NP-MRD: Showing NP-Card for (-)-tetrahydropalmatine (NP0030764)

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Record Information

Version

2.0

Created at

2021-06-19 22:02:18 UTC

Updated at

2021-06-29 23:58:56 UTC

NP-MRD ID

NP0030764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-tetrahydropalmatine

Provided By

JEOL Database JEOL Logo

Description

Tetrahydropalmatine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (-)-tetrahydropalmatine is found in Annona cherimolia, Chasmanthera dependens, Chasmanthera dependens Hochst. , Cocculus laurifolius, Corydalis ambigua, Corydalis aurea, Corydalis balansae, Corydalis bungeana , Corydalis caseana, Corydalis cava , Corydalis decumbens , Corydalis heterocarpa, Corydalis intermedia, Corydalis nobilis, Corydalis ochroleuca, Corydalis pallida, Corydalis racemosa, Corydalis remota, Corydalis saxicola, Corydalis solida , Corydalis turtschaninovii, Corydalis turtschaninowii, Corydalis yanhusuo , Croton hemiargyreus, Enantia chlorantha , Fibraurea chloroleuca Miers, Fibraurea recisa, Fibraurea tinctoria Lour., Fumaria bastardii, Gloucium vitellinum Boiss and Buhse, Hyperbaena columbica (Eichl.) Miers, Leontice leontopetalum Linn. , Parabaena sagittata, Phellodendron amurense , Phellodendron chinense var.glabriusculum , Pseudofumaria alba, Stephania bancroftii, Stephania bancroftii Bailey, Stephania delavayi Diels, Stephania dicentrinifera H.S.Lo & M.Yang, Stephania dielsiana Wu, Stephania discflora Hand.-Mazz., Stephania epigaea H.S.Lo, Stephania glabra (Roxb.) Miers , Stephania kuinanensis H.S.Lo & M.Yang, Stephania lincangensis, Stephania macrantha, Stephania officinarum, Stephania pierrei, Stephania rotunda , Stephania sinica, Stephania suberosa, Stephania venosa, Stephania yunnanensis, Stephanina aculeata, Stephanina bancroftii, Stephanina officinarum, Thalictrum minus and Zanthoxylum taediosum. (-)-tetrahydropalmatine was first documented in 1999 (PMID: 17260290). Based on a literature review a small amount of articles have been published on Tetrahydropalmatine (PMID: 10680579) (PMID: 12709895) (PMID: 19544352).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100023D          

 51 54  0  0  0  0            999 V2000
    3.7069   -6.2644    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928   -5.6246   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -4.3012   -0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -3.5284    0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6937   -2.1862    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261   -1.5778    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200   -2.3671   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -3.7003   -1.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -4.3206   -2.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9925   -5.1476   -3.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778   -0.1246    0.1773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4562    0.6691   -1.1516 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1386    2.1382   -0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389    2.9177   -2.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    4.2712   -1.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5296    4.8560   -0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    6.1826   -0.6555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    6.3879    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993    4.1029    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494    4.6613    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014    5.5002    1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    2.7334    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051    1.8953    1.5086 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1707    0.6198    1.1868 N   0  0  1  0  0  0  0  0  0  0  0  0
    2.3678   -0.1764    2.4003 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2392   -1.3931    2.0837 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7098   -5.8259    0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371   -6.2395    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -7.3141    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -3.9480    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6028   -1.9567   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0224   -4.7736   -3.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547   -6.1790   -2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201   -5.1494   -4.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.1715    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.5836   -1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    0.2509   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298    2.4698   -3.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892    4.8667   -2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    6.5051    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    5.5852   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    7.3219   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    5.7400    2.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107    4.9904    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9668    6.4410    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.7195    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    2.4651    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8811    0.4161    3.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053   -0.4939    2.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2947   -2.0266    2.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2585   -1.0714    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  2  0  0  0  0
 22 13  2  0  0  0  0
  3  8  2  0  0  0  0
 13 14  1  0  0  0  0
  5 26  1  0  0  0  0
 14 15  2  0  0  0  0
  6 11  1  0  0  0  0
 15 16  1  0  0  0  0
 24 25  1  0  0  0  0
 16 19  2  0  0  0  0
 19 22  1  0  0  0  0
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  3  2  1  0  0  0  0
 24 11  1  0  0  0  0
  8  9  1  0  0  0  0
  5  4  2  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  9 10  1  0  0  0  0
  5  6  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 24 23  1  0  0  0  0
 16 17  1  0  0  0  0
 11 12  1  0  0  0  0
 17 18  1  0  0  0  0
 12 13  1  0  0  0  0
 11 35  1  1  0  0  0
  7 31  1  0  0  0  0
  4 30  1  0  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 23 46  1  0  0  0  0
 23 47  1  0  0  0  0
 14 38  1  0  0  0  0
 15 39  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 10 32  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 21 43  1  0  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
 18 40  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    3.7069   -6.2644    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928   -5.6246   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -4.3012   -0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -3.5284    0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6937   -2.1862    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261   -1.5778    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200   -2.3671   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -3.7003   -1.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -4.3206   -2.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9925   -5.1476   -3.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778   -0.1246    0.1773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4562    0.6691   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386    2.1382   -0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389    2.9177   -2.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    4.2712   -1.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5296    4.8560   -0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    6.1826   -0.6555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    6.3879    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993    4.1029    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494    4.6613    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014    5.5002    1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    2.7334    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051    1.8953    1.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1707    0.6198    1.1868 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678   -0.1764    2.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392   -1.3931    2.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7098   -5.8259    0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371   -6.2395    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -7.3141    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -3.9480    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6028   -1.9567   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0224   -4.7736   -3.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547   -6.1790   -2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201   -5.1494   -4.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.1715    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.5836   -1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    0.2509   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2892    4.8667   -2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    6.5051    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    5.5852   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    7.3219   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    5.7400    2.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107    4.9904    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9668    6.4410    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.7195    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    2.4651    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8811    0.4161    3.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053   -0.4939    2.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2947   -2.0266    2.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2585   -1.0714    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
  8  7  1  0
  7  6  2  0
 22 13  2  0
  3  8  2  0
 13 14  1  0
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 14 15  2  0
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 24 25  1  0
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 10 33  1  0
 10 34  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
M  END


  Mrv1652306202100023D          

 51 54  0  0  0  0            999 V2000
    3.7069   -6.2644    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928   -5.6246   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -4.3012   -0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -3.5284    0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6937   -2.1862    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261   -1.5778    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200   -2.3671   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -3.7003   -1.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -4.3206   -2.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9925   -5.1476   -3.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778   -0.1246    0.1773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4562    0.6691   -1.1516 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1386    2.1382   -0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389    2.9177   -2.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    4.2712   -1.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5296    4.8560   -0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    6.1826   -0.6555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    6.3879    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993    4.1029    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494    4.6613    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014    5.5002    1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    2.7334    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051    1.8953    1.5086 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1707    0.6198    1.1868 N   0  0  1  0  0  0  0  0  0  0  0  0
    2.3678   -0.1764    2.4003 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2392   -1.3931    2.0837 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7098   -5.8259    0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371   -6.2395    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -7.3141    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -3.9480    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6028   -1.9567   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0224   -4.7736   -3.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547   -6.1790   -2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201   -5.1494   -4.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.1715    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.5836   -1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    0.2509   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298    2.4698   -3.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892    4.8667   -2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    6.5051    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    5.5852   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    7.3219   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    5.7400    2.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107    4.9904    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9668    6.4410    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.7195    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    2.4651    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8811    0.4161    3.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053   -0.4939    2.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2947   -2.0266    2.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2585   -1.0714    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  2  0  0  0  0
 22 13  2  0  0  0  0
  3  8  2  0  0  0  0
 13 14  1  0  0  0  0
  5 26  1  0  0  0  0
 14 15  2  0  0  0  0
  6 11  1  0  0  0  0
 15 16  1  0  0  0  0
 24 25  1  0  0  0  0
 16 19  2  0  0  0  0
 19 22  1  0  0  0  0
 25 26  1  0  0  0  0
  3  2  1  0  0  0  0
 24 11  1  0  0  0  0
  8  9  1  0  0  0  0
  5  4  2  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  9 10  1  0  0  0  0
  5  6  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 24 23  1  0  0  0  0
 16 17  1  0  0  0  0
 11 12  1  0  0  0  0
 17 18  1  0  0  0  0
 12 13  1  0  0  0  0
 11 35  1  1  0  0  0
  7 31  1  0  0  0  0
  4 30  1  0  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 23 46  1  0  0  0  0
 23 47  1  0  0  0  0
 14 38  1  0  0  0  0
 15 39  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 10 32  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 21 43  1  0  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
 18 40  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030764

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C2=C(C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])N1C([H])([H])C([H])([H])C3=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C3[C@]1([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1

> <INCHI_KEY>
AEQDJSLRWYMAQI-KRWDZBQOSA-N

> <FORMULA>
C21H25NO4

> <MOLECULAR_WEIGHT>
355.434

> <EXACT_MASS>
355.178358289

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
40.59794463936008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12bS)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
3.1479747203333344

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.344725834166826

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
101.35549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrahydropalmatine

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    3.7069   -6.2644    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928   -5.6246   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -4.3012   -0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -3.5284    0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6937   -2.1862    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261   -1.5778    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200   -2.3671   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -3.7003   -1.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -4.3206   -2.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9925   -5.1476   -3.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778   -0.1246    0.1773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4562    0.6691   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386    2.1382   -0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389    2.9177   -2.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    4.2712   -1.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5296    4.8560   -0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    6.1826   -0.6555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    6.3879    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993    4.1029    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494    4.6613    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014    5.5002    1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    2.7334    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051    1.8953    1.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1707    0.6198    1.1868 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678   -0.1764    2.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392   -1.3931    2.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7098   -5.8259    0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371   -6.2395    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -7.3141    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -3.9480    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6028   -1.9567   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0224   -4.7736   -3.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547   -6.1790   -2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201   -5.1494   -4.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.1715    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.5836   -1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    0.2509   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298    2.4698   -3.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892    4.8667   -2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    6.5051    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    5.5852   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    7.3219   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    5.7400    2.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107    4.9904    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9668    6.4410    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.7195    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    2.4651    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8811    0.4161    3.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053   -0.4939    2.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2947   -2.0266    2.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2585   -1.0714    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
  8  7  1  0
  7  6  2  0
 22 13  2  0
  3  8  2  0
 13 14  1  0
  5 26  1  0
 14 15  2  0
  6 11  1  0
 15 16  1  0
 24 25  1  0
 16 19  2  0
 19 22  1  0
 25 26  1  0
  3  2  1  0
 24 11  1  0
  8  9  1  0
  5  4  2  0
  2  1  1  0
  4  3  1  0
  9 10  1  0
  5  6  1  0
 19 20  1  0
 20 21  1  0
 24 23  1  0
 16 17  1  0
 11 12  1  0
 17 18  1  0
 12 13  1  0
 11 35  1  1
  7 31  1  0
  4 30  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 12 36  1  0
 12 37  1  0
 23 46  1  0
 23 47  1  0
 14 38  1  0
 15 39  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.707  -6.264   0.488  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.893  -5.625  -0.485  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.593  -4.301  -0.300  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.083  -3.528   0.758  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.694  -2.186   0.924  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.826  -1.578   0.001  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.320  -2.367  -1.043  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.717  -3.700  -1.216  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.124  -4.321  -2.288  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.992  -5.148  -3.057  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.378  -0.125   0.177  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.456   0.669  -1.152  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.139   2.138  -0.986  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.839   2.918  -2.113  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.537   4.271  -1.972  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.530   4.856  -0.707  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.188   6.183  -0.656  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.996   6.388   0.117  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.899   4.103   0.416  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.949   4.661   1.670  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.101   5.500   1.791  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.192   2.733   0.289  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.505   1.895   1.509  0.00  0.00           C+0
HETATM   24  N   UNK     0       2.171   0.620   1.187  0.00  0.00           N+0
HETATM   25  C   UNK     0       2.368  -0.176   2.400  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.239  -1.393   2.084  0.00  0.00           C+0
HETATM   27  H   UNK     0       4.710  -5.826   0.513  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.237  -6.239   1.477  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.812  -7.314   0.197  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.769  -3.948   1.488  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.603  -1.957  -1.750  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.022  -4.774  -3.081  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.955  -6.179  -2.695  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.620  -5.149  -4.087  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.330  -0.172   0.510  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.462   0.584  -1.585  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.747   0.251  -1.876  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.830   2.470  -3.104  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.289   4.867  -2.846  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.751   6.505   1.176  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.730   5.585  -0.022  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.455   7.322  -0.222  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.226   5.740   2.851  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.011   4.990   1.452  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.967   6.441   1.249  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.567   1.720   2.052  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.176   2.465   2.163  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.881   0.416   3.168  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.405  -0.494   2.824  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.295  -2.027   2.977  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.258  -1.071   1.836  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    8    2    4                                                  
CONECT    4    5    3   30                                                  
CONECT    5   26    4    6                                                  
CONECT    6    7   11    5                                                  
CONECT    7    8    6   31                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   32   33   34                                             
CONECT   11    6   24   12   35                                             
CONECT   12   11   13   36   37                                             
CONECT   13   22   14   12                                                  
CONECT   14   13   15   38                                                  
CONECT   15   14   16   39                                                  
CONECT   16   15   19   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   40   41   42                                             
CONECT   19   16   22   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   43   44   45                                             
CONECT   22   23   13   19                                                  
CONECT   23   22   24   46   47                                             
CONECT   24   25   11   23                                                  
CONECT   25   24   26   48   49                                             
CONECT   26    5   25   50   51                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    7                                                            
CONECT   32   10                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   11                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   18                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   21                                                            
CONECT   44   21                                                            
CONECT   45   21                                                            
CONECT   46   23                                                            
CONECT   47   23                                                            
CONECT   48   25                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  108    0
END

RDKit          3D

51 54  0  0  0  0  0  0  0  0999 V2000
    3.7069   -6.2644    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928   -5.6246   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -4.3012   -0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -3.5284    0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6937   -2.1862    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261   -1.5778    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200   -2.3671   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -3.7003   -1.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -4.3206   -2.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9925   -5.1476   -3.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778   -0.1246    0.1773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4562    0.6691   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386    2.1382   -0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389    2.9177   -2.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    4.2712   -1.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5296    4.8560   -0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    6.1826   -0.6555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    6.3879    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993    4.1029    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494    4.6613    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014    5.5002    1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    2.7334    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051    1.8953    1.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1707    0.6198    1.1868 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678   -0.1764    2.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392   -1.3931    2.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7098   -5.8259    0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371   -6.2395    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -7.3141    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -3.9480    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6028   -1.9567   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0224   -4.7736   -3.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547   -6.1790   -2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201   -5.1494   -4.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.1715    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.5836   -1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    0.2509   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298    2.4698   -3.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892    4.8667   -2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    6.5051    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    5.5852   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    7.3219   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    5.7400    2.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107    4.9904    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9668    6.4410    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.7195    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    2.4651    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8811    0.4161    3.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053   -0.4939    2.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2947   -2.0266    2.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2585   -1.0714    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
  8  7  1  0
  7  6  2  0
 22 13  2  0
  3  8  2  0
 13 14  1  0
  5 26  1  0
 14 15  2  0
  6 11  1  0
 15 16  1  0
 24 25  1  0
 16 19  2  0
 19 22  1  0
 25 26  1  0
  3  2  1  0
 24 11  1  0
  8  9  1  0
  5  4  2  0
  2  1  1  0
  4  3  1  0
  9 10  1  0
  5  6  1  0
 19 20  1  0
 20 21  1  0
 24 23  1  0
 16 17  1  0
 11 12  1  0
 17 18  1  0
 12 13  1  0
 11 35  1  1
  7 31  1  0
  4 30  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 12 36  1  0
 12 37  1  0
 23 46  1  0
 23 47  1  0
 14 38  1  0
 15 39  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(-)-Tetrahydropalmatine	ChEBI
(S)-(-)-Tetrahydropalmatine	ChEBI
(S)-Tetrahydropalmatine	ChEBI
2,3,9,10-Tetramethoxy-13aalpha-berbine	ChEBI
L-Tetrahydropalmatine	ChEBI
(S)-Isomer OF tetrahydropalmatine	MeSH
5,8,13,13a-tetrahydro-2,3,9,10-Tetramethoxy-6H-dibenzo(a,g)quinolizine	MeSH
HCL(+-)-Isomer OF tetrahydropalmatine	MeSH
HCL(R)-Isomer OF tetrahydropalmatine	MeSH
(+-)-Isomer OF tetrahydropalmatine	MeSH
HCL OF Tetrahydropalmatine	MeSH
HCL(S)-Isomer OF tetrahydropalmatine	MeSH
Rotundium	MeSH
Gindarin	MeSH
Tetrahydropalmitine	MeSH
levo-Tetrahydropalmatine	MeSH
Corydalis b	MeSH
Rotundine	MeSH
(R)-Isomer
corydalis b OF tetrahydropalmatine

Chemical Formula

C₂₁H₂₅NO₄

Average Mass

355.4340 Da

Monoisotopic Mass

355.17836 Da

IUPAC Name

(12bS)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

Traditional Name

tetrahydropalmatine

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C2=C(C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])N1C([H])([H])C([H])([H])C3=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C3[C@]1([H])C2([H])[H]

InChI Identifier

InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1

InChI Key

AEQDJSLRWYMAQI-KRWDZBQOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Annona cherimolia	Plant	KNApSAcK
Chasmanthera dependens	LOTUS Database	35616633
Chasmanthera dependens Hochst	KNApSAcK Database	22123792
Chasmanthera dependens Hochst.	Plant	KNApSAcK
Cocculus laurifolius	LOTUS Database	35616633
Corydalis ambigua	LOTUS Database	35616633
Corydalis aurea	LOTUS Database	35616633
Corydalis balansae	LOTUS Database	35616633
Corydalis bungeana	Plant	KNApSAcK
Corydalis caseana	LOTUS Database	35616633
Corydalis caseana A.Gray.	KNApSAcK Database	22123792
Corydalis cava	Plant	KNApSAcK
Corydalis decumbens	Plant	KNApSAcK
Corydalis heterocarpa	LOTUS Database	35616633
Corydalis intermedia	Plant	KNApSAcK
Corydalis nobilis	Plant	KNApSAcK
Corydalis ochroleuca	Plant	KNApSAcK
Corydalis pallida	Plant	KNApSAcK
Corydalis racemosa	Plant	KNApSAcK
Corydalis remota	Plant	KNApSAcK
Corydalis saxicola	LOTUS Database	35616633
Corydalis solida	Plant	KNApSAcK
Corydalis turtschaninovii	LOTUS Database	35616633
Corydalis turtschaninowii	Plant	KNApSAcK
Corydalis yanhusuo	Plant	KNApSAcK
Croton hemiargyreus	Plant	KNApSAcK
Enantia chlorantha	Plant	KNApSAcK
Fibraurea chloroleuca	Plant	KNApSAcK
Fibraurea recisa	LOTUS Database	35616633
Fibraurea tinctoria	Plant	KNApSAcK
Fumaria bastardii	Plant	KNApSAcK
Gloucium vitellinum Boiss and Buhse	-	KNApSAcK
Hyperbaena columbica (Eichl.) Miers	Plant	KNApSAcK
Leontice leontopetalum Linn.	Plant	KNApSAcK
Parabaena sagittata	LOTUS Database	35616633
Parabaena sagittata Miers	KNApSAcK Database	22123792
Phellodendron amurense	Plant	KNApSAcK
Phellodendron chinense var.glabriusculum	Plant	KNApSAcK
Pseudofumaria alba	LOTUS Database	35616633
Stephania bancroftii	JEOL database	Blanchfield, J. T., et al., Phytochemistry 63, 711 (2003)
Stephania bancroftii Bailey	Plant	KNApSAcK
Stephania bancroftii F.M.Bailey	KNApSAcK Database	22123792
Stephania brachyandra Diels	KNApSAcK Database	22123792
Stephania delavayi	Plant	KNApSAcK
Stephania dicentrinifera H.S.Lo & M.Yang	Plant	KNApSAcK
Stephania dicentrinifera H.S.Lo.et.M.Yang	KNApSAcK Database	22123792
Stephania dielsiana Wu	Plant	KNApSAcK
Stephania dielsiana Y.C.Wu	KNApSAcK Database	22123792
Stephania discflora Hand.-Mazz.	Plant	KNApSAcK
Stephania dolichopoda Diels	KNApSAcK Database	22123792
Stephania epigaea	Plant	KNApSAcK
Stephania glabra (Roxb.) Miers	Plant	KNApSAcK
Stephania glabra Miers	KNApSAcK Database	22123792
Stephania hainanensis H.S.Lo & Y.	KNApSAcK Database	22123792
Stephania intermedia	KNApSAcK Database	22123792
Stephania kuinanensis H.S.Lo & M.Yang	Plant	KNApSAcK
Stephania kuinanensis H.S.Lo.	KNApSAcK Database	22123792
Stephania kwangsiensis H.S.Lo	KNApSAcK Database	22123792
Stephania lincangensis	Plant	KNApSAcK
Stephania macrantha	Plant	KNApSAcK
Stephania mashanica H.S.Lo & B.N.	KNApSAcK Database	22123792
Stephania micrantha H.S.Lo	KNApSAcK Database	22123792
Stephania officinarum	Plant	KNApSAcK
Stephania pierrei	LOTUS Database	35616633
Stephania pierrei Diels	KNApSAcK Database	22123792
Stephania rotunda	Plant	KNApSAcK
Stephania sasakii Hayata	KNApSAcK Database	22123792
Stephania sinica	Plant	KNApSAcK
Stephania sinica Diels	KNApSAcK Database	22123792
Stephania suberosa	LOTUS Database	35616633
Stephania suberosa Forman	KNApSAcK Database	22123792
Stephania succinifera H.S.Lo	KNApSAcK Database	22123792
Stephania tetrandra S.Moore	KNApSAcK Database	22123792
Stephania venosa	LOTUS Database	35616633
Stephania venosa Spreng	KNApSAcK Database	22123792
Stephania viridiflavens H.S.Lo & M.Yang	KNApSAcK Database	22123792
Stephania yunnanensis	Plant	KNApSAcK
Stephania yunnanensis H.S Lo	KNApSAcK Database	22123792
Stephanina aculeata	-	KNApSAcK
Stephanina bancroftii	-	KNApSAcK
Stephanina officinarum	-	KNApSAcK
Thalictrum minus	Plant	KNApSAcK
Xylopia vieillardi	KNApSAcK Database	22123792
Zanthoxylum taediosum	Plant	KNApSAcK

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroprotoberberine skeleton
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:16563 )
berberine alkaloid (CHEBI:16563 )
Isoquinoline alkaloids (C02890 )

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	3.09	ALOGPS
logP	3.15	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	5.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.36 m³·mol⁻¹	ChemAxon
Polarizability	40.6 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

DB12093

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Tetrahydropalmatine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16563

Good Scents ID

Not Available

References

General References

Ng TB, Liu F, Wang ZT: Antioxidative activity of natural products from plants. Life Sci. 2000 Jan 14;66(8):709-23. doi: 10.1016/s0024-3205(99)00642-6. [PubMed:10680579 ]
Halbsguth C, Meissner O, Haberlein H: Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site. Planta Med. 2003 Apr;69(4):305-9. doi: 10.1055/s-2003-38869. [PubMed:12709895 ]
Chen JJ, Duh CY, Chen IS: New tetrahydroprotoberberine N-oxide alkaloids and cytotoxic constituents of Corydalis tashiroi. Planta Med. 1999 Oct;65(7):643-7. doi: 10.1055/s-1999-14090. [PubMed:17260290 ]
Hong Z, Wen J, Zhang Q, Fan G, Chai Y, Wu Y: Study on the stereoselective excretion of tetrahydropalmatine enantiomers in rats and identification of in vivo metabolites by liquid chromatography-tandem mass spectrometry. Chirality. 2010 Mar;22(3):355-60. doi: 10.1002/chir.20750. [PubMed:19544352 ]
Blanchfield, J. T., et al. (2003). Blanchfield, J. T., et al., Phytochemistry 63, 711 (2003) . Phytochem..

Showing NP-Card for (-)-tetrahydropalmatine (NP0030764)

MOL for NP0030764 ((-)-tetrahydropalmatine)

3D MOL for NP0030764 ((-)-tetrahydropalmatine)

3D SDF for NP0030764 ((-)-tetrahydropalmatine)

3D-SDF for NP0030764 ((-)-tetrahydropalmatine)

PDB for NP0030764 ((-)-tetrahydropalmatine)

3D PDB for NP0030764 ((-)-tetrahydropalmatine)

SMILES for NP0030764 ((-)-tetrahydropalmatine)

INCHI for NP0030764 ((-)-tetrahydropalmatine)

Structure for NP0030764 ((-)-tetrahydropalmatine)

3D Structure for NP0030764 ((-)-tetrahydropalmatine)