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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-23 07:03:32 UTC

Update Date

2022-09-22 18:34:59 UTC

HMDB ID

HMDB0302150

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Osthol

Description

Osthol, also known as 7-methoxy-8-(3-methylpent-2-enyl)coumarin, belongs to coumarins and derivatives class of compounds. Those are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Osthol is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Osthol can be found in a number of food items such as wild celery, lemon, parsley, and wild carrot, which makes osthol a potential biomarker for the consumption of these food products. Osthol is an O-methylated coumarin. It is a calcium channel blocker, found in plants such as Cnidium monnieri, Angelica archangelica and Angelica pubescens .

Structure

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

HMDB0302150
     RDKit          3D
Osthol
 34 35  0  0  0  0  0  0  0  0999 V2000
    0.0363    3.3075    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    2.0278    0.0493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725    1.1045    0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204    1.4741    0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0290    0.5404    0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127   -0.7353    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8437   -1.6533    0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -2.9137   -0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084   -3.2089   -0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349   -4.3584   -1.4459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892   -2.2803   -0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.0692   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5274   -0.1520   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8348   -0.5297   -0.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854   -0.7904    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104   -0.1159    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -0.4043    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3563    0.9536   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003    3.9718    0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394    3.7467    0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116    3.2816    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880    2.4748    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087    0.8321    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8287   -1.3991    0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3611   -3.6716   -0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479    0.2762   -1.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7118   -1.4405   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -1.5565    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7954   -0.8532    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4360   -1.1325    2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1578    0.5533    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0776    0.7671   -1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550    1.9222   -0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4686    1.0310   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13  3  1  0
 12  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
M  END


  Mrv0541 02241215262D          

 18 19  0  0  0  0            999 V2000
    1.0308    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3716   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.4433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3716   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5158    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5158    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    2.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  0  0  0  0
  2  3  2  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302150

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C=CC(=O)OC2=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3

> <INCHI_KEY>
MBRLOUHOWLUMFF-UHFFFAOYSA-N

> <FORMULA>
C15H16O3

> <MOLECULAR_WEIGHT>
244.2857

> <EXACT_MASS>
244.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.33844022351429

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.3542553490000007

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8409774360376465

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
72.2546

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
osthole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302150
     RDKit          3D
Osthol
 34 35  0  0  0  0  0  0  0  0999 V2000
    0.0363    3.3075    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    2.0278    0.0493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725    1.1045    0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204    1.4741    0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0290    0.5404    0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127   -0.7353    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8437   -1.6533    0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -2.9137   -0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084   -3.2089   -0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349   -4.3584   -1.4459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892   -2.2803   -0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.0692   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5274   -0.1520   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8348   -0.5297   -0.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854   -0.7904    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104   -0.1159    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -0.4043    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3563    0.9536   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003    3.9718    0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394    3.7467    0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116    3.2816    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880    2.4748    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087    0.8321    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8287   -1.3991    0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3611   -3.6716   -0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479    0.2762   -1.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7118   -1.4405   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -1.5565    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7954   -0.8532    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4360   -1.1325    2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1578    0.5533    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0776    0.7671   -1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550    1.9222   -0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4686    1.0310   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13  3  1  0
 12  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.924   1.924   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.924   0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.694  -0.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.692   0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.078  -0.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.696  -0.384   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.310   0.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.310   1.924   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.692  -4.234   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.692  -2.694   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.694  -1.924   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.924  -2.694   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.310  -1.924   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.310  -0.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.696   0.384   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.696   1.924   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.310   2.694   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.310   4.234   0.000  0.00  0.00           O+0
CONECT    1    2   17                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    7                                                       
CONECT    6    7                                                            
CONECT    7    5    6    8                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11                                                       
CONECT   11    3   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    2   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17    1   16   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0302150
HETATM    1  C1  UNL     1       0.036   3.308   0.549  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.252   2.028   0.049  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.772   1.104   0.040  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.020   1.474   0.536  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.029   0.540   0.517  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.813  -0.735   0.018  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.844  -1.653   0.012  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.570  -2.914  -0.499  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.308  -3.209  -0.973  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.035  -4.358  -1.446  1.00  0.00           O  
HETATM   11  O3  UNL     1      -1.389  -2.280  -0.930  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.556  -1.069  -0.468  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.527  -0.152  -0.461  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.835  -0.530  -0.987  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.785  -0.790   0.091  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.910  -0.116   0.195  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.883  -0.404   1.326  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.356   0.954  -0.733  1.00  0.00           C  
HETATM   19  H1  UNL     1       0.900   3.972   0.348  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.839   3.747   0.032  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.212   3.282   1.633  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.188   2.475   0.927  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.009   0.832   0.907  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.829  -1.399   0.390  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.361  -3.672  -0.522  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.148   0.276  -1.662  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.712  -1.440  -1.628  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.592  -1.557   0.848  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.795  -0.853   0.914  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.436  -1.132   2.029  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.158   0.553   1.807  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.078   0.767  -1.794  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.955   1.922  -0.353  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.469   1.031  -0.712  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   22
CONECT    5    6    6   23
CONECT    6    7   12
CONECT    7    8    8   24
CONECT    8    9   25
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   26   27
CONECT   15   16   16   28
CONECT   16   17   18
CONECT   17   29   30   31
CONECT   18   32   33   34
END

HMDB0302150
     RDKit          3D
Osthol
 34 35  0  0  0  0  0  0  0  0999 V2000
    0.0363    3.3075    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    2.0278    0.0493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725    1.1045    0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204    1.4741    0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0290    0.5404    0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127   -0.7353    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8437   -1.6533    0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -2.9137   -0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084   -3.2089   -0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349   -4.3584   -1.4459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892   -2.2803   -0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.0692   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5274   -0.1520   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8348   -0.5297   -0.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854   -0.7904    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104   -0.1159    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -0.4043    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3563    0.9536   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003    3.9718    0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394    3.7467    0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116    3.2816    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880    2.4748    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087    0.8321    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8287   -1.3991    0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3611   -3.6716   -0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479    0.2762   -1.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7118   -1.4405   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -1.5565    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7954   -0.8532    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4360   -1.1325    2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1578    0.5533    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0776    0.7671   -1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550    1.9222   -0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4686    1.0310   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13  3  1  0
 12  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Methoxy-8-(3-methylpent-2-enyl)coumarin	MeSH
Osthol	MeSH

Chemical Formula

C₁₅H₁₆O₃

Average Molecular Weight

244.2857

Monoisotopic Molecular Weight

244.109944378

IUPAC Name

7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Traditional Name

osthole

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=CC(=O)OC2=C1CC=C(C)C

InChI Identifier

InChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3

InChI Key

MBRLOUHOWLUMFF-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coumarins (CHEBI:69832 )
botanical anti-fungal agent (CHEBI:69832 )
coumarins (C09280 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302150)

Food

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Dill (FooDB: FOOD00013)
Parsley (FooDB: FOOD00131)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Process

Not Available

Role

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	3.41	ALOGPS
logP	3.35	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.25 m³·mol⁻¹	ChemAxon
Polarizability	26.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	153.224	32859911
AllCCS	[M+H-H2O]+	149.218	32859911
AllCCS	[M+Na]+	158.024	32859911
AllCCS	[M+NH4]+	156.95	32859911
AllCCS	[M-H]-	157.689	32859911
AllCCS	[M+Na-2H]-	157.345	32859911
AllCCS	[M+HCOO]-	157.085	32859911
DeepCCS	[M+H]+	156.691	30932474
DeepCCS	[M-H]-	154.295	30932474
DeepCCS	[M-2H]-	187.285	30932474
DeepCCS	[M+Na]+	162.618	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	16.7098 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1773.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	334.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	170.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	193.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	83.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	475.5 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	481.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	953.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	406.3 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	1240.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	301.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	335.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	333.0 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
MS	Mass Spectrum (Electron Ionization)	splash10-0f9l-3970000000-4f98b2489c4119cf70b6	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 10V, Positive-QTOF	splash10-0002-0090000000-2fc5799b180de518e4ef	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 20V, Positive-QTOF	splash10-00kb-3190000000-257f4ccd908ffa56c6c1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 40V, Positive-QTOF	splash10-0gb9-9820000000-11f5c9b9fcef5d41d09d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 10V, Negative-QTOF	splash10-0006-0190000000-a4fb35683e1aa8dd5101	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 20V, Negative-QTOF	splash10-0006-0490000000-81e15af3a3d9a535f2e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 40V, Negative-QTOF	splash10-001i-1920000000-570d40b95f6d7db0366f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 10V, Positive-QTOF	splash10-000j-0970000000-56ccbf122c5f7c9f4d8a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 20V, Positive-QTOF	splash10-000i-0910000000-9884c3353133eaaf2dd0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 40V, Positive-QTOF	splash10-0fi3-9620000000-5f4ce0cf72069169ff7d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 10V, Negative-QTOF	splash10-0006-0090000000-204ca24ee8ee58d6cd7a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 20V, Negative-QTOF	splash10-01r6-0390000000-1cad35d7e2037c07eb0c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthol 40V, Negative-QTOF	splash10-00e9-0900000000-8b8323aa5449829b6278	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10228

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1046251

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Osthol (HMDB0302150)

MOL for HMDB0302150 (Osthol)

3D MOL for HMDB0302150 (Osthol)

3D SDF for HMDB0302150 (Osthol)

3D-SDF for HMDB0302150 (Osthol)

PDB for HMDB0302150 (Osthol)

3D PDB for HMDB0302150 (Osthol)

SMILES for HMDB0302150 (Osthol)

INCHI for HMDB0302150 (Osthol)

Structure for HMDB0302150 (Osthol)

3D Structure for HMDB0302150 (Osthol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra