NP-MRD: Showing NP-Card for 5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol (NP0202236)

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Record Information

Version

2.0

Created at

2022-09-04 21:25:20 UTC

Updated at

2022-09-04 21:25:20 UTC

NP-MRD ID

NP0202236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol

Description

Mulberrofuran H belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol is found in Morus alba and Morus mongolica. Mulberrofuran H is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241501092D          

 33 38  0  0  0  0            999 V2000
    3.3021    0.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0418    0.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461    1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    3.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1846    2.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247    2.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    1.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076    2.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736    3.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568    3.9564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4565    3.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0733    3.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072    2.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1244    2.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9583    1.2445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8562    3.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1058    4.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9308    4.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4787    4.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2868    4.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8346    5.2407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5470    3.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9991    3.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1910    3.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5269    2.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381    2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0550    2.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3128    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2537    1.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886    1.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789    1.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2189    1.0365    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  2  0  0  0  0
  4 26  1  0  0  0  0
 26 27  2  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
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
M  END

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
   -3.1284   -3.1439   -1.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439   -1.7711   -1.1306 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2397   -1.2948   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071   -0.1761   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448   -0.0542   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    1.1572   -0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095    2.3585   -0.5711 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830    1.2170   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6613    0.0950   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1186    0.2283    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8221    1.4051   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1496    1.1239    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2595    1.9288    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5205    1.3665    0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5783   -0.0025    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8405   -0.5686    0.6300 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4620   -0.8126    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2157   -0.2584    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9833   -0.7185    0.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287   -1.1171   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -1.1888   -0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0953   -2.4515   -0.0863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4092    1.0133   -0.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421    0.5892   -1.5691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5982   -0.7574   -2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7492    0.5426   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3445    1.7440   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3017    1.7710    0.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6658    0.5778    1.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6210    0.5599    2.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0981   -0.6064    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1272   -0.6240    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5586   -1.8590   -0.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3783   -3.1700   -2.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0915   -3.4712   -2.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9209   -3.8465   -0.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9606   -1.9178    0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2446    3.2437   -0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3304    2.2053   -0.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245    2.3993   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1947    3.0131    0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4173    1.9831    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9646   -1.5743    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5348   -1.8876    0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076   -2.0136    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6760   -3.2572    0.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170    1.6663   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8777    1.5651   -1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0151    1.3720   -2.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7265   -0.7918   -2.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402   -1.0435   -2.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0496    2.6845   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7557    2.7259    1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0564    1.4159    2.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3654   -1.5737    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2 25  1  0
 25 24  1  0
 24 23  1  0
 23  4  1  0
  4  3  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 20  1  0
 20 21  2  0
 21 22  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
  3  2  1  0
 21  5  1  0
 19 10  1  0
 32 26  1  0
 33  2  1  0
 18 12  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 25 50  1  0
 25 51  1  0
 24 49  1  6
 23 47  1  0
 23 48  1  0
  3 37  1  0
  7 38  1  0
  8 39  1  0
 20 45  1  0
 22 46  1  0
 11 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 31 55  1  0
M  END


  Mrv1533004241501092D          

 33 38  0  0  0  0            999 V2000
    3.3021    0.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0418    0.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461    1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    3.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1846    2.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247    2.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    1.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076    2.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736    3.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568    3.9564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4565    3.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0733    3.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072    2.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1244    2.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9583    1.2445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8562    3.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1058    4.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9308    4.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4787    4.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2868    4.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8346    5.2407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5470    3.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9991    3.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1910    3.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5269    2.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381    2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0550    2.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3128    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2537    1.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886    1.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789    1.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2189    1.0365    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  2  0  0  0  0
  4 26  1  0  0  0  0
 26 27  2  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
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(CC(=C1)C1=C(O)C=C(C=C1O)C1=CC3=CC=C(O)C=C3O1)C1=CC=C(O)C=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C27H22O6/c1-27-12-16(20-5-4-19(29)11-25(20)33-27)6-17(13-27)26-21(30)7-15(8-22(26)31)23-9-14-2-3-18(28)10-24(14)32-23/h2-5,7-11,13,16,28-31H,6,12H2,1H3

> <INCHI_KEY>
ZVTKGVROAGDVCH-UHFFFAOYSA-N

> <FORMULA>
C27H22O6

> <MOLECULAR_WEIGHT>
442.467

> <EXACT_MASS>
442.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
47.40992506773731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
5.164971984

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.121814433102527

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.524004147876985

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8616061449622685

> <JCHEM_POLAR_SURFACE_AREA>
103.29

> <JCHEM_REFRACTIVITY>
123.8772

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.164   0.363   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.678   1.824   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.566   3.575   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.409   5.643   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.945   5.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.953   4.368   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.842   2.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.414   4.854   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.724   6.363   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.573   7.385   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.185   6.848   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.337   5.826   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.027   4.317   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.565   3.831   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.256   2.323   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.798   6.312   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.264   7.779   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.804   7.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.827   8.941   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.335   8.631   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.358   9.783   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      17.821   7.170   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.798   6.018   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.290   6.328   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.050   5.415   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.244   4.635   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.969   5.499   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.584   4.826   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.473   3.290   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.912   2.618   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.749   2.427   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.134   3.099   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.142   1.935   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   33                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24   16                                                       
CONECT   26    4   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26   33                                                  
CONECT   33   32    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₂O₆

Average Mass

442.4670 Da

Monoisotopic Mass

442.14164 Da

IUPAC Name

5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol

Traditional Name

5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

CC12CC(CC(=C1)C1=C(O)C=C(C=C1O)C1=CC3=CC=C(O)C=C3O1)C1=CC=C(O)C=C1O2

InChI Identifier

InChI=1S/C27H22O6/c1-27-12-16(20-5-4-19(29)11-25(20)33-27)6-17(13-27)26-21(30)7-15(8-22(26)31)23-9-14-2-3-18(28)10-24(14)32-23/h2-5,7-11,13,16,28-31H,6,12H2,1H3

InChI Key

ZVTKGVROAGDVCH-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
Morus alba	LOTUS Database	35616633
Morus mongolica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
4'-prenylated 2-arybenzofuran
2-phenylbenzofuran
Phenylbenzofuran
Chromane
Benzopyran
1-benzopyran
Benzofuran
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	4.7	ALOGPS
logP	5.16	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.52	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	123.88 m³·mol⁻¹	ChemAxon
Polarizability	47.41 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21636209

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol (NP0202236)

MOL for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)

3D MOL for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)

3D SDF for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)

3D-SDF for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)

PDB for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)

3D PDB for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)

SMILES for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)

INCHI for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)

Structure for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)

3D Structure for NP0202236 (5-(6-hydroxy-1-benzofuran-2-yl)-2-{5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-11-yl}benzene-1,3-diol)