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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:29:30 UTC

Update Date

2022-03-07 02:53:50 UTC

HMDB ID

HMDB0033732

Secondary Accession Numbers

HMDB33732

Metabolite Identification

Common Name

Pisatin

Description

Pisatin, also known as (S,S)-pisatin, 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. Pisatin has been detected, but not quantified in, several different foods, such as teas (Camellia sinensis), common peas (Pisum sativum), red tea, herbs and spices, and black tea. This could make pisatin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Pisatin.

Structure

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

HMDB0033732
     RDKit          3D
Pisatin
 37 41  0  0  0  0  0  0  0  0999 V2000
   -6.3079    0.2724   -0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6324   -0.6859    0.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2579   -0.6244    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -1.5745    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -1.5403    1.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671   -0.5331    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1301    0.4151   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4980    0.3816   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955    1.4380   -0.6939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    1.2179   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865    0.8136    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4450    1.7767    1.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121    0.4470    0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912    1.1658    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3835    0.5373   -0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120   -0.8218   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -1.5110   -0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9983   -0.9019   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779   -1.3855   -0.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -0.5214    0.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7228   -1.1437   -0.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461    0.0076   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6957    1.0220   -0.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0425    0.1281   -1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4124    0.0723   -0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0719    1.3148   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906   -2.3744    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -2.3257    1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0259    1.1231   -0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057    0.3373   -1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151    2.0901   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    2.3489    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    2.2138    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -2.5640   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2749   -0.8058    1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8749    0.3155   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3664   -0.1255    0.1480 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 20 11  1  0
 20  6  1  0
 18 13  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 14 33  1  0
 17 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
M  END


  Mrv0541 02241218592D          

 23 27  0  0  0  0            999 V2000
   -1.4562   -1.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7412   -1.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276   -1.8384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874   -1.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874   -0.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4410   -0.9364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1443    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276   -0.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7412   -0.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -0.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698   -0.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698   -1.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848   -1.8384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652    0.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505    1.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2701    1.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8834    1.8384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5984    1.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4266    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056    0.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1217   -0.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984   -1.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 23  1  0  0  0  0
 14 15  2  0  0  0  0
 14 22  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033732

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C3OC4=C(C=C5OCOC5=C4)C3(O)COC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O6/c1-19-9-2-3-10-12(4-9)20-7-17(18)11-5-14-15(22-8-21-14)6-13(11)23-16(10)17/h2-6,16,18H,7-8H2,1H3

> <INCHI_KEY>
LZMRDTLRSDRUSU-UHFFFAOYSA-N

> <FORMULA>
C17H14O6

> <MOLECULAR_WEIGHT>
314.2895

> <EXACT_MASS>
314.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.731171579758104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2(10),3,8,13,15,17-hexaen-1-ol

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.7808418036666658

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.975073455591103

> <JCHEM_PKA_STRONGEST_BASIC>
-4.121902870524452

> <JCHEM_POLAR_SURFACE_AREA>
66.38000000000001

> <JCHEM_REFRACTIVITY>
77.935

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2(10),3,8,13,15,17-hexaen-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033732
     RDKit          3D
Pisatin
 37 41  0  0  0  0  0  0  0  0999 V2000
   -6.3079    0.2724   -0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6324   -0.6859    0.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2579   -0.6244    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -1.5745    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -1.5403    1.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671   -0.5331    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1301    0.4151   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4980    0.3816   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955    1.4380   -0.6939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    1.2179   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865    0.8136    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4450    1.7767    1.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121    0.4470    0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912    1.1658    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3835    0.5373   -0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120   -0.8218   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -1.5110   -0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9983   -0.9019   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779   -1.3855   -0.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -0.5214    0.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7228   -1.1437   -0.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461    0.0076   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6957    1.0220   -0.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0425    0.1281   -1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4124    0.0723   -0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0719    1.3148   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906   -2.3744    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -2.3257    1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0259    1.1231   -0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057    0.3373   -1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151    2.0901   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    2.3489    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    2.2138    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -2.5640   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2749   -0.8058    1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8749    0.3155   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3664   -0.1255    0.1480 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 20 11  1  0
 20  6  1  0
 18 13  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 14 33  1  0
 17 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.718  -3.432   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.384  -2.661   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.052  -3.432   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.283  -2.661   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.283  -1.121   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.690  -1.748   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.269   1.155   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.052  -0.351   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.384  -1.121   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.718  -0.351   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.050  -1.121   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.050  -2.661   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.385  -3.432   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.428  -0.092   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.802   1.317   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.708   2.562   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.238   2.400   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.382   3.432   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.717   2.661   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.396   1.155   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.864   0.993   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.961  -0.251   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.717  -2.659   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8   14                                             
CONECT    6    5                                                            
CONECT    7    8   15                                                       
CONECT    8    5    7    9                                                  
CONECT    9    2    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    1   11   13                                                  
CONECT   13   12   23                                                       
CONECT   14    5   15   22                                                  
CONECT   15    7   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   17   20   22                                                  
CONECT   22   14   21                                                       
CONECT   23   13                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0033732
HETATM    1  C1  UNL     1      -6.308   0.272  -0.691  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.632  -0.686   0.067  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.258  -0.624   0.245  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.597  -1.575   0.995  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.232  -1.540   1.191  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.467  -0.533   0.631  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.130   0.415  -0.118  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.498   0.382  -0.315  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.395   1.438  -0.694  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.009   1.218  -0.868  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.587   0.814   0.457  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.445   1.777   1.430  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.012   0.447   0.208  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.191   1.166   0.239  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.384   0.537  -0.044  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.412  -0.822  -0.364  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.205  -1.511  -0.385  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.998  -0.902  -0.104  1.00  0.00           C  
HETATM   19  O4  UNL     1       0.678  -1.386  -0.064  1.00  0.00           O  
HETATM   20  C16 UNL     1      -0.003  -0.521   0.857  1.00  0.00           C  
HETATM   21  O5  UNL     1       5.723  -1.144  -0.590  1.00  0.00           O  
HETATM   22  C17 UNL     1       6.546   0.008  -0.559  1.00  0.00           C  
HETATM   23  O6  UNL     1       5.696   1.022  -0.083  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.042   0.128  -1.756  1.00  0.00           H  
HETATM   25  H2  UNL     1      -7.412   0.072  -0.575  1.00  0.00           H  
HETATM   26  H3  UNL     1      -6.072   1.315  -0.372  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.191  -2.374   1.442  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.764  -2.326   1.798  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.026   1.123  -0.902  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.106   0.337  -1.547  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.515   2.090  -1.301  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.349   2.349   1.293  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.122   2.214   0.491  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.251  -2.564  -0.635  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.275  -0.806   1.889  1.00  0.00           H  
HETATM   36  H13 UNL     1       6.875   0.315  -1.581  1.00  0.00           H  
HETATM   37  H14 UNL     1       7.366  -0.125   0.148  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   20
CONECT    7    8    8    9
CONECT    8   29
CONECT    9   10
CONECT   10   11   30   31
CONECT   11   12   13   20
CONECT   12   32
CONECT   13   14   14   18
CONECT   14   15   33
CONECT   15   16   16   23
CONECT   16   17   21
CONECT   17   18   18   34
CONECT   18   19
CONECT   19   20
CONECT   20   35
CONECT   21   22
CONECT   22   23   36   37
END

HMDB0033732
     RDKit          3D
Pisatin
 37 41  0  0  0  0  0  0  0  0999 V2000
   -6.3079    0.2724   -0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6324   -0.6859    0.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2579   -0.6244    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -1.5745    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -1.5403    1.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671   -0.5331    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1301    0.4151   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4980    0.3816   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955    1.4380   -0.6939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    1.2179   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865    0.8136    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4450    1.7767    1.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121    0.4470    0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912    1.1658    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3835    0.5373   -0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120   -0.8218   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -1.5110   -0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9983   -0.9019   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779   -1.3855   -0.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -0.5214    0.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7228   -1.1437   -0.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461    0.0076   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6957    1.0220   -0.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0425    0.1281   -1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4124    0.0723   -0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0719    1.3148   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906   -2.3744    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -2.3257    1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0259    1.1231   -0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057    0.3373   -1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151    2.0901   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    2.3489    1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    2.2138    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -2.5640   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2749   -0.8058    1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8749    0.3155   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3664   -0.1255    0.1480 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 20 11  1  0
 20  6  1  0
 18 13  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 14 33  1  0
 17 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Pisatin	MeSH
Pisatin, (6ar-cis)-isomer	MeSH
Pisatin, (6as-cis)-isomer	MeSH
(S,S)-Pisatin	MeSH
(+)-Pisatin	MeSH
6a-Hydroxy-3-methoxy-8,9-methylenedioxypterocarpan	HMDB
Pisatin	MeSH

Chemical Formula

C₁₇H₁₄O₆

Average Molecular Weight

314.2895

Monoisotopic Molecular Weight

314.07903818

IUPAC Name

16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2(10),3,8,13,15,17-hexaen-1-ol

Traditional Name

16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2(10),3,8,13,15,17-hexaen-1-ol

CAS Registry Number

469-01-2

SMILES

COC1=CC=C2C3OC4=C(C=C5OCOC5=C4)C3(O)COC2=C1

InChI Identifier

InChI=1S/C17H14O6/c1-19-9-2-3-10-12(4-9)20-7-17(18)11-5-14-15(22-8-21-14)6-13(11)23-16(10)17/h2-6,16,18H,7-8H2,1H3

InChI Key

LZMRDTLRSDRUSU-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

Isoflavanol
Pterocarpan
Isoflavan
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Benzofuran
Coumaran
Anisole
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Oxacycle
Ether
Acetal
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-3944 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033732)
Cell membrane (HMDB: HMDB0033732)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033732)

Source

Exogenous

Exogenous (HMDB: HMDB0033732)

Food

Food (HMDB: HMDB0033732)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033732)
Fabaceae (HMDB: HMDB0033732)

Process

Not Available

Role

Biological role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0033732)

Pesticide (HMDB: HMDB0033732)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	61 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.58	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.77 g/L	ALOGPS
logP	1.75	ALOGPS
logP	1.78	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.98	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.94 m³·mol⁻¹	ChemAxon
Polarizability	31.73 Å³	ChemAxon
Number of Rings	5	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]+	171.061	31661259
DarkChem	[M-H]-	174.674	31661259
DeepCCS	[M+H]+	176.567	30932474
DeepCCS	[M-H]-	174.209	30932474
DeepCCS	[M-2H]-	207.67	30932474
DeepCCS	[M+Na]+	182.897	30932474
AllCCS	[M+H]+	173.3	32859911
AllCCS	[M+H-H2O]+	169.8	32859911
AllCCS	[M+NH4]+	176.6	32859911
AllCCS	[M+Na]+	177.5	32859911
AllCCS	[M-H]-	177.3	32859911
AllCCS	[M+Na-2H]-	176.4	32859911
AllCCS	[M+HCOO]-	175.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pisatin	COC1=CC=C2C3OC4=C(C=C5OCOC5=C4)C3(O)COC2=C1	4027.1	Standard polar	33892256
Pisatin	COC1=CC=C2C3OC4=C(C=C5OCOC5=C4)C3(O)COC2=C1	2532.0	Standard non polar	33892256
Pisatin	COC1=CC=C2C3OC4=C(C=C5OCOC5=C4)C3(O)COC2=C1	2755.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pisatin,1TMS,isomer #1	COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C)C3=CC4=C(C=C3OC21)OCO4	2736.2	Semi standard non polar	33892256
Pisatin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C(C)(C)C)C3=CC4=C(C=C3OC21)OCO4	3047.4	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 - Pisatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-06sa-1691000000-274d0a6517fe3252562b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pisatin GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9328000000-e689e98a16aeffb2e091	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pisatin 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 - Pisatin 10V, Positive-QTOF	splash10-014i-0009000000-51ff895d3d542958b762	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 20V, Positive-QTOF	splash10-014i-0039000000-0352732548637eab03f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 40V, Positive-QTOF	splash10-00di-7930000000-ac982921a96b24070af6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 10V, Negative-QTOF	splash10-03di-0009000000-226bc1be39e0a6889bbb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 20V, Negative-QTOF	splash10-03di-0039000000-32e07322e048d0dfd736	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 40V, Negative-QTOF	splash10-0fr2-1090000000-82ba48e1b539fc3da501	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 10V, Negative-QTOF	splash10-03di-0009000000-7c7169b7540bc9455826	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 20V, Negative-QTOF	splash10-03di-0049000000-3be945fe734b9b554664	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 40V, Negative-QTOF	splash10-0101-1690000000-1c2eba349da0683de3b2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 10V, Positive-QTOF	splash10-014i-0009000000-2ba875095a8aafa31ef7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 20V, Positive-QTOF	splash10-014i-0119000000-4b39bd2e26b1cc32f4d0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pisatin 40V, Positive-QTOF	splash10-004r-0922000000-d989845b9f9595ff4ac4	2021-09-25	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

FDB011855

KNApSAcK ID

C00000651

Chemspider ID

3682780

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pisatin

METLIN ID

Not Available

PubChem Compound

4484953

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Pisatin (HMDB0033732)

MOL for HMDB0033732 (Pisatin)

3D MOL for HMDB0033732 (Pisatin)

3D SDF for HMDB0033732 (Pisatin)

3D-SDF for HMDB0033732 (Pisatin)

PDB for HMDB0033732 (Pisatin)

3D PDB for HMDB0033732 (Pisatin)

SMILES for HMDB0033732 (Pisatin)

INCHI for HMDB0033732 (Pisatin)

Structure for HMDB0033732 (Pisatin)

3D Structure for HMDB0033732 (Pisatin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra