NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0255012)

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Record Information

Version

2.0

Created at

2022-09-07 19:21:06 UTC

Updated at

2022-09-07 19:21:06 UTC

NP-MRD ID

NP0255012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(2S,3R,4S,5S,6R)-2-{[(1R)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. (2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Phellodendron amurense. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-2-{[(1R)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221212D          

 32 35  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    5.0013   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  1  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  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
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
    3.0453   -1.6429    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5846   -1.0302   -0.4853 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7481   -2.0259   -1.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018   -2.4215   -2.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -1.8212   -1.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0816   -2.4836   -1.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768   -1.9736   -1.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2710   -2.7163   -1.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -0.7558   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -0.1729    0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3964   -0.4659    0.3241 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1653    0.5387   -0.2953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4819    0.3231    0.0885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4674    0.8035   -0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7400    0.5467   -0.4751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6723    1.0064    1.4221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8393    0.5926    2.0580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811    0.6797    2.2737 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5802    1.7510    2.3639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989   -0.5189    1.8100 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4732   -1.6490    2.0448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.0809   -0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3410   -0.5942   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6849    0.0449   -0.9392 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8237    1.1777    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2525    1.6344   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2059    1.1304    0.8459 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5166    1.5534    0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9335    2.5168   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2467    2.9639   -0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9774    3.0246   -0.9178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6688    2.6114   -0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540   -1.1112    1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7862   -1.7365    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7200   -2.6663    0.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1467   -2.9487   -1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604   -1.6872   -2.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -2.0007   -3.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475   -3.5236   -2.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -3.4579   -2.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473   -3.5889   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7073   -1.4240   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6565   -0.7621    0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3592    1.8891   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3161    0.1868   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7974   -0.3082    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7182    2.1034    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4831    1.3437    2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8342    0.4931    3.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0961    2.5939    2.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7706   -0.5915    2.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1278   -1.5233    2.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2856    0.8751    0.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0316    0.3453   -1.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6392    0.8681    1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1778    2.0369   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9299    0.3722    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2569    1.1477    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5953    3.7294    0.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2889    3.7828   -1.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    3.0161   -1.5794 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  2  0
 23 24  1  0
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 25 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
 24  2  1  0
 32 26  1  0
 23  5  1  0
 20 11  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  6 40  1  0
  8 41  1  0
 11 42  1  6
 13 43  1  1
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  6
 17 48  1  0
 18 49  1  1
 19 50  1  0
 20 51  1  1
 21 52  1  0
 22 53  1  0
 24 54  1  6
 25 55  1  0
 25 56  1  0
 27 57  1  0
 28 58  1  0
 30 59  1  0
 31 60  1  0
 32 61  1  0
M  END


  Mrv1652309072221212D          

 32 35  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    5.0013   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
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 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
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  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  1  0  0  0
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 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255012

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2=CC(O)=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C2[C@H]1CC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO8/c1-24-7-6-13-9-17(27)18(31-23-22(30)21(29)20(28)19(11-25)32-23)10-15(13)16(24)8-12-2-4-14(26)5-3-12/h2-5,9-10,16,19-23,25-30H,6-8,11H2,1H3/t16-,19-,20-,21+,22-,23-/m1/s1

> <INCHI_KEY>
HWKIERCNYOLMLM-FHCTVQHNSA-N

> <FORMULA>
C23H29NO8

> <MOLECULAR_WEIGHT>
447.484

> <EXACT_MASS>
447.189316898

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.61308402060993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(1R)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
0.6718008176850953

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.3684333425779

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.693302216446781

> <JCHEM_PKA_STRONGEST_BASIC>
8.31633389669339

> <JCHEM_POLAR_SURFACE_AREA>
143.08

> <JCHEM_REFRACTIVITY>
115.0352

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(1R)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -4.620   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  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20                                                            
CONECT   22    9   23                                                       
CONECT   23   22    5   24                                                  
CONECT   24   23    2   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   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                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₉NO₈

Average Mass

447.4840 Da

Monoisotopic Mass

447.18932 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{[(1R)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5S,6R)-2-{[(1R)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CN1CCC2=CC(O)=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C2[C@H]1CC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C23H29NO8/c1-24-7-6-13-9-17(27)18(31-23-22(30)21(29)20(28)19(11-25)32-23)10-15(13)16(24)8-12-2-4-14(26)5-3-12/h2-5,9-10,16,19-23,25-30H,6-8,11H2,1H3/t16-,19-,20-,21+,22-,23-/m1/s1

InChI Key

HWKIERCNYOLMLM-FHCTVQHNSA-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
Phellodendron amurense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Acetal
Oxacycle
Azacycle
Polyol
Amine
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary 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	0.67	ChemAxon
pKa (Strongest Acidic)	9.69	ChemAxon
pKa (Strongest Basic)	8.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	143.08 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.04 m³·mol⁻¹	ChemAxon
Polarizability	46.61 Å³	ChemAxon
Number of Rings	4	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

163040028

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0255012)

MOL for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0255012 ((2s,3r,4s,5s,6r)-2-{[(1r)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)