NP-MRD: Showing NP-Card for Phebaclavin F (NP0001523)

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Record Information

Version

2.0

Created at

2020-08-25 00:17:29 UTC

Updated at

2021-08-10 02:54:57 UTC

NP-MRD ID

NP0001523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phebaclavin F

Description

Methyl (2E)-4-(7,8-dihydroxy-2-oxo-2H-chromen-3-yl)-4-hydroxy-2-methylbut-2-enoate belongs to the class of organic compounds known as 7,8-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively. Phebaclavin F is found in Phebalium clavatum. Based on a literature review very few articles have been published on methyl (2E)-4-(7,8-dihydroxy-2-oxo-2H-chromen-3-yl)-4-hydroxy-2-methylbut-2-enoate.

Structure

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


  Mrv1652308252002172D          

 36 37  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 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
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -0.4125    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
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  7 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
M  END

NP0001523
     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    5.9455   -1.9860    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411   -1.1697   -0.2812 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8228   -0.7992    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5487   -1.2044    1.4127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    0.0550   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    0.5066   -1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299    0.4289   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841    1.2855   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    2.5929   -0.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6159    1.0701   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0865   -0.2178   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135   -0.4157    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9130   -1.7031    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2297   -1.8870    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0498   -0.7995    0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3868   -1.0144    1.2472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414    0.4627    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3577    1.5572    0.9236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2239    0.6796    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    1.8856    0.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5015    2.1007   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0490    3.2771   -0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377   -2.8186   -0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5219   -2.4000    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8446   -1.3443    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3838    0.4113   -2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7938   -0.1187   -2.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247    1.5962   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4679    0.0900    0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8975    1.0294   -1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701    3.0793   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4389   -1.0853   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2492   -2.5333    0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6453   -2.8958    0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9899   -0.2131    1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0472    2.4978    0.8233 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
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 10  1  0
 19 12  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
  9 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 18 36  1  0
M  END


  Mrv1652308252002172D          

 36 37  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 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
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -0.4125    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
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  7 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001523

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O7/c1-7(14(19)21-2)5-11(17)9-6-8-3-4-10(16)12(18)13(8)22-15(9)20/h3-6,11,16-18H,1-2H3/b7-5+

> <INCHI_KEY>
WEUHPGXFFBPCGM-FNORWQNLSA-N

> <FORMULA>
C15H14O7

> <MOLECULAR_WEIGHT>
306.27

> <EXACT_MASS>
306.073952791

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.340794130570366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
1.9329414526666664

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.022998518423535

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.982501617222599

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2968257657395164

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
76.91690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001523
     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    5.9455   -1.9860    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411   -1.1697   -0.2812 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8228   -0.7992    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5487   -1.2044    1.4127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    0.0550   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    0.5066   -1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299    0.4289   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841    1.2855   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    2.5929   -0.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6159    1.0701   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0865   -0.2178   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135   -0.4157    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9130   -1.7031    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2297   -1.8870    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0498   -0.7995    0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3868   -1.0144    1.2472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414    0.4627    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3577    1.5572    0.9236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2239    0.6796    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    1.8856    0.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5015    2.1007   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0490    3.2771   -0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377   -2.8186   -0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5219   -2.4000    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8446   -1.3443    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3838    0.4113   -2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7938   -0.1187   -2.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247    1.5962   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4679    0.0900    0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8975    1.0294   -1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701    3.0793   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4389   -1.0853   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2492   -2.5333    0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6453   -2.8958    0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9899   -0.2131    1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0472    2.4978    0.8233 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
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 10  1  0
 19 12  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
  9 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 18 36  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  H   UNK     0      -1.334  -5.390   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       0.000   1.540   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      -2.667   0.000   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       2.667   1.540   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       8.208  -0.770   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       4.001   2.310   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       9.542   6.160   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       8.002   7.700   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.462   6.160   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0       7.232   0.206   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       9.336   0.770   0.000  0.00  0.00           H+0
HETATM   36  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   11                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8   18                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3   12                                                  
CONECT   12   11                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    7                                                       
CONECT   19   15   20   21   23                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   19   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   33                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   25   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

COMPND    NP0001523
HETATM    1  C1  UNL     1       5.945  -1.986   0.435  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.041  -1.170  -0.281  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.823  -0.799   0.271  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.549  -1.204   1.413  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.897   0.055  -0.501  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.280   0.507  -1.856  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.730   0.429  -0.011  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.784   1.285  -0.766  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.204   2.593  -0.619  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.616   1.070  -0.376  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.086  -0.218  -0.227  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.414  -0.416   0.142  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.913  -1.703   0.300  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.230  -1.887   0.666  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.050  -0.800   0.875  1.00  0.00           C  
HETATM   16  O4  UNL     1      -6.387  -1.014   1.247  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.541   0.463   0.715  1.00  0.00           C  
HETATM   18  O5  UNL     1      -5.358   1.557   0.924  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.224   0.680   0.349  1.00  0.00           C  
HETATM   20  O6  UNL     1      -2.756   1.886   0.201  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.501   2.101  -0.148  1.00  0.00           C  
HETATM   22  O7  UNL     1      -1.049   3.277  -0.291  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.338  -2.819  -0.207  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.522  -2.400   1.356  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.845  -1.344   0.654  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.384   0.411  -2.029  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.794  -0.119  -2.634  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.025   1.596  -1.995  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.468   0.090   0.979  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.897   1.029  -1.860  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.970   3.079  -1.449  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.439  -1.085  -0.392  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.249  -2.533   0.130  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.645  -2.896   0.796  1.00  0.00           H  
HETATM   35  H13 UNL     1      -6.990  -0.213   1.401  1.00  0.00           H  
HETATM   36  H14 UNL     1      -5.047   2.498   0.823  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   10   30
CONECT    9   31
CONECT   10   11   11   21
CONECT   11   12   32
CONECT   12   13   13   19
CONECT   13   14   33
CONECT   14   15   15   34
CONECT   15   16   17
CONECT   16   35
CONECT   17   18   19   19
CONECT   18   36
CONECT   19   20
CONECT   20   21
CONECT   21   22   22
END

NP0001523
     RDKit          3D

36 37  0  0  0  0  0  0  0  0999 V2000
    5.9455   -1.9860    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411   -1.1697   -0.2812 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8228   -0.7992    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5487   -1.2044    1.4127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    0.0550   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    0.5066   -1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299    0.4289   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841    1.2855   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    2.5929   -0.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6159    1.0701   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0865   -0.2178   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135   -0.4157    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9130   -1.7031    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2297   -1.8870    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0498   -0.7995    0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3868   -1.0144    1.2472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414    0.4627    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3577    1.5572    0.9236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2239    0.6796    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    1.8856    0.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5015    2.1007   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0490    3.2771   -0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377   -2.8186   -0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5219   -2.4000    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8446   -1.3443    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3838    0.4113   -2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7938   -0.1187   -2.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247    1.5962   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4679    0.0900    0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8975    1.0294   -1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701    3.0793   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4389   -1.0853   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2492   -2.5333    0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6453   -2.8958    0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9899   -0.2131    1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0472    2.4978    0.8233 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
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 10  1  0
 19 12  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
  9 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 18 36  1  0
M  END

View in JSmol

Synonyms

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

Chemical Formula

C₁₅H₁₄O₇

Average Mass

306.2700 Da

Monoisotopic Mass

306.07395 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H14O7/c1-7(14(19)21-2)5-11(17)9-6-8-3-4-10(16)12(18)13(8)22-15(9)20/h3-6,11,16-18H,1-2H3/b7-5+

InChI Key

WEUHPGXFFBPCGM-FNORWQNLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300Mz MHz, Methanol, 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, Methanol, simulated)	rgf8b@missouri.edu	Not Available	Not Available	2020-08-25	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Phebalium clavatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,8-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7,8-dihydroxycoumarins

Alternative Parents

Substituents

7,8-dihydroxycoumarin
7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Pyranone
Fatty acyl
Benzenoid
Pyran
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic alcohol
Alcohol
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	1.61	ALOGPS
logP	1.93	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.92 m³·mol⁻¹	ChemAxon
Polarizability	29.34 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

Not Available

Chemspider ID

9067377

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10892114

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phebaclavin F (NP0001523)

MOL for NP0001523 (Phebaclavin F)

3D MOL for NP0001523 (Phebaclavin F)

3D SDF for NP0001523 (Phebaclavin F)

3D-SDF for NP0001523 (Phebaclavin F)

PDB for NP0001523 (Phebaclavin F)

3D PDB for NP0001523 (Phebaclavin F)

SMILES for NP0001523 (Phebaclavin F)

INCHI for NP0001523 (Phebaclavin F)

Structure for NP0001523 (Phebaclavin F)

3D Structure for NP0001523 (Phebaclavin F)