Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 18:30:11 UTC

Update Date

2021-09-23 18:30:11 UTC

HMDB ID

HMDB0302533

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Heraclenin

Description

Heraclenin is a member of the class of compounds known as psoralens. Psoralens are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Heraclenin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Heraclenin can be found in carrot, lemon, and wild carrot, which makes heraclenin a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302533
     RDKit          3D
Heraclenin
 35 38  0  0  0  0  0  0  0  0999 V2000
    5.1336    0.2142    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170   -0.2476    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084   -1.5177    1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236   -0.1985   -1.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164    0.7331   -0.1239 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3293    0.6231    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425    0.6475   -0.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9934    0.5544   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988    1.7063   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779    2.9712   -0.0192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940    3.7331    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949    2.9230    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0551    1.6448    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    0.4396    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877   -0.7272    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725   -1.9066    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9774   -3.0812    0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6413   -2.9520   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227   -4.0371   -0.5360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315   -1.7973   -0.3979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6534   -0.6501   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7951   -0.0307   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5095   -0.2686    1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552    1.3089    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559   -1.9100    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834   -2.2911    0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325   -1.4397    2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161    1.7694   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502    1.5201    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439   -0.2593    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3890    4.8224    0.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692    3.2782    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7519    0.4168    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7278   -1.9447    0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753   -4.0469    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  5  2  1  0
 21  8  1  0
 13  9  1  0
 21 15  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  6
  6 29  1  0
  6 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
M  END


  Mrv0541 02241221202D          

 21 24  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 O   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
    1.4289    0.0000    0.0000 O   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
    2.8579    0.8250    0.0000 O   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    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7309    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046    3.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3778    2.7051    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
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    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
    2.8579   -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
    1.4289   -1.6500    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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  5 13  2  0  0  0  0
 13 14  1  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
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  4 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302533

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)O[C@H]1COC1=C2OC=CC2=CC2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-16(2)11(21-16)8-19-15-13-10(5-6-18-13)7-9-3-4-12(17)20-14(9)15/h3-7,11H,8H2,1-2H3/t11-/m0/s1

> <INCHI_KEY>
CTJZWFCPUDPLME-NSHDSACASA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.03452402439358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.323230061666666

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3921706521845603

> <JCHEM_POLAR_SURFACE_AREA>
61.2

> <JCHEM_REFRACTIVITY>
74.65459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302533
     RDKit          3D
Heraclenin
 35 38  0  0  0  0  0  0  0  0999 V2000
    5.1336    0.2142    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170   -0.2476    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084   -1.5177    1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236   -0.1985   -1.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164    0.7331   -0.1239 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3293    0.6231    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425    0.6475   -0.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9934    0.5544   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988    1.7063   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779    2.9712   -0.0192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940    3.7331    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949    2.9230    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0551    1.6448    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    0.4396    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877   -0.7272    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725   -1.9066    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9774   -3.0812    0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6413   -2.9520   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227   -4.0371   -0.5360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315   -1.7973   -0.3979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6534   -0.6501   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7951   -0.0307   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5095   -0.2686    1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552    1.3089    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559   -1.9100    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834   -2.2911    0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325   -1.4397    2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161    1.7694   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502    1.5201    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439   -0.2593    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3890    4.8224    0.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692    3.2782    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7519    0.4168    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7278   -1.9447    0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753   -4.0469    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  5  2  1  0
 21  8  1  0
 13  9  1  0
 21 15  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  6
  6 29  1  0
  6 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  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       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   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  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.231   5.184   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.771   5.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.422   6.579   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.305   5.050   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   10                                                       
CONECT   10    9    8   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    4   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0302533
HETATM    1  C1  UNL     1       5.134   0.214   0.552  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.717  -0.248   0.325  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.308  -1.518   1.035  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.224  -0.199  -1.002  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.716   0.733  -0.124  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.329   0.623   0.408  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.342   0.647  -0.604  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.993   0.554  -0.265  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.699   1.706  -0.013  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.378   2.971  -0.019  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.394   3.733   0.289  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.495   2.923   0.524  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.055   1.645   0.333  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.699   0.440   0.426  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.988  -0.727   0.172  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.673  -1.907   0.277  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.977  -3.081   0.026  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.641  -2.952  -0.311  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.023  -4.037  -0.536  1.00  0.00           O  
HETATM   20  O5  UNL     1      -1.031  -1.797  -0.398  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.653  -0.650  -0.168  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.795  -0.031  -0.303  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.510  -0.269   1.467  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.155   1.309   0.738  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.356  -1.910   0.624  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.083  -2.291   0.760  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.333  -1.440   2.126  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.116   1.769  -0.309  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.150   1.520   1.062  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.244  -0.259   1.072  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.389   4.822   0.354  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.469   3.278   0.797  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.752   0.417   0.696  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.728  -1.945   0.547  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.475  -4.047   0.096  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    5
CONECT    3   25   26   27
CONECT    4    5
CONECT    5    6   28
CONECT    6    7   29   30
CONECT    7    8
CONECT    8    9    9   21
CONECT    9   10   13
CONECT   10   11
CONECT   11   12   12   31
CONECT   12   13   32
CONECT   13   14   14
CONECT   14   15   33
CONECT   15   16   21   21
CONECT   16   17   17   34
CONECT   17   18   35
CONECT   18   19   19   20
CONECT   20   21
END

HMDB0302533
     RDKit          3D
Heraclenin
 35 38  0  0  0  0  0  0  0  0999 V2000
    5.1336    0.2142    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170   -0.2476    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084   -1.5177    1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236   -0.1985   -1.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164    0.7331   -0.1239 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3293    0.6231    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425    0.6475   -0.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9934    0.5544   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988    1.7063   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779    2.9712   -0.0192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940    3.7331    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949    2.9230    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0551    1.6448    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    0.4396    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877   -0.7272    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725   -1.9066    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9774   -3.0812    0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6413   -2.9520   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227   -4.0371   -0.5360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315   -1.7973   -0.3979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6534   -0.6501   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7951   -0.0307   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5095   -0.2686    1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552    1.3089    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559   -1.9100    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834   -2.2911    0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325   -1.4397    2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161    1.7694   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502    1.5201    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439   -0.2593    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3890    4.8224    0.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692    3.2782    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7519    0.4168    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7278   -1.9447    0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753   -4.0469    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  5  2  1  0
 21  8  1  0
 13  9  1  0
 21 15  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  6
  6 29  1  0
  6 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

9-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC1(C)O[C@H]1COC1=C2OC=CC2=CC2=C1OC(=O)C=C2

InChI Identifier

InChI=1S/C16H14O5/c1-16(2)11(21-16)8-19-15-13-10(5-6-18-13)7-9-3-4-12(17)20-14(9)15/h3-7,11H,8H2,1-2H3/t11-/m0/s1

InChI Key

CTJZWFCPUDPLME-NSHDSACASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Benzopyran
1-benzopyran
Benzofuran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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

Fruit

Citrus

Lemon (FooDB: FOOD00054)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

anticoagulant (HMDB: HMDB0302533)

Biological role

anti inflammatory (HMDB: HMDB0302533)

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	2.78	ALOGPS
logP	2.32	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.65 m³·mol⁻¹	ChemAxon
Polarizability	29.03 Å³	ChemAxon
Number of Rings	4	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
AllCCS	[M+H]+	164.154	32859911
AllCCS	[M+H-H2O]+	160.472	32859911
AllCCS	[M+Na]+	168.557	32859911
AllCCS	[M+NH4]+	167.573	32859911
AllCCS	[M-H]-	170.085	32859911
AllCCS	[M+Na-2H]-	169.285	32859911
AllCCS	[M+HCOO]-	168.534	32859911
DeepCCS	[M+H]+	163.295	30932474
DeepCCS	[M-H]-	160.937	30932474
DeepCCS	[M-2H]-	193.899	30932474
DeepCCS	[M+Na]+	169.388	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 10V, Positive-QTOF	splash10-000i-1090000000-f2b8b263f1878c0e4956	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 20V, Positive-QTOF	splash10-000i-5090000000-dc004f4a68076cd91783	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 40V, Positive-QTOF	splash10-0udr-7890000000-67d0547f6870d524a051	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 10V, Negative-QTOF	splash10-0f79-0090000000-91150f41df4c4d3a91db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 20V, Negative-QTOF	splash10-0udi-0390000000-dcf03410d711e8dbb428	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 40V, Negative-QTOF	splash10-0a4i-0910000000-640a73d2e70f3ef22775	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 10V, Positive-QTOF	splash10-0udr-0090000000-76d787fb1f8e47a752eb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 20V, Positive-QTOF	splash10-0udr-1090000000-1934514aff6810e56f24	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 40V, Positive-QTOF	splash10-0zi1-3960000000-035ad490698f9b50beb7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 10V, Negative-QTOF	splash10-000i-0090000000-968438c85a381522a87d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 20V, Negative-QTOF	splash10-0f79-0290000000-9237c409253e778aa100	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heraclenin 40V, Negative-QTOF	splash10-0udi-0490000000-1b59cad6b4fc3d04c6f1	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB005034

KNApSAcK ID

Not Available

Chemspider ID

16905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17897

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

Not Available

Showing metabocard for Heraclenin (HMDB0302533)

MOL for HMDB0302533 (Heraclenin)

3D MOL for HMDB0302533 (Heraclenin)

3D SDF for HMDB0302533 (Heraclenin)

3D-SDF for HMDB0302533 (Heraclenin)

PDB for HMDB0302533 (Heraclenin)

3D PDB for HMDB0302533 (Heraclenin)

SMILES for HMDB0302533 (Heraclenin)

INCHI for HMDB0302533 (Heraclenin)

Structure for HMDB0302533 (Heraclenin)

3D Structure for HMDB0302533 (Heraclenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra