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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:47:00 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034008

Secondary Accession Numbers

HMDB34008

Metabolite Identification

Common Name

Methylnissolin

Description

Methylnissolin belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, methylnissolin is considered to be a flavonoid. Methylnissolin has been detected, but not quantified in, alfalfas (Medicago sativa) and pulses. This could make methylnissolin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methylnissolin.

Structure

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

HMDB0034008
     RDKit          3D
Methylnissolin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -5.8129    0.2063    0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429   -0.4842   -0.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3709   -0.0119    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1999    1.1887    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273    1.6575    1.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296    0.9095    0.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622   -0.2914    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431   -0.7244   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3927   -1.9480   -0.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331   -2.0158   -2.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148   -0.8331   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438   -0.2971    0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692   -0.3968    0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2798   -1.5061    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414   -1.6443    0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3006   -0.6608   -0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6437   -0.8057   -0.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5733    0.4297   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2253    0.5893   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923    1.6770   -0.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    1.8812   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289    1.1248    0.8996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0878   -0.0848    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7018    1.2914    0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6078   -0.1141   -0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0386    1.8006    1.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384    2.6078    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368   -1.0380   -2.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3575   -2.5686   -2.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5812   -2.6757   -2.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8380   -0.8285    1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851   -2.2861    1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2112   -2.5064    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2169   -0.1693   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0674    1.2084   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    1.5012   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682    2.9515   -0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8729    1.6438    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 12  1  0
 22  6  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  1  0
M  END


  Mrv0541 05061307302D          

 22 25  0  0  0  0            999 V2000
   -0.9390   -2.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -4.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -3.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    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
 11  4  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  2  0  0  0  0
 17 13  2  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 19  1  1  0  0  0  0
 19 13  1  0  0  0  0
 20  2  1  0  0  0  0
 20 17  1  0  0  0  0
 21  8  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034008

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-19-13-6-5-10-12-8-21-14-7-9(18)3-4-11(14)15(12)22-16(10)17(13)20-2/h3-7,12,15,18H,8H2,1-2H3

> <INCHI_KEY>
UOVGCLXUTLXAEC-UHFFFAOYSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.3059

> <EXACT_MASS>
300.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.96005970337123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14,15-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.3515521306666667

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.420752477509364

> <JCHEM_PKA_STRONGEST_BASIC>
-4.323038009923046

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
79.52430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14,15-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034008
     RDKit          3D
Methylnissolin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -5.8129    0.2063    0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429   -0.4842   -0.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3709   -0.0119    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1999    1.1887    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273    1.6575    1.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296    0.9095    0.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622   -0.2914    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431   -0.7244   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3927   -1.9480   -0.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331   -2.0158   -2.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148   -0.8331   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438   -0.2971    0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692   -0.3968    0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2798   -1.5061    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414   -1.6443    0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3006   -0.6608   -0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6437   -0.8057   -0.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5733    0.4297   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2253    0.5893   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923    1.6770   -0.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    1.8812   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289    1.1248    0.8996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0878   -0.0848    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7018    1.2914    0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6078   -0.1141   -0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0386    1.8006    1.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384    2.6078    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368   -1.0380   -2.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3575   -2.5686   -2.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5812   -2.6757   -2.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8380   -0.8285    1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851   -2.2861    1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2112   -2.5064    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2169   -0.1693   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0674    1.2084   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    1.5012   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682    2.9515   -0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8729    1.6438    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 12  1  0
 22  6  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 22 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      -1.753  -4.262   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.429  -7.592   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.134  -6.760   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    6   10                                                       
CONECT    6    5   13                                                       
CONECT    7    9   14                                                       
CONECT    8   12   21                                                       
CONECT    9    3    7   18                                                  
CONECT   10    5   12   16                                                  
CONECT   11    4   14   15                                                  
CONECT   12    8   10   15                                                  
CONECT   13    6   17   19                                                  
CONECT   14    7   11   21                                                  
CONECT   15   11   12   22                                                  
CONECT   16   10   17   22                                                  
CONECT   17   13   16   20                                                  
CONECT   18    9                                                            
CONECT   19    1   13                                                       
CONECT   20    2   17                                                       
CONECT   21    8   14                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0034008
HETATM    1  C1  UNL     1      -5.813   0.206   0.165  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.643  -0.484  -0.170  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.371  -0.012   0.135  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.200   1.189   0.797  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.927   1.658   1.100  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.830   0.910   0.731  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.962  -0.291   0.070  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.243  -0.724  -0.214  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.393  -1.948  -0.888  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.433  -2.016  -2.300  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.315  -0.833  -0.179  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.144  -0.297   0.863  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.569  -0.397   0.552  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.280  -1.506   0.978  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.641  -1.644   0.705  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.301  -0.661  -0.003  1.00  0.00           C  
HETATM   17  O4  UNL     1       6.644  -0.806  -0.268  1.00  0.00           O  
HETATM   18  C14 UNL     1       4.573   0.430  -0.414  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.225   0.589  -0.156  1.00  0.00           C  
HETATM   20  O5  UNL     1       2.492   1.677  -0.564  1.00  0.00           O  
HETATM   21  C16 UNL     1       1.132   1.881  -0.311  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.629   1.125   0.900  1.00  0.00           C  
HETATM   23  H1  UNL     1      -6.088  -0.085   1.199  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.702   1.291   0.025  1.00  0.00           H  
HETATM   25  H3  UNL     1      -6.608  -0.114  -0.565  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.039   1.801   1.101  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.838   2.608   1.623  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.337  -1.038  -2.784  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.357  -2.569  -2.571  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.581  -2.676  -2.601  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.838  -0.828   1.783  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.785  -2.286   1.532  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.211  -2.506   1.031  1.00  0.00           H  
HETATM   34  H12 UNL     1       7.217  -0.169  -0.764  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.067   1.208  -0.968  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.560   1.501  -1.198  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.868   2.951  -0.216  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.873   1.644   1.844  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   22
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10
CONECT   10   28   29   30
CONECT   11   12
CONECT   12   13   22   31
CONECT   13   14   14   19
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17   18
CONECT   17   34
CONECT   18   19   19   35
CONECT   19   20
CONECT   20   21
CONECT   21   22   36   37
CONECT   22   38
END

HMDB0034008
     RDKit          3D
Methylnissolin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -5.8129    0.2063    0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429   -0.4842   -0.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3709   -0.0119    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1999    1.1887    0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273    1.6575    1.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296    0.9095    0.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622   -0.2914    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431   -0.7244   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3927   -1.9480   -0.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331   -2.0158   -2.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148   -0.8331   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438   -0.2971    0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692   -0.3968    0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2798   -1.5061    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414   -1.6443    0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3006   -0.6608   -0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6437   -0.8057   -0.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5733    0.4297   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2253    0.5893   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923    1.6770   -0.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    1.8812   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289    1.1248    0.8996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0878   -0.0848    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7018    1.2914    0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6078   -0.1141   -0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0386    1.8006    1.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384    2.6078    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368   -1.0380   -2.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3575   -2.5686   -2.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5812   -2.6757   -2.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8380   -0.8285    1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851   -2.2861    1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2112   -2.5064    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2169   -0.1693   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0674    1.2084   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    1.5012   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682    2.9515   -0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8729    1.6438    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 12  1  0
 22  6  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-Methoxymedicarpin	HMDB
3-Hydroxy-9,10-dimethoxypterocarpan	HMDB
Astrapterocarpan	HMDB

Chemical Formula

C₁₇H₁₆O₅

Average Molecular Weight

300.3059

Monoisotopic Molecular Weight

300.099773622

IUPAC Name

14,15-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

Traditional Name

14,15-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

CAS Registry Number

73340-41-7

SMILES

COC1=C(OC)C2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2

InChI Identifier

InChI=1S/C17H16O5/c1-19-13-6-5-10-12-8-21-14-7-9(18)3-4-11(14)15(12)22-16(10)17(13)20-2/h3-7,12,15,18H,8H2,1-2H3

InChI Key

UOVGCLXUTLXAEC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Chromane
1-benzopyran
Benzopyran
Coumaran
Benzofuran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070054 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034008)
Cell membrane (HMDB: HMDB0034008)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034008)

Source

Exogenous

Exogenous (HMDB: HMDB0034008)

Food

Food (HMDB: HMDB0034008)

Herb and spice

Herb

Alfalfa (FooDB: FOOD00286)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0034008)
Fabaceae (HMDB: HMDB0034008)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034008)

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
Water Solubility	0.091 g/L	ALOGPS
logP	2.88	ALOGPS
logP	2.35	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.52 m³·mol⁻¹	ChemAxon
Polarizability	30.96 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.329	31661259
DarkChem	[M-H]-	170.67	31661259
DeepCCS	[M+H]+	170.78	30932474
DeepCCS	[M-H]-	168.422	30932474
DeepCCS	[M-2H]-	202.479	30932474
DeepCCS	[M+Na]+	177.706	30932474
AllCCS	[M+H]+	170.4	32859911
AllCCS	[M+H-H2O]+	166.8	32859911
AllCCS	[M+NH4]+	173.8	32859911
AllCCS	[M+Na]+	174.7	32859911
AllCCS	[M-H]-	175.1	32859911
AllCCS	[M+Na-2H]-	174.4	32859911
AllCCS	[M+HCOO]-	173.9	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.	6.51 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3123 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.67 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1926.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	275.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	136.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	547.9 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	558.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1090.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	432.7 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	1271.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	347.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	348.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	299.7 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	31.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methylnissolin	COC1=C(OC)C2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2	3752.2	Standard polar	33892256
Methylnissolin	COC1=C(OC)C2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2	2581.2	Standard non polar	33892256
Methylnissolin	COC1=C(OC)C2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2	2772.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methylnissolin,1TMS,isomer #1	COC1=CC=C2C(=C1OC)OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21	2691.1	Semi standard non polar	33892256
Methylnissolin,1TBDMS,isomer #1	COC1=CC=C2C(=C1OC)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21	2942.1	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 - Methylnissolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ru9-0490000000-7b7b87b3c375cc5fbd7c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylnissolin GC-MS (1 TMS) - 70eV, Positive	splash10-0adi-2329000000-7af9e37010c0dfada26f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylnissolin 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 - Methylnissolin 10V, Positive-QTOF	splash10-0udi-0019000000-2486ecb82882a86c39f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 20V, Positive-QTOF	splash10-0udi-0169000000-d687330f56b5384c52cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 40V, Positive-QTOF	splash10-00xs-9870000000-1f3f4dbb27287c4110de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 10V, Negative-QTOF	splash10-0002-0090000000-89e39719e9c02d923511	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 20V, Negative-QTOF	splash10-0002-0090000000-7d343563881b9782e9af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 40V, Negative-QTOF	splash10-0gx0-0490000000-e2d5a07be005e0329ea4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 10V, Negative-QTOF	splash10-0002-0090000000-c8e04b941de97dd002f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 20V, Negative-QTOF	splash10-0002-0090000000-89e3db12b1a28200d297	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 40V, Negative-QTOF	splash10-0f6t-0390000000-f1abac09a375810c67d5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 10V, Positive-QTOF	splash10-0udi-0009000000-7fd5921050e52686aed7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 20V, Positive-QTOF	splash10-0udi-0109000000-d2103f39dd75204ef847	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylnissolin 40V, Positive-QTOF	splash10-00r2-0950000000-c6372111becdc61e34ab	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB012244

KNApSAcK ID

C00009617

Chemspider ID

4477965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319733

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1839751

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 Methylnissolin (HMDB0034008)

MOL for HMDB0034008 (Methylnissolin)

3D MOL for HMDB0034008 (Methylnissolin)

3D SDF for HMDB0034008 (Methylnissolin)

3D-SDF for HMDB0034008 (Methylnissolin)

PDB for HMDB0034008 (Methylnissolin)

3D PDB for HMDB0034008 (Methylnissolin)

SMILES for HMDB0034008 (Methylnissolin)

INCHI for HMDB0034008 (Methylnissolin)

Structure for HMDB0034008 (Methylnissolin)

3D Structure for HMDB0034008 (Methylnissolin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra