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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:47 UTC

Update Date

2022-03-07 02:52:40 UTC

HMDB ID

HMDB0030745

Secondary Accession Numbers

HMDB30745

Metabolite Identification

Common Name

(R)-Heraclenol

Description

(R)-Heraclenol 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 (R)-Heraclenol has been detected, but not quantified in, herbs and spices. This could make (R)-heraclenol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Heraclenol.

Structure

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

HMDB0030745
     RDKit          3D
(R)-Heraclenol
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.8208    1.5218   -0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519    0.1103    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946   -0.5902   -1.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0108   -0.4870    1.0804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    0.3018    0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9338    1.1181    1.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1951   -0.9910    0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -0.7895    1.4944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1755   -0.2537    0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923    1.0841    0.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369    2.1304    1.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6037    3.2328    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    2.9277    0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6386    1.5713    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4757    0.7357   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654   -0.6259   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047   -1.4724   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6841   -2.7940   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5275   -3.2083   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2704   -4.4451   -0.6012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7634   -2.3600    0.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295   -1.0791    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101    2.2152    0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6195    1.8459   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8948    1.5154    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7320    0.0521   -2.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778   -0.8785   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -1.4975   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1615   -1.4591    0.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005    0.7631   -0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607    0.6348    2.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570   -1.7114    0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353   -1.5450    1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3898    4.2435    1.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    3.5995    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772    1.1072   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -1.0380   -1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3153   -3.4852   -1.7078 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
  2  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22  9  1  0
 14 10  1  0
 22 16  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
M  END


  Mrv0541 05061305282D          

 22 24  0  0  0  0            999 V2000
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 C   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
    2.8579    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -4.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 11  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 16  1  0  0  0  0
 20  6  1  0  0  0  0
 20 13  1  0  0  0  0
 21  8  1  0  0  0  0
 21 15  1  0  0  0  0
 22 12  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030745

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(O)C(O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-16(2,19)11(17)8-21-15-13-10(5-6-20-13)7-9-3-4-12(18)22-14(9)15/h3-7,11,17,19H,8H2,1-2H3

> <INCHI_KEY>
FOINLJRVEBYARJ-UHFFFAOYSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.2946

> <EXACT_MASS>
304.094688244

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.49664720061971

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(2,3-dihydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.161526489333333

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.118688122121622

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.196270602008596

> <JCHEM_PKA_STRONGEST_BASIC>
-3.121923440699545

> <JCHEM_POLAR_SURFACE_AREA>
89.13000000000001

> <JCHEM_REFRACTIVITY>
78.16470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(2,3-dihydroxy-3-methylbutoxy)furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030745
     RDKit          3D
(R)-Heraclenol
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.8208    1.5218   -0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519    0.1103    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946   -0.5902   -1.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0108   -0.4870    1.0804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    0.3018    0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9338    1.1181    1.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1951   -0.9910    0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -0.7895    1.4944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1755   -0.2537    0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923    1.0841    0.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369    2.1304    1.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6037    3.2328    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    2.9277    0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6386    1.5713    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4757    0.7357   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654   -0.6259   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047   -1.4724   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6841   -2.7940   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5275   -3.2083   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2704   -4.4451   -0.6012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7634   -2.3600    0.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295   -1.0791    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101    2.2152    0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6195    1.8459   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8948    1.5154    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7320    0.0521   -2.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778   -0.8785   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -1.4975   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1615   -1.4591    0.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005    0.7631   -0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607    0.6348    2.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570   -1.7114    0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353   -1.5450    1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3898    4.2435    1.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    3.5995    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772    1.1072   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -1.0380   -1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3153   -3.4852   -1.7078 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
  2  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22  9  1  0
 14 10  1  0
 22 16  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  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       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.772  -6.366   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.232  -9.034   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3    4    9                                                       
CONECT    4    3   12                                                       
CONECT    5    6   10                                                       
CONECT    6    5   20                                                       
CONECT    7    9   10                                                       
CONECT    8   11   21                                                       
CONECT    9    3    7   14                                                  
CONECT   10    5    7   13                                                  
CONECT   11    8   16   17                                                  
CONECT   12    4   18   22                                                  
CONECT   13   10   15   20                                                  
CONECT   14    9   15   22                                                  
CONECT   15   13   14   21                                                  
CONECT   16    1    2   11   19                                             
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   16                                                            
CONECT   20    6   13                                                       
CONECT   21    8   15                                                       
CONECT   22   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0030745
HETATM    1  C1  UNL     1      -3.821   1.522  -0.096  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.252   0.110   0.093  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.295  -0.590  -1.224  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.011  -0.487   1.080  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.829   0.302   0.611  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.934   1.118   1.735  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.195  -0.991   1.000  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.082  -0.789   1.494  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.176  -0.254   0.908  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.492   1.084   0.968  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.937   2.130   1.524  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.604   3.233   1.318  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.704   2.928   0.561  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.639   1.571   0.338  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.476   0.736  -0.354  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.165  -0.626  -0.423  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.005  -1.472  -1.119  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.684  -2.794  -1.174  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.527  -3.208  -0.523  1.00  0.00           C  
HETATM   20  O5  UNL     1       2.270  -4.445  -0.601  1.00  0.00           O  
HETATM   21  O6  UNL     1       1.763  -2.360   0.126  1.00  0.00           O  
HETATM   22  C16 UNL     1       2.030  -1.079   0.207  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.310   2.215   0.602  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.620   1.846  -1.119  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.895   1.515   0.181  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.732   0.052  -2.016  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.278  -0.878  -1.605  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.926  -1.497  -1.140  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.162  -1.459   0.904  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.200   0.763  -0.179  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.561   0.635   2.356  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.157  -1.711   0.129  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.835  -1.545   1.749  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.390   4.244   1.651  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.492   3.599   0.194  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.377   1.107  -0.852  1.00  0.00           H  
HETATM   37  H15 UNL     1       4.883  -1.038  -1.590  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.315  -3.485  -1.708  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    5
CONECT    3   26   27   28
CONECT    4   29
CONECT    5    6    7   30
CONECT    6   31
CONECT    7    8   32   33
CONECT    8    9
CONECT    9   10   10   22
CONECT   10   11   14
CONECT   11   12
CONECT   12   13   13   34
CONECT   13   14   35
CONECT   14   15   15
CONECT   15   16   36
CONECT   16   17   22   22
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   21
CONECT   21   22
END

HMDB0030745
     RDKit          3D
(R)-Heraclenol
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.8208    1.5218   -0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519    0.1103    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946   -0.5902   -1.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0108   -0.4870    1.0804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    0.3018    0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9338    1.1181    1.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1951   -0.9910    0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -0.7895    1.4944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1755   -0.2537    0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923    1.0841    0.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369    2.1304    1.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6037    3.2328    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    2.9277    0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6386    1.5713    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4757    0.7357   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654   -0.6259   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047   -1.4724   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6841   -2.7940   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5275   -3.2083   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2704   -4.4451   -0.6012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7634   -2.3600    0.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295   -1.0791    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101    2.2152    0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6195    1.8459   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8948    1.5154    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7320    0.0521   -2.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778   -0.8785   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -1.4975   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1615   -1.4591    0.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005    0.7631   -0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607    0.6348    2.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570   -1.7114    0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353   -1.5450    1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3898    4.2435    1.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    3.5995    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772    1.1072   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -1.0380   -1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3153   -3.4852   -1.7078 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
  2  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22  9  1  0
 14 10  1  0
 22 16  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Heraclenol	HMDB

Chemical Formula

C₁₆H₁₆O₆

Average Molecular Weight

304.2946

Monoisotopic Molecular Weight

304.094688244

IUPAC Name

9-(2,3-dihydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-(2,3-dihydroxy-3-methylbutoxy)furo[3,2-g]chromen-7-one

CAS Registry Number

26091-76-9

SMILES

CC(C)(O)C(O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

InChI Identifier

InChI=1S/C16H16O6/c1-16(2,19)11(17)8-21-15-13-10(5-6-20-13)7-9-3-4-12(18)22-14(9)15/h3-7,11,17,19H,8H2,1-2H3

InChI Key

FOINLJRVEBYARJ-UHFFFAOYSA-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
Tertiary alcohol
Furan
1,2-diol
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030745)
Cytoplasm (HMDB: HMDB0030745)

Source

Exogenous

Exogenous (HMDB: HMDB0030745)

Food

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Endogenous (HMDB: HMDB0030745)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	117 - 118 °C	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
Water Solubility	0.29 g/L	ALOGPS
logP	1.82	ALOGPS
logP	1.16	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.2	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.16 m³·mol⁻¹	ChemAxon
Polarizability	30.5 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]+	168.25	31661259
DarkChem	[M-H]-	167.368	31661259
DeepCCS	[M+H]+	166.172	30932474
DeepCCS	[M-H]-	163.814	30932474
DeepCCS	[M-2H]-	196.843	30932474
DeepCCS	[M+Na]+	172.266	30932474
AllCCS	[M+H]+	168.2	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	171.3	32859911
AllCCS	[M+Na]+	172.2	32859911
AllCCS	[M-H]-	172.4	32859911
AllCCS	[M+Na-2H]-	172.0	32859911
AllCCS	[M+HCOO]-	171.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.24 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5038 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1661.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	278.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	82.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	431.1 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	472.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	796.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	360.3 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	1237.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	301.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	304.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	302.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	267.6 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	26.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Heraclenol	CC(C)(O)C(O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2	3696.9	Standard polar	33892256
(R)-Heraclenol	CC(C)(O)C(O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2	2554.4	Standard non polar	33892256
(R)-Heraclenol	CC(C)(O)C(O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2	2709.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Heraclenol,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)C(O)COC1=C2OC=CC2=CC2=C1OC(=O)C=C2	2718.2	Semi standard non polar	33892256
(R)-Heraclenol,1TMS,isomer #2	CC(C)(O)C(COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C	2699.2	Semi standard non polar	33892256
(R)-Heraclenol,2TMS,isomer #1	CC(C)(O[Si](C)(C)C)C(COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C	2713.7	Semi standard non polar	33892256
(R)-Heraclenol,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C(O)COC1=C2OC=CC2=CC2=C1OC(=O)C=C2	2972.2	Semi standard non polar	33892256
(R)-Heraclenol,1TBDMS,isomer #2	CC(C)(O)C(COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C(C)(C)C	2961.8	Semi standard non polar	33892256
(R)-Heraclenol,2TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C(COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C(C)(C)C	3204.3	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 - (R)-Heraclenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9140000000-00effd3606a3a93b19c6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Heraclenol GC-MS (2 TMS) - 70eV, Positive	splash10-001i-9644600000-ba97ef6ea2f2909d3c08	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Heraclenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Heraclenol , positive-QTOF	splash10-0udj-0980000000-2a9d336c59b7427c787d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Heraclenol , positive-QTOF	splash10-0udi-0690000000-1c26fc27ceded773623e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Heraclenol 10V, Positive-QTOF	splash10-0uxr-0090000000-4d8c75807d4194c90cf7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Heraclenol 20V, Positive-QTOF	splash10-0udi-2190000000-189cf5b0ff180b30a931	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Heraclenol 40V, Positive-QTOF	splash10-0002-3910000000-45458632ebeb4baa67f6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 10V, Positive-QTOF	splash10-0a4r-1079000000-5119de69b212b99ecdc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 20V, Positive-QTOF	splash10-0k9i-4292000000-6e174f1e87ddc2795f45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 40V, Positive-QTOF	splash10-0udr-8590000000-39ec641aaebce3f7a37c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 10V, Negative-QTOF	splash10-0udi-1198000000-db757ffc17838cf04727	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 20V, Negative-QTOF	splash10-0udi-0390000000-7d8b88d917de246f5659	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 40V, Negative-QTOF	splash10-0a4i-0910000000-d57b4f343ba87a8aa1bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 10V, Negative-QTOF	splash10-0udi-0019000000-cd51f5d9186655cf2f11	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 20V, Negative-QTOF	splash10-0uxu-3191000000-1dc4aa373094d670f4a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 40V, Negative-QTOF	splash10-0uk9-0490000000-3d798eaf31ebdd35d69e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 10V, Positive-QTOF	splash10-0zfr-0095000000-c1fc5235bb39ff83f6e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 20V, Positive-QTOF	splash10-0udi-2190000000-c48273e3db9dd4283b56	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Heraclenol 40V, Positive-QTOF	splash10-052b-3940000000-452da60eb625532848ff	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB002674

KNApSAcK ID

Not Available

Chemspider ID

290709

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

328236

PDB ID

Not Available

ChEBI ID

93899

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

(R)-Heraclenol → {[3-hydroxy-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)butan-2-yl]oxy}sulfonic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

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

Reactions

(R)-Heraclenol → 3,4,5-trihydroxy-6-{[3-hydroxy-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)butan-2-yl]oxy}oxane-2-carboxylic acid	details
(R)-Heraclenol → 3,4,5-trihydroxy-6-{[3-hydroxy-2-methyl-4-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)butan-2-yl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for (R)-Heraclenol (HMDB0030745)

MOL for HMDB0030745 ((R)-Heraclenol)

3D MOL for HMDB0030745 ((R)-Heraclenol)

3D SDF for HMDB0030745 ((R)-Heraclenol)

3D-SDF for HMDB0030745 ((R)-Heraclenol)

PDB for HMDB0030745 ((R)-Heraclenol)

3D PDB for HMDB0030745 ((R)-Heraclenol)

SMILES for HMDB0030745 ((R)-Heraclenol)

INCHI for HMDB0030745 ((R)-Heraclenol)

Structure for HMDB0030745 ((R)-Heraclenol)

3D Structure for HMDB0030745 ((R)-Heraclenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions