NP-MRD: Showing NP-Card for (1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene (NP0208221)

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Record Information

Version

2.0

Created at

2022-09-05 05:08:22 UTC

Updated at

2022-09-05 05:08:22 UTC

NP-MRD ID

NP0208221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene

Description

Phyltetralin belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. (1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene is found in Phyllanthus urinaria and Phyllanthus virgatus. (1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene was first documented in 2019 (PMID: 31440162). Based on a literature review a small amount of articles have been published on Phyltetralin (PMID: 32512613) (PMID: 32611404) (PMID: 32606305) (PMID: 32532192).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052207082D          

 30 32  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    4.2868   -1.6500    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
    2.8579   -1.6500    0.0000 C   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  1  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
    2.1434   -2.8875    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 17 26  1  0  0  0  0
 16 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -3.5730    4.5267   -1.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9703    3.7980   -0.5946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9546    2.9687   -1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3915    2.2433    0.1375 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4420    1.4357    0.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3232   -0.0368    0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466   -0.8088    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2724   -2.1625    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095   -2.9365    0.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7026   -2.3862    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0003   -2.7159    0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818   -4.0767   -0.0068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575   -4.7593   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8943   -1.9123    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555   -0.5644    0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0653    0.3878    0.7720 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3809   -0.2728    0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9524   -0.7181    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780   -1.3488    1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8888   -1.5612    0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1251   -2.1921    0.7111 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6976   -2.6418    1.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2884   -1.1032   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205   -1.3244   -1.6087 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5194   -0.9039   -2.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0696   -0.4729   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1171    1.5100   -0.1898 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0422    2.4766   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    3.1091    1.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860    3.9887    0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9989    3.8045   -2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8608    5.2475   -2.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3640    5.1495   -1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3266    2.2754   -1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916    3.6374   -1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046    3.0643    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4223    1.5659    1.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4705    1.7237    0.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551   -0.3738    0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0008   -2.0223    1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4204   -3.2152   -0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7588   -1.5692   -0.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -5.7445   -0.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3641   -5.0241    1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -4.1770   -0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154   -2.3434    0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0608    0.8017    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473   -0.5858    2.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6214   -1.6986    2.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070   -3.4819    2.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7056   -3.0689    1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8051   -1.8055    2.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0211   -1.4327   -3.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5889    0.1806   -3.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4539   -1.2715   -2.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448   -0.1348   -1.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    1.0840   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7924    3.2683   -0.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9981    2.0379   -0.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1985    3.3887    0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1203    4.6876    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924    4.4857    1.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 27  1  0
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 29 30  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 27  4  1  0
 26 17  1  0
 15  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  1
  5 37  1  0
  5 38  1  0
  7 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 16 47  1  1
 27 57  1  6
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 18 48  1  0
 19 49  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
M  END


  Mrv1652309052207082D          

 30 32  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    4.2868   -1.6500    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
    2.8579   -1.6500    0.0000 C   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  1  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
    2.1434   -2.8875    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 17 26  1  0  0  0  0
 16 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@H]1CC2=CC(OC)=C(OC)C=C2[C@H]([C@@H]1COC)C1=CC=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-25-13-17-9-16-11-22(29-5)23(30-6)12-18(16)24(19(17)14-26-2)15-7-8-20(27-3)21(10-15)28-4/h7-8,10-12,17,19,24H,9,13-14H2,1-6H3/t17-,19-,24-/m1/s1

> <INCHI_KEY>
CZZKSEXMNQGXJU-ROMRWMGNSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.22604950240857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3S)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene

> <JCHEM_LOGP>
3.358479455000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6790965807022995

> <JCHEM_POLAR_SURFACE_AREA>
55.38000000000001

> <JCHEM_REFRACTIVITY>
116.33960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   17                                                       
CONECT   27   16    4   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

(1R,2S,3S)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene

Traditional Name

(1R,2S,3S)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene

CAS Registry Number

Not Available

SMILES

COC[C@H]1CC2=CC(OC)=C(OC)C=C2[C@H]([C@@H]1COC)C1=CC=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C24H32O6/c1-25-13-17-9-16-11-22(29-5)23(30-6)12-18(16)24(19(17)14-26-2)15-7-8-20(27-3)21(10-15)28-4/h7-8,10-12,17,19,24H,9,13-14H2,1-6H3/t17-,19-,24-/m1/s1

InChI Key

CZZKSEXMNQGXJU-ROMRWMGNSA-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
Phyllanthus urinaria	LOTUS Database	35616633
Phyllanthus virgatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
Tetralin
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Dialkyl ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.36	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.38 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	116.34 m³·mol⁻¹	ChemAxon
Polarizability	46.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

9398835

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11223782

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Conrado GG, Grazzia N, de Oliveira ADSS, Franco CH, Moraes CB, Gadelha FR, Miguel DC, Garcia VL: Prospecting and Identifying Phyllanthus amarus Lignans with Antileishmanial and Antitrypanosomal Activity. Planta Med. 2020 Jul;86(11):782-789. doi: 10.1055/a-1179-1003. Epub 2020 Jun 8. [PubMed:32512613 ]
Ismail EN, Jantan I, Vidyadaran S, Jamal JA, Azmi N: Phyllanthus amarus prevents LPS-mediated BV2 microglial activation via MyD88 and NF-kappaB signaling pathways. BMC Complement Med Ther. 2020 Jul 1;20(1):202. doi: 10.1186/s12906-020-02961-0. [PubMed:32611404 ]
Nikule HA, Nitnaware KM, Chambhare MR, Kadam NS, Borde MY, Nikam TD: In-vitro propagation, callus culture and bioactive lignan production in Phyllanthus tenellus Roxb: a new source of phyllanthin, hypophyllanthin and phyltetralin. Sci Rep. 2020 Jun 30;10(1):10668. doi: 10.1038/s41598-020-67637-8. [PubMed:32606305 ]
Mohamed SIA, Jantan I, Nafiah MA, Seyed MA, Chan KM: Lignans and Polyphenols of Phyllanthus amarus Schumach and Thonn Induce Apoptosis in HCT116 Human Colon Cancer Cells through Caspases-Dependent Pathway. Curr Pharm Biotechnol. 2021;22(2):262-273. doi: 10.2174/1389201021666200612173029. [PubMed:32532192 ]
Jantan I, Haque MA, Ilangkovan M, Arshad L: An Insight Into the Modulatory Effects and Mechanisms of Action of Phyllanthus Species and Their Bioactive Metabolites on the Immune System. Front Pharmacol. 2019 Aug 7;10:878. doi: 10.3389/fphar.2019.00878. eCollection 2019. [PubMed:31440162 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene (NP0208221)

MOL for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)

3D MOL for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)

3D SDF for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)

3D-SDF for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)

PDB for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)

3D PDB for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)

SMILES for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)

INCHI for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)

Structure for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)

3D Structure for NP0208221 ((1r,2s,3s)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-bis(methoxymethyl)-1,2,3,4-tetrahydronaphthalene)