NP-MRD: Showing NP-Card for 5-hydroxy-7-methoxyflavone (NP0024982)

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Record Information

Version

2.0

Created at

2021-06-19 17:13:24 UTC

Updated at

2021-06-29 23:49:38 UTC

NP-MRD ID

NP0024982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-7-methoxyflavone

Provided By

JEOL Database JEOL Logo

Description

Tectochrysin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 5-hydroxy-7-methoxyflavone is found in Alnus sieboldiana, Andrographis macrobotrys, Apis mellifera, Boesenbergia rotunda, Celosia cristata, Hedychium spicatum, Helichrysum kraussii, Helichrysum schimperi, Muntingia calabura, Oroxylum indicum, Picea abies, Pinus armandii, Pinus monticola, Pinus morrisonicola, Piper aduncum, Piper sylvaticum, Pongamia pinnata, Populus balsamifera, Populus deltoides, Populus laurifolia and Populus nigra. 5-hydroxy-7-methoxyflavone was first documented in 2013 (PMID: 23583435). Based on a literature review a small amount of articles have been published on Tectochrysin (PMID: 24727421) (PMID: 25083589) (PMID: 34206940) (PMID: 33878335).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119133D          

 32 34  0  0  0  0            999 V2000
   -6.5753    1.3229    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4315    1.0456   -0.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.4266    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3306    0.0394    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888   -0.5867    2.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104   -0.9391    3.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.8292    1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -1.4857    1.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -1.8468    2.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -1.6883    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0491   -1.2650   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004   -1.4474   -1.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4506   -1.1873   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.3573   -2.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -1.7837   -3.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -2.0362   -3.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558   -1.8659   -2.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017   -0.6532   -1.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398   -0.4451   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2801    0.1813   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3164    1.8157   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3286    2.0092    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0241    0.3992    0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590    0.2088    2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -1.3678    3.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -2.1871    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -0.8360   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -1.1514   -2.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -1.9144   -4.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -2.3648   -4.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824   -2.0696   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3161    0.4826   -1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0  0  0  0
 11 18  1  0  0  0  0
 19  7  1  0  0  0  0
  8  9  2  0  0  0  0
  3  4  2  0  0  0  0
 12 13  2  0  0  0  0
  3 20  1  0  0  0  0
 13 14  1  0  0  0  0
  4  5  1  0  0  0  0
 14 15  2  0  0  0  0
  5  7  2  0  0  0  0
 15 16  1  0  0  0  0
 19 20  2  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
 11 12  1  0  0  0  0
 19 18  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  3  2  1  0  0  0  0
  8 10  1  0  0  0  0
  2  1  1  0  0  0  0
  4 24  1  0  0  0  0
 20 32  1  0  0  0  0
 10 26  1  0  0  0  0
 13 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
  6 25  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -6.5753    1.3229    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4315    1.0456   -0.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.4266    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3306    0.0394    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888   -0.5867    2.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104   -0.9391    3.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.8292    1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -1.4857    1.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -1.8468    2.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -1.6883    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0491   -1.2650   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004   -1.4474   -1.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4506   -1.1873   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.3573   -2.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -1.7837   -3.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -2.0362   -3.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558   -1.8659   -2.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017   -0.6532   -1.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398   -0.4451   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2801    0.1813   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3164    1.8157   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3286    2.0092    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0241    0.3992    0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590    0.2088    2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -1.3678    3.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -2.1871    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -0.8360   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -1.1514   -2.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -1.9144   -4.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -2.3648   -4.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824   -2.0696   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3161    0.4826   -1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11 18  1  0
 19  7  1  0
  8  9  2  0
  3  4  2  0
 12 13  2  0
  3 20  1  0
 13 14  1  0
  4  5  1  0
 14 15  2  0
  5  7  2  0
 15 16  1  0
 19 20  2  0
 16 17  2  0
 17 12  1  0
 11 12  1  0
 19 18  1  0
  5  6  1  0
  7  8  1  0
  3  2  1  0
  8 10  1  0
  2  1  1  0
  4 24  1  0
 20 32  1  0
 10 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
  6 25  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END


  Mrv1652306192119133D          

 32 34  0  0  0  0            999 V2000
   -6.5753    1.3229    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4315    1.0456   -0.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.4266    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3306    0.0394    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888   -0.5867    2.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104   -0.9391    3.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.8292    1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -1.4857    1.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -1.8468    2.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -1.6883    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0491   -1.2650   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004   -1.4474   -1.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4506   -1.1873   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.3573   -2.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -1.7837   -3.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -2.0362   -3.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558   -1.8659   -2.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017   -0.6532   -1.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398   -0.4451   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2801    0.1813   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3164    1.8157   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3286    2.0092    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0241    0.3992    0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590    0.2088    2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -1.3678    3.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -2.1871    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -0.8360   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -1.1514   -2.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -1.9144   -4.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -2.3648   -4.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824   -2.0696   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3161    0.4826   -1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0  0  0  0
 11 18  1  0  0  0  0
 19  7  1  0  0  0  0
  8  9  2  0  0  0  0
  3  4  2  0  0  0  0
 12 13  2  0  0  0  0
  3 20  1  0  0  0  0
 13 14  1  0  0  0  0
  4  5  1  0  0  0  0
 14 15  2  0  0  0  0
  5  7  2  0  0  0  0
 15 16  1  0  0  0  0
 19 20  2  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
 11 12  1  0  0  0  0
 19 18  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  3  2  1  0  0  0  0
  8 10  1  0  0  0  0
  2  1  1  0  0  0  0
  4 24  1  0  0  0  0
 20 32  1  0  0  0  0
 10 26  1  0  0  0  0
 13 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
  6 25  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024982

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-9,17H,1H3

> <INCHI_KEY>
IRZVHDLBAYNPCT-UHFFFAOYSA-N

> <FORMULA>
C16H12O4

> <MOLECULAR_WEIGHT>
268.2641

> <EXACT_MASS>
268.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.211289975479247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-7-methoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.1561485113333334

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.18373475709686

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.365716193842765

> <JCHEM_PKA_STRONGEST_BASIC>
-4.745726102201751

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
75.41530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tectochrysin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -6.5753    1.3229    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4315    1.0456   -0.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.4266    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3306    0.0394    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888   -0.5867    2.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104   -0.9391    3.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.8292    1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -1.4857    1.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -1.8468    2.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -1.6883    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0491   -1.2650   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004   -1.4474   -1.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4506   -1.1873   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.3573   -2.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -1.7837   -3.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -2.0362   -3.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558   -1.8659   -2.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017   -0.6532   -1.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398   -0.4451   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2801    0.1813   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3164    1.8157   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3286    2.0092    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0241    0.3992    0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590    0.2088    2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -1.3678    3.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -2.1871    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -0.8360   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -1.1514   -2.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -1.9144   -4.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -2.3648   -4.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824   -2.0696   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3161    0.4826   -1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11 18  1  0
 19  7  1  0
  8  9  2  0
  3  4  2  0
 12 13  2  0
  3 20  1  0
 13 14  1  0
  4  5  1  0
 14 15  2  0
  5  7  2  0
 15 16  1  0
 19 20  2  0
 16 17  2  0
 17 12  1  0
 11 12  1  0
 19 18  1  0
  5  6  1  0
  7  8  1  0
  3  2  1  0
  8 10  1  0
  2  1  1  0
  4 24  1  0
 20 32  1  0
 10 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
  6 25  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -6.575   1.323   0.366  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.431   1.046  -0.434  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.380   0.427   0.185  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.331   0.039   1.526  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.189  -0.587   2.027  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.210  -0.939   3.350  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.093  -0.829   1.195  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.878  -1.486   1.688  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.780  -1.847   2.856  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.212  -1.688   0.723  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.049  -1.265  -0.539  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.100  -1.447  -1.559  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.451  -1.187  -1.277  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.430  -1.357  -2.260  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.072  -1.784  -3.537  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.736  -2.036  -3.835  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.756  -1.866  -2.853  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.102  -0.653  -1.014  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.140  -0.445  -0.141  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.280   0.181  -0.645  0.00  0.00           C+0
HETATM   21  H   UNK     0      -7.316   1.816  -0.271  0.00  0.00           H+0
HETATM   22  H   UNK     0      -6.329   2.009   1.183  0.00  0.00           H+0
HETATM   23  H   UNK     0      -7.024   0.399   0.746  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.159   0.209   2.205  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.351  -1.368   3.568  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.101  -2.187   1.086  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.756  -0.836  -0.295  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.472  -1.151  -2.028  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.835  -1.914  -4.301  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.453  -2.365  -4.832  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.282  -2.070  -3.108  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.316   0.483  -1.689  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    3    1                                                       
CONECT    3    4   20    2                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    7    6                                                  
CONECT    6    5   25                                                       
CONECT    7   19    5    8                                                  
CONECT    8    9    7   10                                                  
CONECT    9    8                                                            
CONECT   10   11    8   26                                                  
CONECT   11   10   18   12                                                  
CONECT   12   13   17   11                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16   29                                                  
CONECT   16   15   17   30                                                  
CONECT   17   16   12   31                                                  
CONECT   18   11   19                                                       
CONECT   19    7   20   18                                                  
CONECT   20    3   19   32                                                  
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    4                                                            
CONECT   25    6                                                            
CONECT   26   10                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   20                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

RDKit          3D

32 34  0  0  0  0  0  0  0  0999 V2000
   -6.5753    1.3229    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4315    1.0456   -0.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.4266    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3306    0.0394    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888   -0.5867    2.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104   -0.9391    3.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.8292    1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -1.4857    1.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -1.8468    2.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -1.6883    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0491   -1.2650   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004   -1.4474   -1.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4506   -1.1873   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.3573   -2.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0725   -1.7837   -3.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -2.0362   -3.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558   -1.8659   -2.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017   -0.6532   -1.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398   -0.4451   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2801    0.1813   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3164    1.8157   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3286    2.0092    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0241    0.3992    0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590    0.2088    2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -1.3678    3.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -2.1871    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -0.8360   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -1.1514   -2.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -1.9144   -4.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -2.3648   -4.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824   -2.0696   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3161    0.4826   -1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11 18  1  0
 19  7  1  0
  8  9  2  0
  3  4  2  0
 12 13  2  0
  3 20  1  0
 13 14  1  0
  4  5  1  0
 14 15  2  0
  5  7  2  0
 15 16  1  0
 19 20  2  0
 16 17  2  0
 17 12  1  0
 11 12  1  0
 19 18  1  0
  5  6  1  0
  7  8  1  0
  3  2  1  0
  8 10  1  0
  2  1  1  0
  4 24  1  0
 20 32  1  0
 10 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
  6 25  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-7-methoxyflavone	ChEBI
Techtochrysin	Kegg

Chemical Formula

C₁₆H₁₂O₄

Average Mass

268.2641 Da

Monoisotopic Mass

268.07356 Da

IUPAC Name

5-hydroxy-7-methoxy-2-phenyl-4H-chromen-4-one

Traditional Name

tectochrysin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H12O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-9,17H,1H3

InChI Key

IRZVHDLBAYNPCT-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
Alnus sieboldiana	LOTUS Database	35616633
Alpinia oxyphylla	KNApSAcK Database	22123792
Andrographis macrobotrys	LOTUS Database	35616633
Apis mellifera	LOTUS Database	35616633
Baccharis viminea	KNApSAcK Database	22123792
Boesenbergia pandurata	KNApSAcK Database	22123792
Boesenbergia rotunda	LOTUS Database	35616633
Celosia cristata	LOTUS Database	35616633
Cistus populifolius	KNApSAcK Database	22123792
Collinsonia canadensis	KNApSAcK Database	22123792
Comptonia peregrina	KNApSAcK Database	22123792
Flourensia laurifolia	KNApSAcK Database	22123792
Godmania aesculifolia	KNApSAcK Database	22123792
Hedychium spicatum	LOTUS Database	35616633
Helichrysum kraussii	LOTUS Database	35616633
Helichrysum schimperi	LOTUS Database	35616633
Heliotropium pycnophyllum	KNApSAcK Database	22123792
Hoslundia opposita	KNApSAcK Database	22123792
Kaempferia parviflora	KNApSAcK Database	22123792
Lychnophora markgravii	KNApSAcK Database	22123792
Muntingia calabura	LOTUS Database	35616633
Nuxia sphaerocephala	KNApSAcK Database	22123792
Oroxylum indicum	LOTUS Database	35616633
Pelargonium crispum	KNApSAcK Database	22123792
Picea abies	LOTUS Database	35616633
Pinus armandii	LOTUS Database	35616633
Pinus monticola	LOTUS Database	35616633
Pinus morrisonicola	LOTUS Database	35616633
Pinus spp.	KNApSAcK Database	22123792
Piper aduncum	LOTUS Database	35616633
Piper manii	KNApSAcK Database	22123792
Piper sylvaticum	LOTUS Database	35616633
Piper sylvaticum Roxb.	KNApSAcK Database	22123792
Pongamia pinnata	LOTUS Database	35616633
Populus balsamifera	LOTUS Database	35616633
Populus davidiana	KNApSAcK Database	22123792
Populus deltoides	LOTUS Database	35616633
Populus laurifolia	LOTUS Database	35616633
Populus nigra	LOTUS Database	35616633
Populus spp.	KNApSAcK Database	22123792
Prunus avium	KNApSAcK Database	22123792
Prunus cerasus	KNApSAcK Database	22123792
Prunus spp.	KNApSAcK Database	22123792
Taxus chinensis	KNApSAcK Database	22123792
Uvaria rufa	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:9426 )
monohydroxyflavone (CHEBI:9426 )
flavones (C11621 )
Flavones and Flavonols (C11621 )
Flavones and Flavonols (LMPK12110190 )

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	3.71	ALOGPS
logP	3.16	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.37	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.42 m³·mol⁻¹	ChemAxon
Polarizability	28.21 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

HMDB0150664

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Techtochrysin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

9426

Good Scents ID

rw1698461

References

General References

Zhang J, Wang S, Li Y, Xu P, Chen F, Tan Y, Duan J: Anti-diarrheal constituents of Alpinia oxyphylla. Fitoterapia. 2013 Sep;89:149-56. doi: 10.1016/j.fitote.2013.04.001. Epub 2013 Apr 12. [PubMed:23583435 ]
Chen F, Li HL, Tan YF, Guan WW, Zhang JQ, Li YH, Zhao YS, Qin ZM: Different accumulation profiles of multiple components between pericarp and seed of Alpinia oxyphylla capsular fruit as determined by UFLC-MS/MS. Molecules. 2014 Apr 10;19(4):4510-23. doi: 10.3390/molecules19044510. [PubMed:24727421 ]
Oh SB, Hwang CJ, Song SY, Jung YY, Yun HM, Sok CH, Sung HC, Yi JM, Park DH, Ham YW, Han SB, Hwang BY, Hong JT: Anti-cancer effect of tectochrysin in NSCLC cells through overexpression of death receptor and inactivation of STAT3. Cancer Lett. 2014 Oct 10;353(1):95-103. doi: 10.1016/j.canlet.2014.07.007. Epub 2014 Jul 30. [PubMed:25083589 ]
Alotaibi A, Ebiloma GU, Williams R, Alfayez IA, Natto MJ, Alenezi S, Siheri W, AlQarni M, Igoli JO, Fearnley J, De Koning HP, Watson DG: Activity of Compounds from Temperate Propolis against Trypanosoma brucei and Leishmania mexicana. Molecules. 2021 Jun 26;26(13). pii: molecules26133912. doi: 10.3390/molecules26133912. [PubMed:34206940 ]
Fang L, Yan Y, Xu Z, He Z, Zhou S, Jiang X, Wu F, Yuan X, Zhang T, Yu D: Tectochrysin ameliorates murine allergic airway inflammation by suppressing Th2 response and oxidative stress. Eur J Pharmacol. 2021 Jul 5;902:174100. doi: 10.1016/j.ejphar.2021.174100. Epub 2021 Apr 18. [PubMed:33878335 ]
Park, Y., et al. (2007). Park, Y., et al, Magn. Reson. Chem. 45, 1072 (2007). Mag. Reson. Chem..

Showing NP-Card for 5-hydroxy-7-methoxyflavone (NP0024982)

MOL for NP0024982 (5-hydroxy-7-methoxyflavone)

3D MOL for NP0024982 (5-hydroxy-7-methoxyflavone)

3D SDF for NP0024982 (5-hydroxy-7-methoxyflavone)

3D-SDF for NP0024982 (5-hydroxy-7-methoxyflavone)

PDB for NP0024982 (5-hydroxy-7-methoxyflavone)

3D PDB for NP0024982 (5-hydroxy-7-methoxyflavone)

SMILES for NP0024982 (5-hydroxy-7-methoxyflavone)

INCHI for NP0024982 (5-hydroxy-7-methoxyflavone)

Structure for NP0024982 (5-hydroxy-7-methoxyflavone)

3D Structure for NP0024982 (5-hydroxy-7-methoxyflavone)