NP-MRD: Showing NP-Card for Versicoumarin C (NP0044004)

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Record Information

Version

1.0

Created at

2021-06-22 17:44:57 UTC

Updated at

2021-06-22 17:44:57 UTC

NP-MRD ID

NP0044004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Versicoumarin C

Description

CHEMBL3798284 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. Versicoumarin C is found in Aspergillus versicolor. It was first documented in 2014 (Ye, et al.). Based on a literature review very few articles have been published on CHEMBL3798284.

Structure

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

NP0044004
     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    2.1805    3.3237    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9133    3.1268   -0.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0869    2.2932    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9757    2.7700    1.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8221    4.0540    1.9154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    1.9131    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    0.6314    1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2203    0.1665    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041    1.0196   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    0.5444   -1.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281    0.0199   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.1852   -0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -2.1010   -1.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451   -1.7231   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3828   -1.2082   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481   -1.5733   -0.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0946   -2.9249   -0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863   -1.5245    1.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860   -0.2403    1.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    0.1983    2.6342 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656    2.7945    1.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056    4.3955    0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206    2.9175   -0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677    4.6305    1.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769    2.2182    2.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2735   -0.0746   -1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0923    1.4721   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6198    0.5872    0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -1.5854   -2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299   -2.7339   -1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5325   -2.7844   -2.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9188   -1.2345    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813   -2.8238   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5974   -1.4970   -0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927   -1.9206    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9334   -1.4031   -1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -0.8277   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9342   -3.7677   -0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053   -3.0353   -1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1209   -2.9079   -1.2312 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
  9  3  1  0
 19  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  6
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  END


  Mrv1652306222119442D          

 20 21  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.1434    2.0625    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
  7 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(=O)O[C@H](C)CC2=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O4/c1-9(2)5-6-11-12-7-10(3)20-16(18)13(12)8-14(17)15(11)19-4/h5,8,10,17H,6-7H2,1-4H3/t10-/m1/s1

> <INCHI_KEY>
GBZUPJOFJRYUPJ-SNVBAGLBSA-N

> <FORMULA>
C16H20O4

> <MOLECULAR_WEIGHT>
276.332

> <EXACT_MASS>
276.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.320761533178114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-7-hydroxy-6-methoxy-3-methyl-5-(3-methylbut-2-en-1-yl)-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
3.500516723

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.990505470484933

> <JCHEM_PKA_STRONGEST_BASIC>
-4.919613756712436

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
78.49859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-7-hydroxy-6-methoxy-3-methyl-5-(3-methylbut-2-en-1-yl)-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0044004
     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    2.1805    3.3237    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9133    3.1268   -0.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0869    2.2932    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9757    2.7700    1.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8221    4.0540    1.9154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    1.9131    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    0.6314    1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2203    0.1665    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041    1.0196   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    0.5444   -1.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281    0.0199   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.1852   -0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -2.1010   -1.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451   -1.7231   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3828   -1.2082   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481   -1.5733   -0.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0946   -2.9249   -0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863   -1.5245    1.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860   -0.2403    1.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    0.1983    2.6342 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656    2.7945    1.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056    4.3955    0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206    2.9175   -0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677    4.6305    1.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769    2.2182    2.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2735   -0.0746   -1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0923    1.4721   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6198    0.5872    0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -1.5854   -2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299   -2.7339   -1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5325   -2.7844   -2.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9188   -1.2345    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813   -2.8238   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5974   -1.4970   -0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927   -1.9206    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9334   -1.4031   -1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -0.8277   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9342   -3.7677   -0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053   -3.0353   -1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1209   -2.9079   -1.2312 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
  9  3  1  0
 19  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  6
 17 38  1  0
 17 39  1  0
 17 40  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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    2                                                       
CONECT   13    7                                                            
CONECT   14    6   15                                                       
CONECT   15   14                                                            
CONECT   16    5   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    NP0044004
HETATM    1  C1  UNL     1       2.181   3.324   0.508  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.913   3.127  -0.001  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.087   2.293   0.439  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.976   2.770   1.415  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.822   4.054   1.915  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.962   1.913   1.819  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.098   0.631   1.306  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.220   0.167   0.346  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.204   1.020  -0.084  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.798   0.544  -1.093  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.028   0.020  -0.508  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.467  -1.185  -0.807  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.776  -2.101  -1.741  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.745  -1.723  -0.193  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.383  -1.208  -0.168  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.848  -1.573  -0.157  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.095  -2.925  -0.789  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.286  -1.524   1.199  1.00  0.00           O  
HETATM   19  C16 UNL     1      -3.186  -0.240   1.766  1.00  0.00           C  
HETATM   20  O4  UNL     1      -3.963   0.198   2.634  1.00  0.00           O  
HETATM   21  H1  UNL     1       2.266   2.794   1.487  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.406   4.396   0.717  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.921   2.918  -0.243  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.068   4.630   1.569  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.677   2.218   2.567  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.274  -0.075  -1.813  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.092   1.472  -1.703  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.620   0.587   0.189  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.293  -1.585  -2.583  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.030  -2.734  -1.195  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.533  -2.784  -2.241  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.919  -1.235   0.776  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.681  -2.824  -0.111  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.597  -1.497  -0.866  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.893  -1.921   0.566  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.933  -1.403  -1.147  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.378  -0.828  -0.778  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.934  -3.768  -0.107  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.405  -3.035  -1.661  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.121  -2.908  -1.231  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5    6
CONECT    5   24
CONECT    6    7    7   25
CONECT    7    8   19
CONECT    8    9    9   15
CONECT    9   10
CONECT   10   11   26   27
CONECT   11   12   12   28
CONECT   12   13   14
CONECT   13   29   30   31
CONECT   14   32   33   34
CONECT   15   16   35   36
CONECT   16   17   18   37
CONECT   17   38   39   40
CONECT   18   19
CONECT   19   20   20
END

NP0044004
     RDKit          3D

40 41  0  0  0  0  0  0  0  0999 V2000
    2.1805    3.3237    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9133    3.1268   -0.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0869    2.2932    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9757    2.7700    1.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8221    4.0540    1.9154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    1.9131    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    0.6314    1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2203    0.1665    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041    1.0196   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    0.5444   -1.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281    0.0199   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.1852   -0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -2.1010   -1.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451   -1.7231   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3828   -1.2082   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481   -1.5733   -0.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0946   -2.9249   -0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863   -1.5245    1.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860   -0.2403    1.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    0.1983    2.6342 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656    2.7945    1.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056    4.3955    0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206    2.9175   -0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677    4.6305    1.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769    2.2182    2.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2735   -0.0746   -1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0923    1.4721   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6198    0.5872    0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -1.5854   -2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299   -2.7339   -1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5325   -2.7844   -2.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9188   -1.2345    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813   -2.8238   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5974   -1.4970   -0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927   -1.9206    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9334   -1.4031   -1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -0.8277   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9342   -3.7677   -0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053   -3.0353   -1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1209   -2.9079   -1.2312 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
  9  3  1  0
 19  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  6
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₄

Average Mass

276.3320 Da

Monoisotopic Mass

276.13616 Da

IUPAC Name

(3R)-7-hydroxy-6-methoxy-3-methyl-5-(3-methylbut-2-en-1-yl)-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

(3R)-7-hydroxy-6-methoxy-3-methyl-5-(3-methylbut-2-en-1-yl)-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(=O)O[C@H](C)CC2=C1CC=C(C)C

InChI Identifier

InChI=1S/C16H20O4/c1-9(2)5-6-11-12-7-10(3)20-16(18)13(12)8-14(17)15(11)19-4/h5,8,10,17H,6-7H2,1-4H3/t10-/m1/s1

InChI Key

GBZUPJOFJRYUPJ-SNVBAGLBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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
Aspergillus versicolor	Linigton's dataset	Yan-qing Ye, Cong-Fang Xia, Juan-Xia Yang, Ying Qin, Ming Zhou, Xue-Mei Gao, Gang Du, Hai-Ying Ya...

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
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
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	3.22	ALOGPS
logP	3.5	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.5 m³·mol⁻¹	ChemAxon
Polarizability	30.32 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

58927845

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127045809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yan-qing Ye, Cong-Fang Xia, Juan-Xia Yang, Ying Qin, Ming Zhou, Xue-Mei Gao, Gang Du, Hai-Ying Yang, Xue-Mei Li and Qiu-Fen Hu (2014). Yan-qing Ye, Cong-Fang Xia, Juan-Xia Yang, Ying Qin, Ming Zhou, Xue-Mei Gao, Gang Du, Hai-Ying Yang, Xue-Mei Li and Qiu-Fen Hu. Isocoumarins from the fermentation products of an endophytic fungus of Aspergillus versicolor DOI: 10.1016/j.phytol.2014.09.016. Phytochemistry Letters.

Showing NP-Card for Versicoumarin C (NP0044004)

MOL for NP0044004 (Versicoumarin C)

3D MOL for NP0044004 (Versicoumarin C)

3D SDF for NP0044004 (Versicoumarin C)

3D-SDF for NP0044004 (Versicoumarin C)

PDB for NP0044004 (Versicoumarin C)

3D PDB for NP0044004 (Versicoumarin C)

SMILES for NP0044004 (Versicoumarin C)

INCHI for NP0044004 (Versicoumarin C)

Structure for NP0044004 (Versicoumarin C)

3D Structure for NP0044004 (Versicoumarin C)