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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:49:35 UTC

Update Date

2022-03-07 02:56:54 UTC

HMDB ID

HMDB0041167

Secondary Accession Numbers

HMDB41167

Metabolite Identification

Common Name

(-)-Shinpterocarpin

Description

(-)-Shinpterocarpin 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 (-)-Shinpterocarpin has been detected, but not quantified in, several different foods, such as teas (Camellia sinensis), red tea, herbal tea, black tea, and green tea. This could make (-)-shinpterocarpin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on (-)-Shinpterocarpin.

Structure

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

HMDB0041167
     RDKit          3D
(-)-Shinpterocarpin
 42 46  0  0  0  0  0  0  0  0999 V2000
    4.2225    2.2276   -1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0516    0.8809   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4144    0.2310   -0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819    1.1512    1.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3346    0.6255    1.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729   -0.2284    0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0644   -0.5036   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -1.3274   -1.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155   -1.8726   -1.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3855   -1.6041    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.7871    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477   -0.5194    2.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4962   -0.5341    2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -1.3071    1.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -0.4417    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8873    0.7604    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467    1.3403   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801    0.7423   -1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5521    1.3465   -2.3197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1381   -0.4541   -1.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -1.0454   -0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -2.2425   -0.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583   -2.1422    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    0.0492   -1.1145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7427    3.0469   -0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396    2.2066   -2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3067    2.4874   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -0.1275   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0529    0.9311    0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2387   -0.6532    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0679    1.7949    1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    0.8372    2.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7507   -1.5226   -2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528   -2.5071   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -0.9593    3.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8381    0.5376    2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0806   -1.9684    2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590    1.2013    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1486    2.2942    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0153    2.2182   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2187   -0.9625   -2.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5018   -3.2002    0.8296 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
 24  2  1  0
 11  6  1  0
 23 14  1  0
 23 10  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  1  0
M  END

  Mrv0541 05061312262D          

 24 28  0  0  0  0            999 V2000
    7.6127   -1.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5027   -2.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6080   -1.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3925   -1.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192   -3.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1398   -3.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7724   -1.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5930   -1.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507   -2.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108   -0.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4371   -2.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0060   -1.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2880   -1.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9831   -2.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264   -1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6242   -2.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8351   -2.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -1.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9291   -2.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3473   -2.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1313   -1.0485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -2.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4447   -2.7266    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
  8  7  2  0  0  0  0
 11  3  1  0  0  0  0
 11  9  2  0  0  0  0
 12  4  1  0  0  0  0
 13  7  1  0  0  0  0
 14  5  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16 13  2  0  0  0  0
 17  9  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  1  0  0  0  0
 18 14  2  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 21 11  1  0  0  0  0
 22 10  1  0  0  0  0
 22 18  1  0  0  0  0
 23 17  1  0  0  0  0
 23 19  1  0  0  0  0
 24 16  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041167

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=C(C=C1)C1=C(C=C2)C2OC3=C(C=CC(O)=C3)C2CO1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O4/c1-20(2)8-7-13-16(24-20)6-5-14-18(13)22-10-15-12-4-3-11(21)9-17(12)23-19(14)15/h3-9,15,19,21H,10H2,1-2H3

> <INCHI_KEY>
QGPHRCQDTPCIQI-UHFFFAOYSA-N

> <FORMULA>
C20H18O4

> <MOLECULAR_WEIGHT>
322.3545

> <EXACT_MASS>
322.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.81518586207583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),4(9),5,7,14(19),15,20-heptaen-6-ol

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
3.5675180639999997

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.552918611868835

> <JCHEM_PKA_STRONGEST_BASIC>
-4.424283050683855

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
90.99130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),4(9),5,7,14(19),15,20-heptaen-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041167
     RDKit          3D
(-)-Shinpterocarpin
 42 46  0  0  0  0  0  0  0  0999 V2000
    4.2225    2.2276   -1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0516    0.8809   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4144    0.2310   -0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819    1.1512    1.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3346    0.6255    1.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729   -0.2284    0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0644   -0.5036   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -1.3274   -1.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155   -1.8726   -1.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3855   -1.6041    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.7871    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477   -0.5194    2.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4962   -0.5341    2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -1.3071    1.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -0.4417    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8873    0.7604    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467    1.3403   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801    0.7423   -1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5521    1.3465   -2.3197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1381   -0.4541   -1.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -1.0454   -0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -2.2425   -0.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583   -2.1422    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    0.0492   -1.1145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7427    3.0469   -0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396    2.2066   -2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3067    2.4874   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -0.1275   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0529    0.9311    0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2387   -0.6532    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0679    1.7949    1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    0.8372    2.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7507   -1.5226   -2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528   -2.5071   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -0.9593    3.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8381    0.5376    2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0806   -1.9684    2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590    1.2013    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1486    2.2942    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0153    2.2182   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2187   -0.9625   -2.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5018   -3.2002    0.8296 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
 24  2  1  0
 11  6  1  0
 23 14  1  0
 23 10  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  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      14.210  -2.981   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.005  -4.950   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.135  -2.654   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.599  -2.177   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.063  -6.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.594  -6.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.775  -2.277   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.307  -2.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.961  -5.190   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.180  -1.797   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.816  -4.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.745  -3.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.871  -3.523   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.435  -4.610   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.276  -3.044   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.499  -4.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.426  -4.713   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.339  -3.364   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.903  -4.450   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.934  -3.843   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.648  -4.637   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.712  -1.957   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.760  -5.482   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.030  -5.090   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3    4   11                                                       
CONECT    4    3   12                                                       
CONECT    5    6   14                                                       
CONECT    6    5   16                                                       
CONECT    7    8   13                                                       
CONECT    8    7   20                                                       
CONECT    9   11   17                                                       
CONECT   10   15   22                                                       
CONECT   11    3    9   21                                                  
CONECT   12    4   15   17                                                  
CONECT   13    7   16   18                                                  
CONECT   14    5   18   19                                                  
CONECT   15   10   12   19                                                  
CONECT   16    6   13   24                                                  
CONECT   17    9   12   23                                                  
CONECT   18   13   14   22                                                  
CONECT   19   14   15   23                                                  
CONECT   20    1    2    8   24                                             
CONECT   21   11                                                            
CONECT   22   10   18                                                       
CONECT   23   17   19                                                       
CONECT   24   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0041167
HETATM    1  C1  UNL     1       4.222   2.228  -1.004  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.052   0.881  -0.312  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.414   0.231  -0.079  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.482   1.151   1.029  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.335   0.625   1.372  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.573  -0.228   0.487  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.064  -0.504  -0.761  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.331  -1.327  -1.615  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.116  -1.873  -1.227  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.386  -1.604   0.020  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.362  -0.787   0.842  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.148  -0.519   2.097  1.00  0.00           O  
HETATM   13  C12 UNL     1      -1.496  -0.534   2.424  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.371  -1.307   1.494  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.239  -0.442   0.658  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.887   0.760   0.887  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.647   1.340  -0.102  1.00  0.00           C  
HETATM   18  C17 UNL     1      -4.780   0.742  -1.337  1.00  0.00           C  
HETATM   19  O2  UNL     1      -5.552   1.346  -2.320  1.00  0.00           O  
HETATM   20  C18 UNL     1      -4.138  -0.454  -1.573  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.364  -1.045  -0.565  1.00  0.00           C  
HETATM   22  O3  UNL     1      -2.625  -2.243  -0.564  1.00  0.00           O  
HETATM   23  C20 UNL     1      -1.658  -2.142   0.499  1.00  0.00           C  
HETATM   24  O4  UNL     1       3.265   0.049  -1.114  1.00  0.00           O  
HETATM   25  H1  UNL     1       3.743   3.047  -0.431  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.740   2.207  -2.003  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.307   2.487  -1.079  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.853  -0.128  -1.030  1.00  0.00           H  
HETATM   29  H5  UNL     1       6.053   0.931   0.475  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.239  -0.653   0.558  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.068   1.795   1.680  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.940   0.837   2.354  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.751  -1.523  -2.595  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.453  -2.507  -1.881  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.602  -0.959   3.442  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.838   0.538   2.477  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.081  -1.968   2.075  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.759   1.201   1.871  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.149   2.294   0.110  1.00  0.00           H  
HETATM   40  H16 UNL     1      -6.015   2.218  -2.137  1.00  0.00           H  
HETATM   41  H17 UNL     1      -4.219  -0.962  -2.542  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.502  -3.200   0.830  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   24
CONECT    3   28   29   30
CONECT    4    5    5   31
CONECT    5    6   32
CONECT    6    7    7   11
CONECT    7    8   24
CONECT    8    9    9   33
CONECT    9   10   34
CONECT   10   11   11   23
CONECT   11   12
CONECT   12   13
CONECT   13   14   35   36
CONECT   14   15   23   37
CONECT   15   16   16   21
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   20
CONECT   19   40
CONECT   20   21   21   41
CONECT   21   22
CONECT   22   23
CONECT   23   42
END

HMDB0041167
     RDKit          3D
(-)-Shinpterocarpin
 42 46  0  0  0  0  0  0  0  0999 V2000
    4.2225    2.2276   -1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0516    0.8809   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4144    0.2310   -0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819    1.1512    1.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3346    0.6255    1.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729   -0.2284    0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0644   -0.5036   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -1.3274   -1.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155   -1.8726   -1.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3855   -1.6041    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.7871    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477   -0.5194    2.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4962   -0.5341    2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -1.3071    1.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -0.4417    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8873    0.7604    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467    1.3403   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801    0.7423   -1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5521    1.3465   -2.3197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1381   -0.4541   -1.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -1.0454   -0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -2.2425   -0.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583   -2.1422    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    0.0492   -1.1145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7427    3.0469   -0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396    2.2066   -2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3067    2.4874   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -0.1275   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0529    0.9311    0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2387   -0.6532    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0679    1.7949    1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    0.8372    2.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7507   -1.5226   -2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528   -2.5071   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -0.9593    3.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8381    0.5376    2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0806   -1.9684    2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590    1.2013    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1486    2.2942    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0153    2.2182   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2187   -0.9625   -2.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5018   -3.2002    0.8296 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
 24  2  1  0
 11  6  1  0
 23 14  1  0
 23 10  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Shinpterocarpin	HMDB

Chemical Formula

C₂₀H₁₈O₄

Average Molecular Weight

322.3545

Monoisotopic Molecular Weight

322.120509064

IUPAC Name

17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),4(9),5,7,14(19),15,20-heptaen-6-ol

Traditional Name

17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),4(9),5,7,14(19),15,20-heptaen-6-ol

CAS Registry Number

157414-04-5

SMILES

CC1(C)OC2=C(C=C1)C1=C(C=C2)C2OC3=C(C=CC(O)=C3)C2CO1

InChI Identifier

InChI=1S/C20H18O4/c1-20(2)8-7-13-16(24-20)6-5-14-18(13)22-10-15-12-4-3-11(21)9-17(12)23-19(14)15/h3-9,15,19,21H,10H2,1-2H3

InChI Key

QGPHRCQDTPCIQI-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
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Coumaran
Benzofuran
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041167)
Cell membrane (HMDB: HMDB0041167)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041167)

Source

Exogenous

Exogenous (HMDB: HMDB0041167)

Food

Food (HMDB: HMDB0041167)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0041167)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041167)

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	0.0072 g/L	ALOGPS
logP	4.13	ALOGPS
logP	3.57	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.99 m³·mol⁻¹	ChemAxon
Polarizability	34.82 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]+	172.468	31661259
DarkChem	[M-H]-	174.107	31661259
DeepCCS	[M+H]+	179.483	30932474
DeepCCS	[M-H]-	177.122	30932474
DeepCCS	[M-2H]-	211.467	30932474
DeepCCS	[M+Na]+	186.644	30932474
AllCCS	[M+H]+	179.0	32859911
AllCCS	[M+H-H2O]+	175.5	32859911
AllCCS	[M+NH4]+	182.2	32859911
AllCCS	[M+Na]+	183.2	32859911
AllCCS	[M-H]-	184.0	32859911
AllCCS	[M+Na-2H]-	183.3	32859911
AllCCS	[M+HCOO]-	182.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Shinpterocarpin	CC1(C)OC2=C(C=C1)C1=C(C=C2)C2OC3=C(C=CC(O)=C3)C2CO1	3834.7	Standard polar	33892256
(-)-Shinpterocarpin	CC1(C)OC2=C(C=C1)C1=C(C=C2)C2OC3=C(C=CC(O)=C3)C2CO1	2776.3	Standard non polar	33892256
(-)-Shinpterocarpin	CC1(C)OC2=C(C=C1)C1=C(C=C2)C2OC3=C(C=CC(O)=C3)C2CO1	2984.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Shinpterocarpin,1TMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OCC2C4=CC=C(O[Si](C)(C)C)C=C4OC32)O1	2799.3	Semi standard non polar	33892256
(-)-Shinpterocarpin,1TBDMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OCC2C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4OC32)O1	3064.5	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 - (-)-Shinpterocarpin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ac0-1956000000-32b44fe3b629c95bbf3e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Shinpterocarpin GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-3759000000-7640ffa71a96ba5550ed	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Shinpterocarpin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Shinpterocarpin 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 - (-)-Shinpterocarpin 10V, Positive-QTOF	splash10-00fr-0719000000-ca2661321bf8ec415f15	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 20V, Positive-QTOF	splash10-06fr-1896000000-3bc14a4ada1da03c6523	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 40V, Positive-QTOF	splash10-014i-4900000000-c9c342bf72604ac0e1cf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 10V, Negative-QTOF	splash10-00di-0009000000-632d884e2f1281f9eeb5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 20V, Negative-QTOF	splash10-00di-0059000000-681ec9a85ffe1724e66e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 40V, Negative-QTOF	splash10-0a70-0190000000-0ba58c07ea4844b92d73	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 10V, Positive-QTOF	splash10-00di-0009000000-17eb34705e2ef23f703b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 20V, Positive-QTOF	splash10-00di-0019000000-e2c0e8f86ed078922027	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 40V, Positive-QTOF	splash10-00kb-2985000000-10c3568e8c9bccf00861	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 10V, Negative-QTOF	splash10-00di-0009000000-a4f58630e05faac231a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 20V, Negative-QTOF	splash10-00di-0079000000-8fe1f3f07e4a4ffbd391	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Shinpterocarpin 40V, Negative-QTOF	splash10-00fr-2298000000-7f8e5ea1034f0f7380a0	2021-09-23	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

FDB021058

KNApSAcK ID

C00018979

Chemspider ID

35015118

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85114192

PDB ID

Not Available

ChEBI ID

175114

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1890151

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 (-)-Shinpterocarpin (HMDB0041167)

MOL for HMDB0041167 ((-)-Shinpterocarpin)

3D MOL for HMDB0041167 ((-)-Shinpterocarpin)

3D SDF for HMDB0041167 ((-)-Shinpterocarpin)

3D-SDF for HMDB0041167 ((-)-Shinpterocarpin)

PDB for HMDB0041167 ((-)-Shinpterocarpin)

3D PDB for HMDB0041167 ((-)-Shinpterocarpin)

SMILES for HMDB0041167 ((-)-Shinpterocarpin)

INCHI for HMDB0041167 ((-)-Shinpterocarpin)

Structure for HMDB0041167 ((-)-Shinpterocarpin)

3D Structure for HMDB0041167 ((-)-Shinpterocarpin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra