NP-MRD: Showing NP-Card for Phellinsin A (NP0003545)

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Record Information

Version

1.0

Created at

2020-12-09 00:46:06 UTC

Updated at

2021-07-15 16:46:42 UTC

NP-MRD ID

NP0003545

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phellinsin A

Provided By

NPAtlas

Description

Phellinsin A is found in Phellinus. It was first documented in 2000 (PMID: 11099223). Based on a literature review very few articles have been published on (4E)-2-(3,4-dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-5-oxooxolane-3-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 40 42  0  0  0  0            999 V2000
   -0.1028   -3.8605   -2.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -2.8628   -1.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5558   -2.5047   -0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813   -1.4412   -0.0172 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5701   -0.6215    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428   -0.2625    1.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0510    0.5087    1.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.9486    0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9620    1.7291    0.9284 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773    0.6021   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967    1.0685   -1.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676   -0.1691   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -0.6596   -0.7693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1344    0.5506   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020    0.8100    1.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9116    1.4811   -0.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529   -1.7737   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.9157   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441   -0.8935   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8368   -0.4679   -1.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7918    0.4729   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265    0.9813    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6604    1.9295    0.8833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360    0.5512    1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583    1.0614    2.5619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -0.3874    0.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -1.8511    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3252   -0.6092    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    0.7838    2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2181    1.9803    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479    0.8212   -2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011   -0.4333   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.4823   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9240    2.4641   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -2.9170   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.8243   -2.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5776    0.8124   -1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3990    2.2656    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216    0.7476    3.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -0.6960    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 24 26  2  0  0  0  0
 17  2  1  0  0  0  0
 26 19  1  0  0  0  0
 12  5  1  0  0  0  0
  4 27  1  1  0  0  0
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  9 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  6  0  0  0
 16 34  1  0  0  0  0
 18 35  1  0  0  0  0
 20 36  1  0  0  0  0
 21 37  1  0  0  0  0
 23 38  1  0  0  0  0
 25 39  1  0  0  0  0
 26 40  1  0  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -0.1028   -3.8605   -2.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -2.8628   -1.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5558   -2.5047   -0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813   -1.4412   -0.0172 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5701   -0.6215    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428   -0.2625    1.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0510    0.5087    1.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.9486    0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9620    1.7291    0.9284 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773    0.6021   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967    1.0685   -1.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676   -0.1691   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -0.6596   -0.7693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1344    0.5506   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020    0.8100    1.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9116    1.4811   -0.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529   -1.7737   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.9157   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441   -0.8935   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8368   -0.4679   -1.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7918    0.4729   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265    0.9813    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6604    1.9295    0.8833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360    0.5512    1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583    1.0614    2.5619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -0.3874    0.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -1.8511    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3252   -0.6092    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    0.7838    2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2181    1.9803    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479    0.8212   -2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011   -0.4333   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.4823   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9240    2.4641   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -2.9170   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.8243   -2.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5776    0.8124   -1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3990    2.2656    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216    0.7476    3.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -0.6960    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 17  2  1  0
 26 19  1  0
 12  5  1  0
  4 27  1  1
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  6
 16 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
 25 39  1  0
 26 40  1  0
M  END


  Mrv1652306242117483D          

 40 42  0  0  0  0            999 V2000
   -0.1028   -3.8605   -2.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -2.8628   -1.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5558   -2.5047   -0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813   -1.4412   -0.0172 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5701   -0.6215    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428   -0.2625    1.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0510    0.5087    1.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.9486    0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9620    1.7291    0.9284 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773    0.6021   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967    1.0685   -1.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676   -0.1691   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -0.6596   -0.7693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1344    0.5506   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020    0.8100    1.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9116    1.4811   -0.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529   -1.7737   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.9157   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441   -0.8935   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8368   -0.4679   -1.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7918    0.4729   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265    0.9813    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6604    1.9295    0.8833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360    0.5512    1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583    1.0614    2.5619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -0.3874    0.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -1.8511    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3252   -0.6092    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    0.7838    2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2181    1.9803    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479    0.8212   -2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011   -0.4333   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.4823   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9240    2.4641   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -2.9170   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.8243   -2.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5776    0.8124   -1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3990    2.2656    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216    0.7476    3.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -0.6960    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 24 26  2  0  0  0  0
 17  2  1  0  0  0  0
 26 19  1  0  0  0  0
 12  5  1  0  0  0  0
  4 27  1  1  0  0  0
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  9 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  6  0  0  0
 16 34  1  0  0  0  0
 18 35  1  0  0  0  0
 20 36  1  0  0  0  0
 21 37  1  0  0  0  0
 23 38  1  0  0  0  0
 25 39  1  0  0  0  0
 26 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003545

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1([H])\C(=C(\[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])C(=O)O[C@@]1([H])C1=C([H])C([H])=C(O[H])C(O[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O8/c19-11-3-1-8(6-13(11)21)5-10-15(17(23)24)16(26-18(10)25)9-2-4-12(20)14(22)7-9/h1-7,15-16,19-22H,(H,23,24)/b10-5+/t15-,16+/m1/s1

> <INCHI_KEY>
OIVDIVRTEKNHDH-BJMVGYQFSA-N

> <FORMULA>
C18H14O8

> <MOLECULAR_WEIGHT>
358.302

> <EXACT_MASS>
358.068867411

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.064191518577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4E)-2-(3,4-dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-5-oxooxolane-3-carboxylic acid

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.3859621296666664

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.9006926866862

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.356958842542541

> <JCHEM_PKA_STRONGEST_BASIC>
-6.286456830820804

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
88.7468

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4E)-2-(3,4-dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-5-oxooxolane-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -0.1028   -3.8605   -2.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -2.8628   -1.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5558   -2.5047   -0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813   -1.4412   -0.0172 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5701   -0.6215    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428   -0.2625    1.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0510    0.5087    1.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.9486    0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9620    1.7291    0.9284 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773    0.6021   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967    1.0685   -1.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676   -0.1691   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -0.6596   -0.7693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1344    0.5506   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020    0.8100    1.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9116    1.4811   -0.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529   -1.7737   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.9157   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441   -0.8935   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8368   -0.4679   -1.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7918    0.4729   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265    0.9813    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6604    1.9295    0.8833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360    0.5512    1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583    1.0614    2.5619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -0.3874    0.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -1.8511    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3252   -0.6092    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    0.7838    2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2181    1.9803    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479    0.8212   -2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011   -0.4333   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.4823   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9240    2.4641   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -2.9170   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.8243   -2.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5776    0.8124   -1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3990    2.2656    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216    0.7476    3.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -0.6960    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
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  4 13  1  0
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 14 15  2  0
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 17 18  2  0
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 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 17  2  1  0
 26 19  1  0
 12  5  1  0
  4 27  1  1
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  6
 16 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
 25 39  1  0
 26 40  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -0.103  -3.861  -2.034  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.282  -2.863  -1.390  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.556  -2.505  -0.939  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.381  -1.441  -0.017  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.570  -0.622   0.190  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.943  -0.263   1.478  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.051   0.509   1.757  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.831   0.949   0.720  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.962   1.729   0.928  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.477   0.602  -0.570  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.297   1.069  -1.608  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.368  -0.169  -0.837  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.263  -0.660  -0.769  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.134   0.551  -0.124  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.202   0.810   1.057  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.912   1.481  -0.796  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.653  -1.774  -0.949  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.927  -1.916  -0.844  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.844  -0.894  -0.415  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.837  -0.468  -1.258  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.792   0.473  -0.855  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.726   0.981   0.426  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.660   1.930   0.883  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.736   0.551   1.254  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.658   1.061   2.562  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.784  -0.387   0.853  0.00  0.00           C+0
HETATM   27  H   UNK     0       1.004  -1.851   0.924  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.325  -0.609   2.317  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.334   0.784   2.767  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.218   1.980   1.867  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.048   0.821  -2.557  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.101  -0.433  -1.847  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.730  -0.482  -1.792  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.924   2.464  -0.560  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.383  -2.917  -1.104  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.953  -0.824  -2.283  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.578   0.812  -1.515  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.399   2.266   0.300  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.922   0.748   3.192  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.020  -0.696   1.590  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13   27                                             
CONECT    5    4    6   12                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   30                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10   31                                                       
CONECT   12   10    5   32                                                  
CONECT   13    4   14   17   33                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   34                                                       
CONECT   17   13   18    2                                                  
CONECT   18   17   19   35                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21   36                                                  
CONECT   21   20   22   37                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   38                                                       
CONECT   24   22   25   26                                                  
CONECT   25   24   39                                                       
CONECT   26   24   19   40                                                  
CONECT   27    4                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    9                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   16                                                            
CONECT   35   18                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
CONECT   38   23                                                            
CONECT   39   25                                                            
CONECT   40   26                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

RDKit          3D

40 42  0  0  0  0  0  0  0  0999 V2000
   -0.1028   -3.8605   -2.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -2.8628   -1.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5558   -2.5047   -0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813   -1.4412   -0.0172 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5701   -0.6215    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428   -0.2625    1.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0510    0.5087    1.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.9486    0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9620    1.7291    0.9284 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773    0.6021   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967    1.0685   -1.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676   -0.1691   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -0.6596   -0.7693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1344    0.5506   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020    0.8100    1.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9116    1.4811   -0.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529   -1.7737   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.9157   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441   -0.8935   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8368   -0.4679   -1.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7918    0.4729   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265    0.9813    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6604    1.9295    0.8833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360    0.5512    1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583    1.0614    2.5619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -0.3874    0.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -1.8511    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3252   -0.6092    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    0.7838    2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2181    1.9803    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479    0.8212   -2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011   -0.4333   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.4823   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9240    2.4641   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -2.9170   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.8243   -2.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5776    0.8124   -1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3990    2.2656    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216    0.7476    3.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -0.6960    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 17  2  1  0
 26 19  1  0
 12  5  1  0
  4 27  1  1
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  6
 16 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
 25 39  1  0
 26 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(4E)-2-(3,4-Dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-5-oxooxolane-3-carboxylate	Generator

Chemical Formula

C₁₈H₁₄O₈

Average Mass

358.3020 Da

Monoisotopic Mass

358.06887 Da

IUPAC Name

(2R,3R,4E)-2-(3,4-dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-5-oxooxolane-3-carboxylic acid

Traditional Name

(2R,3R,4E)-2-(3,4-dihydroxyphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]-5-oxooxolane-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1C(OC(=O)\C1=C\C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C18H14O8/c19-11-3-1-8(6-13(11)21)5-10-15(17(23)24)16(26-18(10)25)9-2-4-12(20)14(22)7-9/h1-7,15-16,19-22H,(H,23,24)/b10-5+

InChI Key

OIVDIVRTEKNHDH-BJMVGYQFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phellinus	NPAtlas	11099223

Species Where Detected

Species Name	Source	Reference
Phellinus sp. PL3	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.82	ALOGPS
logP	2.39	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.75 m³·mol⁻¹	ChemAxon
Polarizability	34.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA014897

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8219485

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10043921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hwang EI, Yun BS, Kim YK, Kwon BM, Kim HG, Lee HB, Jeong WJ, Kim SU: Phellinsin A, a novel chitin synthases inhibitor produced by Phellinus sp. PL3. J Antibiot (Tokyo). 2000 Sep;53(9):903-11. doi: 10.7164/antibiotics.53.903. [PubMed:11099223 ]

Showing NP-Card for Phellinsin A (NP0003545)

MOL for NP0003545 (Phellinsin A)

3D MOL for NP0003545 (Phellinsin A)

3D SDF for NP0003545 (Phellinsin A)

3D-SDF for NP0003545 (Phellinsin A)

PDB for NP0003545 (Phellinsin A)

3D PDB for NP0003545 (Phellinsin A)

SMILES for NP0003545 (Phellinsin A)

INCHI for NP0003545 (Phellinsin A)

Structure for NP0003545 (Phellinsin A)

3D Structure for NP0003545 (Phellinsin A)