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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:41:45 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033921

Secondary Accession Numbers

HMDB33921

Metabolite Identification

Common Name

3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one

Description

3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one has been detected, but not quantified in, herbs and spices. This could make 3-(1,1-dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one.

Structure

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

HMDB0033921
     RDKit          3D
3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.7532   -0.2564    1.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202    0.7514    1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1654    0.4163   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -0.8980   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5546    1.5461   -1.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6777    0.3368   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    0.5474    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4485    0.4473    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583    0.6489    1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270    0.5469    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.2450    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488    0.1446    0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3778    0.3495    1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111    0.0378   -0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -0.2625   -1.8725 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -1.5446   -2.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426    0.1417   -0.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2936   -0.0522   -1.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    0.0359   -1.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6985   -0.1579   -2.5572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -1.2870    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0785   -0.0750    2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8347    1.7497    1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7638   -1.0110   -0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9420   -0.9719   -1.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1218   -1.7140   -0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861    2.0520   -0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914    1.1906   -2.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    2.3082   -1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210    0.7802    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084    0.8913    2.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    0.7161    2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0308   -0.2083    2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4164    0.0308    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3889    1.4423    1.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857   -2.2901   -1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633   -1.7229   -3.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4322   -1.5931   -2.5550 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  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19  6  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END


  Mrv0541 05061307262D          

 20 21  0  0  0  0            999 V2000
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   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
    1.4289    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  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
    2.1434   -0.4125    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
    0.7145   -1.2375    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
    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    2.8579   -1.6500    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
 10  9  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16  6  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18  4  1  0  0  0  0
 18 12  1  0  0  0  0
 19  5  1  0  0  0  0
 19 14  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033921

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C(C=C1)C=C(C(=O)O2)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O4/c1-6-16(2,3)11-9-10-7-8-12(18-4)14(19-5)13(10)20-15(11)17/h6-9H,1H2,2-5H3

> <INCHI_KEY>
YSFZHXKUZLVBRX-UHFFFAOYSA-N

> <FORMULA>
C16H18O4

> <MOLECULAR_WEIGHT>
274.3117

> <EXACT_MASS>
274.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.39782263470341

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,8-dimethoxy-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
3.0357831333333327

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.633501534640391

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
77.10190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8-dimethoxy-3-(2-methylbut-3-en-2-yl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033921
     RDKit          3D
3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.7532   -0.2564    1.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202    0.7514    1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1654    0.4163   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -0.8980   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5546    1.5461   -1.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6777    0.3368   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    0.5474    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4485    0.4473    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583    0.6489    1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270    0.5469    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.2450    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488    0.1446    0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3778    0.3495    1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111    0.0378   -0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -0.2625   -1.8725 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -1.5446   -2.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426    0.1417   -0.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2936   -0.0522   -1.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    0.0359   -1.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6985   -0.1579   -2.5572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -1.2870    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0785   -0.0750    2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8347    1.7497    1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7638   -1.0110   -0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9420   -0.9719   -1.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1218   -1.7140   -0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861    2.0520   -0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914    1.1906   -2.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    2.3082   -1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210    0.7802    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084    0.8913    2.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    0.7161    2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0308   -0.2083    2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4164    0.0308    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3889    1.4423    1.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857   -2.2901   -1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633   -1.7229   -3.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4322   -1.5931   -2.5550 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  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19  6  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  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      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.232   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.772  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6    1   16                                                       
CONECT    7    8   10                                                       
CONECT    8    7   12                                                       
CONECT    9   10   11                                                       
CONECT   10    7    9   13                                                  
CONECT   11    9   15   16                                                  
CONECT   12    8   14   18                                                  
CONECT   13   10   14   20                                                  
CONECT   14   12   13   19                                                  
CONECT   15   11   17   20                                                  
CONECT   16    2    3    6   11                                             
CONECT   17   15                                                            
CONECT   18    4   12                                                       
CONECT   19    5   14                                                       
CONECT   20   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0033921
HETATM    1  C1  UNL     1      -3.753  -0.256   1.897  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.620   0.751   1.043  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.165   0.416  -0.345  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.787  -0.898  -0.754  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.555   1.546  -1.271  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.678   0.337  -0.338  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.919   0.547   0.789  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.449   0.447   0.675  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.258   0.649   1.774  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.627   0.547   1.652  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.189   0.245   0.438  1.00  0.00           C  
HETATM   12  O1  UNL     1       4.549   0.145   0.320  1.00  0.00           O  
HETATM   13  C12 UNL     1       5.378   0.350   1.439  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.411   0.038  -0.679  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.029  -0.263  -1.873  1.00  0.00           O  
HETATM   16  C14 UNL     1       3.334  -1.545  -2.331  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.043   0.142  -0.548  1.00  0.00           C  
HETATM   18  O3  UNL     1       0.294  -0.052  -1.598  1.00  0.00           O  
HETATM   19  C16 UNL     1      -1.013   0.036  -1.523  1.00  0.00           C  
HETATM   20  O4  UNL     1      -1.698  -0.158  -2.557  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.549  -1.287   1.630  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.079  -0.075   2.914  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.835   1.750   1.358  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.764  -1.011  -0.236  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.942  -0.972  -1.854  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.122  -1.714  -0.373  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.486   2.052  -0.944  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.591   1.191  -2.306  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.734   2.308  -1.230  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.421   0.780   1.708  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.808   0.891   2.749  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.226   0.716   2.555  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.031  -0.208   2.330  1.00  0.00           H  
HETATM   34  H14 UNL     1       6.416   0.031   1.189  1.00  0.00           H  
HETATM   35  H15 UNL     1       5.389   1.442   1.708  1.00  0.00           H  
HETATM   36  H16 UNL     1       3.086  -2.290  -1.562  1.00  0.00           H  
HETATM   37  H17 UNL     1       2.763  -1.723  -3.290  1.00  0.00           H  
HETATM   38  H18 UNL     1       4.432  -1.593  -2.555  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   23
CONECT    3    4    5    6
CONECT    4   24   25   26
CONECT    5   27   28   29
CONECT    6    7    7   19
CONECT    7    8   30
CONECT    8    9    9   17
CONECT    9   10   31
CONECT   10   11   11   32
CONECT   11   12   14
CONECT   12   13
CONECT   13   33   34   35
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   36   37   38
CONECT   17   18
CONECT   18   19
CONECT   19   20   20
END

HMDB0033921
     RDKit          3D
3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.7532   -0.2564    1.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202    0.7514    1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1654    0.4163   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -0.8980   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5546    1.5461   -1.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6777    0.3368   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    0.5474    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4485    0.4473    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583    0.6489    1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270    0.5469    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.2450    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488    0.1446    0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3778    0.3495    1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111    0.0378   -0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -0.2625   -1.8725 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -1.5446   -2.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426    0.1417   -0.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2936   -0.0522   -1.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    0.0359   -1.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6985   -0.1579   -2.5572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -1.2870    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0785   -0.0750    2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8347    1.7497    1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7638   -1.0110   -0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9420   -0.9719   -1.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1218   -1.7140   -0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861    2.0520   -0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914    1.1906   -2.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    2.3082   -1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210    0.7802    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084    0.8913    2.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    0.7161    2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0308   -0.2083    2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4164    0.0308    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3889    1.4423    1.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857   -2.2901   -1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633   -1.7229   -3.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4322   -1.5931   -2.5550 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  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19  6  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one, 9ci	HMDB
3-(1,1-Dimethylallyl)-7,8-dimethoxycoumarin	HMDB

Chemical Formula

C₁₆H₁₈O₄

Average Molecular Weight

274.3117

Monoisotopic Molecular Weight

274.120509064

IUPAC Name

7,8-dimethoxy-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one

Traditional Name

7,8-dimethoxy-3-(2-methylbut-3-en-2-yl)chromen-2-one

CAS Registry Number

30310-54-4

SMILES

COC1=C(OC)C2=C(C=C1)C=C(C(=O)O2)C(C)(C)C=C

InChI Identifier

InChI=1S/C16H18O4/c1-6-16(2,3)11-9-10-7-8-12(18-4)14(19-5)13(10)20-15(11)17/h6-9H,1H2,2-5H3

InChI Key

YSFZHXKUZLVBRX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033921)

Cellular substructure

Membrane (HMDB: HMDB0033921)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033921)

Source

Exogenous

Food

Food (HMDB: HMDB0033921)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033921)

Not Available

Nutrient (HMDB: HMDB0033921)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	85 - 86 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	20.65 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.72	ALOGPS
logP	3.04	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.1 m³·mol⁻¹	ChemAxon
Polarizability	29.4 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.582	31661259
DarkChem	[M-H]-	162.177	31661259
DeepCCS	[M+H]+	169.735	30932474
DeepCCS	[M-H]-	167.377	30932474
DeepCCS	[M-2H]-	200.701	30932474
DeepCCS	[M+Na]+	175.928	30932474
AllCCS	[M+H]+	161.8	32859911
AllCCS	[M+H-H2O]+	158.1	32859911
AllCCS	[M+NH4]+	165.2	32859911
AllCCS	[M+Na]+	166.2	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	168.0	32859911
AllCCS	[M+HCOO]-	167.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one	COC1=C(OC)C2=C(C=C1)C=C(C(=O)O2)C(C)(C)C=C	2953.2	Standard polar	33892256
3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one	COC1=C(OC)C2=C(C=C1)C=C(C(=O)O2)C(C)(C)C=C	2227.0	Standard non polar	33892256
3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one	COC1=C(OC)C2=C(C=C1)C=C(C(=O)O2)C(C)(C)C=C	2216.8	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 - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6s-1190000000-a567df37d47ad2477dd3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 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 - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 10V, Positive-QTOF	splash10-004i-0090000000-0ce4e3e7154a3672563f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-016r-7090000000-94f55fc8a18ebb424b56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 40V, Positive-QTOF	splash10-014i-9150000000-86ec0023edf8fbeefd81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 10V, Negative-QTOF	splash10-00di-0090000000-d1c644cefb75370bd8a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 20V, Negative-QTOF	splash10-05fr-0190000000-0b776f49650f21d1f6b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 40V, Negative-QTOF	splash10-08g3-2970000000-0f519ea6c5ce34df0f92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 10V, Positive-QTOF	splash10-004i-0090000000-9ba2fc14dec0ffa21c75	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-0002-0090000000-651c091aa1d6d0a4e1db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 40V, Positive-QTOF	splash10-0j4i-3590000000-03c415e5b4a5e7ea0a67	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 10V, Negative-QTOF	splash10-00di-0090000000-b03c805fc5d67115d290	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 20V, Negative-QTOF	splash10-00di-0090000000-70c7c26e59fd742f7335	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one 40V, Negative-QTOF	splash10-004i-2890000000-d78dfc102030e4f96688	2021-09-23	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

FDB012120

KNApSAcK ID

Not Available

Chemspider ID

10294194

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21678648

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1839271

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 3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one (HMDB0033921)

MOL for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

3D MOL for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

3D SDF for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

3D-SDF for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

PDB for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

3D PDB for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

SMILES for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

INCHI for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

Structure for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

3D Structure for HMDB0033921 (3-(1,1-Dimethyl-2-propenyl)-7,8-dimethoxy-2H-1-benzopyran-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra