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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:41 UTC

Update Date

2022-03-07 02:52:40 UTC

HMDB ID

HMDB0030729

Secondary Accession Numbers

HMDB30729

Metabolite Identification

Common Name

Gravelliferone

Description

Gravelliferone belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Based on a literature review very few articles have been published on Gravelliferone.

Structure

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

HMDB0030729
     RDKit          3D
Gravelliferone
 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.2997    2.1479   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8463    1.2737    0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2158   -0.0112    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1200   -0.1483   -1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1439   -1.1193    0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355   -0.1650    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -0.3425   -0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084   -0.4770    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6084   -0.6551   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -0.7979    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0269   -0.9680   -0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7258    0.3358   -0.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0006    0.5781   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9694   -0.4938   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5535    1.9610   -0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0096   -0.7578    1.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2633   -0.8998    2.1213 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -0.5769    2.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3404   -0.4415    1.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4091   -0.2717    2.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5940   -0.1398    1.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6299    0.0265    2.6975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7482    3.0661   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2415    1.9841   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9314    1.4900    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455   -1.1816   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1775   -0.1521   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027    0.6313   -1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -1.5105    1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1687   -0.6954    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1472   -1.9627   -0.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439   -0.3740   -1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -0.6884   -1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738   -1.3036   -1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7390   -1.6905   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    1.2162   -1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9271   -0.2505   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.4710    0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6817   -1.4975   -0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055    2.2509    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4478    1.9822   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7986    2.6897   -1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0839   -1.0414    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169   -0.5485    3.4553 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
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 10 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  6  1  0
 19  8  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
M  END


  Mrv0541 05061305282D          

 22 23  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
   -2.1434   -0.4125    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
    3.8743    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
    5.0013    0.4125    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
    0.0000    0.0000    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
    2.8579    0.0000    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    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
    2.1434   -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
    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
    0.0000   -1.6500    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
    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  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  2  0  0  0  0
 16 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  1  0  0  0  0
 19  4  1  0  0  0  0
 19  5  1  0  0  0  0
 19  6  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 18  2  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030729

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O3/c1-6-19(4,5)15-10-14-9-13(8-7-12(2)3)16(20)11-17(14)22-18(15)21/h6-7,9-11,20H,1,8H2,2-5H3

> <INCHI_KEY>
HEPYYVMIJBDNIM-UHFFFAOYSA-N

> <FORMULA>
C19H22O3

> <MOLECULAR_WEIGHT>
298.3762

> <EXACT_MASS>
298.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.14194329348399

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-6-(3-methylbut-2-en-1-yl)-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
5.14

> <JCHEM_LOGP>
4.776127342333333

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.604606799447563

> <JCHEM_PKA_STRONGEST_BASIC>
-7.028705624701476

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
90.39919999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-6-(3-methylbut-2-en-1-yl)-3-(2-methylbut-3-en-2-yl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030729
     RDKit          3D
Gravelliferone
 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.2997    2.1479   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8463    1.2737    0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2158   -0.0112    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1200   -0.1483   -1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1439   -1.1193    0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355   -0.1650    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -0.3425   -0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084   -0.4770    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6084   -0.6551   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -0.7979    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0269   -0.9680   -0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7258    0.3358   -0.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0006    0.5781   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9694   -0.4938   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5535    1.9610   -0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0096   -0.7578    1.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2633   -0.8998    2.1213 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -0.5769    2.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3404   -0.4415    1.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4091   -0.2717    2.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5940   -0.1398    1.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6299    0.0265    2.6975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7482    3.0661   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2415    1.9841   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9314    1.4900    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455   -1.1816   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1775   -0.1521   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027    0.6313   -1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -1.5105    1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1687   -0.6954    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1472   -1.9627   -0.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439   -0.3740   -1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -0.6884   -1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738   -1.3036   -1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7390   -1.6905   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    1.2162   -1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9271   -0.2505   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.4710    0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6817   -1.4975   -0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055    2.2509    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4478    1.9822   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7986    2.6897   -1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0839   -1.0414    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169   -0.5485    3.4553 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
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 10 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  6  1  0
 19  8  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.232   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.772  -1.334   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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   19                                                            
CONECT    5   19                                                            
CONECT    6    1   19                                                       
CONECT    7    8   12                                                       
CONECT    8    7   13                                                       
CONECT    9   13   14                                                       
CONECT   10   14   15                                                       
CONECT   11   16   17                                                       
CONECT   12    2    3    7                                                  
CONECT   13    8    9   16                                                  
CONECT   14    9   10   17                                                  
CONECT   15   10   18   19                                                  
CONECT   16   11   13   20                                                  
CONECT   17   11   14   22                                                  
CONECT   18   15   21   22                                                  
CONECT   19    4    5    6   15                                             
CONECT   20   16                                                            
CONECT   21   18                                                            
CONECT   22   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0030729
HETATM    1  C1  UNL     1      -5.300   2.148  -0.502  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.846   1.274   0.383  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.216  -0.011   0.023  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.120  -0.148  -1.506  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.144  -1.119   0.457  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.835  -0.165   0.605  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.738  -0.343  -0.213  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.508  -0.477   0.405  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.608  -0.655  -0.377  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.888  -0.798   0.192  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.027  -0.968  -0.743  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.726   0.336  -0.860  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.001   0.578  -0.730  1.00  0.00           C  
HETATM   14  C14 UNL     1       5.969  -0.494  -0.432  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.553   1.961  -0.875  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.010  -0.758   1.545  1.00  0.00           C  
HETATM   17  O1  UNL     1       3.263  -0.900   2.121  1.00  0.00           O  
HETATM   18  C17 UNL     1       0.890  -0.577   2.380  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.340  -0.441   1.778  1.00  0.00           C  
HETATM   20  O2  UNL     1      -1.409  -0.272   2.502  1.00  0.00           O  
HETATM   21  C19 UNL     1      -2.594  -0.140   1.960  1.00  0.00           C  
HETATM   22  O3  UNL     1      -3.630   0.027   2.697  1.00  0.00           O  
HETATM   23  H1  UNL     1      -5.748   3.066  -0.150  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.241   1.984  -1.561  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.931   1.490   1.446  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.745  -1.182  -1.676  1.00  0.00           H  
HETATM   27  H5  UNL     1      -5.178  -0.152  -1.863  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.503   0.631  -1.949  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.830  -1.511   1.446  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.169  -0.695   0.538  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.147  -1.963  -0.270  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.844  -0.374  -1.296  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.520  -0.688  -1.449  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.674  -1.304  -1.746  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.739  -1.690  -0.300  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.077   1.216  -1.088  1.00  0.00           H  
HETATM   37  H15 UNL     1       6.927  -0.250  -0.968  1.00  0.00           H  
HETATM   38  H16 UNL     1       6.210  -0.471   0.667  1.00  0.00           H  
HETATM   39  H17 UNL     1       5.682  -1.498  -0.782  1.00  0.00           H  
HETATM   40  H18 UNL     1       5.906   2.251   0.146  1.00  0.00           H  
HETATM   41  H19 UNL     1       6.448   1.982  -1.533  1.00  0.00           H  
HETATM   42  H20 UNL     1       4.799   2.690  -1.200  1.00  0.00           H  
HETATM   43  H21 UNL     1       4.084  -1.041   1.577  1.00  0.00           H  
HETATM   44  H22 UNL     1       1.017  -0.548   3.455  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3   25
CONECT    3    4    5    6
CONECT    4   26   27   28
CONECT    5   29   30   31
CONECT    6    7    7   21
CONECT    7    8   32
CONECT    8    9    9   19
CONECT    9   10   33
CONECT   10   11   16   16
CONECT   11   12   34   35
CONECT   12   13   13   36
CONECT   13   14   15
CONECT   14   37   38   39
CONECT   15   40   41   42
CONECT   16   17   18
CONECT   17   43
CONECT   18   19   19   44
CONECT   19   20
CONECT   20   21
CONECT   21   22   22
END

HMDB0030729
     RDKit          3D
Gravelliferone
 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.2997    2.1479   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8463    1.2737    0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2158   -0.0112    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1200   -0.1483   -1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1439   -1.1193    0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355   -0.1650    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -0.3425   -0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084   -0.4770    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6084   -0.6551   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -0.7979    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0269   -0.9680   -0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7258    0.3358   -0.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0006    0.5781   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9694   -0.4938   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5535    1.9610   -0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0096   -0.7578    1.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2633   -0.8998    2.1213 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -0.5769    2.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3404   -0.4415    1.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4091   -0.2717    2.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5940   -0.1398    1.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6299    0.0265    2.6975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7482    3.0661   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2415    1.9841   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9314    1.4900    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455   -1.1816   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1775   -0.1521   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027    0.6313   -1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -1.5105    1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1687   -0.6954    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1472   -1.9627   -0.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439   -0.3740   -1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -0.6884   -1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738   -1.3036   -1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7390   -1.6905   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    1.2162   -1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9271   -0.2505   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.4710    0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6817   -1.4975   -0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055    2.2509    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4478    1.9822   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7986    2.6897   -1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0839   -1.0414    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169   -0.5485    3.4553 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
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 10 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  6  1  0
 19  8  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(1,1-Dimethyl-2-propenyl)-7-hydroxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9ci	HMDB
3-(1,1-Dimethylallyl)-7-hydroxy-6-(3-methyl-2-butenyl)coumarin, 8ci	HMDB
Gravelliferone methyl ether	HMDB

Chemical Formula

C₁₉H₂₂O₃

Average Molecular Weight

298.3762

Monoisotopic Molecular Weight

298.15689457

IUPAC Name

7-hydroxy-6-(3-methylbut-2-en-1-yl)-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one

Traditional Name

7-hydroxy-6-(3-methylbut-2-en-1-yl)-3-(2-methylbut-3-en-2-yl)chromen-2-one

CAS Registry Number

21316-80-3

SMILES

CC(C)=CCC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O

InChI Identifier

InChI=1S/C19H22O3/c1-6-19(4,5)15-10-14-9-13(8-7-12(2)3)16(20)11-17(14)22-18(15)21/h6-7,9-11,20H,1,8H2,2-5H3

InChI Key

HEPYYVMIJBDNIM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
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: HMDB0030729)

Cellular substructure

Membrane (HMDB: HMDB0030729)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030729)

Source

Endogenous

Endogenous (HMDB: HMDB0030729)

Plant

Plant (HMDB: HMDB0030729)

Exogenous

Food

Food (HMDB: HMDB0030729)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	166 - 168 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.71 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	0.011 g/L	ALOGPS
logP	5.14	ALOGPS
logP	4.78	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.6	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.4 m³·mol⁻¹	ChemAxon
Polarizability	34.14 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]+	173.582	31661259
DarkChem	[M-H]-	174.266	31661259
DeepCCS	[M+H]+	169.484	30932474
DeepCCS	[M-H]-	167.126	30932474
DeepCCS	[M-2H]-	200.715	30932474
DeepCCS	[M+Na]+	175.942	30932474
AllCCS	[M+H]+	170.4	32859911
AllCCS	[M+H-H2O]+	166.9	32859911
AllCCS	[M+NH4]+	173.6	32859911
AllCCS	[M+Na]+	174.5	32859911
AllCCS	[M-H]-	174.9	32859911
AllCCS	[M+Na-2H]-	174.5	32859911
AllCCS	[M+HCOO]-	174.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gravelliferone	CC(C)=CCC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O	3257.8	Standard polar	33892256
Gravelliferone	CC(C)=CCC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O	2478.2	Standard non polar	33892256
Gravelliferone	CC(C)=CCC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O	2580.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gravelliferone,1TMS,isomer #1	C=CC(C)(C)C1=CC2=CC(CC=C(C)C)=C(O[Si](C)(C)C)C=C2OC1=O	2516.1	Semi standard non polar	33892256
Gravelliferone,1TBDMS,isomer #1	C=CC(C)(C)C1=CC2=CC(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O	2771.1	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 - Gravelliferone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0569-2090000000-d84e5fd1eaa2c8cbfb3e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gravelliferone GC-MS (1 TMS) - 70eV, Positive	splash10-0a6r-3009000000-d0397661aae55b32bca1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gravelliferone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gravelliferone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gravelliferone , positive-QTOF	splash10-052f-0590000000-3b2f02a552d98e956845	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gravelliferone , positive-QTOF	splash10-000i-1902000000-2de68ea3469d131f254b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 10V, Positive-QTOF	splash10-0002-0090000000-20fc3ac195511a0b396f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 20V, Positive-QTOF	splash10-015d-3090000000-9b0db5399e2e22702eac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 40V, Positive-QTOF	splash10-014i-9240000000-fa228275309a74e9166e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 10V, Negative-QTOF	splash10-0002-0090000000-2468ce82ac20b5a990ad	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 20V, Negative-QTOF	splash10-0002-0190000000-29c3cfcb98b50c664d4f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 40V, Negative-QTOF	splash10-05nr-7980000000-56e920be926feb1aa30a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 10V, Positive-QTOF	splash10-0005-0090000000-6b3a08e1facdccdc945a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 20V, Positive-QTOF	splash10-014j-0190000000-06c381e4ea4fa95222fc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 40V, Positive-QTOF	splash10-0gbd-3390000000-43e586456c0944499df7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 10V, Negative-QTOF	splash10-0002-0090000000-79d5bf1412a00d5e8553	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 20V, Negative-QTOF	splash10-0002-0190000000-480640f7e7c6fa5ca566	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gravelliferone 40V, Negative-QTOF	splash10-0jdi-0590000000-6ae0fb700abbc4163927	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

FDB002655

KNApSAcK ID

Not Available

Chemspider ID

21615441

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14133589

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1822311

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Gravelliferone → 3,4,5-trihydroxy-6-{[6-(3-methylbut-2-en-1-yl)-3-(2-methylbut-3-en-2-yl)-2-oxo-2H-chromen-7-yl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for Gravelliferone (HMDB0030729)

MOL for HMDB0030729 (Gravelliferone)

3D MOL for HMDB0030729 (Gravelliferone)

3D SDF for HMDB0030729 (Gravelliferone)

3D-SDF for HMDB0030729 (Gravelliferone)

PDB for HMDB0030729 (Gravelliferone)

3D PDB for HMDB0030729 (Gravelliferone)

SMILES for HMDB0030729 (Gravelliferone)

INCHI for HMDB0030729 (Gravelliferone)

Structure for HMDB0030729 (Gravelliferone)

3D Structure for HMDB0030729 (Gravelliferone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions