NP-MRD: Showing NP-Card for luteolin 8-acetic acid methyl ester (NP0042805)

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Record Information

Version

1.0

Created at

2021-06-21 00:22:49 UTC

Updated at

2021-06-30 00:18:06 UTC

NP-MRD ID

NP0042805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

luteolin 8-acetic acid methyl ester

Provided By

JEOL Database JEOL Logo

Description

5,7-Dihydroxy-2-(3,4-dihydroxyphenyl)-4-oxo-4H-1-benzopyran-8-acetic acid methyl ester belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). luteolin 8-acetic acid methyl ester is found in Arthraxon hispidus. It was first documented in 2013 (Quan, G.-H., et al.). Based on a literature review very few articles have been published on 5,7-Dihydroxy-2-(3,4-dihydroxyphenyl)-4-oxo-4H-1-benzopyran-8-acetic acid methyl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102223D          

 40 42  0  0  0  0            999 V2000
    0.1081    4.8665    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743    4.1361    0.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4883    2.7822    0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    2.2143    1.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1214    2.1165   -0.3412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4261    0.6506   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126    0.2266    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6964    1.1640    0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -1.1214    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -2.0668    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356   -3.3728    0.5385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935   -1.6671   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3988   -2.6406   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988   -3.8409    0.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364   -2.1153   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8841   -0.7958   -0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021   -0.1922   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    0.9696   -0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8298    1.5723   -0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6847    1.0124   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9105    1.5510   -1.6449 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -0.1312   -2.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534   -0.6725   -2.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -0.7366   -1.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1231   -0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118   -0.3175   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    4.6918    2.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0513    5.9314    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614    4.5947    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    2.2297   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384    2.6590   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5138    0.7210    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988   -1.4522    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -3.9278    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488   -2.8292   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9219    1.4082    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    2.4634    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0327    2.3322   -1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383   -0.0889   -2.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -1.6196   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  2  0  0  0  0
  9 10  1  0  0  0  0
 19 20  1  0  0  0  0
 10 12  2  0  0  0  0
 20 22  2  0  0  0  0
 26  6  2  0  0  0  0
 22 24  1  0  0  0  0
 24 17  2  0  0  0  0
 16 17  1  0  0  0  0
  6  7  1  0  0  0  0
 20 21  1  0  0  0  0
 26 25  1  0  0  0  0
 22 23  1  0  0  0  0
 12 13  1  0  0  0  0
 10 11  1  0  0  0  0
 13 15  1  0  0  0  0
  7  8  1  0  0  0  0
 15 16  2  0  0  0  0
 13 14  2  0  0  0  0
 16 25  1  0  0  0  0
  6  5  1  0  0  0  0
 26 12  1  0  0  0  0
  5  3  1  0  0  0  0
  7  9  2  0  0  0  0
  3  2  1  0  0  0  0
 17 18  1  0  0  0  0
  2  1  1  0  0  0  0
  3  4  2  0  0  0  0
  9 33  1  0  0  0  0
 15 35  1  0  0  0  0
 18 36  1  0  0  0  0
 19 37  1  0  0  0  0
 24 40  1  0  0  0  0
 21 38  1  0  0  0  0
 23 39  1  0  0  0  0
 11 34  1  0  0  0  0
  8 32  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    0.1081    4.8665    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743    4.1361    0.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4883    2.7822    0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    2.2143    1.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1214    2.1165   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261    0.6506   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126    0.2266    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6964    1.1640    0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -1.1214    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -2.0668    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356   -3.3728    0.5385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935   -1.6671   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3988   -2.6406   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988   -3.8409    0.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364   -2.1153   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8841   -0.7958   -0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021   -0.1922   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    0.9696   -0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8298    1.5723   -0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6847    1.0124   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9105    1.5510   -1.6449 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -0.1312   -2.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534   -0.6725   -2.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -0.7366   -1.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1231   -0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118   -0.3175   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    4.6918    2.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0513    5.9314    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614    4.5947    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    2.2297   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384    2.6590   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5138    0.7210    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988   -1.4522    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -3.9278    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488   -2.8292   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9219    1.4082    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    2.4634    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0327    2.3322   -1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383   -0.0889   -2.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -1.6196   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  2  0
  9 10  1  0
 19 20  1  0
 10 12  2  0
 20 22  2  0
 26  6  2  0
 22 24  1  0
 24 17  2  0
 16 17  1  0
  6  7  1  0
 20 21  1  0
 26 25  1  0
 22 23  1  0
 12 13  1  0
 10 11  1  0
 13 15  1  0
  7  8  1  0
 15 16  2  0
 13 14  2  0
 16 25  1  0
  6  5  1  0
 26 12  1  0
  5  3  1  0
  7  9  2  0
  3  2  1  0
 17 18  1  0
  2  1  1  0
  3  4  2  0
  9 33  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
 24 40  1  0
 21 38  1  0
 23 39  1  0
 11 34  1  0
  8 32  1  0
  5 30  1  0
  5 31  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1652306212102223D          

 40 42  0  0  0  0            999 V2000
    0.1081    4.8665    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743    4.1361    0.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4883    2.7822    0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    2.2143    1.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1214    2.1165   -0.3412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4261    0.6506   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126    0.2266    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6964    1.1640    0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -1.1214    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -2.0668    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356   -3.3728    0.5385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935   -1.6671   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3988   -2.6406   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988   -3.8409    0.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364   -2.1153   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8841   -0.7958   -0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021   -0.1922   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    0.9696   -0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8298    1.5723   -0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6847    1.0124   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9105    1.5510   -1.6449 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -0.1312   -2.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534   -0.6725   -2.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -0.7366   -1.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1231   -0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118   -0.3175   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    4.6918    2.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0513    5.9314    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614    4.5947    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    2.2297   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384    2.6590   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5138    0.7210    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988   -1.4522    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -3.9278    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488   -2.8292   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9219    1.4082    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    2.4634    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0327    2.3322   -1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383   -0.0889   -2.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -1.6196   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  2  0  0  0  0
  9 10  1  0  0  0  0
 19 20  1  0  0  0  0
 10 12  2  0  0  0  0
 20 22  2  0  0  0  0
 26  6  2  0  0  0  0
 22 24  1  0  0  0  0
 24 17  2  0  0  0  0
 16 17  1  0  0  0  0
  6  7  1  0  0  0  0
 20 21  1  0  0  0  0
 26 25  1  0  0  0  0
 22 23  1  0  0  0  0
 12 13  1  0  0  0  0
 10 11  1  0  0  0  0
 13 15  1  0  0  0  0
  7  8  1  0  0  0  0
 15 16  2  0  0  0  0
 13 14  2  0  0  0  0
 16 25  1  0  0  0  0
  6  5  1  0  0  0  0
 26 12  1  0  0  0  0
  5  3  1  0  0  0  0
  7  9  2  0  0  0  0
  3  2  1  0  0  0  0
 17 18  1  0  0  0  0
  2  1  1  0  0  0  0
  3  4  2  0  0  0  0
  9 33  1  0  0  0  0
 15 35  1  0  0  0  0
 18 36  1  0  0  0  0
 19 37  1  0  0  0  0
 24 40  1  0  0  0  0
 21 38  1  0  0  0  0
 23 39  1  0  0  0  0
 11 34  1  0  0  0  0
  8 32  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C([H])=C(OC2=C1C([H])([H])C(=O)OC([H])([H])[H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O8/c1-25-16(24)5-9-11(20)6-13(22)17-14(23)7-15(26-18(9)17)8-2-3-10(19)12(21)4-8/h2-4,6-7,19-22H,5H2,1H3

> <INCHI_KEY>
PXIBTNJNDHNAJH-UHFFFAOYSA-N

> <FORMULA>
C18H14O8

> <MOLECULAR_WEIGHT>
358.302

> <EXACT_MASS>
358.068867411

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.800562718714914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]acetate

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.186766157333333

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.025535761990522

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.357971350004984

> <JCHEM_PKA_STRONGEST_BASIC>
-5.385926802930912

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
90.9715

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
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   -0.4883    2.7822    0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    2.2143    1.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4261    0.6506   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126    0.2266    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6964    1.1640    0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9894   -2.0668    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356   -3.3728    0.5385 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8841   -0.7958   -0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5887    0.9696   -0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8298    1.5723   -0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6847    1.0124   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1614    4.5947    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    2.2297   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5488   -2.8292   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9219    1.4082    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    2.4634    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       0.108   4.867   1.753  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.474   4.136   0.673  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.488   2.782   0.861  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.019   2.214   1.838  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.121   2.116  -0.341  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.426   0.651  -0.124  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.713   0.227   0.237  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.696   1.164   0.384  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.001  -1.121   0.450  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.989  -2.067   0.317  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.336  -3.373   0.539  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.694  -1.667  -0.019  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.399  -2.641  -0.142  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.199  -3.841   0.011  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.736  -2.115  -0.444  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.884  -0.796  -0.625  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.202  -0.192  -0.892  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.589   0.970  -0.196  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.830   1.572  -0.430  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.685   1.012  -1.369  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.910   1.551  -1.645  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.308  -0.131  -2.068  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.153  -0.673  -2.994  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.078  -0.737  -1.841  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.852   0.123  -0.551  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.412  -0.318  -0.235  0.00  0.00           C+0
HETATM   27  H   UNK     0      -0.448   4.692   2.679  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.051   5.931   1.511  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.161   4.595   1.874  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.444   2.230  -1.196  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.038   2.659  -0.598  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.514   0.721   0.670  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.999  -1.452   0.722  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.531  -3.928   0.417  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.549  -2.829  -0.487  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.922   1.408   0.546  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.101   2.463   0.126  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.033   2.332  -1.078  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.938  -0.089  -2.981  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.813  -1.620  -2.416  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3   30   31                                             
CONECT    6   26    7    5                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   32                                                       
CONECT    9   10    7   33                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10   34                                                       
CONECT   12   10   13   26                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   16   35                                                  
CONECT   16   17   15   25                                                  
CONECT   17   24   16   18                                                  
CONECT   18   19   17   36                                                  
CONECT   19   18   20   37                                                  
CONECT   20   19   22   21                                                  
CONECT   21   20   38                                                       
CONECT   22   20   24   23                                                  
CONECT   23   22   39                                                       
CONECT   24   22   17   40                                                  
CONECT   25   26   16                                                       
CONECT   26    6   25   12                                                  
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    5                                                            
CONECT   31    5                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
CONECT   34   11                                                            
CONECT   35   15                                                            
CONECT   36   18                                                            
CONECT   37   19                                                            
CONECT   38   21                                                            
CONECT   39   23                                                            
CONECT   40   24                                                            
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
    0.1081    4.8665    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743    4.1361    0.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1214    2.1165   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261    0.6506   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126    0.2266    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6964    1.1640    0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -1.1214    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -2.0668    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356   -3.3728    0.5385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935   -1.6671   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3988   -2.6406   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988   -3.8409    0.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364   -2.1153   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8841   -0.7958   -0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021   -0.1922   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    0.9696   -0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8298    1.5723   -0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6847    1.0124   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9105    1.5510   -1.6449 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -0.1312   -2.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534   -0.6725   -2.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -0.7366   -1.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1231   -0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118   -0.3175   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    4.6918    2.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0513    5.9314    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614    4.5947    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    2.2297   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384    2.6590   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5138    0.7210    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988   -1.4522    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -3.9278    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488   -2.8292   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9219    1.4082    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    2.4634    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0327    2.3322   -1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383   -0.0889   -2.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -1.6196   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  2  0
  9 10  1  0
 19 20  1  0
 10 12  2  0
 20 22  2  0
 26  6  2  0
 22 24  1  0
 24 17  2  0
 16 17  1  0
  6  7  1  0
 20 21  1  0
 26 25  1  0
 22 23  1  0
 12 13  1  0
 10 11  1  0
 13 15  1  0
  7  8  1  0
 15 16  2  0
 13 14  2  0
 16 25  1  0
  6  5  1  0
 26 12  1  0
  5  3  1  0
  7  9  2  0
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 17 18  1  0
  2  1  1  0
  3  4  2  0
  9 33  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
 24 40  1  0
 21 38  1  0
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 11 34  1  0
  8 32  1  0
  5 30  1  0
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  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

View in JSmol

Synonyms

Value	Source
5,7-Dihydroxy-2-(3,4-dihydroxyphenyl)-4-oxo-4H-1-benzopyran-8-acetate methyl ester	Generator

Chemical Formula

C₁₈H₁₄O₈

Average Mass

358.3020 Da

Monoisotopic Mass

358.06887 Da

IUPAC Name

methyl 2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]acetate

Traditional Name

methyl [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]acetate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(=O)C([H])=C(OC2=C1C([H])([H])C(=O)OC([H])([H])[H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C18H14O8/c1-25-16(24)5-9-11(20)6-13(22)17-14(23)7-15(26-18(9)17)8-2-3-10(19)12(21)4-8/h2-4,6-7,19-22H,5H2,1H3

InChI Key

PXIBTNJNDHNAJH-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arthraxon hispidus	JEOL database	Quan, G.-H., et al., Chem. Pharm. Bull. 61, 920 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Methyl ester
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	2.7	ALOGPS
logP	2.19	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.36	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.97 m³·mol⁻¹	ChemAxon
Polarizability	34.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72196833

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Quan, G.-H., et al. (2013). Quan, G.-H., et al., Chem. Pharm. Bull. 61, 920 (2013). Chem. Pharm. Bull..

Showing NP-Card for luteolin 8-acetic acid methyl ester (NP0042805)

MOL for NP0042805 (luteolin 8-acetic acid methyl ester)

3D MOL for NP0042805 (luteolin 8-acetic acid methyl ester)

3D SDF for NP0042805 (luteolin 8-acetic acid methyl ester)

3D-SDF for NP0042805 (luteolin 8-acetic acid methyl ester)

PDB for NP0042805 (luteolin 8-acetic acid methyl ester)

3D PDB for NP0042805 (luteolin 8-acetic acid methyl ester)

SMILES for NP0042805 (luteolin 8-acetic acid methyl ester)

INCHI for NP0042805 (luteolin 8-acetic acid methyl ester)

Structure for NP0042805 (luteolin 8-acetic acid methyl ester)

3D Structure for NP0042805 (luteolin 8-acetic acid methyl ester)