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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:04:56 UTC

Update Date

2021-09-26 23:02:39 UTC

HMDB ID

HMDB0250925

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Decursinol angelate

Description

2,2-dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoate 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. Based on a literature review very few articles have been published on 2,2-dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Decursinol angelate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Decursinol angelate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0250925
     RDKit          3D
Decursinol angelate
 44 46  0  0  0  0  0  0  0  0999 V2000
    3.8897   -0.1921    2.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -1.0579    1.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1467   -1.5124    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9597   -2.3653   -0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7871   -1.1854   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797   -1.6222   -1.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -0.3897    0.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -0.1017   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3946   -0.5843    0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7319   -0.0911    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8697   -0.8311    0.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122   -0.3588    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2678   -1.0798    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693   -0.5417    0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5296    0.6680   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6706    1.0933   -0.6221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4293    1.3224   -0.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510    0.8419   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511    1.5818   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9027    1.1031   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791    1.8488   -0.3983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5389    1.3912   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2449    1.6698   -1.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2148    2.1910    0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038   -0.7511    2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5265   -0.0136    2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687    0.7672    1.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807   -1.3336    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9653   -1.8902   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800   -3.3524   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973   -2.5742   -1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -0.6062   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1310   -0.3330    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -1.6926    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7852   -1.7814    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1546   -2.0115    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3861   -1.0790    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    2.5359   -0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6384    1.2330   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    2.7602   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2395    1.1614   -1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192    3.1565    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658    2.3640    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2498    1.6426    1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  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 04121520452D          

 24 26  0  0  0  0            999 V2000
   -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
   -0.7145   -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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918   -3.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044   -2.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250925

> <DATABASE_NAME>
hmdb

> <SMILES>
CC=C(C)C(=O)OC1CC2=CC3=C(OC(=O)C=C3)C=C2OC1(C)C

> <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

> <INCHI_KEY>
AGABNGOXUSXQDD-UHFFFAOYSA-N

> <FORMULA>
C19H20O5

> <MOLECULAR_WEIGHT>
328.364

> <EXACT_MASS>
328.131073744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.305984557512694

> <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(10),2,8,11-tetraen-6-yl 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>
90.17070000000001

> <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(10),2,8,11-tetraen-6-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250925
     RDKit          3D
Decursinol angelate
 44 46  0  0  0  0  0  0  0  0999 V2000
    3.8897   -0.1921    2.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -1.0579    1.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1467   -1.5124    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9597   -2.3653   -0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7871   -1.1854   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797   -1.6222   -1.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -0.3897    0.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -0.1017   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3946   -0.5843    0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7319   -0.0911    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8697   -0.8311    0.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122   -0.3588    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2678   -1.0798    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693   -0.5417    0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5296    0.6680   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6706    1.0933   -0.6221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4293    1.3224   -0.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510    0.8419   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511    1.5818   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9027    1.1031   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791    1.8488   -0.3983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5389    1.3912   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2449    1.6698   -1.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2148    2.1910    0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038   -0.7511    2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5265   -0.0136    2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687    0.7672    1.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807   -1.3336    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9653   -1.8902   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800   -3.3524   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973   -2.5742   -1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -0.6062   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1310   -0.3330    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -1.6926    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7852   -1.7814    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1546   -2.0115    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3861   -1.0790    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    2.5359   -0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6384    1.2330   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    2.7602   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2395    1.1614   -1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192    3.1565    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658    2.3640    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2498    1.6426    1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  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                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.851  -5.926   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.128  -4.674   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   10   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    8   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0250925
HETATM    1  C1  UNL     1       3.890  -0.192   2.068  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.657  -1.058   1.128  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.147  -1.512   0.007  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.960  -2.365  -0.879  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.787  -1.185  -0.377  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.280  -1.622  -1.466  1.00  0.00           O  
HETATM    7  O2  UNL     1       1.939  -0.390   0.384  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.618  -0.102  -0.039  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.395  -0.584   0.954  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.732  -0.091   0.564  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.870  -0.831   0.860  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.112  -0.359   0.491  1.00  0.00           C  
HETATM   13  C11 UNL     1      -5.268  -1.080   0.775  1.00  0.00           C  
HETATM   14  C12 UNL     1      -6.469  -0.542   0.373  1.00  0.00           C  
HETATM   15  C13 UNL     1      -6.530   0.668  -0.287  1.00  0.00           C  
HETATM   16  O3  UNL     1      -7.671   1.093  -0.622  1.00  0.00           O  
HETATM   17  O4  UNL     1      -5.429   1.322  -0.540  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.251   0.842  -0.172  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.151   1.582  -0.472  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.903   1.103  -0.098  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.779   1.849  -0.398  1.00  0.00           O  
HETATM   22  C17 UNL     1       0.539   1.391  -0.269  1.00  0.00           C  
HETATM   23  C18 UNL     1       1.245   1.670  -1.582  1.00  0.00           C  
HETATM   24  C19 UNL     1       1.215   2.191   0.801  1.00  0.00           C  
HETATM   25  H1  UNL     1       3.004  -0.751   2.430  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.527  -0.014   2.954  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.669   0.767   1.603  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.681  -1.334   1.366  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.965  -1.890  -0.966  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.080  -3.352  -0.345  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.497  -2.574  -1.843  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.437  -0.606  -1.016  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.131  -0.333   1.996  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.417  -1.693   0.897  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.785  -1.781   1.383  1.00  0.00           H  
HETATM   36  H12 UNL     1      -5.155  -2.012   1.290  1.00  0.00           H  
HETATM   37  H13 UNL     1      -7.386  -1.079   0.580  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.210   2.536  -0.993  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.638   1.233  -2.392  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.396   2.760  -1.720  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.239   1.161  -1.593  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.719   3.156   1.009  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.266   2.364   0.492  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.250   1.643   1.767  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

HMDB0250925
     RDKit          3D
Decursinol angelate
 44 46  0  0  0  0  0  0  0  0999 V2000
    3.8897   -0.1921    2.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -1.0579    1.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1467   -1.5124    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9597   -2.3653   -0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7871   -1.1854   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797   -1.6222   -1.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -0.3897    0.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -0.1017   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3946   -0.5843    0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7319   -0.0911    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8697   -0.8311    0.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122   -0.3588    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2678   -1.0798    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693   -0.5417    0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5296    0.6680   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6706    1.0933   -0.6221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4293    1.3224   -0.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510    0.8419   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511    1.5818   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9027    1.1031   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791    1.8488   -0.3983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5389    1.3912   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2449    1.6698   -1.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2148    2.1910    0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038   -0.7511    2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5265   -0.0136    2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687    0.7672    1.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807   -1.3336    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9653   -1.8902   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800   -3.3524   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973   -2.5742   -1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -0.6062   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1310   -0.3330    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -1.6926    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7852   -1.7814    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1546   -2.0115    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3861   -1.0790    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    2.5359   -0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6384    1.2330   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    2.7602   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2395    1.1614   -1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192    3.1565    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658    2.3640    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2498    1.6426    1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  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
2,2-Dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₁₉H₂₀O₅

Average Molecular Weight

328.364

Monoisotopic Molecular Weight

328.131073744

IUPAC Name

5,5-dimethyl-13-oxo-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-6-yl 2-methylbut-2-enoate

Traditional Name

5,5-dimethyl-13-oxo-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-6-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1CC2=CC3=C(OC(=O)C=C3)C=C2OC1(C)C

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

InChI Key

AGABNGOXUSXQDD-UHFFFAOYSA-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

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	35.31 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
DeepCCS	[M+H]+	181.557	30932474
DeepCCS	[M-H]-	179.199	30932474
DeepCCS	[M-2H]-	213.462	30932474
DeepCCS	[M+Na]+	188.701	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.7704 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.59 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2497.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	395.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	626.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	632.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1253.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	556.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1521.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	387.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	286.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Decursinol angelate	CC=C(C)C(=O)OC1CC2=CC3=C(OC(=O)C=C3)C=C2OC1(C)C	3722.5	Standard polar	33892256
Decursinol angelate	CC=C(C)C(=O)OC1CC2=CC3=C(OC(=O)C=C3)C=C2OC1(C)C	2707.4	Standard non polar	33892256
Decursinol angelate	CC=C(C)C(=O)OC1CC2=CC3=C(OC(=O)C=C3)C=C2OC1(C)C	2802.9	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 - Decursinol angelate GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-9031000000-8d52df8e34794b417d96	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Decursinol angelate 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 - Decursinol angelate 10V, Positive-QTOF	splash10-004j-0091000000-d4f892c989b57bf9438c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Decursinol angelate 20V, Positive-QTOF	splash10-004i-0190000000-77b5cc0cb43e81e263cb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Decursinol angelate 40V, Positive-QTOF	splash10-0cgi-1390000000-e43201bb1413b5028aec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Decursinol angelate 10V, Negative-QTOF	splash10-0002-9002000000-3148a0488984da4b6b15	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Decursinol angelate 20V, Negative-QTOF	splash10-0002-9020000000-224c99af45541f51bca3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Decursinol angelate 40V, Negative-QTOF	splash10-0pb9-9010000000-1cb44d6213a18c8bcefb	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

531592

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

611538

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Decursinol angelate (HMDB0250925)

MOL for HMDB0250925 (Decursinol angelate)

3D MOL for HMDB0250925 (Decursinol angelate)

3D SDF for HMDB0250925 (Decursinol angelate)

3D-SDF for HMDB0250925 (Decursinol angelate)

PDB for HMDB0250925 (Decursinol angelate)

3D PDB for HMDB0250925 (Decursinol angelate)

SMILES for HMDB0250925 (Decursinol angelate)

INCHI for HMDB0250925 (Decursinol angelate)

Structure for HMDB0250925 (Decursinol angelate)

3D Structure for HMDB0250925 (Decursinol angelate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra