NP-MRD: Showing NP-Card for 5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol (NP0225489)

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Record Information

Version

2.0

Created at

2022-09-06 04:13:43 UTC

Updated at

2022-09-06 04:13:43 UTC

NP-MRD ID

NP0225489

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol

Description

5,5'-Bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. 5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol is found in Cerbera manghas. 5,5'-Bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251505192D          

 54 59  0  0  0  0            999 V2000
   -1.3373   -2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0824   -3.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -3.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795   -4.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315   -5.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6766   -5.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286   -6.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -5.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5612   -7.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8161   -7.8731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6411   -7.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -7.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807   -6.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8522   -6.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260   -8.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905   -9.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754   -9.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9398  -10.7154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4247  -11.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -9.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5808  -10.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314   -9.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9465   -8.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2519   -9.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7368   -9.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5573   -9.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929   -8.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4079   -8.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7435   -7.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2586   -6.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5875   -8.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1025   -7.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0422  -10.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8672  -10.2842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1222  -11.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4547  -11.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0068  -12.1668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9027  -12.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1576  -12.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6056  -13.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8605  -14.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6675  -14.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9224  -15.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2195  -13.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0265  -14.0791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5785  -13.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9646  -13.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7873  -11.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0027  -11.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3896  -10.7717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385   -5.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9934   -4.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414   -3.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6963   -2.8520    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  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 44 47  2  0  0  0  0
 39 47  1  0  0  0  0
 36 48  1  0  0  0  0
 33 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
  5 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
  3 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END


  Mrv1533004251505192D          

 54 59  0  0  0  0            999 V2000
   -1.3373   -2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0824   -3.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -3.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795   -4.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315   -5.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6766   -5.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286   -6.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -5.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5612   -7.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8161   -7.8731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6411   -7.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -7.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807   -6.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8522   -6.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260   -8.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905   -9.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754   -9.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9398  -10.7154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4247  -11.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -9.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5808  -10.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314   -9.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9465   -8.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2519   -9.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7368   -9.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5573   -9.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929   -8.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4079   -8.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7435   -7.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2586   -6.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5875   -8.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1025   -7.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0422  -10.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8672  -10.2842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1222  -11.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4547  -11.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0068  -12.1668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9027  -12.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1576  -12.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6056  -13.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8605  -14.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6675  -14.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9224  -15.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2195  -13.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0265  -14.0791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5785  -13.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9646  -13.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7873  -11.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0027  -11.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3896  -10.7717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385   -5.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9934   -4.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414   -3.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6963   -2.8520    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  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 44 47  2  0  0  0  0
 39 47  1  0  0  0  0
 36 48  1  0  0  0  0
 33 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
  5 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
  3 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225489

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC2(O)COC(C2CO)C2=CC(OC)=C(O)C(=C2)C2=CC(=CC(OC)=C2O)C2OCC(O)(CC3=CC=C(O)C(OC)=C3)C2CO)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C40H46O14/c1-49-31-9-21(5-7-29(31)43)15-39(47)19-53-37(27(39)17-41)23-11-25(35(45)33(13-23)51-3)26-12-24(14-34(52-4)36(26)46)38-28(18-42)40(48,20-54-38)16-22-6-8-30(44)32(10-22)50-2/h5-14,27-28,37-38,41-48H,15-20H2,1-4H3

> <INCHI_KEY>
JTVJZJDQKYSORU-UHFFFAOYSA-N

> <FORMULA>
C40H46O14

> <MOLECULAR_WEIGHT>
750.794

> <EXACT_MASS>
750.288756161

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
75.93071888717796

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[4-hydroxy-3-(2-hydroxy-5-{4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-3-methoxyphenyl)-5-methoxyphenyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-3-ol

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.644066408000001

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.674894798553415

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.055242482801424

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6753340705825126

> <JCHEM_POLAR_SURFACE_AREA>
217.21999999999997

> <JCHEM_REFRACTIVITY>
195.646

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[4-hydroxy-3-(2-hydroxy-5-{4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-3-methoxyphenyl)-5-methoxyphenyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -2.496  -4.500   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.020  -5.964   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.051  -7.109   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.575  -8.573   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.605  -9.718   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.130 -11.182   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.160 -12.327   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.191 -11.182   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.914 -13.232   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.390 -14.697   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.930 -14.697   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.406 -13.232   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.871 -12.756   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -7.191 -11.250   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.835 -15.942   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.209 -17.349   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.114 -18.595   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.488 -20.002   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.393 -21.248   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.646 -18.434   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.551 -19.680   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.272 -17.027   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.367 -15.781   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.804 -16.866   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.709 -18.112   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.240 -17.951   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -12.867 -16.544   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -11.961 -15.299   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -12.588 -13.892   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -11.683 -12.646   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.430 -15.459   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -9.525 -14.214   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -13.145 -19.197   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -14.685 -19.197   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -15.161 -20.662   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -13.915 -21.567   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -14.946 -22.711   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0     -12.885 -22.711   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -13.361 -24.176   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -12.330 -25.320   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -12.806 -26.785   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -14.313 -27.105   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0     -14.789 -28.570   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0     -15.343 -25.961   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0     -16.849 -26.281   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0     -17.880 -25.137   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -14.867 -24.496   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -12.670 -20.662   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -11.205 -21.138   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0     -10.061 -20.107   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -5.112  -9.397   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -5.588  -7.933   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -4.557  -6.788   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -5.033  -5.324   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   53                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   51                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   12                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22   15                                                       
CONECT   24   22   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   24   32                                                  
CONECT   32   31                                                            
CONECT   33   26   34   48                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38   48                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   47                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   47                                                  
CONECT   45   44   46                                                       
CONECT   46   45                                                            
CONECT   47   44   39                                                       
CONECT   48   36   33   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51    5   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52    3   54                                                  
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₄₆O₁₄

Average Mass

750.7940 Da

Monoisotopic Mass

750.28876 Da

IUPAC Name

5-[4-hydroxy-3-(2-hydroxy-5-{4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-3-methoxyphenyl)-5-methoxyphenyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-3-ol

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(CC2(O)COC(C2CO)C2=CC(OC)=C(O)C(=C2)C2=CC(=CC(OC)=C2O)C2OCC(O)(CC3=CC=C(O)C(OC)=C3)C2CO)=CC=C1O

InChI Identifier

InChI=1S/C40H46O14/c1-49-31-9-21(5-7-29(31)43)15-39(47)19-53-37(27(39)17-41)23-11-25(35(45)33(13-23)51-3)26-12-24(14-34(52-4)36(26)46)38-28(18-42)40(48,20-54-38)16-22-6-8-30(44)32(10-22)50-2/h5-14,27-28,37-38,41-48H,15-20H2,1-4H3

InChI Key

JTVJZJDQKYSORU-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
Cerbera manghas	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,9'-epoxylignans

Alternative Parents

Substituents

7,9p-epoxylignan
Linear 1,7-diphenylheptane skeleton
Biphenyl
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Tertiary alcohol
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.81	ALOGPS
logP	2.64	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	217.22 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	195.65 m³·mol⁻¹	ChemAxon
Polarizability	75.93 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

14033810

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol (NP0225489)

MOL for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)

3D MOL for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)

3D SDF for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)

3D-SDF for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)

PDB for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)

3D PDB for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)

SMILES for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)

INCHI for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)

Structure for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)

3D Structure for NP0225489 (5,5'-bis({4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl})-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diol)