NP-MRD: Showing NP-Card for pratensein (NP0037430)

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Record Information

Version

2.0

Created at

2021-06-20 20:21:23 UTC

Updated at

2021-06-30 00:09:38 UTC

NP-MRD ID

NP0037430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pratensein

Provided By

JEOL Database JEOL Logo

Description

Pratensein, also known as 4776B compound, belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Pratensein has been detected, but not quantified in, a few different foods, such as chickpeas (Cicer arietinum), peanuts (Arachis hypogaea), and pulses. This could make pratensein a potential biomarker for the consumption of these foods. Pratensein is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. pratensein is found in Ammopiptanthus mongolicus, Andira inermis, Andira surinamensis, Astragalus mongholicus, Bolusanthus speciosus, Rosulabryum capillare, Cicer nuristanicum, Cicer pungens, Cicer songaricum, Dalbergia sissoo, Dermatophyllum secundiflorum, Echinosophora koreensis, Iris pseudacorus, Inula britannica , Sophora japonica and Trifolium repens . pratensein was first documented in 2009 (PMID: 19571401). Based on a literature review a small amount of articles have been published on Pratensein (PMID: 23030687) (PMID: 19637114) (PMID: 22494026) (PMID: 29349861).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122213D          

 34 36  0  0  0  0            999 V2000
    5.1231    3.4680    3.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    3.8160    3.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    3.0145    2.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776    1.9149    1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    1.1857    0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471    1.5412    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    0.7648    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    1.3803   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621    0.7844   -1.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -0.5840   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0568   -1.1728   -2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -2.5585   -2.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -3.0938   -2.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -3.3665   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -2.7718   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966   -3.6168    0.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1727   -1.3787   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162   -0.7228    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6694   -1.4098    0.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792    2.6452    1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5527    3.3641    2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    4.4387    3.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527    4.1869    3.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819    2.4709    3.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412    3.5412    2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3096    1.5904    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6225    0.3268    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0328    2.4553   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -0.5580   -2.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -4.0618   -2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -4.4478   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582   -3.0685    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593    2.9516    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    4.7869    3.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0  0  0  0
 15 14  2  0  0  0  0
  6 20  2  0  0  0  0
 17 15  1  0  0  0  0
 20 21  1  0  0  0  0
 14 12  1  0  0  0  0
 21  3  2  0  0  0  0
  3  4  1  0  0  0  0
 12 11  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12 13  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 10  9  1  0  0  0  0
  3  2  1  0  0  0  0
  9  8  1  0  0  0  0
  2  1  1  0  0  0  0
  8  7  2  0  0  0  0
 15 16  1  0  0  0  0
  7 18  1  0  0  0  0
 21 22  1  0  0  0  0
 14 31  1  0  0  0  0
 11 29  1  0  0  0  0
  8 28  1  0  0  0  0
 20 33  1  0  0  0  0
  4 26  1  0  0  0  0
  5 27  1  0  0  0  0
 13 30  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 16 32  1  0  0  0  0
 22 34  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    5.1231    3.4680    3.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    3.8160    3.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    3.0145    2.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776    1.9149    1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    1.1857    0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471    1.5412    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    0.7648    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    1.3803   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621    0.7844   -1.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -0.5840   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0568   -1.1728   -2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -2.5585   -2.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -3.0938   -2.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -3.3665   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -2.7718   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966   -3.6168    0.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1727   -1.3787   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162   -0.7228    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6694   -1.4098    0.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792    2.6452    1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5527    3.3641    2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    4.4387    3.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527    4.1869    3.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819    2.4709    3.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412    3.5412    2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3096    1.5904    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6225    0.3268    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0328    2.4553   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -0.5580   -2.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -4.0618   -2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -4.4478   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582   -3.0685    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593    2.9516    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    4.7869    3.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0
 15 14  2  0
  6 20  2  0
 17 15  1  0
 20 21  1  0
 14 12  1  0
 21  3  2  0
  3  4  1  0
 12 11  2  0
  4  5  2  0
  5  6  1  0
  7  6  1  0
 11 10  1  0
 12 13  1  0
 17 18  1  0
 18 19  2  0
 10  9  1  0
  3  2  1  0
  9  8  1  0
  2  1  1  0
  8  7  2  0
 15 16  1  0
  7 18  1  0
 21 22  1  0
 14 31  1  0
 11 29  1  0
  8 28  1  0
 20 33  1  0
  4 26  1  0
  5 27  1  0
 13 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 16 32  1  0
 22 34  1  0
M  END


  Mrv1652306202122213D          

 34 36  0  0  0  0            999 V2000
    5.1231    3.4680    3.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    3.8160    3.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    3.0145    2.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776    1.9149    1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    1.1857    0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471    1.5412    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    0.7648    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    1.3803   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621    0.7844   -1.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -0.5840   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0568   -1.1728   -2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -2.5585   -2.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -3.0938   -2.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -3.3665   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -2.7718   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966   -3.6168    0.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1727   -1.3787   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162   -0.7228    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6694   -1.4098    0.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792    2.6452    1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5527    3.3641    2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    4.4387    3.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527    4.1869    3.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819    2.4709    3.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412    3.5412    2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3096    1.5904    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6225    0.3268    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0328    2.4553   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -0.5580   -2.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -4.0618   -2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -4.4478   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582   -3.0685    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593    2.9516    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    4.7869    3.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0  0  0  0
 15 14  2  0  0  0  0
  6 20  2  0  0  0  0
 17 15  1  0  0  0  0
 20 21  1  0  0  0  0
 14 12  1  0  0  0  0
 21  3  2  0  0  0  0
  3  4  1  0  0  0  0
 12 11  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12 13  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 10  9  1  0  0  0  0
  3  2  1  0  0  0  0
  9  8  1  0  0  0  0
  2  1  1  0  0  0  0
  8  7  2  0  0  0  0
 15 16  1  0  0  0  0
  7 18  1  0  0  0  0
 21 22  1  0  0  0  0
 14 31  1  0  0  0  0
 11 29  1  0  0  0  0
  8 28  1  0  0  0  0
 20 33  1  0  0  0  0
  4 26  1  0  0  0  0
  5 27  1  0  0  0  0
 13 30  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 16 32  1  0  0  0  0
 22 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(O[H])=C1[H])C(=O)C(=C([H])O2)C1=C([H])C(O[H])=C(OC([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3

> <INCHI_KEY>
FPIOBTBNRZPWJW-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.53648605717334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.9192011239999993

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.113371588850987

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.54659919653317

> <JCHEM_PKA_STRONGEST_BASIC>
-4.765626247355578

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1461

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pratensein

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    5.1231    3.4680    3.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    3.8160    3.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    3.0145    2.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776    1.9149    1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    1.1857    0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471    1.5412    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    0.7648    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    1.3803   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621    0.7844   -1.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -0.5840   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0568   -1.1728   -2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -2.5585   -2.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -3.0938   -2.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -3.3665   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -2.7718   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966   -3.6168    0.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1727   -1.3787   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162   -0.7228    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6694   -1.4098    0.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792    2.6452    1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5527    3.3641    2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    4.4387    3.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527    4.1869    3.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819    2.4709    3.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412    3.5412    2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3096    1.5904    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6225    0.3268    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0328    2.4553   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -0.5580   -2.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -4.0618   -2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -4.4478   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582   -3.0685    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593    2.9516    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    4.7869    3.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0
 15 14  2  0
  6 20  2  0
 17 15  1  0
 20 21  1  0
 14 12  1  0
 21  3  2  0
  3  4  1  0
 12 11  2  0
  4  5  2  0
  5  6  1  0
  7  6  1  0
 11 10  1  0
 12 13  1  0
 17 18  1  0
 18 19  2  0
 10  9  1  0
  3  2  1  0
  9  8  1  0
  2  1  1  0
  8  7  2  0
 15 16  1  0
  7 18  1  0
 21 22  1  0
 14 31  1  0
 11 29  1  0
  8 28  1  0
 20 33  1  0
  4 26  1  0
  5 27  1  0
 13 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 16 32  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       5.123   3.468   3.094  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.743   3.816   3.103  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.905   3.014   2.372  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.278   1.915   1.604  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.304   1.186   0.905  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.947   1.541   0.961  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.064   0.765   0.220  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.976   1.380  -0.551  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.962   0.784  -1.299  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.045  -0.584  -1.272  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.057  -1.173  -2.031  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.187  -2.559  -2.043  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.189  -3.094  -2.798  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.324  -3.366  -1.309  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.315  -2.772  -0.553  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.497  -3.617   0.148  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.173  -1.379  -0.532  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.116  -0.723   0.256  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.669  -1.410   0.903  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.579   2.645   1.741  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.553   3.364   2.428  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.151   4.439   3.176  0.00  0.00           O+0
HETATM   23  H   UNK     0       5.653   4.187   3.727  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.282   2.471   3.518  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.541   3.541   2.084  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.310   1.590   1.524  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.623   0.327   0.316  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.033   2.455  -0.680  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.740  -0.558  -2.611  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.166  -4.062  -2.709  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.417  -4.448  -1.312  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.158  -3.068   0.638  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.459   2.952   1.833  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.971   4.787   3.577  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    3    1                                                       
CONECT    3   21    4    2                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6   27                                                  
CONECT    6   20    5    7                                                  
CONECT    7    6    8   18                                                  
CONECT    8    9    7   28                                                  
CONECT    9   10    8                                                       
CONECT   10   17   11    9                                                  
CONECT   11   12   10   29                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12   30                                                       
CONECT   14   15   12   31                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15   32                                                       
CONECT   17   10   15   18                                                  
CONECT   18   17   19    7                                                  
CONECT   19   18                                                            
CONECT   20    6   21   33                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21   34                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28    8                                                            
CONECT   29   11                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   16                                                            
CONECT   33   20                                                            
CONECT   34   22                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
    5.1231    3.4680    3.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    3.8160    3.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    3.0145    2.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776    1.9149    1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    1.1857    0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471    1.5412    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    0.7648    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    1.3803   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621    0.7844   -1.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -0.5840   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0568   -1.1728   -2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -2.5585   -2.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -3.0938   -2.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -3.3665   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -2.7718   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966   -3.6168    0.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1727   -1.3787   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162   -0.7228    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6694   -1.4098    0.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792    2.6452    1.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5527    3.3641    2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    4.4387    3.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527    4.1869    3.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819    2.4709    3.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412    3.5412    2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3096    1.5904    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6225    0.3268    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0328    2.4553   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -0.5580   -2.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -4.0618   -2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -4.4478   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582   -3.0685    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593    2.9516    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    4.7869    3.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0
 15 14  2  0
  6 20  2  0
 17 15  1  0
 20 21  1  0
 14 12  1  0
 21  3  2  0
  3  4  1  0
 12 11  2  0
  4  5  2  0
  5  6  1  0
  7  6  1  0
 11 10  1  0
 12 13  1  0
 17 18  1  0
 18 19  2  0
 10  9  1  0
  3  2  1  0
  9  8  1  0
  2  1  1  0
  8  7  2  0
 15 16  1  0
  7 18  1  0
 21 22  1  0
 14 31  1  0
 11 29  1  0
  8 28  1  0
 20 33  1  0
  4 26  1  0
  5 27  1  0
 13 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 16 32  1  0
 22 34  1  0
M  END

View in JSmol

Synonyms

Value	Source
3',5,7-Trihydroxy-4'-methoxyisoflavone	ChEBI
3'-Hydroxy-biochanin a	ChEBI
3'-Hydroxybiochanin a	ChEBI
5,7,3'-Trihydroxy-4'-methoxyisoflavone	ChEBI
5,7-Dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
4776b Compound	HMDB
4'-Methoxy-3',5,7-trihydroxyisoflavone	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2629 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

pratensein

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C(O[H])=C1[H])C(=O)C(=C([H])O2)C1=C([H])C(O[H])=C(OC([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3

InChI Key

FPIOBTBNRZPWJW-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ammopiptanthus mongolicus	LOTUS Database	35616633
Andira inermis	LOTUS Database	35616633
Andira surinamensis	JEOL database	Almeida, J. G. L., et al, Magn. Reson. Chem. 46, 103 (2008)
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Astragalus mongholicus	LOTUS Database	35616633
Bolusanthus speciosus	LOTUS Database	35616633
Bryum capillare	LOTUS Database	35616633
Cicer arietinum	KNApSAcK Database	22123792
Cicer nuristanicum	LOTUS Database	35616633
Cicer pungens	LOTUS Database	35616633
Cicer songaricum	LOTUS Database	35616633
Dalbergia parviflora	KNApSAcK Database	22123792
Dalbergia sissoo	LOTUS Database	35616633
Dermatophyllum secundiflorum	LOTUS Database	35616633
Echinosophora koreensis	LOTUS Database	35616633
Glycyrrhiza glabra	KNApSAcK Database	22123792
Glycyrrhiza inflata	KNApSAcK Database	22123792
Glycyrrhiza uralensis	KNApSAcK Database	22123792
Inula britannica	KNApSAcK Database	22123792
Inula britannica var.chinensis	KNApSAcK Database	22123792
Iris pseudacorus	LOTUS Database	35616633
Medicago truncatula	KNApSAcK Database	22123792
Monopteryx inpae	KNApSAcK Database	22123792
Pentanema britannicum	Plant	KNApSAcK
Sophora japonica	KNApSAcK Database	22123792
Sophora secundiflora	KNApSAcK Database	22123792
Styphnolobium japonicum	Plant	KNApSAcK
Thermopsis spp.	KNApSAcK Database	22123792
Trifolium pratense	KNApSAcK Database	22123792
Trifolium repens	Plant	KNApSAcK
Trifolium subterraneum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.05	ALOGPS
logP	2.92	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.55	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.15 m³·mol⁻¹	ChemAxon
Polarizability	29.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030617

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Pratensein

METLIN ID

Not Available

PubChem Compound

5281803

PDB ID

Not Available

ChEBI ID

8359

Good Scents ID

Not Available

References

General References

Shajib MT, Pedersen HA, Mortensen AG, Kudsk P, Fomsgaard IS: Phytotoxic effect, uptake, and transformation of biochanin A in selected weed species. J Agric Food Chem. 2012 Oct 31;60(43):10715-22. doi: 10.1021/jf3023589. Epub 2012 Oct 18. [PubMed:23030687 ]
Yang Y, Jiang W, Wang L, Zhang ZB, Si SY, Hong B: Characterization of the isoflavone pratensein as a novel transcriptional up-regulator of scavenger receptor class B type I in HepG2 cells. Biol Pharm Bull. 2009 Jul;32(7):1289-94. doi: 10.1248/bpb.32.1289. [PubMed:19571401 ]
Chen QC, Zhang WY, Jin W, Lee IS, Min BS, Jung HJ, Na M, Lee S, Bae K: Flavonoids and isoflavonoids from Sophorae Flos improve glucose uptake in vitro. Planta Med. 2010 Jan;76(1):79-81. doi: 10.1055/s-0029-1185944. Epub 2009 Jul 27. [PubMed:19637114 ]
Li X, Zhang SD, Jin HZ, Dong F, Shan L, Zhang WD: A new flavonol from Oxytropis ochrocephala Bunge. Nat Prod Res. 2013;27(6):554-7. doi: 10.1080/14786419.2012.678350. Epub 2012 Apr 11. [PubMed:22494026 ]
Du G, Fu L, Jia J, Pang X, Yu H, Zhang Y, Fan G, Gao X, Han L: Validated UPLC-MS/MS method for quantification of seven compounds in rat plasma and tissues: Application to pharmacokinetic and tissue distribution studies in rats after oral administration of extract of Eclipta prostrata L. Biomed Chromatogr. 2018 Jun;32(6):e4191. doi: 10.1002/bmc.4191. Epub 2018 Feb 27. [PubMed:29349861 ]
Almeida, J. G. L., et al. (2008). Almeida, J. G. L., et al, Magn. Reson. Chem. 46, 103 (2008). Mag. Reson. Chem..

Showing NP-Card for pratensein (NP0037430)

MOL for NP0037430 (pratensein)

3D MOL for NP0037430 (pratensein)

3D SDF for NP0037430 (pratensein)

3D-SDF for NP0037430 (pratensein)

PDB for NP0037430 (pratensein)

3D PDB for NP0037430 (pratensein)

SMILES for NP0037430 (pratensein)

INCHI for NP0037430 (pratensein)

Structure for NP0037430 (pratensein)

3D Structure for NP0037430 (pratensein)