NP-MRD: Showing NP-Card for Phebaclavin B (NP0001519)

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Record Information

Version

2.0

Created at

2020-08-24 23:24:16 UTC

Updated at

2021-08-10 02:54:55 UTC

NP-MRD ID

NP0001519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phebaclavin B

Description

Methyl (2E)-4-(7-hydroxy-8-methoxy-2-oxo-2H-chromen-3-yl)-2-methylbut-2-enoate belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Based on a literature review very few articles have been published on methyl (2E)-4-(7-hydroxy-8-methoxy-2-oxo-2H-chromen-3-yl)-2-methylbut-2-enoate.

Structure

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


  Mrv1652308252001242D          

 38 39  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.1730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3112   -0.6893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6815   -0.0480    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 10 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
M  END

NP0001519
     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    6.0733    1.7045   -1.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2509    1.3310   -0.7062 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831    0.4704   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    0.0027   -2.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681    0.1108    0.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7177    0.6615    1.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -0.7058    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -1.1132    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -0.8063    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -1.8328    0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -1.5149    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0323   -2.5253    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548   -2.2643   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7797   -0.9603   -0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1213   -0.6905   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9427    0.0737    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935    1.3797    0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3312    2.2098   -0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6001   -0.2143    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7728    0.7402    0.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4953    0.4592    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925    1.4023    1.4587 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159    2.7454   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9374    1.0038   -1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4251    1.6792   -2.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6819    1.2173    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8426   -0.1754    2.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9551    1.3876    1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -1.0863   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347   -2.2156    1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7857   -0.6463    2.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4353   -2.8298    0.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6279   -3.5249   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0597   -3.0480   -0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4719    0.2538   -0.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8136    1.7352   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8809    3.1723   -0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560    2.4137   -0.9758 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
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  9  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END


  Mrv1652308252001242D          

 38 39  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.1730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3112   -0.6893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6815   -0.0480    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 10 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001519

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-9(15(18)21-3)4-5-11-8-10-6-7-12(17)14(20-2)13(10)22-16(11)19/h4,6-8,17H,5H2,1-3H3/b9-4+

> <INCHI_KEY>
VOYTXVCFUOMPAS-RUDMXATFSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.48602379956919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-4-(7-hydroxy-8-methoxy-2-oxo-2H-chromen-3-yl)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.503739115666666

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.358792305443307

> <JCHEM_PKA_STRONGEST_BASIC>
-4.96153381537874

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
80.03769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-4-(7-hydroxy-8-methoxy-2-oxochromen-3-yl)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001519
     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    6.0733    1.7045   -1.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2509    1.3310   -0.7062 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831    0.4704   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    0.0027   -2.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681    0.1108    0.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7177    0.6615    1.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -0.7058    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -1.1132    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -0.8063    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -1.8328    0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -1.5149    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0323   -2.5253    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548   -2.2643   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7797   -0.9603   -0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1213   -0.6905   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9427    0.0737    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935    1.3797    0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3312    2.2098   -0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6001   -0.2143    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7728    0.7402    0.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4953    0.4592    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925    1.4023    1.4587 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159    2.7454   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9374    1.0038   -1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4251    1.6792   -2.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6819    1.2173    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8426   -0.1754    2.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9551    1.3876    1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -1.0863   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347   -2.2156    1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7857   -0.6463    2.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4353   -2.8298    0.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6279   -3.5249   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0597   -3.0480   -0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4719    0.2538   -0.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8136    1.7352   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8809    3.1723   -0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560    2.4137   -0.9758 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
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  9  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 25-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-AUG-20         0                                  
HETATM    1  H   UNK     0      -4.001  -2.310   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       0.564  -6.724   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0       2.667  -6.160   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0       2.104  -4.056   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       0.000   1.540   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      -2.667   0.000   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       2.667   1.540   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       6.181  -1.287   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       6.872  -0.090   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       4.001   2.310   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       9.542   6.160   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.002   7.700   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.462   6.160   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0       7.232   0.206   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       9.336   0.770   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       8.772   2.874   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    4   11   21                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    3   15                                                  
CONECT   15   14                                                            
CONECT   16   11   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   10                                                       
CONECT   22   18   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   35                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   27   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

COMPND    NP0001519
HETATM    1  C1  UNL     1       6.073   1.704  -1.820  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.251   1.331  -0.706  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.183   0.470  -0.870  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.926   0.003  -2.029  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.368   0.111   0.284  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.718   0.661   1.601  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.336  -0.706   0.188  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.467  -1.113   1.304  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.029  -0.806   1.025  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.843  -1.833   0.648  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.157  -1.515   0.394  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.032  -2.525   0.019  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.355  -2.264  -0.246  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.780  -0.960  -0.125  1.00  0.00           C  
HETATM   15  O3  UNL     1      -6.121  -0.690  -0.393  1.00  0.00           O  
HETATM   16  C13 UNL     1      -3.943   0.074   0.245  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.393   1.380   0.359  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.331   2.210  -0.782  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.600  -0.214   0.510  1.00  0.00           C  
HETATM   20  O5  UNL     1      -1.773   0.740   0.864  1.00  0.00           O  
HETATM   21  C16 UNL     1      -0.495   0.459   1.115  1.00  0.00           C  
HETATM   22  O6  UNL     1       0.292   1.402   1.459  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.416   2.745  -1.569  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.937   1.004  -1.897  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.425   1.679  -2.713  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.682   1.217   1.591  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.843  -0.175   2.323  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.955   1.388   1.905  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.148  -1.086  -0.825  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.535  -2.216   1.481  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.786  -0.646   2.271  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.435  -2.830   0.576  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.628  -3.525  -0.054  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.060  -3.048  -0.543  1.00  0.00           H  
HETATM   35  H13 UNL     1      -6.472   0.254  -0.315  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.814   1.735  -1.667  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.881   3.172  -0.579  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.256   2.414  -0.976  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    7    7
CONECT    6   26   27   28
CONECT    7    8   29
CONECT    8    9   30   31
CONECT    9   10   10   21
CONECT   10   11   32
CONECT   11   12   12   19
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   16
CONECT   15   35
CONECT   16   17   19   19
CONECT   17   18
CONECT   18   36   37   38
CONECT   19   20
CONECT   20   21
CONECT   21   22   22
END

NP0001519
     RDKit          3D

38 39  0  0  0  0  0  0  0  0999 V2000
    6.0733    1.7045   -1.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2509    1.3310   -0.7062 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831    0.4704   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    0.0027   -2.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681    0.1108    0.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7177    0.6615    1.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -0.7058    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -1.1132    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -0.8063    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -1.8328    0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -1.5149    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0323   -2.5253    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548   -2.2643   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7797   -0.9603   -0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1213   -0.6905   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9427    0.0737    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935    1.3797    0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3312    2.2098   -0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6001   -0.2143    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7728    0.7402    0.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4953    0.4592    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925    1.4023    1.4587 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159    2.7454   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9374    1.0038   -1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4251    1.6792   -2.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6819    1.2173    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8426   -0.1754    2.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9551    1.3876    1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -1.0863   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347   -2.2156    1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7857   -0.6463    2.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4353   -2.8298    0.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6279   -3.5249   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0597   -3.0480   -0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4719    0.2538   -0.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8136    1.7352   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8809    3.1723   -0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560    2.4137   -0.9758 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
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  9  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl (2E)-4-(7-hydroxy-8-methoxy-2-oxo-2H-chromen-3-yl)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

methyl (2E)-4-(7-hydroxy-8-methoxy-2-oxo-2H-chromen-3-yl)-2-methylbut-2-enoate

Traditional Name

methyl (2E)-4-(7-hydroxy-8-methoxy-2-oxochromen-3-yl)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H16O6/c1-9(15(18)21-3)4-5-11-8-10-6-7-12(17)14(20-2)13(10)22-16(11)19/h4,6-8,17H,5H2,1-3H3/b9-4+

InChI Key

VOYTXVCFUOMPAS-RUDMXATFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300Mz MHz, CDCL3, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300Mz, CDCL3, simulated)	rgf8b@missouri.edu	Not Available	Not Available	2020-08-24	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Phebalium clavatum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

7-hydroxycoumarin
Benzopyran
1-benzopyran
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Fatty acid ester
Pyranone
Fatty acyl
Benzenoid
Pyran
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

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	2.89	ALOGPS
logP	2.5	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.36	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.04 m³·mol⁻¹	ChemAxon
Polarizability	30.49 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045363

Chemspider ID

9165529

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10990334

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Phebaclavin B (NP0001519)

MOL for NP0001519 (Phebaclavin B)

3D MOL for NP0001519 (Phebaclavin B)

3D SDF for NP0001519 (Phebaclavin B)

3D-SDF for NP0001519 (Phebaclavin B)

PDB for NP0001519 (Phebaclavin B)

3D PDB for NP0001519 (Phebaclavin B)

SMILES for NP0001519 (Phebaclavin B)

INCHI for NP0001519 (Phebaclavin B)

Structure for NP0001519 (Phebaclavin B)

3D Structure for NP0001519 (Phebaclavin B)