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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:14:32 UTC

Update Date

2022-03-07 02:56:41 UTC

HMDB ID

HMDB0040670

Secondary Accession Numbers

HMDB40670

Metabolite Identification

Common Name

Acutilobin

Description

Acutilobin belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Acutilobin has been detected, but not quantified in, green vegetables. This could make acutilobin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Acutilobin.

Structure

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

HMDB0040670
     RDKit          3D
Acutilobin
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.9507    1.3344   -1.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1998    0.9524   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2846    0.4772    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6725    0.1329    1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323    0.3060    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397    0.6038   -1.1604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901   -0.1899    0.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -0.3422    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4308    0.4957    1.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7104    0.3319    0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632    1.3311    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8195    1.1650   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7793    2.1697   -0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9490    2.0329   -1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1091    0.8757   -1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1859    0.7135   -2.5414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2075   -0.0733   -1.8992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0747    0.0464   -1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154   -0.9281   -1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334   -0.8004   -0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9734   -1.8367   -0.5690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -1.7599    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333   -2.0582    1.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -2.7800    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9135    1.7344   -2.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6280    0.4842   -2.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2354    2.1751   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2118    1.0617    0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7744   -0.9597    2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823    0.4256    2.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5464    0.7099    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505   -0.0185   -0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430    1.5593    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    0.1089    2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703    2.2163    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5582    3.0380    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6883    2.8217   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2584   -1.8408   -1.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354   -1.7073    2.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -1.7080    1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5624   -3.1760    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247   -2.7746    1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -3.7736    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -2.5765   -0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22  8  1  0
 20 10  1  0
 18 12  2  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 19 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
M  END


  Mrv0541 05061312022D          

 24 26  0  0  0  0            999 V2000
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652    1.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0170    1.7181    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
    4.2868    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
    0.7145   -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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    0.0000    0.0000    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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   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
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  2  0  0  0  0
 11  2  1  0  0  0  0
 11  5  2  0  0  0  0
 12  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 18 11  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  2  0  0  0  0
 21 18  2  0  0  0  0
 22 14  1  0  0  0  0
 22 17  1  0  0  0  0
 23 16  1  0  0  0  0
 23 18  1  0  0  0  0
 24 15  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040670

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(\C)C(=O)OC1CC2=C(OC1(C)C)C=C1OC(=O)C=CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O5/c1-5-11(2)18(21)23-16-9-13-8-12-6-7-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/b11-5-

> <INCHI_KEY>
AGABNGOXUSXQDD-WZUFQYTHSA-N

> <FORMULA>
C19H20O5

> <MOLECULAR_WEIGHT>
328.3591

> <EXACT_MASS>
328.13107375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.232433552334676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,5-dimethyl-13-oxo-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),9,11-tetraen-6-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
3.9453308416666673

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8919257245617835

> <JCHEM_POLAR_SURFACE_AREA>
61.83000000000001

> <JCHEM_REFRACTIVITY>
90.17069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,5-dimethyl-13-oxo-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),9,11-tetraen-6-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040670
     RDKit          3D
Acutilobin
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.9507    1.3344   -1.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1998    0.9524   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2846    0.4772    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6725    0.1329    1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323    0.3060    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397    0.6038   -1.1604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901   -0.1899    0.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -0.3422    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4308    0.4957    1.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7104    0.3319    0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632    1.3311    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8195    1.1650   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7793    2.1697   -0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9490    2.0329   -1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1091    0.8757   -1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1859    0.7135   -2.5414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2075   -0.0733   -1.8992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0747    0.0464   -1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154   -0.9281   -1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334   -0.8004   -0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9734   -1.8367   -0.5690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -1.7599    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333   -2.0582    1.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -2.7800    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9135    1.7344   -2.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6280    0.4842   -2.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2354    2.1751   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2118    1.0617    0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7744   -0.9597    2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823    0.4256    2.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5464    0.7099    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505   -0.0185   -0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430    1.5593    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    0.1089    2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703    2.2163    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5582    3.0380    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6883    2.8217   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2584   -1.8408   -1.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354   -1.7073    2.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -1.7080    1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5624   -3.1760    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247   -2.7746    1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -3.7736    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -2.5765   -0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22  8  1  0
 20 10  1  0
 18 12  2  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 19 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 24 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      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.242   2.208   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.032   3.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   11                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    1   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   17                                                       
CONECT    8   12   13                                                       
CONECT    9   13   16                                                       
CONECT   10   14   15                                                       
CONECT   11    2    5   18                                                  
CONECT   12    6    8   14                                                  
CONECT   13    8    9   15                                                  
CONECT   14   10   12   22                                                  
CONECT   15   10   13   24                                                  
CONECT   16    9   19   23                                                  
CONECT   17    7   20   22                                                  
CONECT   18   11   21   23                                                  
CONECT   19    3    4   16   24                                             
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   14   17                                                       
CONECT   23   16   18                                                       
CONECT   24   15   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0040670
HETATM    1  C1  UNL     1       4.951   1.334  -1.725  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.200   0.952  -0.311  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.285   0.477   0.509  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.673   0.133   1.909  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.932   0.306   0.018  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.640   0.604  -1.160  1.00  0.00           O  
HETATM    7  O2  UNL     1       1.890  -0.190   0.806  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.600  -0.342   0.304  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.431   0.496   1.031  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.710   0.332   0.239  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.663   1.331   0.276  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.820   1.165  -0.449  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.779   2.170  -0.413  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.949   2.033  -1.128  1.00  0.00           C  
HETATM   15  C13 UNL     1      -6.109   0.876  -1.862  1.00  0.00           C  
HETATM   16  O3  UNL     1      -7.186   0.714  -2.541  1.00  0.00           O  
HETATM   17  O4  UNL     1      -5.208  -0.073  -1.899  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.075   0.046  -1.213  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.115  -0.928  -1.233  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.933  -0.800  -0.515  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.973  -1.837  -0.569  1.00  0.00           O  
HETATM   22  C17 UNL     1       0.084  -1.760   0.367  1.00  0.00           C  
HETATM   23  C18 UNL     1      -0.533  -2.058   1.735  1.00  0.00           C  
HETATM   24  C19 UNL     1       1.148  -2.780   0.131  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.913   1.734  -2.138  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.628   0.484  -2.358  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.235   2.175  -1.781  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.212   1.062   0.116  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.774  -0.960   2.039  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.782   0.426   2.538  1.00  0.00           H  
HETATM   31  H7  UNL     1       5.546   0.710   2.253  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.551  -0.019  -0.771  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.143   1.559   1.088  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.651   0.109   2.047  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.470   2.216   0.876  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.558   3.038   0.193  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.688   2.822  -1.092  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.258  -1.841  -1.820  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.135  -1.707   2.558  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.561  -1.708   1.817  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.562  -3.176   1.845  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.825  -2.775   1.013  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.658  -3.774   0.073  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.715  -2.577  -0.801  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   28
CONECT    3    4    5
CONECT    4   29   30   31
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   22   32
CONECT    9   10   33   34
CONECT   10   11   11   20
CONECT   11   12   35
CONECT   12   13   18   18
CONECT   13   14   14   36
CONECT   14   15   37
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19
CONECT   19   20   20   38
CONECT   20   21
CONECT   21   22
CONECT   22   23   24
CONECT   23   39   40   41
CONECT   24   42   43   44
END

HMDB0040670
     RDKit          3D
Acutilobin
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.9507    1.3344   -1.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1998    0.9524   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2846    0.4772    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6725    0.1329    1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323    0.3060    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397    0.6038   -1.1604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901   -0.1899    0.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -0.3422    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4308    0.4957    1.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7104    0.3319    0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632    1.3311    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8195    1.1650   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7793    2.1697   -0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9490    2.0329   -1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1091    0.8757   -1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1859    0.7135   -2.5414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2075   -0.0733   -1.8992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0747    0.0464   -1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154   -0.9281   -1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334   -0.8004   -0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9734   -1.8367   -0.5690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -1.7599    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333   -2.0582    1.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -2.7800    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9135    1.7344   -2.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6280    0.4842   -2.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2354    2.1751   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2118    1.0617    0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7744   -0.9597    2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823    0.4256    2.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5464    0.7099    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505   -0.0185   -0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430    1.5593    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    0.1089    2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703    2.2163    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5582    3.0380    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6883    2.8217   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2584   -1.8408   -1.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354   -1.7073    2.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -1.7080    1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5624   -3.1760    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247   -2.7746    1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -3.7736    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -2.5765   -0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22  8  1  0
 20 10  1  0
 18 12  2  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 19 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Decursinol angelate	HMDB
2,2-Dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl (2Z)-2-methylbut-2-enoic acid	Generator
Decursinol	MeSH
Decursin	MeSH

Chemical Formula

C₁₉H₂₀O₅

Average Molecular Weight

328.3591

Monoisotopic Molecular Weight

328.13107375

IUPAC Name

5,5-dimethyl-13-oxo-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),9,11-tetraen-6-yl (2Z)-2-methylbut-2-enoate

Traditional Name

5,5-dimethyl-13-oxo-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),9,11-tetraen-6-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

130848-06-5

SMILES

C\C=C(\C)C(=O)OC1CC2=C(OC1(C)C)C=C1OC(=O)C=CC1=C2

InChI Identifier

InChI=1S/C19H20O5/c1-5-11(2)18(21)23-16-9-13-8-12-6-7-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/b11-5-

InChI Key

AGABNGOXUSXQDD-WZUFQYTHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Fatty acid ester
Pyran
Fatty acyl
Benzenoid
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	94 - 95 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.28 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	0.0054 g/L	ALOGPS
logP	3.85	ALOGPS
logP	3.95	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.17 m³·mol⁻¹	ChemAxon
Polarizability	35.23 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]+	178.41	31661259
DarkChem	[M-H]-	176.327	31661259
DeepCCS	[M+H]+	175.54	30932474
DeepCCS	[M-H]-	173.182	30932474
DeepCCS	[M-2H]-	207.35	30932474
DeepCCS	[M+Na]+	182.577	30932474
AllCCS	[M+H]+	178.3	32859911
AllCCS	[M+H-H2O]+	175.1	32859911
AllCCS	[M+NH4]+	181.3	32859911
AllCCS	[M+Na]+	182.1	32859911
AllCCS	[M-H]-	183.4	32859911
AllCCS	[M+Na-2H]-	183.0	32859911
AllCCS	[M+HCOO]-	182.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acutilobin	C\C=C(\C)C(=O)OC1CC2=C(OC1(C)C)C=C1OC(=O)C=CC1=C2	3722.5	Standard polar	33892256
Acutilobin	C\C=C(\C)C(=O)OC1CC2=C(OC1(C)C)C=C1OC(=O)C=CC1=C2	2707.6	Standard non polar	33892256
Acutilobin	C\C=C(\C)C(=O)OC1CC2=C(OC1(C)C)C=C1OC(=O)C=CC1=C2	2802.7	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 - Acutilobin GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-9041000000-bea0dde665100dd0d4c7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acutilobin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acutilobin 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 - Acutilobin 10V, Positive-QTOF	splash10-004i-2936000000-b10f7f12d7ecf0d0ce4b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 20V, Positive-QTOF	splash10-056r-5921000000-93942338974ef626d10d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 40V, Positive-QTOF	splash10-0a59-4900000000-85ff534a2a6476b029a7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 10V, Negative-QTOF	splash10-004i-2029000000-d3ebc5733b233de15ebb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 20V, Negative-QTOF	splash10-0kea-9676000000-66c02a5616633154f1b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 40V, Negative-QTOF	splash10-0kbb-9230000000-dfeecaba87a74e2f1d11	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 10V, Positive-QTOF	splash10-004i-0090000000-42ff11c1ee50cd9976b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 20V, Positive-QTOF	splash10-004i-0290000000-72ea2effe3585c03d3ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 40V, Positive-QTOF	splash10-03gr-2590000000-218ce72c43822d117315	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 10V, Negative-QTOF	splash10-0002-9001000000-403bc457fe109d73af9d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 20V, Negative-QTOF	splash10-0002-9000000000-a259ffd02f4671d0241b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acutilobin 40V, Negative-QTOF	splash10-0pb9-9010000000-f5c8ff8115ecb83371f8	2021-09-22	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

FDB020467

KNApSAcK ID

C00054857

Chemspider ID

4525412

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5376051

PDB ID

Not Available

ChEBI ID

141534

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1885301

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 Acutilobin (HMDB0040670)

MOL for HMDB0040670 (Acutilobin)

3D MOL for HMDB0040670 (Acutilobin)

3D SDF for HMDB0040670 (Acutilobin)

3D-SDF for HMDB0040670 (Acutilobin)

PDB for HMDB0040670 (Acutilobin)

3D PDB for HMDB0040670 (Acutilobin)

SMILES for HMDB0040670 (Acutilobin)

INCHI for HMDB0040670 (Acutilobin)

Structure for HMDB0040670 (Acutilobin)

3D Structure for HMDB0040670 (Acutilobin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra