NP-MRD: Showing NP-Card for gnaphaliin A (NP0034378)

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Record Information

Version

2.0

Created at

2021-06-20 18:07:29 UTC

Updated at

2021-06-30 00:04:43 UTC

NP-MRD ID

NP0034378

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gnaphaliin A

Provided By

JEOL Database JEOL Logo

Description

Gnaphaliin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, gnaphaliin is considered to be a flavonoid. gnaphaliin A is found in Achyrocline flaccida, Gnaphalium liebmannii and Muntingia calabura. gnaphaliin A was first documented in 2007 (PMID: 17084992). Based on a literature review a significant number of articles have been published on Gnaphaliin (PMID: 34227310) (PMID: 34275800) (PMID: 28787672) (PMID: 27061296) (PMID: 25710523) (PMID: 25517209).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120073D          

 37 39  0  0  0  0            999 V2000
    3.6151    2.8341   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570    2.2054    0.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771    2.0907   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6946    0.9310   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560   -0.3051    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533   -1.4970   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628   -2.6822    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733   -2.6910    1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8725   -1.5172    2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -0.3316    1.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814    0.7408   -0.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.7939   -1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    1.5799   -2.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9606    0.3981   -2.2154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -0.3787   -1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250    2.6340   -2.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    2.4413   -3.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446    3.8946   -2.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684    4.1072   -2.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5422    5.3700   -2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    3.0589   -1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    3.2651   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007    4.3813   -0.7209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675    3.9200    0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155    2.5566   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599    2.4961    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0147   -1.5103   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395   -3.5977   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -3.6126    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -1.5222    3.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    0.5726    2.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -1.0666   -0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594    0.2424   -0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183   -0.9845   -1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2023    1.4969   -3.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022    4.7003   -3.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747    5.3911   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 19 18  1  0  0  0  0
  5  6  2  0  0  0  0
 21 19  2  0  0  0  0
  6  7  1  0  0  0  0
 18 16  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 16 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
 13 12  2  0  0  0  0
 13 14  1  0  0  0  0
 12 11  1  0  0  0  0
 14 15  1  0  0  0  0
 21 22  1  0  0  0  0
 16 17  1  0  0  0  0
 22  3  1  0  0  0  0
 19 20  1  0  0  0  0
  3  4  2  0  0  0  0
  3  2  1  0  0  0  0
  4 11  1  0  0  0  0
  2  1  1  0  0  0  0
 12 21  1  0  0  0  0
 22 23  2  0  0  0  0
 18 36  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  0  0  0  0
  9 30  1  0  0  0  0
 10 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 17 35  1  0  0  0  0
 20 37  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.6151    2.8341   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570    2.2054    0.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771    2.0907   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6946    0.9310   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560   -0.3051    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533   -1.4970   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628   -2.6822    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733   -2.6910    1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8725   -1.5172    2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -0.3316    1.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814    0.7408   -0.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.7939   -1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    1.5799   -2.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9606    0.3981   -2.2154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -0.3787   -1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250    2.6340   -2.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    2.4413   -3.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446    3.8946   -2.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684    4.1072   -2.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5422    5.3700   -2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    3.0589   -1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    3.2651   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007    4.3813   -0.7209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675    3.9200    0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155    2.5566   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599    2.4961    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0147   -1.5103   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395   -3.5977   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -3.6126    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -1.5222    3.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    0.5726    2.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -1.0666   -0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594    0.2424   -0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183   -0.9845   -1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2023    1.4969   -3.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022    4.7003   -3.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747    5.3911   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 19 18  1  0
  5  6  2  0
 21 19  2  0
  6  7  1  0
 18 16  2  0
  7  8  2  0
  8  9  1  0
 16 13  1  0
  9 10  2  0
 10  5  1  0
 13 12  2  0
 13 14  1  0
 12 11  1  0
 14 15  1  0
 21 22  1  0
 16 17  1  0
 22  3  1  0
 19 20  1  0
  3  4  2  0
  3  2  1  0
  4 11  1  0
  2  1  1  0
 12 21  1  0
 22 23  2  0
 18 36  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 20 37  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END


  Mrv1652306202120073D          

 37 39  0  0  0  0            999 V2000
    3.6151    2.8341   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570    2.2054    0.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771    2.0907   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6946    0.9310   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560   -0.3051    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533   -1.4970   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628   -2.6822    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733   -2.6910    1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8725   -1.5172    2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -0.3316    1.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814    0.7408   -0.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.7939   -1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    1.5799   -2.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9606    0.3981   -2.2154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -0.3787   -1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250    2.6340   -2.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    2.4413   -3.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446    3.8946   -2.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684    4.1072   -2.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5422    5.3700   -2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    3.0589   -1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    3.2651   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007    4.3813   -0.7209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675    3.9200    0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155    2.5566   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599    2.4961    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0147   -1.5103   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395   -3.5977   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -3.6126    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -1.5222    3.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    0.5726    2.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -1.0666   -0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594    0.2424   -0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183   -0.9845   -1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2023    1.4969   -3.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022    4.7003   -3.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747    5.3911   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 19 18  1  0  0  0  0
  5  6  2  0  0  0  0
 21 19  2  0  0  0  0
  6  7  1  0  0  0  0
 18 16  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 16 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
 13 12  2  0  0  0  0
 13 14  1  0  0  0  0
 12 11  1  0  0  0  0
 14 15  1  0  0  0  0
 21 22  1  0  0  0  0
 16 17  1  0  0  0  0
 22  3  1  0  0  0  0
 19 20  1  0  0  0  0
  3  4  2  0  0  0  0
  3  2  1  0  0  0  0
  4 11  1  0  0  0  0
  2  1  1  0  0  0  0
 12 21  1  0  0  0  0
 22 23  2  0  0  0  0
 18 36  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  0  0  0  0
  9 30  1  0  0  0  0
 10 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 17 35  1  0  0  0  0
 20 37  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034378

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C(OC([H])([H])[H])=C(OC2=C1OC([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O6/c1-21-15-11(19)8-10(18)12-13(20)17(22-2)14(23-16(12)15)9-6-4-3-5-7-9/h3-8,18-19H,1-2H3

> <INCHI_KEY>
OWQLBLNRUZULFV-UHFFFAOYSA-N

> <FORMULA>
C17H14O6

> <MOLECULAR_WEIGHT>
314.2895

> <EXACT_MASS>
314.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.224162259812562

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3,8-dimethoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
2.7185862309999997

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.500302836775253

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.906353694887822

> <JCHEM_PKA_STRONGEST_BASIC>
-4.62087084380131

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
84.1148

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gnaphaliin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.6151    2.8341   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570    2.2054    0.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771    2.0907   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6946    0.9310   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560   -0.3051    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533   -1.4970   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628   -2.6822    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733   -2.6910    1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8725   -1.5172    2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -0.3316    1.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814    0.7408   -0.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.7939   -1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    1.5799   -2.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9606    0.3981   -2.2154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -0.3787   -1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250    2.6340   -2.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    2.4413   -3.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446    3.8946   -2.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684    4.1072   -2.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5422    5.3700   -2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    3.0589   -1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    3.2651   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007    4.3813   -0.7209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675    3.9200    0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155    2.5566   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599    2.4961    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0147   -1.5103   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395   -3.5977   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -3.6126    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -1.5222    3.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    0.5726    2.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -1.0666   -0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594    0.2424   -0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183   -0.9845   -1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2023    1.4969   -3.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022    4.7003   -3.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747    5.3911   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 19 18  1  0
  5  6  2  0
 21 19  2  0
  6  7  1  0
 18 16  2  0
  7  8  2  0
  8  9  1  0
 16 13  1  0
  9 10  2  0
 10  5  1  0
 13 12  2  0
 13 14  1  0
 12 11  1  0
 14 15  1  0
 21 22  1  0
 16 17  1  0
 22  3  1  0
 19 20  1  0
  3  4  2  0
  3  2  1  0
  4 11  1  0
  2  1  1  0
 12 21  1  0
 22 23  2  0
 18 36  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 20 37  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.615   2.834  -0.030  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.557   2.205   0.689  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.377   2.091  -0.030  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.695   0.931  -0.088  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.156  -0.305   0.578  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.253  -1.497  -0.157  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.663  -2.682   0.459  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.973  -2.691   1.817  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.873  -1.517   2.561  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.462  -0.332   1.946  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.481   0.741  -0.791  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.063   1.794  -1.443  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.265   1.580  -2.131  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.961   0.398  -2.215  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.007  -0.379  -1.020  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.825   2.634  -2.866  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.978   2.441  -3.577  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.245   3.895  -2.891  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.068   4.107  -2.182  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.542   5.370  -2.240  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.472   3.059  -1.465  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.787   3.265  -0.733  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.301   4.381  -0.721  0.00  0.00           O+0
HETATM   24  H   UNK     0       3.567   3.920   0.089  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.615   2.557  -1.089  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.560   2.496   0.407  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.015  -1.510  -1.218  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.740  -3.598  -0.122  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.293  -3.613   2.297  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.113  -1.522   3.621  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.386   0.573   2.546  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.158  -1.067  -0.981  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.059   0.242  -0.120  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.918  -0.985  -1.057  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.202   1.497  -3.464  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.702   4.700  -3.457  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.275   5.391  -1.691  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    3    1                                                       
CONECT    3   22    4    2                                                  
CONECT    4    5    3   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10   30                                                  
CONECT   10    9    5   31                                                  
CONECT   11   12    4                                                       
CONECT   12   13   11   21                                                  
CONECT   13   16   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   32   33   34                                             
CONECT   16   18   13   17                                                  
CONECT   17   16   35                                                       
CONECT   18   19   16   36                                                  
CONECT   19   18   21   20                                                  
CONECT   20   19   37                                                       
CONECT   21   19   22   12                                                  
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   15                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   20                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
    3.6151    2.8341   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570    2.2054    0.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771    2.0907   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6946    0.9310   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560   -0.3051    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533   -1.4970   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628   -2.6822    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733   -2.6910    1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8725   -1.5172    2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -0.3316    1.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814    0.7408   -0.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.7939   -1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    1.5799   -2.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9606    0.3981   -2.2154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -0.3787   -1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250    2.6340   -2.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    2.4413   -3.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446    3.8946   -2.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684    4.1072   -2.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5422    5.3700   -2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    3.0589   -1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    3.2651   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007    4.3813   -0.7209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675    3.9200    0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155    2.5566   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599    2.4961    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0147   -1.5103   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395   -3.5977   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -3.6126    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -1.5222    3.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    0.5726    2.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -1.0666   -0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594    0.2424   -0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183   -0.9845   -1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2023    1.4969   -3.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022    4.7003   -3.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747    5.3911   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 19 18  1  0
  5  6  2  0
 21 19  2  0
  6  7  1  0
 18 16  2  0
  7  8  2  0
  8  9  1  0
 16 13  1  0
  9 10  2  0
 10  5  1  0
 13 12  2  0
 13 14  1  0
 12 11  1  0
 14 15  1  0
 21 22  1  0
 16 17  1  0
 22  3  1  0
 19 20  1  0
  3  4  2  0
  3  2  1  0
  4 11  1  0
  2  1  1  0
 12 21  1  0
 22 23  2  0
 18 36  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 20 37  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END

View in JSmol

Synonyms

Value	Source
3-O-Methyl-8-methoxygalangin	HMDB
5,7-Dihydroxy-3,8-dimethoxy-2-phenyl-4H-1-benzopyran-4-one	HMDB
5,7-Dihydroxy-3,8-dimethoxyflavone	HMDB
Gnaphalin	HMDB

Chemical Formula

C₁₇H₁₄O₆

Average Mass

314.2895 Da

Monoisotopic Mass

314.07904 Da

IUPAC Name

5,7-dihydroxy-3,8-dimethoxy-2-phenyl-4H-chromen-4-one

Traditional Name

gnaphaliin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(=O)C(OC([H])([H])[H])=C(OC2=C1OC([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

InChI Identifier

InChI=1S/C17H14O6/c1-21-15-11(19)8-10(18)12-13(20)17(22-2)14(23-16(12)15)9-6-4-3-5-7-9/h3-8,18-19H,1-2H3

InChI Key

OWQLBLNRUZULFV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Achyrocline flaccida	LOTUS Database	35616633
Achyrocline spp.	KNApSAcK Database	22123792
Anaphalis margaritacea	KNApSAcK Database	22123792
Gnaphalium liebmannii	JEOL database	Rodriguez-Ramos, F., et al, J. Nat. Prod. 72, 1061 (2009)
Gnaphalium luteo-album	KNApSAcK Database	22123792
Gnaphalium microcephalum	KNApSAcK Database	22123792
Gnaphalium obtusifolium	KNApSAcK Database	22123792
Gnaphalium robustum	KNApSAcK Database	22123792
Gymnosperma glutinosum	KNApSAcK Database	22123792
Helichrysum aureum	KNApSAcK Database	22123792
Helichrysum bracteiferum	KNApSAcK Database	22123792
Helichrysum italicum	KNApSAcK Database	22123792
Helichrysum picardii	KNApSAcK Database	22123792
Muntingia calabura	LOTUS Database	35616633
Nothofagus alessandri	KNApSAcK Database	22123792
Nothofagus spp.	KNApSAcK Database	22123792
Ozothamnus ericifolius	KNApSAcK Database	22123792
Ozothamnus purpurescens	KNApSAcK Database	22123792
Woodsia scopulina	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
3-methoxychromone
Chromone
1-benzopyran
Benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12113093 )

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	3.24	ALOGPS
logP	2.72	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.91	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.11 m³·mol⁻¹	ChemAxon
Polarizability	31.22 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

HMDB0030544

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002418

KNApSAcK ID

C00004556

Chemspider ID

8148502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9972910

PDB ID

Not Available

ChEBI ID

656980

Good Scents ID

rw1820881

References

General References

Shen S, Yang Y, Wang J, Chen X, Liu T, Zhuo Q: [Analysis of differences between unifloral honeys from different botanical origins based on non-targeted metabolomics by ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry]. Se Pu. 2021 Mar;39(3):291-300. doi: 10.3724/SP.J.1123.2020.06029. [PubMed:34227310 ]
Kanwal N, Rasul A, Shah MA, Jabeen F, Sultana T: In silico-based identification of phytochemicals as novel human phosphoglycerate mutase 1 (PGAM1) inhibitors for cancer therapy. Pak J Pharm Sci. 2021 Mar;34(2(Supplementary)):665-670. [PubMed:34275800 ]
Pereira CG, Barreira L, Bijttebier S, Pieters L, Neves V, Rodrigues MJ, Rivas R, Varela J, Custodio L: Chemical profiling of infusions and decoctions of Helichrysum italicum subsp. picardii by UHPLC-PDA-MS and in vitro biological activities comparatively with green tea (Camellia sinensis) and rooibos tisane (Aspalathus linearis). J Pharm Biomed Anal. 2017 Oct 25;145:593-603. doi: 10.1016/j.jpba.2017.07.007. Epub 2017 Jul 18. [PubMed:28787672 ]
Rodriguez-Ramos F, Andrade-Moreno MA, Alfaro-Romero A, Balderas-Lopez JL, Navarrete A: Gnaphaliin A and gnaphaliin B synergize the relaxant effect of salbutamol but not of ipratropium in guinea pig trachea. J Pharm Pharmacol. 2016 Apr;68(4):533-41. doi: 10.1111/jphp.12536. Epub 2016 Apr 7. [PubMed:27061296 ]
Demarque DP, Fitts SM, Boaretto AG, da Silva JC, Vieira MC, Franco VN, Teixeira CB, Toffoli-Kadri MC, Carollo CA: Optimization and technological development strategies of an antimicrobial extract from Achyrocline alata assisted by statistical design. PLoS One. 2015 Feb 24;10(2):e0118574. doi: 10.1371/journal.pone.0118574. eCollection 2015. [PubMed:25710523 ]
Casero C, Machin F, Mendez-Alvarez S, Demo M, Ravelo AG, Perez-Hernandez N, Joseph-Nathan P, Estevez-Braun A: Structure and antimicrobial activity of phloroglucinol derivatives from Achyrocline satureioides. J Nat Prod. 2015 Jan 23;78(1):93-102. doi: 10.1021/np500735f. Epub 2014 Dec 17. [PubMed:25517209 ]
Rodriguez-Ramos F, Sanchez-Estrada VH, Alfaro-Romero A, Tapia-Alvarez GR, Navarrete A: Development and validation of a column high-performance liquid chromatography method for quantification of ganaphaliin A and B in inflorescences of Gnaphalium liebmannii Sch. Bp ex Klatt. J AOAC Int. 2011 Jul-Aug;94(4):1076-81. [PubMed:21919340 ]
Rodriguez-Ramos F, Gonzalez-Andrade M, Navarrete A: Gnaphaliin A and B relax smooth muscle of guinea-pig trachea and rat aorta via phosphodiesterase inhibition. J Pharm Pharmacol. 2011 Jul;63(7):926-35. doi: 10.1111/j.2042-7158.2011.01275.x. Epub 2011 May 19. [PubMed:21635258 ]
Rodriguez-Ramos F, Navarrete A: Solving the confusion of gnaphaliin structure: gnaphaliin A and gnaphaliin B identified as active principles of Gnaphalium liebmannii with tracheal smooth muscle relaxant properties. J Nat Prod. 2009 Jun;72(6):1061-4. doi: 10.1021/np800746j. [PubMed:19505084 ]
Schinella GR, Tournier HA, Manez S, de Buschiazzo PM, Del Carmen Recio M, Rios JL: Tiliroside and gnaphaliin inhibit human low density lipoprotein oxidation. Fitoterapia. 2007 Jan;78(1):1-6. doi: 10.1016/j.fitote.2006.09.018. Epub 2006 Sep 23. [PubMed:17084992 ]
Rodriguez-Ramos, F., et al. (2009). Rodriguez-Ramos, F., et al, J. Nat. Prod. 72, 1061 (2009). J. Nat. Prod..

Showing NP-Card for gnaphaliin A (NP0034378)

MOL for NP0034378 (gnaphaliin A)

3D MOL for NP0034378 (gnaphaliin A)

3D SDF for NP0034378 (gnaphaliin A)

3D-SDF for NP0034378 (gnaphaliin A)

PDB for NP0034378 (gnaphaliin A)

3D PDB for NP0034378 (gnaphaliin A)

SMILES for NP0034378 (gnaphaliin A)

INCHI for NP0034378 (gnaphaliin A)

Structure for NP0034378 (gnaphaliin A)

3D Structure for NP0034378 (gnaphaliin A)