NP-MRD: Showing NP-Card for 4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol (NP0173246)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 10:21:06 UTC

Updated at

2022-09-03 10:21:06 UTC

NP-MRD ID

NP0173246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol

Description

4-[7-Hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol belongs to the class of organic compounds known as 2'-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 2'-position. 4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol is found in Dendrolobium lanceolatum. 4-[7-Hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191522372D          

 31 33  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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
    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
    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 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 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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    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  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
   -4.7865    4.6276   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5071    3.3410    0.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3976    2.5964    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4027    3.0208   -0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300    2.2158   -1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2276    0.9669   -0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    0.5257    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0455   -0.8366    0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0737   -1.2797    1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8059   -2.3419    1.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920   -3.0996    0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8509   -2.8004    2.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097    1.3302    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3023    0.8635    1.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    0.1774   -0.7861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0281    0.7587   -1.3758 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8666   -0.3602   -1.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756   -0.7110   -3.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259   -1.7988   -3.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3824   -2.5631   -2.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487   -3.6728   -2.9645 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860   -2.2275   -1.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9640   -3.0285   -0.3476 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5300   -1.1302   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639   -0.7286    0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    0.3215    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490    0.2238    1.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858   -0.9161    2.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4396    1.3570    1.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4797    1.5302   -2.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744    2.7113   -1.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9124    5.2055   -0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3897    5.2308    0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4388    4.5271   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4767    4.0136   -1.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -1.5285    0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0649   -0.8254    1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474   -0.7463    2.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786   -3.9656    0.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6974   -2.4770   -0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362   -3.4719    0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9898   -2.1441    3.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5368   -3.7928    2.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8282   -2.9336    2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1173    1.4204    1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3935    1.4470   -0.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4398   -0.0780   -3.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950   -2.0497   -4.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6217   -4.2171   -2.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498   -2.8697    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6528   -1.5569    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -0.2030    0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5088    1.2053    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1307   -0.5838    3.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6525   -1.3571    2.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2941   -1.6348    2.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204    2.1976    2.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8192    1.6538    0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3448    1.0051    2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754    1.9041   -3.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244    0.9036   -3.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4695    3.2582   -1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6732    3.3900   -2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 15  1  0
 15 16  1  0
 16 30  1  0
 30 31  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  3
 27 28  1  0
 27 29  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  2  0
 13 14  1  0
 13  3  1  0
 31  5  1  0
 24 17  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
 16 46  1  1
 30 60  1  0
 30 61  1  0
 31 62  1  0
 31 63  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
M  END


  Mrv1533004191522372D          

 31 33  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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
    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
    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 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 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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    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  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(OC(CC2)C2=CC=C(O)C(O)=C2CC=C(C)C)C(CC=C(C)C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O5/c1-15(2)6-9-19-18(11-12-21(27)24(19)28)22-13-8-17-14-23(30-5)25(29)20(26(17)31-22)10-7-16(3)4/h6-7,11-12,14,22,27-29H,8-10,13H2,1-5H3

> <INCHI_KEY>
VPRXRGLNLDGXIE-UHFFFAOYSA-N

> <FORMULA>
C26H32O5

> <MOLECULAR_WEIGHT>
424.537

> <EXACT_MASS>
424.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.24650257408855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol

> <ALOGPS_LOGP>
5.06

> <JCHEM_LOGP>
6.473038677

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.10280490694761

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.027394811351591

> <JCHEM_PKA_STRONGEST_BASIC>
-4.581779575310138

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
125.60609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11    3   18                                                  
CONECT   18   17                                                            
CONECT   19    8   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₅

Average Mass

424.5370 Da

Monoisotopic Mass

424.22497 Da

IUPAC Name

4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol

Traditional Name

4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(OC(CC2)C2=CC=C(O)C(O)=C2CC=C(C)C)C(CC=C(C)C)=C1O

InChI Identifier

InChI=1S/C26H32O5/c1-15(2)6-9-19-18(11-12-21(27)24(19)28)22-13-8-17-14-23(30-5)25(29)20(26(17)31-22)10-7-16(3)4/h6-7,11-12,14,22,27-29H,8-10,13H2,1-5H3

InChI Key

VPRXRGLNLDGXIE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dendrolobium lanceolatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

2'-prenylated flavans

Alternative Parents

Substituents

2'-prenylated flavan
8-prenylated flavan
6-methoxyflavonoid-skeleton
7-hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Anisole
Catechol
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	5.06	ALOGPS
logP	6.47	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	125.61 m³·mol⁻¹	ChemAxon
Polarizability	48.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21580162

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol (NP0173246)

MOL for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)

3D MOL for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)

3D SDF for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)

3D-SDF for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)

PDB for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)

3D PDB for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)

SMILES for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)

INCHI for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)

Structure for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)

3D Structure for NP0173246 (4-[7-hydroxy-6-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-2-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol)