
 16 32  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₆O₄

Average Mass

224.2560 Da

Monoisotopic Mass

224.10486 Da

IUPAC Name

(3S,4R)-8-methoxy-3,5-dimethyl-3,4-dihydro-1H-2-benzopyran-4,6-diol

Traditional Name

(3S,4R)-8-methoxy-3,5-dimethyl-3,4-dihydro-1H-2-benzopyran-4,6-diol

CAS Registry Number

Not Available

SMILES

COC1=C2CO[C@@H](C)[C@H](O)C2=C(C)C(O)=C1

InChI Identifier

InChI=1S/C12H16O4/c1-6-9(13)4-10(15-3)8-5-16-7(2)12(14)11(6)8/h4,7,12-14H,5H2,1-3H3/t7-,12-/m0/s1

InChI Key

FWQJAZKWNXACKB-MADCSZMMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium sp. WN-11-1-3-1-2	Linigton's dataset	Raha S.Orfali, Amal H.Aly, Weaam Ebrahim, Rudiyansyah, Peter Proksch. Isochroman and isocoumarin ...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	0.71	ALOGPS
logP	1.44	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.05 m³·mol⁻¹	ChemAxon
Polarizability	23.62 Å³	ChemAxon
Number of Rings	2	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

78442035

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585712

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Raha S.Orfali, Amal H.Aly, Weaam Ebrahim, Rudiyansyah, Peter Proksch (2015). Raha S.Orfali, Amal H.Aly, Weaam Ebrahim, Rudiyansyah, Peter Proksch. Isochroman and isocoumarin derivatives from hypersaline lake sediment-derived fungus Penicillium sp. DOI: 10.1016/j.phytol.2015.06.003. Phytochemistry Letters.

Showing NP-Card for (3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol (NP0043784)

MOL for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)

3D MOL for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)

3D SDF for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)

3D-SDF for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)

PDB for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)

3D PDB for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)

SMILES for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)

INCHI for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)

Structure for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)

3D Structure for NP0043784 ((3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol)