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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:27:31 UTC

Update Date

2021-09-23 16:27:32 UTC

HMDB ID

HMDB0302268

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nodakenetic

Description

Nodakenetic, also known as (-)-marmesin or marmesin, (R)-isomer, 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. Nodakenetic is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Nodakenetic can be found in wild celery, which makes nodakenetic a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302268
     RDKit          3D
Nodakenetic
 32 34  0  0  0  0  0  0  0  0999 V2000
   -4.0900   -0.3516    0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0664    0.3356   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4617    1.7828   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424   -0.3002   -1.5268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6940    0.3423    0.3021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0671   -1.0164    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -0.6992    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5696   -1.3459    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.7666    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822   -1.4054    0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1436   -0.7621    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1342    0.4654   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1745    1.0906   -0.8589 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9913    1.0458   -0.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505    0.4790   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543    1.1428   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    0.5517   -0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    1.0401   -0.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7990   -0.9587   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923    0.4169    1.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420   -1.0253    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882    2.2788    0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3911    1.8636   -1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5944    2.2812   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289   -0.3597   -1.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7106    0.8137    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487   -1.7525   -0.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594   -1.3671    1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -2.3110    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9567   -2.3888    0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1045   -1.2371    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6933    2.1175   -1.1938 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  5  1  0
 17  7  1  0
 15  9  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 16 32  1  0
M  END


  Mrv1533007131513302D          

 19 21  0  0  1  0            999 V2000
   -2.2784    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030    2.2580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  6  1  0  0  0  0
 13  4  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 12 14  1  6  0  0  0
 15 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  1  0  0  0  0
 12 19  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302268

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC2=C(O1)C=C1OC(=O)C=CC1=C2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3/t12-/m1/s1

> <INCHI_KEY>
FWYSBEAFFPBAQU-GFCCVEGCSA-N

> <FORMULA>
C14H14O4

> <MOLECULAR_WEIGHT>
246.262

> <EXACT_MASS>
246.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.70352027386889

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-(2-hydroxypropan-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
1.7323936069999994

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.296805394683403

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1063773203654783

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
66.3409

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-marmesin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302268
     RDKit          3D
Nodakenetic
 32 34  0  0  0  0  0  0  0  0999 V2000
   -4.0900   -0.3516    0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0664    0.3356   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4617    1.7828   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424   -0.3002   -1.5268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6940    0.3423    0.3021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0671   -1.0164    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -0.6992    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5696   -1.3459    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.7666    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822   -1.4054    0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1436   -0.7621    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1342    0.4654   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1745    1.0906   -0.8589 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9913    1.0458   -0.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505    0.4790   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543    1.1428   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    0.5517   -0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    1.0401   -0.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7990   -0.9587   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923    0.4169    1.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420   -1.0253    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882    2.2788    0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3911    1.8636   -1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5944    2.2812   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289   -0.3597   -1.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7106    0.8137    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487   -1.7525   -0.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594   -1.3671    1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -2.3110    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9567   -2.3888    0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1045   -1.2371    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6933    2.1175   -1.1938 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  5  1  0
 17  7  1  0
 15  9  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -4.253   2.843   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.713   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.713   4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      -1.872   4.215   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    4    8                                                       
CONECT    4    3   13                                                       
CONECT    5    8    9                                                       
CONECT    6    9   12                                                       
CONECT    7   10   11                                                       
CONECT    8    3    5   10                                                  
CONECT    9    5    6   11                                                  
CONECT   10    7    8   18                                                  
CONECT   11    7    9   17                                                  
CONECT   12    6   14   17   19                                             
CONECT   13    4   15   18                                                  
CONECT   14    1    2   12   16                                             
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17   11   12                                                       
CONECT   18   10   13                                                       
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0302268
HETATM    1  C1  UNL     1      -4.090  -0.352   0.570  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.066   0.336  -0.286  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.462   1.783  -0.536  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.042  -0.300  -1.527  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.694   0.342   0.302  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.067  -1.016   0.413  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.382  -0.699   0.209  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.570  -1.346   0.478  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.784  -0.767   0.156  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.982  -1.405   0.421  1.00  0.00           C  
HETATM   11  C10 UNL     1       5.144  -0.762   0.070  1.00  0.00           C  
HETATM   12  C11 UNL     1       5.134   0.465  -0.521  1.00  0.00           C  
HETATM   13  O2  UNL     1       6.175   1.091  -0.859  1.00  0.00           O  
HETATM   14  O3  UNL     1       3.991   1.046  -0.760  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.850   0.479  -0.446  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.654   1.143  -0.723  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.457   0.552  -0.396  1.00  0.00           C  
HETATM   18  O4  UNL     1      -0.839   1.040  -0.585  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.799  -0.959  -0.031  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.692   0.417   1.101  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.642  -1.025   1.326  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.588   2.279   0.464  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.391   1.864  -1.135  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.594   2.281  -1.023  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.129  -0.360  -1.905  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.711   0.814   1.314  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.449  -1.753  -0.290  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.159  -1.367   1.478  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.537  -2.311   0.944  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.957  -2.389   0.895  1.00  0.00           H  
HETATM   31  H13 UNL     1       6.105  -1.237   0.264  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.693   2.118  -1.194  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    5
CONECT    3   22   23   24
CONECT    4   25
CONECT    5    6   18   26
CONECT    6    7   27   28
CONECT    7    8    8   17
CONECT    8    9   29
CONECT    9   10   15   15
CONECT   10   11   11   30
CONECT   11   12   31
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   32
CONECT   17   18
END

HMDB0302268
     RDKit          3D
Nodakenetic
 32 34  0  0  0  0  0  0  0  0999 V2000
   -4.0900   -0.3516    0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0664    0.3356   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4617    1.7828   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424   -0.3002   -1.5268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6940    0.3423    0.3021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0671   -1.0164    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -0.6992    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5696   -1.3459    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.7666    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822   -1.4054    0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1436   -0.7621    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1342    0.4654   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1745    1.0906   -0.8589 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9913    1.0458   -0.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505    0.4790   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543    1.1428   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    0.5517   -0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    1.0401   -0.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7990   -0.9587   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923    0.4169    1.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420   -1.0253    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882    2.2788    0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3911    1.8636   -1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5944    2.2812   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289   -0.3597   -1.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7106    0.8137    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487   -1.7525   -0.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594   -1.3671    1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -2.3110    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9567   -2.3888    0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1045   -1.2371    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6933    2.1175   -1.1938 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  5  1  0
 17  7  1  0
 15  9  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Marmesin	ChEBI
(R)-2-(1-Hydroxy-1-methylethyl)-2,3-dihydro-7H-furo(3,2-g)(1)benzopyran-7-one	ChEBI
Marmesin	MeSH
Marmesin, (R)-isomer	MeSH
Nodakenetin	MeSH

Chemical Formula

C₁₄H₁₄O₄

Average Molecular Weight

246.262

Monoisotopic Molecular Weight

246.089208931

IUPAC Name

(2R)-2-(2-hydroxypropan-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

Traditional Name

(-)-marmesin

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC2=C(O1)C=C1OC(=O)C=CC1=C2)C(C)(C)O

InChI Identifier

InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3/t12-/m1/s1

InChI Key

FWYSBEAFFPBAQU-GFCCVEGCSA-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
Coumaran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

marmesin (CHEBI:49083 )
Furanocoumarins (C09278 )

Ontology

Not Available

Wild celery (FooDB: FOOD00015)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.98	ALOGPS
logP	1.73	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.34 m³·mol⁻¹	ChemAxon
Polarizability	25.7 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
AllCCS	[M+H]+	155.203	32859911
AllCCS	[M+H-H2O]+	151.274	32859911
AllCCS	[M+Na]+	159.908	32859911
AllCCS	[M+NH4]+	158.856	32859911
AllCCS	[M-H]-	160.259	32859911
AllCCS	[M+Na-2H]-	159.907	32859911
AllCCS	[M+HCOO]-	159.639	32859911
DeepCCS	[M+H]+	157.837	30932474
DeepCCS	[M-H]-	155.479	30932474
DeepCCS	[M-2H]-	189.93	30932474
DeepCCS	[M+Na]+	164.856	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 - Nodakenetic 10V, Positive-QTOF	splash10-002b-0090000000-1e79c1f020b61645f076	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 20V, Positive-QTOF	splash10-004j-0190000000-40afedd63981faa16804	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 40V, Positive-QTOF	splash10-01p9-3940000000-dbf2f2671711a438ee87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 10V, Negative-QTOF	splash10-0002-0090000000-d67ae6a47c04aa84c49b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 20V, Negative-QTOF	splash10-0002-0390000000-47033284f5fc203ed7ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 40V, Negative-QTOF	splash10-003i-1940000000-2854bff13b00322ef7e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 10V, Positive-QTOF	splash10-0002-0090000000-9c784d3e69b8766c47d3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 20V, Positive-QTOF	splash10-002b-0090000000-c8a0d2a152848bb3c37f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 40V, Positive-QTOF	splash10-0a59-1920000000-32b8f235651555b3be9c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 10V, Negative-QTOF	splash10-0002-0090000000-4a890656b917e493d11c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 20V, Negative-QTOF	splash10-0005-0290000000-5205e328ccf3efb9b832	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nodakenetic 40V, Negative-QTOF	splash10-000i-0940000000-3a3ced09e58d628073e4	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

132623

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1841611

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Nodakenetic (HMDB0302268)

MOL for HMDB0302268 (Nodakenetic)

3D MOL for HMDB0302268 (Nodakenetic)

3D SDF for HMDB0302268 (Nodakenetic)

3D-SDF for HMDB0302268 (Nodakenetic)

PDB for HMDB0302268 (Nodakenetic)

3D PDB for HMDB0302268 (Nodakenetic)

SMILES for HMDB0302268 (Nodakenetic)

INCHI for HMDB0302268 (Nodakenetic)

Structure for HMDB0302268 (Nodakenetic)

3D Structure for HMDB0302268 (Nodakenetic)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra