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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:45:31 UTC

Update Date

2022-03-07 02:55:22 UTC

HMDB ID

HMDB0037507

Secondary Accession Numbers

HMDB37507

Metabolite Identification

Common Name

Folerogenin

Description

Folerogenin is found in root vegetables. Folerogenin is isolated from licorice (Glycyrrhiza glabra) leaves Nadolol is a nonselective beta-adrenergic receptor antagonist with a long half-life, and is structurally similar to propranolol. Clinical pharmacology studies have demonstrated beta-blocking activity by showing (1) reduction in heart rate and cardiac output at rest and on exercise, (2) reduction of systolic and diastolic blood pressure at rest and on exercise, (3) inhibition of isoproterenol-induced tachycardia, and (4) reduction of reflex orthostatic tachycardia. Nadolol has no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, nadolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.

Structure

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

HMDB0037507
     RDKit          3D
Folerogenin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.2887    2.6444   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9163    2.5725    0.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957    1.3855    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7857    0.2205   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569   -0.9769   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6663   -2.1289   -0.7446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.9407    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    0.2430    0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8789    1.4144    0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013    0.2220    0.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738   -0.8792    0.7633 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4459   -0.4648    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401   -1.1350   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -0.7409   -0.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0527    0.3821   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3477    0.8026   -0.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853    1.0844    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077    0.6780    0.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691   -1.8774   -0.2719 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7023   -1.3710   -1.5449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8942   -2.1213   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3844   -3.2396    0.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6202    3.6627   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4221    2.0702   -1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9061    2.1367    0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223    0.1941   -0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511   -3.0056   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753    2.3176    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0546   -1.4250    1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.0405   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985   -1.3138   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7406    1.6196   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7137    1.9812    1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178    1.2420    1.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834   -2.8269   -0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -0.3860   -1.5310 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  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
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  9  3  1  0
 18 12  1  0
 21  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 11 29  1  1
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
M  END


  Mrv0541 04261301292D          

 22 24  0  0  0  0            999 V2000
    2.8574    0.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426    0.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    0.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    1.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426    1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574    1.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5707    1.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -0.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    0.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426    0.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426   -0.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -1.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -2.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -0.7910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7147    0.0184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8559    0.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5707    0.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -1.2031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 11 19  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 18  3  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0037507

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C2C(=O)[C@@H](O)[C@H](OC2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,15-18,20H,1H3/t15-,16-/m1/s1

> <INCHI_KEY>
LZLGHWHSUZVUFZ-HZPDHXFCSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.2788

> <EXACT_MASS>
302.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.139849594420895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
2.265843645666667

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.941597916788426

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.291140087000118

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9292704190853494

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
77.11030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037507
     RDKit          3D
Folerogenin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.2887    2.6444   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9163    2.5725    0.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957    1.3855    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7857    0.2205   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569   -0.9769   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6663   -2.1289   -0.7446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.9407    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    0.2430    0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8789    1.4144    0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013    0.2220    0.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738   -0.8792    0.7633 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4459   -0.4648    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401   -1.1350   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -0.7409   -0.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0527    0.3821   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3477    0.8026   -0.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853    1.0844    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077    0.6780    0.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691   -1.8774   -0.2719 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7023   -1.3710   -1.5449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8942   -2.1213   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3844   -3.2396    0.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6202    3.6627   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4221    2.0702   -1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9061    2.1367    0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223    0.1941   -0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511   -3.0056   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753    2.3176    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0546   -1.4250    1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.0405   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985   -1.3138   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7406    1.6196   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7137    1.9812    1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178    1.2420    1.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834   -2.8269   -0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -0.3860   -1.5310 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  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
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  9  3  1  0
 18 12  1  0
 21  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 11 29  1  1
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
M  END

HEADER    PROTEIN                                 26-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-13         0                                  
HETATM    1  C   UNK     0       5.334   0.804   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.000   0.034   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.666   0.804   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.666   2.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.000   3.116   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.334   2.343   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.665   3.113   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000  -3.811   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -2.275   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.332  -1.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.332   0.037   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.666   0.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.000   0.037   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.000  -1.502   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.666  -2.272   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.666  -3.811   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -1.477   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   0.034   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000   0.807   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.331   0.807   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.665   0.037   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.668  -2.246   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10   17                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16   15                                                            
CONECT   17    9   18   22                                                  
CONECT   18   17   19    3                                                  
CONECT   19   11   18                                                       
CONECT   20   13   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0037507
HETATM    1  C1  UNL     1      -5.289   2.644  -0.072  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.916   2.573   0.267  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.196   1.386   0.182  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.786   0.221  -0.236  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.057  -0.977  -0.321  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.666  -2.129  -0.745  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.731  -0.941   0.031  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.121   0.243   0.458  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.879   1.414   0.529  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.201   0.222   0.795  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.074  -0.879   0.763  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.446  -0.465   0.404  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.240  -1.135  -0.487  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.528  -0.741  -0.823  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.053   0.382  -0.239  1.00  0.00           C  
HETATM   16  O4  UNL     1       6.348   0.803  -0.559  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.285   1.084   0.663  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.008   0.678   0.985  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.569  -1.877  -0.272  1.00  0.00           C  
HETATM   20  O5  UNL     1       0.702  -1.371  -1.545  1.00  0.00           O  
HETATM   21  C16 UNL     1      -0.894  -2.121  -0.005  1.00  0.00           C  
HETATM   22  O6  UNL     1      -1.384  -3.240   0.178  1.00  0.00           O  
HETATM   23  H1  UNL     1      -5.620   3.663  -0.290  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.422   2.070  -1.035  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.906   2.137   0.685  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.822   0.194  -0.510  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.251  -3.006  -0.857  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.375   2.318   0.866  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.055  -1.425   1.740  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.858  -2.041  -0.976  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.098  -1.314  -1.532  1.00  0.00           H  
HETATM   32  H10 UNL     1       6.741   1.620  -0.140  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.714   1.981   1.125  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.418   1.242   1.696  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.083  -2.827  -0.087  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.896  -0.386  -1.531  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   21
CONECT    8    9    9   10
CONECT    9   28
CONECT   10   11
CONECT   11   12   19   29
CONECT   12   13   13   18
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16   17
CONECT   16   32
CONECT   17   18   18   33
CONECT   18   34
CONECT   19   20   21   35
CONECT   20   36
CONECT   21   22   22
END

HMDB0037507
     RDKit          3D
Folerogenin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.2887    2.6444   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9163    2.5725    0.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957    1.3855    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7857    0.2205   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569   -0.9769   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6663   -2.1289   -0.7446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.9407    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    0.2430    0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8789    1.4144    0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013    0.2220    0.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738   -0.8792    0.7633 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4459   -0.4648    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401   -1.1350   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -0.7409   -0.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0527    0.3821   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3477    0.8026   -0.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853    1.0844    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077    0.6780    0.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691   -1.8774   -0.2719 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7023   -1.3710   -1.5449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8942   -2.1213   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3844   -3.2396    0.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6202    3.6627   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4221    2.0702   -1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9061    2.1367    0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223    0.1941   -0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511   -3.0056   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753    2.3176    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0546   -1.4250    1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.0405   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985   -1.3138   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7406    1.6196   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7137    1.9812    1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178    1.2420    1.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834   -2.8269   -0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -0.3860   -1.5310 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  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
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  9  3  1  0
 18 12  1  0
 21  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 11 29  1  1
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Anabet	HMDB
Corgard	HMDB
Corgaretic	HMDB
Corzide	HMDB
Isoauroside	HMDB
Nadic	HMDB
Nadolol	HMDB
Nadolol (JP15/usp/inn)	HMDB
Nadololum	HMDB
Solgol	HMDB

Chemical Formula

C₁₆H₁₄O₆

Average Molecular Weight

302.2788

Monoisotopic Molecular Weight

302.07903818

IUPAC Name

(2R,3S)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R,3S)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

35815-06-6

SMILES

COC1=CC(O)=C2C(=O)[C@@H](O)[C@H](OC2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,15-18,20H,1H3/t15-,16-/m1/s1

InChI Key

LZLGHWHSUZVUFZ-HZPDHXFCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Flavanonol
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037507)
Cytoplasm (HMDB: HMDB0037507)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037507)

Source

Endogenous

Plant

Plant (HMDB: HMDB0037507)

Exogenous

Food

Food (HMDB: HMDB0037507)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Process

Not Available

Role

Industrial application

Drug (HMDB: HMDB0037507)

Biological role

Nutrient

Nutrient (HMDB: HMDB0037507)

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	5875 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.54 g/L	ALOGPS
logP	1.78	ALOGPS
logP	2.27	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.11 m³·mol⁻¹	ChemAxon
Polarizability	30.14 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]+	171.709	31661259
DarkChem	[M-H]-	171.102	31661259
DeepCCS	[M+H]+	174.739	30932474
DeepCCS	[M-H]-	172.363	30932474
DeepCCS	[M-2H]-	206.481	30932474
DeepCCS	[M+Na]+	181.581	30932474
AllCCS	[M+H]+	171.2	32859911
AllCCS	[M+H-H2O]+	167.5	32859911
AllCCS	[M+NH4]+	174.5	32859911
AllCCS	[M+Na]+	175.5	32859911
AllCCS	[M-H]-	171.0	32859911
AllCCS	[M+Na-2H]-	170.5	32859911
AllCCS	[M+HCOO]-	170.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Folerogenin	COC1=CC(O)=C2C(=O)[C@@H](O)[C@H](OC2=C1)C1=CC=C(O)C=C1	4026.8	Standard polar	33892256
Folerogenin	COC1=CC(O)=C2C(=O)[C@@H](O)[C@H](OC2=C1)C1=CC=C(O)C=C1	2855.9	Standard non polar	33892256
Folerogenin	COC1=CC(O)=C2C(=O)[C@@H](O)[C@H](OC2=C1)C1=CC=C(O)C=C1	2884.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Folerogenin,1TMS,isomer #1	COC1=CC2=C(C(=O)[C@@H](O)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C1	2861.9	Semi standard non polar	33892256
Folerogenin,1TMS,isomer #2	COC1=CC(O)=C2C(=O)[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C=C3)OC2=C1	2767.3	Semi standard non polar	33892256
Folerogenin,1TMS,isomer #3	COC1=CC(O)=C2C(=O)[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)OC2=C1	2851.8	Semi standard non polar	33892256
Folerogenin,2TMS,isomer #1	COC1=CC2=C(C(=O)[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C1	2714.5	Semi standard non polar	33892256
Folerogenin,2TMS,isomer #2	COC1=CC2=C(C(=O)[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)O2)C(O[Si](C)(C)C)=C1	2792.1	Semi standard non polar	33892256
Folerogenin,2TMS,isomer #3	COC1=CC(O)=C2C(=O)[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)OC2=C1	2691.5	Semi standard non polar	33892256
Folerogenin,3TMS,isomer #1	COC1=CC2=C(C(=O)[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)O2)C(O[Si](C)(C)C)=C1	2724.6	Semi standard non polar	33892256
Folerogenin,1TBDMS,isomer #1	COC1=CC2=C(C(=O)[C@@H](O)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3114.4	Semi standard non polar	33892256
Folerogenin,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C=C3)OC2=C1	3028.1	Semi standard non polar	33892256
Folerogenin,1TBDMS,isomer #3	COC1=CC(O)=C2C(=O)[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)OC2=C1	3121.2	Semi standard non polar	33892256
Folerogenin,2TBDMS,isomer #1	COC1=CC2=C(C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3205.9	Semi standard non polar	33892256
Folerogenin,2TBDMS,isomer #2	COC1=CC2=C(C(=O)[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3327.1	Semi standard non polar	33892256
Folerogenin,2TBDMS,isomer #3	COC1=CC(O)=C2C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)OC2=C1	3225.1	Semi standard non polar	33892256
Folerogenin,3TBDMS,isomer #1	COC1=CC2=C(C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3431.3	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 - Folerogenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-0950000000-de2029bc14e7db044c3b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Folerogenin GC-MS (3 TMS) - 70eV, Positive	splash10-0uka-9820550000-5b30b68052967e7e8cb0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Folerogenin 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 - Folerogenin 10V, Positive-QTOF	splash10-0udi-0139000000-3d001fea9798a00fa93a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folerogenin 20V, Positive-QTOF	splash10-0v4i-0943000000-9058f0c38fbb5883ca55	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folerogenin 40V, Positive-QTOF	splash10-00di-3900000000-c31b22a759a19c82ea1c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folerogenin 10V, Negative-QTOF	splash10-0udi-0219000000-0b14661f38b7633fbbee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folerogenin 20V, Negative-QTOF	splash10-0v4r-1944000000-182176261c015d80cb5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folerogenin 40V, Negative-QTOF	splash10-00rm-5910000000-ab9ec644ac85d4ed0128	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folerogenin 10V, Positive-QTOF	splash10-0udi-0409000000-a2ab31c5228f28769ce4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folerogenin 20V, Positive-QTOF	splash10-014i-0900000000-a7ee695a918b69294573	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Folerogenin 40V, Positive-QTOF	splash10-014i-0900000000-ff30aa4d3f57671329de	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

FDB016583

KNApSAcK ID

C00020493

Chemspider ID

30777189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319509

PDB ID

Not Available

ChEBI ID

7444

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1861631

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Folerogenin (HMDB0037507)

MOL for HMDB0037507 (Folerogenin)

3D MOL for HMDB0037507 (Folerogenin)

3D SDF for HMDB0037507 (Folerogenin)

3D-SDF for HMDB0037507 (Folerogenin)

PDB for HMDB0037507 (Folerogenin)

3D PDB for HMDB0037507 (Folerogenin)

SMILES for HMDB0037507 (Folerogenin)

INCHI for HMDB0037507 (Folerogenin)

Structure for HMDB0037507 (Folerogenin)

3D Structure for HMDB0037507 (Folerogenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra