NP-MRD: Showing NP-Card for (1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol (NP0203110)

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Record Information

Version

2.0

Created at

2022-09-04 22:29:39 UTC

Updated at

2022-09-04 22:29:39 UTC

NP-MRD ID

NP0203110

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol

Description

Fraxiresinol belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. (1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol is found in Fraxinus chinensis, Fraxinus mandshurica, Gentiana lutea, Salvia santolinifolia and Salvia trijuga. (1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol was first documented in 2004 (PMID: 15270567). Fraxiresinol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 26697686) (PMID: 16864436).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006292D          

 30 33  0  0  0  0            999 V2000
   -1.3862    1.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7188    1.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7188   -0.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513    1.4356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6631    1.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6631    2.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862   -0.1336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1006   -0.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -0.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1006   -1.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.6510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5188    0.6510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1313    0.6510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9563    0.6510    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    3.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    2.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    3.0856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    1.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -0.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -1.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441   -1.7836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -1.7836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    1.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    1.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3775    3.9106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    4.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9585   -0.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441   -0.1336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  5  1  0  0  0  0
  1 15  1  0  0  0  0
 13  5  1  0  0  0  0
  2 13  1  0  0  0  0
 13 15  1  0  0  0  0
 15  9  1  0  0  0  0
  4  2  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  2  0  0  0  0
  6  8  1  0  0  0  0
 17  7  1  0  0  0  0
 17 18  2  0  0  0  0
  8 20  2  0  0  0  0
 20 18  1  0  0  0  0
  9 10  1  6  0  0  0
 12 10  2  0  0  0  0
 11 10  1  0  0  0  0
 11 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 24  2  0  0  0  0
 24 12  1  0  0  0  0
 15 16  1  6  0  0  0
 18 19  1  0  0  0  0
 20 25  1  0  0  0  0
 22 23  1  0  0  0  0
 25 26  1  0  0  0  0
 13 14  1  6  0  0  0
 30 29  1  0  0  0  0
 21 30  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    4.9710    0.0191   -3.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6906   -0.4389   -2.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235   -0.5803   -1.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7967   -0.2819   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2532   -0.4277    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8498   -0.1383    0.6744 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7593    0.6138    1.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5721    1.2781    1.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1358    1.0472    0.5368 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7386    2.1488   -0.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -0.2166    0.5126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3882   -0.0644    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0277    1.0682    0.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299    1.1415    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1106    2.2735    1.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4091    3.3944    1.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1821    0.0927    0.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5825    0.1942    0.3812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5356   -1.0486   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2791   -2.1310   -0.4896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6139   -3.2820   -0.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1715   -1.1033    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282   -0.9605   -0.5652 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214   -0.1983   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0679    0.6051   -0.3327 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0771   -0.8870    1.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4060   -1.1950    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9379   -1.0400   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2733   -1.3452   -0.3645 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6546    0.3878   -4.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148   -0.8078   -3.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2797    0.8585   -3.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1473    0.0821   -1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3175   -1.1073    0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575    0.8277    2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758    2.3731    2.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3028    2.9618    0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881   -0.7983    1.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176    1.9270    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7105    3.1544    2.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1344    4.1298    2.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    3.9153    0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0830   -0.5983    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8222   -3.0545   -1.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3359   -4.0000   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1607   -3.7590   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6868   -2.0155   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607    0.5529   -1.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675   -0.8163   -1.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719    1.4956   -0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754   -1.0189    2.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0368   -1.5558    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8233   -1.6722    0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 11  9  1  0
  9 10  1  6
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
  9 25  1  0
  4  5  1  0
  6 25  1  0
 22 12  1  0
 25 50  1  6
 24 48  1  0
 24 49  1  0
 11 38  1  1
 13 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 10 37  1  0
  8 35  1  0
  8 36  1  0
  6 34  1  1
 26 51  1  0
 27 52  1  0
 29 53  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
M  END


  Mrv1652309272006292D          

 30 33  0  0  0  0            999 V2000
   -1.3862    1.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7188    1.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7188   -0.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513    1.4356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6631    1.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6631    2.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862   -0.1336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1006   -0.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -0.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1006   -1.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.6510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5188    0.6510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1313    0.6510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9563    0.6510    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    3.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    2.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    3.0856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    1.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -0.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -1.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441   -1.7836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -1.7836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    1.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    1.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3775    3.9106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    4.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9585   -0.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441   -0.1336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  5  1  0  0  0  0
  1 15  1  0  0  0  0
 13  5  1  0  0  0  0
  2 13  1  0  0  0  0
 13 15  1  0  0  0  0
 15  9  1  0  0  0  0
  4  2  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  2  0  0  0  0
  6  8  1  0  0  0  0
 17  7  1  0  0  0  0
 17 18  2  0  0  0  0
  8 20  2  0  0  0  0
 20 18  1  0  0  0  0
  9 10  1  6  0  0  0
 12 10  2  0  0  0  0
 11 10  1  0  0  0  0
 11 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 24  2  0  0  0  0
 24 12  1  0  0  0  0
 15 16  1  6  0  0  0
 18 19  1  0  0  0  0
 20 25  1  0  0  0  0
 22 23  1  0  0  0  0
 25 26  1  0  0  0  0
 13 14  1  6  0  0  0
 30 29  1  0  0  0  0
 21 30  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203110

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CO[C@H](C3=CC(OC)=C(O)C(OC)=C3)[C@@]1(O)CO[C@@H]2C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O8/c1-25-15-6-11(4-5-14(15)22)19-13-9-28-20(21(13,24)10-29-19)12-7-16(26-2)18(23)17(8-12)27-3/h4-8,13,19-20,22-24H,9-10H2,1-3H3/t13-,19-,20-,21-/m1/s1

> <INCHI_KEY>
IIWORNRJBHZPOA-PJBPFLDMSA-N

> <FORMULA>
C21H24O8

> <MOLECULAR_WEIGHT>
404.415

> <EXACT_MASS>
404.147117733

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.7557137044688

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3aS,4R,6aR)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-ol

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.5700795906666662

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.005080113010173

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20497190186402

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7860679017828835

> <JCHEM_POLAR_SURFACE_AREA>
106.84000000000002

> <JCHEM_REFRACTIVITY>
102.44449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3aS,4R,6aR)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1H-furo[3,4-c]furan-3a-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -2.588   2.680   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.096  -0.249   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.342   3.585   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.342  -1.155   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.096   2.680   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.238   3.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.238   4.990   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.572   2.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.588  -0.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.921  -1.019   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.255  -0.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.921  -2.559   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.572   1.215   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.968   1.215   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.112   1.215   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -3.652   1.215   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       2.572   5.760   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.905   4.990   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.239   5.760   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.905   3.450   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.589  -1.019   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.589  -2.559   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -7.922  -3.329   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.255  -3.329   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.239   2.680   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.573   3.450   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.571   7.300   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.905   8.070   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.256  -1.019   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.922  -0.249   0.000  0.00  0.00           O+0
CONECT    1    3   15                                                       
CONECT    2   13    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3   13    6                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   17                                                       
CONECT    8    6   20                                                       
CONECT    9   15    4   10                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10   21                                                       
CONECT   12   10   24                                                       
CONECT   13    5    2   15   14                                             
CONECT   14   13                                                            
CONECT   15    1   13    9   16                                             
CONECT   16   15                                                            
CONECT   17    7   18   27                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18                                                            
CONECT   20    8   18   25                                                  
CONECT   21   11   22   30                                                  
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   22   12                                                       
CONECT   25   20   26                                                       
CONECT   26   25                                                            
CONECT   27   17   28                                                       
CONECT   28   27                                                            
CONECT   29   30                                                            
CONECT   30   29   21                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
(+)-Fraxiresinol	PhytoBank
Pseuderesinol	PhytoBank

Chemical Formula

C₂₁H₂₄O₈

Average Mass

404.4150 Da

Monoisotopic Mass

404.14712 Da

IUPAC Name

(1S,3aS,4R,6aR)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-ol

Traditional Name

(1S,3aS,4R,6aR)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1H-furo[3,4-c]furan-3a-ol

CAS Registry Number

Not Available

SMILES

[H][C@]12CO[C@H](C3=CC(OC)=C(O)C(OC)=C3)[C@@]1(O)CO[C@@H]2C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C21H24O8/c1-25-15-6-11(4-5-14(15)22)19-13-9-28-20(21(13,24)10-29-19)12-7-16(26-2)18(23)17(8-12)27-3/h4-8,13,19-20,22-24H,9-10H2,1-3H3/t13-,19-,20-,21-/m1/s1

InChI Key

IIWORNRJBHZPOA-PJBPFLDMSA-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
Fraxinus chinensis	LOTUS Database	35616633
Fraxinus mandshurica	LOTUS Database	35616633
Gentiana lutea	LOTUS Database	35616633
Salvia santolinifolia	LOTUS Database	35616633
Salvia trijuga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Not Available

Direct Parent

Furanoid lignans

Alternative Parents

Substituents

Furanoid lignan
Furofuran lignan skeleton
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Furofuran
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxolane
Tertiary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
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	1.8	ALOGPS
logP	1.57	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.2	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.44 m³·mol⁻¹	ChemAxon
Polarizability	39.76 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

10264198

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21632950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin S, Zhang YL, Liu MT, Zi JC, Gan ML, Song WX, Fan XN, Wang XN, Yang YC, Shi JG: Chemical constituents from branch of Fraxinus sieboldiana. Zhongguo Zhong Yao Za Zhi. 2015 Jul;40(13):2602-11. [PubMed:26697686 ]
Li S, An TY, Li J, Shen Q, Lou FC, Hu LH: PTP1B inhibitors from Saussrurea lappa. J Asian Nat Prod Res. 2006 Apr-May;8(3):281-6. doi: 10.1080/10286020412331286434. [PubMed:16864436 ]
Piccinelli AL, Arana S, Caceres A, di Villa Bianca Rd, Sorrentino R, Rastrelli L: New lignans from the roots of Valeriana prionophylla with antioxidative and vasorelaxant activities. J Nat Prod. 2004 Jul;67(7):1135-40. doi: 10.1021/np049879c. [PubMed:15270567 ]
LOTUS database [Link]

Showing NP-Card for (1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol (NP0203110)

MOL for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)

3D MOL for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)

3D SDF for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)

3D-SDF for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)

PDB for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)

3D PDB for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)

SMILES for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)

INCHI for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)

Structure for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)

3D Structure for NP0203110 ((1s,3as,4r,6ar)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol)