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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:19:44 UTC

Update Date

2022-03-07 02:55:11 UTC

HMDB ID

HMDB0037086

Secondary Accession Numbers

HMDB37086

Metabolite Identification

Common Name

5,8-Dimethoxychalepensin

Description

5,8-Dimethoxychalepensin belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. 5,8-Dimethoxychalepensin has been detected, but not quantified in, herbs and spices. This could make 5,8-dimethoxychalepensin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,8-Dimethoxychalepensin.

Structure

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

HMDB0037086
     RDKit          3D
5,8-Dimethoxychalepensin
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.1986    1.8152   -1.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.5180   -1.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581   -0.0733   -0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709    0.7892    0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356   -1.3912   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -0.3420    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802   -0.0356   -0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779   -0.3148   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -0.0248   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6861    0.5326   -2.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859    1.9436   -2.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588   -0.2996   -0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3268   -0.1284   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1878   -0.5927   -0.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5310   -1.0215    1.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2710   -0.8579    0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599   -1.1458    1.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2667   -1.7052    2.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3812   -0.9207    3.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8903   -0.8754    1.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462   -1.1479    1.8450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643   -0.8985    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -1.1863    2.1904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653    2.5110   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803    2.2647   -2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8707   -0.1096   -2.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    1.3553    1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    0.1181    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5769    1.4002    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3040   -1.6321    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -1.3024   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405   -2.2241   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    0.4018   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4266    2.5001   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7251    2.2801   -2.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9387    2.2221   -3.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4993    0.2935   -1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2613   -0.6075   -0.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.1641    4.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3758   -1.5820    4.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3451   -0.3621    3.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  6  1  0
 20  8  1  0
 16 12  2  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  END

  Mrv0541 05061309342D          

 23 25  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.9520    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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5564    0.4125    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
    4.2868    0.8250    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
    1.4289    0.8250    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
    4.2868    0.0000    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
    1.4289    0.0000    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  8  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18  3  1  0  0  0  0
 18  6  1  0  0  0  0
 18 12  1  0  0  0  0
 19 17  2  0  0  0  0
 20  4  1  0  0  0  0
 20 13  1  0  0  0  0
 21  5  1  0  0  0  0
 21 16  1  0  0  0  0
 22  8  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037086

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C(=C2)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O5/c1-6-18(2,3)12-9-11-13(20-4)10-7-8-22-14(10)16(21-5)15(11)23-17(12)19/h6-9H,1H2,2-5H3

> <INCHI_KEY>
KHRPPPVMZUBIOV-UHFFFAOYSA-N

> <FORMULA>
C18H18O5

> <MOLECULAR_WEIGHT>
314.3325

> <EXACT_MASS>
314.115423686

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.88502611440407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,9-dimethoxy-6-(2-methylbut-3-en-2-yl)-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
3.194906534

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.068362641199514

> <JCHEM_POLAR_SURFACE_AREA>
57.900000000000006

> <JCHEM_REFRACTIVITY>
85.943

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,9-dimethoxy-6-(2-methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037086
     RDKit          3D
5,8-Dimethoxychalepensin
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.1986    1.8152   -1.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.5180   -1.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581   -0.0733   -0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709    0.7892    0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356   -1.3912   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -0.3420    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802   -0.0356   -0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779   -0.3148   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -0.0248   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6861    0.5326   -2.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859    1.9436   -2.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588   -0.2996   -0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3268   -0.1284   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1878   -0.5927   -0.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5310   -1.0215    1.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2710   -0.8579    0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599   -1.1458    1.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2667   -1.7052    2.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3812   -0.9207    3.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8903   -0.8754    1.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462   -1.1479    1.8450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643   -0.8985    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -1.1863    2.1904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653    2.5110   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803    2.2647   -2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8707   -0.1096   -2.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    1.3553    1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    0.1181    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5769    1.4002    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3040   -1.6321    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -1.3024   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405   -2.2241   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    0.4018   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4266    2.5001   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7251    2.2801   -2.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9387    2.2221   -3.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4993    0.2935   -1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2613   -0.6075   -0.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.1641    4.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3758   -1.5820    4.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3451   -0.3621    3.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  6  1  0
 20  8  1  0
 16 12  2  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564   0.976   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104   3.644   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.467   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.372   0.770   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.467  -0.476   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   18                                                            
CONECT    3   18                                                            
CONECT    4   20                                                            
CONECT    5   21                                                            
CONECT    6    1   18                                                       
CONECT    7    8   10                                                       
CONECT    8    7   22                                                       
CONECT    9   11   12                                                       
CONECT   10    7   13   14                                                  
CONECT   11    9   13   15                                                  
CONECT   12    9   17   18                                                  
CONECT   13   10   11   20                                                  
CONECT   14   10   16   22                                                  
CONECT   15   11   16   23                                                  
CONECT   16   14   15   21                                                  
CONECT   17   12   19   23                                                  
CONECT   18    2    3    6   12                                             
CONECT   19   17                                                            
CONECT   20    4   13                                                       
CONECT   21    5   16                                                       
CONECT   22    8   14                                                       
CONECT   23   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0037086
HETATM    1  C1  UNL     1       3.199   1.815  -1.779  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.030   0.518  -1.596  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.058  -0.073  -0.251  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.771   0.789   0.768  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.836  -1.391  -0.320  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.645  -0.342   0.193  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.580  -0.036  -0.628  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.678  -0.315  -0.142  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.787  -0.025  -0.931  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.686   0.533  -2.184  1.00  0.00           O  
HETATM   11  C10 UNL     1      -1.686   1.944  -2.411  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.059  -0.300  -0.457  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.327  -0.128  -0.995  1.00  0.00           C  
HETATM   14  C13 UNL     1      -5.188  -0.593  -0.042  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.531  -1.021   1.008  1.00  0.00           O  
HETATM   16  C14 UNL     1      -3.271  -0.858   0.785  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.160  -1.146   1.569  1.00  0.00           C  
HETATM   18  O3  UNL     1      -2.267  -1.705   2.826  1.00  0.00           O  
HETATM   19  C16 UNL     1      -2.381  -0.921   3.989  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.890  -0.875   1.105  1.00  0.00           C  
HETATM   21  O4  UNL     1       0.146  -1.148   1.845  1.00  0.00           O  
HETATM   22  C18 UNL     1       1.364  -0.898   1.422  1.00  0.00           C  
HETATM   23  O5  UNL     1       2.340  -1.186   2.190  1.00  0.00           O  
HETATM   24  H1  UNL     1       3.365   2.511  -0.952  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.180   2.265  -2.768  1.00  0.00           H  
HETATM   26  H3  UNL     1       2.871  -0.110  -2.454  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.020   1.355   1.328  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.275   0.118   1.522  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.577   1.400   0.327  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.304  -1.632   0.659  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.661  -1.302  -1.057  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.141  -2.224  -0.546  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.701   0.402  -1.606  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.427   2.500  -1.477  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.725   2.280  -2.684  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.939   2.222  -3.160  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.499   0.294  -1.972  1.00  0.00           H  
HETATM   38  H15 UNL     1      -6.261  -0.608  -0.135  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.582  -0.164   4.082  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.376  -1.582   4.879  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.345  -0.362   3.906  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3   26
CONECT    3    4    5    6
CONECT    4   27   28   29
CONECT    5   30   31   32
CONECT    6    7    7   22
CONECT    7    8   33
CONECT    8    9    9   20
CONECT    9   10   12
CONECT   10   11
CONECT   11   34   35   36
CONECT   12   13   16   16
CONECT   13   14   14   37
CONECT   14   15   38
CONECT   15   16
CONECT   16   17
CONECT   17   18   20   20
CONECT   18   19
CONECT   19   39   40   41
CONECT   20   21
CONECT   21   22
CONECT   22   23   23
END

HMDB0037086
     RDKit          3D
5,8-Dimethoxychalepensin
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.1986    1.8152   -1.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.5180   -1.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581   -0.0733   -0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709    0.7892    0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356   -1.3912   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -0.3420    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802   -0.0356   -0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779   -0.3148   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -0.0248   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6861    0.5326   -2.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859    1.9436   -2.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588   -0.2996   -0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3268   -0.1284   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1878   -0.5927   -0.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5310   -1.0215    1.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2710   -0.8579    0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599   -1.1458    1.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2667   -1.7052    2.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3812   -0.9207    3.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8903   -0.8754    1.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462   -1.1479    1.8450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643   -0.8985    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -1.1863    2.1904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653    2.5110   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803    2.2647   -2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8707   -0.1096   -2.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    1.3553    1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    0.1181    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5769    1.4002    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3040   -1.6321    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -1.3024   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405   -2.2241   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    0.4018   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4266    2.5001   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7251    2.2801   -2.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9387    2.2221   -3.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4993    0.2935   -1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2613   -0.6075   -0.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.1641    4.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3758   -1.5820    4.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3451   -0.3621    3.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  6  1  0
 20  8  1  0
 16 12  2  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₅

Average Molecular Weight

314.3325

Monoisotopic Molecular Weight

314.115423686

IUPAC Name

4,9-dimethoxy-6-(2-methylbut-3-en-2-yl)-7H-furo[3,2-g]chromen-7-one

Traditional Name

4,9-dimethoxy-6-(2-methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one

CAS Registry Number

42438-50-6

SMILES

COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C(=C2)C(C)(C)C=C

InChI Identifier

InChI=1S/C18H18O5/c1-6-18(2,3)12-9-11-13(20-4)10-7-8-22-14(10)16(21-5)15(11)23-17(12)19/h6-9H,1H2,2-5H3

InChI Key

KHRPPPVMZUBIOV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

8-methoxypsoralens

Alternative Parents

Substituents

5-methoxypsoralen
8-methoxypsoralen
1-benzopyran
Benzopyran
Benzofuran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037086)
Cell membrane (HMDB: HMDB0037086)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037086)

Source

Exogenous

Exogenous (HMDB: HMDB0037086)

Food

Food (HMDB: HMDB0037086)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037086)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037086)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	132 - 134 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.86	ALOGPS
logP	3.19	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.94 m³·mol⁻¹	ChemAxon
Polarizability	32.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	172.813	31661259
DarkChem	[M-H]-	174.146	31661259
DeepCCS	[M+H]+	173.794	30932474
DeepCCS	[M-H]-	171.436	30932474
DeepCCS	[M-2H]-	205.615	30932474
DeepCCS	[M+Na]+	180.842	30932474
AllCCS	[M+H]+	170.9	32859911
AllCCS	[M+H-H2O]+	167.4	32859911
AllCCS	[M+NH4]+	174.1	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	178.0	32859911
AllCCS	[M+Na-2H]-	177.5	32859911
AllCCS	[M+HCOO]-	177.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,8-Dimethoxychalepensin	COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C(=C2)C(C)(C)C=C	3236.8	Standard polar	33892256
5,8-Dimethoxychalepensin	COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C(=C2)C(C)(C)C=C	2497.7	Standard non polar	33892256
5,8-Dimethoxychalepensin	COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C(=C2)C(C)(C)C=C	2552.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,8-Dimethoxychalepensin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01z1-1190000000-31b44a59e096ea1c16df	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,8-Dimethoxychalepensin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 10V, Positive-QTOF	splash10-014i-1019000000-5b6f3458684fc64cdd81	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 20V, Positive-QTOF	splash10-014i-9056000000-f78365c8d1aa58a1e7c9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 40V, Positive-QTOF	splash10-014i-9080000000-f9a8193b649b2aae0c7b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 10V, Negative-QTOF	splash10-03di-0039000000-026ad563dcf97651baa2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 20V, Negative-QTOF	splash10-03dj-0095000000-50a11c163de93844471e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 40V, Negative-QTOF	splash10-0uxs-0090000000-09bc7d8d8ea343ea71fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 10V, Positive-QTOF	splash10-014i-0009000000-62e672a7971e1fba3855	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 20V, Positive-QTOF	splash10-00kr-0093000000-993dc7f1e9dfd677fed4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 40V, Positive-QTOF	splash10-0300-1290000000-e6e73702a1af53b083c0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 10V, Negative-QTOF	splash10-03di-0009000000-758807c1b3917e30ae58	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 20V, Negative-QTOF	splash10-03di-0098000000-acecc94eaf4a60cfe7f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dimethoxychalepensin 40V, Negative-QTOF	splash10-014i-0191000000-aedf4e38bd613faa1381	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016074

KNApSAcK ID

Not Available

Chemspider ID

30777177

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101718033

PDB ID

Not Available

ChEBI ID

175031

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 5,8-Dimethoxychalepensin (HMDB0037086)

MOL for HMDB0037086 (5,8-Dimethoxychalepensin)

3D MOL for HMDB0037086 (5,8-Dimethoxychalepensin)

3D SDF for HMDB0037086 (5,8-Dimethoxychalepensin)

3D-SDF for HMDB0037086 (5,8-Dimethoxychalepensin)

PDB for HMDB0037086 (5,8-Dimethoxychalepensin)

3D PDB for HMDB0037086 (5,8-Dimethoxychalepensin)

SMILES for HMDB0037086 (5,8-Dimethoxychalepensin)

INCHI for HMDB0037086 (5,8-Dimethoxychalepensin)

Structure for HMDB0037086 (5,8-Dimethoxychalepensin)

3D Structure for HMDB0037086 (5,8-Dimethoxychalepensin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra