NP-MRD: Showing NP-Card for Ophioglonol prenyl ether (NP0001559)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-09-21 21:13:45 UTC

Updated at

2021-08-10 02:55:14 UTC

NP-MRD ID

NP0001559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ophioglonol prenyl ether

Description

2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(3-methylbut-2-en-1-yl)oxy]methyl}-4H-chromen-4-one 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). Ophioglonol prenyl ether was first documented in 2005 (PMID: 15787440). Based on a literature review very few articles have been published on 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(3-methylbut-2-en-1-yl)oxy]methyl}-4H-chromen-4-one.

Structure

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


  Mrv1533004191517202D          

 28 30  0  0  0  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 27  1  0  0  0  0
  2 28  1  0  0  0  0
M  END

NP0001559
     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    4.9737   -1.0749   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    0.3450   -0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979    1.1920   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5853    0.8471   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307    0.0847   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434    0.6936   -1.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035   -0.0066   -1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6139    0.3569   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7594   -0.3072   -0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190   -1.5187   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1467   -2.3276    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6793   -3.4441   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3390   -3.8354   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8860   -4.9837   -2.4077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393   -3.0669   -2.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590   -3.4202   -3.8284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061   -1.9224   -1.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5478    0.1695    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049    1.2217    1.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2023    1.6263    2.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9802    2.7378    3.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    3.0827    4.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8443    3.4700    3.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9129    3.0910    2.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1932    3.8383    2.0411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613    1.9614    1.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249    1.5153    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7038    2.1504    0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0425   -1.3144   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794   -1.3633   -1.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6638   -1.6778    0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7593    2.2565   -0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8089    0.8559   -0.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620    1.0427    0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879    1.8967    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439   -0.9856   -0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380   -0.0067    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545    0.3386   -2.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -1.0563   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158   -2.0162    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870   -4.0598   -0.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -5.2346   -3.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982   -2.8354   -4.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385   -1.3617   -2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0803    1.0010    2.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8065    3.8785    5.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    4.3388    3.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590    3.8272    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 27  8  1  0
 17 10  1  0
 26 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  0
M  END


  Mrv1533004191517202D          

 28 30  0  0  0  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 27  1  0  0  0  0
  2 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCOCC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O7/c1-11(2)5-6-27-10-14-20(26)19-17(25)8-13(22)9-18(19)28-21(14)12-3-4-15(23)16(24)7-12/h3-5,7-9,22-25H,6,10H2,1-2H3

> <INCHI_KEY>
CBVYNPBPPIHKOV-UHFFFAOYSA-N

> <FORMULA>
C21H20O7

> <MOLECULAR_WEIGHT>
384.384

> <EXACT_MASS>
384.120902984

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
40.059356901566105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(3-methylbut-2-en-1-yl)oxy]methyl}-4H-chromen-4-one

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
3.522275738000001

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.02102923272742

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.522595913180736

> <JCHEM_PKA_STRONGEST_BASIC>
-4.157634458438723

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
104.89599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(3-methylbut-2-en-1-yl)oxy]methyl}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001559
     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    4.9737   -1.0749   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    0.3450   -0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979    1.1920   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5853    0.8471   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307    0.0847   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434    0.6936   -1.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035   -0.0066   -1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6139    0.3569   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7594   -0.3072   -0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190   -1.5187   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1467   -2.3276    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6793   -3.4441   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3390   -3.8354   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8860   -4.9837   -2.4077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393   -3.0669   -2.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590   -3.4202   -3.8284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061   -1.9224   -1.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5478    0.1695    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049    1.2217    1.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2023    1.6263    2.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9802    2.7378    3.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    3.0827    4.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8443    3.4700    3.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9129    3.0910    2.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1932    3.8383    2.0411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613    1.9614    1.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249    1.5153    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7038    2.1504    0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0425   -1.3144   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794   -1.3633   -1.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6638   -1.6778    0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7593    2.2565   -0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8089    0.8559   -0.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620    1.0427    0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879    1.8967    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439   -0.9856   -0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380   -0.0067    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545    0.3386   -2.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -1.0563   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158   -2.0162    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870   -4.0598   -0.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -5.2346   -3.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982   -2.8354   -4.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385   -1.3617   -2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0803    1.0010    2.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8065    3.8785    5.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    4.3388    3.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590    3.8272    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 27  8  1  0
 17 10  1  0
 26 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  0
M  END

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18                                                  
CONECT   18   17    7   19                                                  
CONECT   19   18                                                            
CONECT   20    8   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20                                                       
CONECT   28    2                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    NP0001559
HETATM    1  C1  UNL     1       4.974  -1.075  -0.755  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.790   0.345  -0.365  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.998   1.192  -0.213  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.585   0.847  -0.160  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.331   0.085  -0.288  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.543   0.694  -1.268  1.00  0.00           O  
HETATM    7  C6  UNL     1       0.304  -0.007  -1.366  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.614   0.357  -0.284  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.759  -0.307  -0.006  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.219  -1.519  -0.674  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.147  -2.328   0.023  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.679  -3.444  -0.546  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.339  -3.835  -1.823  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.886  -4.984  -2.408  1.00  0.00           O  
HETATM   15  C13 UNL     1      -2.439  -3.067  -2.525  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.059  -3.420  -3.828  1.00  0.00           O  
HETATM   17  C14 UNL     1      -1.906  -1.922  -1.919  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.548   0.169   0.971  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.305   1.222   1.677  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.202   1.626   2.674  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.980   2.738   3.444  1.00  0.00           C  
HETATM   22  O5  UNL     1      -3.920   3.083   4.421  1.00  0.00           O  
HETATM   23  C18 UNL     1      -1.844   3.470   3.225  1.00  0.00           C  
HETATM   24  C19 UNL     1      -0.913   3.091   2.225  1.00  0.00           C  
HETATM   25  O6  UNL     1       0.193   3.838   2.041  1.00  0.00           O  
HETATM   26  C20 UNL     1      -1.161   1.961   1.459  1.00  0.00           C  
HETATM   27  C21 UNL     1      -0.325   1.515   0.472  1.00  0.00           C  
HETATM   28  O7  UNL     1       0.704   2.150   0.231  1.00  0.00           O  
HETATM   29  H1  UNL     1       6.043  -1.314  -0.899  1.00  0.00           H  
HETATM   30  H2  UNL     1       4.379  -1.363  -1.649  1.00  0.00           H  
HETATM   31  H3  UNL     1       4.664  -1.678   0.142  1.00  0.00           H  
HETATM   32  H4  UNL     1       5.759   2.256  -0.400  1.00  0.00           H  
HETATM   33  H5  UNL     1       6.809   0.856  -0.901  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.362   1.043   0.839  1.00  0.00           H  
HETATM   35  H7  UNL     1       3.488   1.897   0.126  1.00  0.00           H  
HETATM   36  H8  UNL     1       2.544  -0.986  -0.607  1.00  0.00           H  
HETATM   37  H9  UNL     1       1.838  -0.007   0.670  1.00  0.00           H  
HETATM   38  H10 UNL     1      -0.054   0.339  -2.364  1.00  0.00           H  
HETATM   39  H11 UNL     1       0.613  -1.056  -1.411  1.00  0.00           H  
HETATM   40  H12 UNL     1      -3.416  -2.016   1.041  1.00  0.00           H  
HETATM   41  H13 UNL     1      -4.387  -4.060  -0.010  1.00  0.00           H  
HETATM   42  H14 UNL     1      -3.612  -5.235  -3.343  1.00  0.00           H  
HETATM   43  H15 UNL     1      -1.398  -2.835  -4.312  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.239  -1.362  -2.583  1.00  0.00           H  
HETATM   45  H17 UNL     1      -4.080   1.001   2.794  1.00  0.00           H  
HETATM   46  H18 UNL     1      -3.807   3.878   5.006  1.00  0.00           H  
HETATM   47  H19 UNL     1      -1.640   4.339   3.803  1.00  0.00           H  
HETATM   48  H20 UNL     1       0.959   3.827   1.472  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4    4
CONECT    3   32   33   34
CONECT    4    5   35
CONECT    5    6   36   37
CONECT    6    7
CONECT    7    8   38   39
CONECT    8    9    9   27
CONECT    9   10   18
CONECT   10   11   11   17
CONECT   11   12   40
CONECT   12   13   13   41
CONECT   13   14   15
CONECT   14   42
CONECT   15   16   17   17
CONECT   16   43
CONECT   17   44
CONECT   18   19
CONECT   19   20   20   26
CONECT   20   21   45
CONECT   21   22   23   23
CONECT   22   46
CONECT   23   24   47
CONECT   24   25   26   26
CONECT   25   48
CONECT   26   27
CONECT   27   28   28
END

NP0001559
     RDKit          3D

48 50  0  0  0  0  0  0  0  0999 V2000
    4.9737   -1.0749   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    0.3450   -0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979    1.1920   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5853    0.8471   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307    0.0847   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434    0.6936   -1.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035   -0.0066   -1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6139    0.3569   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7594   -0.3072   -0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190   -1.5187   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1467   -2.3276    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6793   -3.4441   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3390   -3.8354   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8860   -4.9837   -2.4077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393   -3.0669   -2.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590   -3.4202   -3.8284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061   -1.9224   -1.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5478    0.1695    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049    1.2217    1.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2023    1.6263    2.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9802    2.7378    3.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    3.0827    4.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8443    3.4700    3.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9129    3.0910    2.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1932    3.8383    2.0411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613    1.9614    1.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249    1.5153    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7038    2.1504    0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0425   -1.3144   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794   -1.3633   -1.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6638   -1.6778    0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7593    2.2565   -0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8089    0.8559   -0.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620    1.0427    0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879    1.8967    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439   -0.9856   -0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380   -0.0067    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545    0.3386   -2.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -1.0563   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158   -2.0162    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870   -4.0598   -0.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -5.2346   -3.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982   -2.8354   -4.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385   -1.3617   -2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0803    1.0010    2.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8065    3.8785    5.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    4.3388    3.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590    3.8272    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 27  8  1  0
 17 10  1  0
 26 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₇

Average Mass

384.3840 Da

Monoisotopic Mass

384.12090 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(3-methylbut-2-en-1-yl)oxy]methyl}-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(3-methylbut-2-en-1-yl)oxy]methyl}chromen-4-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCOCC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C21H20O7/c1-11(2)5-6-27-10-14-20(26)19-17(25)8-13(22)9-18(19)28-21(14)12-3-4-15(23)16(24)7-12/h3-5,7-9,22-25H,6,10H2,1-2H3

InChI Key

CBVYNPBPPIHKOV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500Mz MHz, DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500Mz, DMSO, simulated)	rgf8b@missouri.edu	Not Available	Not Available	2020-09-21	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Ophioglossum petiolatum	KNApSAcK Database	22123792

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
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	3.42	ALOGPS
logP	3.52	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	6.52	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.9 m³·mol⁻¹	ChemAxon
Polarizability	40.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042809

Chemspider ID

9649410

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11474580

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin YL, Shen CC, Huang YJ, Chang YY: Homoflavonoids from Ophioglossum petiolatum. J Nat Prod. 2005 Mar;68(3):381-4. doi: 10.1021/np0401819. [PubMed:15787440 ]

Showing NP-Card for Ophioglonol prenyl ether (NP0001559)

MOL for NP0001559 (Ophioglonol prenyl ether)

3D MOL for NP0001559 (Ophioglonol prenyl ether)

3D SDF for NP0001559 (Ophioglonol prenyl ether)

3D-SDF for NP0001559 (Ophioglonol prenyl ether)

PDB for NP0001559 (Ophioglonol prenyl ether)

3D PDB for NP0001559 (Ophioglonol prenyl ether)

SMILES for NP0001559 (Ophioglonol prenyl ether)

INCHI for NP0001559 (Ophioglonol prenyl ether)

Structure for NP0001559 (Ophioglonol prenyl ether)

3D Structure for NP0001559 (Ophioglonol prenyl ether)