NP-MRD: Showing NP-Card for Phebaclavin D (NP0001521)

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Record Information

Version

2.0

Created at

2020-08-24 23:51:20 UTC

Updated at

2021-08-10 02:54:56 UTC

NP-MRD ID

NP0001521

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phebaclavin D

Description

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

Structure

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


  Mrv1652308252001512D          

 39 40  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   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
   -2.5559    0.3020    0.0000 H   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
   -1.7309   -1.1270    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
   -1.4289   -1.6500    0.0000 H   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 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
    1.4289   -0.0000    0.0000 O   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
    2.8579   -0.0000    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   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
    3.2704   -3.1895    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   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -1.9520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177   -0.5230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -2.4750    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  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
M  END

NP0001521
     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    6.7798    1.0576    1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8560    0.4097    0.4318 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957    0.6699    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0837    1.5206    1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6166   -0.0399   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1701   -1.0422   -1.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3117    0.1475   -0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.5759   -1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311    0.0680   -2.6949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -0.6364   -1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705    0.4386   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932    0.2703   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7523    1.3071    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0693    1.1544    0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6762   -0.0779    0.6392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0196   -0.2296    1.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7254    0.8780    1.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9535   -1.1391    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5342   -2.3915    0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -0.9600   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9074   -1.9480   -0.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6443   -1.8303   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758   -2.8779   -1.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7007    0.4365    1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3403    1.2780    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0383    2.0375    0.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735   -0.7875   -2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2768   -1.0694   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094   -2.0681   -1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778    0.8635    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.6058   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606    0.6933   -2.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006    1.3840   -0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816    2.2731    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497    1.9961    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9152    1.6496    0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6902    0.5137    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1956    1.3971    2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0164   -3.1646   -0.3580 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
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 10  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
M  END


  Mrv1652308252001512D          

 39 40  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   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
   -2.5559    0.3020    0.0000 H   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
   -1.7309   -1.1270    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
   -1.4289   -1.6500    0.0000 H   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 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
    1.4289   -0.0000    0.0000 O   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
    2.8579   -0.0000    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   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
    3.2704   -3.1895    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   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -1.9520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177   -0.5230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -2.4750    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  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001521

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C2=C1OC(=O)C(=C2[H])C([H])(O[H])C(\[H])=C(\C(=O)OC([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O7/c1-8(15(19)22-3)6-11(17)10-7-9-4-5-12(21-2)13(18)14(9)23-16(10)20/h4-7,11,17-18H,1-3H3/b8-6+

> <INCHI_KEY>
LOHUNZDPICOFEB-SOFGYWHQSA-N

> <FORMULA>
C16H16O7

> <MOLECULAR_WEIGHT>
320.297

> <EXACT_MASS>
320.089602855

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.452659403951408

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
2.078835508666666

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.754623127686113

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.701112773904741

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2968301454355453

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
81.3992

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001521
     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    6.7798    1.0576    1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8560    0.4097    0.4318 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957    0.6699    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0837    1.5206    1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6166   -0.0399   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1701   -1.0422   -1.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3117    0.1475   -0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.5759   -1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311    0.0680   -2.6949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -0.6364   -1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705    0.4386   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932    0.2703   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7523    1.3071    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0693    1.1544    0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6762   -0.0779    0.6392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0196   -0.2296    1.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7254    0.8780    1.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9535   -1.1391    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5342   -2.3915    0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -0.9600   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9074   -1.9480   -0.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6443   -1.8303   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758   -2.8779   -1.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7007    0.4365    1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3403    1.2780    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0383    2.0375    0.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735   -0.7875   -2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2768   -1.0694   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094   -2.0681   -1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778    0.8635    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.6058   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606    0.6933   -2.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006    1.3840   -0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816    2.2731    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497    1.9961    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9152    1.6496    0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6902    0.5137    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1956    1.3971    2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0164   -3.1646   -0.3580 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
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 10  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  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       1.334   2.310   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0      -4.771   0.564   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0      -5.335  -1.540   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0      -3.231  -2.104   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  H   UNK     0      -2.667  -3.080   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       0.000  -4.620   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       2.667  -4.620   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       6.105  -5.954   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       6.668  -0.770   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      12.773  -3.644   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      13.337  -1.540   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      11.233  -0.976   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0       6.462  -4.620   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       8.002  -6.160   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       9.542  -4.620   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
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   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   22                                                  
CONECT   20   19   14   21                                                  
CONECT   21   20                                                            
CONECT   22   19   23   24   26                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   22   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   36                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   28   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

COMPND    NP0001521
HETATM    1  C1  UNL     1       6.780   1.058   1.291  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.856   0.410   0.432  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.496   0.670   0.454  1.00  0.00           C  
HETATM    4  O2  UNL     1       4.084   1.521   1.279  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.617  -0.040  -0.462  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.170  -1.042  -1.421  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.312   0.148  -0.506  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.438  -0.576  -1.436  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.431   0.068  -2.695  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.035  -0.636  -1.004  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.670   0.439  -0.505  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.993   0.270  -0.127  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.752   1.307   0.379  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.069   1.154   0.760  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.676  -0.078   0.639  1.00  0.00           C  
HETATM   16  O4  UNL     1      -6.020  -0.230   1.028  1.00  0.00           O  
HETATM   17  C13 UNL     1      -6.725   0.878   1.536  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.953  -1.139   0.138  1.00  0.00           C  
HETATM   19  O5  UNL     1      -4.534  -2.391   0.004  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.618  -0.960  -0.241  1.00  0.00           C  
HETATM   21  O6  UNL     1      -1.907  -1.948  -0.720  1.00  0.00           O  
HETATM   22  C16 UNL     1      -0.644  -1.830  -1.092  1.00  0.00           C  
HETATM   23  O7  UNL     1      -0.076  -2.878  -1.540  1.00  0.00           O  
HETATM   24  H1  UNL     1       7.701   0.437   1.382  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.340   1.278   2.283  1.00  0.00           H  
HETATM   26  H3  UNL     1       7.038   2.037   0.828  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.873  -0.788  -2.473  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.277  -1.069  -1.315  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.809  -2.068  -1.211  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.878   0.863   0.172  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.795  -1.606  -1.642  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.661   0.693  -2.762  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.201   1.384  -0.414  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.282   2.273   0.476  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.650   1.996   1.159  1.00  0.00           H  
HETATM   36  H13 UNL     1      -6.915   1.650   0.759  1.00  0.00           H  
HETATM   37  H14 UNL     1      -7.690   0.514   1.959  1.00  0.00           H  
HETATM   38  H15 UNL     1      -6.196   1.397   2.360  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.016  -3.165  -0.358  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    7    7
CONECT    6   27   28   29
CONECT    7    8   30
CONECT    8    9   10   31
CONECT    9   32
CONECT   10   11   11   22
CONECT   11   12   33
CONECT   12   13   13   20
CONECT   13   14   34
CONECT   14   15   15   35
CONECT   15   16   18
CONECT   16   17
CONECT   17   36   37   38
CONECT   18   19   20   20
CONECT   19   39
CONECT   20   21
CONECT   21   22
CONECT   22   23   23
END

NP0001521
     RDKit          3D

39 40  0  0  0  0  0  0  0  0999 V2000
    6.7798    1.0576    1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8560    0.4097    0.4318 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957    0.6699    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0837    1.5206    1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6166   -0.0399   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1701   -1.0422   -1.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3117    0.1475   -0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.5759   -1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311    0.0680   -2.6949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -0.6364   -1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705    0.4386   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932    0.2703   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7523    1.3071    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0693    1.1544    0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6762   -0.0779    0.6392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0196   -0.2296    1.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7254    0.8780    1.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9535   -1.1391    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5342   -2.3915    0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184   -0.9600   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9074   -1.9480   -0.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6443   -1.8303   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758   -2.8779   -1.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7007    0.4365    1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3403    1.2780    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0383    2.0375    0.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8735   -0.7875   -2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2768   -1.0694   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094   -2.0681   -1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778    0.8635    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.6058   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606    0.6933   -2.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006    1.3840   -0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816    2.2731    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497    1.9961    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9152    1.6496    0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6902    0.5137    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1956    1.3971    2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0164   -3.1646   -0.3580 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
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 10  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

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

Chemical Formula

C₁₆H₁₆O₇

Average Mass

320.2970 Da

Monoisotopic Mass

320.08960 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C2=C1OC(=O)C(=C2[H])C([H])(O[H])C(\[H])=C(\C(=O)OC([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C16H16O7/c1-8(15(19)22-3)6-11(17)10-7-9-4-5-12(21-2)13(18)14(9)23-16(10)20/h4-7,11,17-18H,1-3H3/b8-6+

InChI Key

LOHUNZDPICOFEB-SOFGYWHQSA-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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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 hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

Hydroxycoumarins

Alternative Parents

Substituents

Hydroxycoumarin
Benzopyran
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Pyranone
Fatty acyl
Pyran
Benzenoid
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Ether
Organic oxide
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aromatic 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	2.03	ALOGPS
logP	2.08	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.7	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.4 m³·mol⁻¹	ChemAxon
Polarizability	31.45 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

9933711

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11759012

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Phebaclavin D (NP0001521)

MOL for NP0001521 (Phebaclavin D)

3D MOL for NP0001521 (Phebaclavin D)

3D SDF for NP0001521 (Phebaclavin D)

3D-SDF for NP0001521 (Phebaclavin D)

PDB for NP0001521 (Phebaclavin D)

3D PDB for NP0001521 (Phebaclavin D)

SMILES for NP0001521 (Phebaclavin D)

INCHI for NP0001521 (Phebaclavin D)

Structure for NP0001521 (Phebaclavin D)

3D Structure for NP0001521 (Phebaclavin D)