NP-MRD: Showing NP-Card for (9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene (NP0282751)

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Record Information

Version

2.0

Created at

2022-09-09 09:42:39 UTC

Updated at

2022-09-09 09:42:40 UTC

NP-MRD ID

NP0282751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene

Description

(S)-glaucine, also known as tusidil or tussiglaucin, belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof (S)-glaucine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene is found in Annona purpurea, Annona reticulata, Berberis cretica, Berberis heteropoda, Berberis integerrima, Berberis nummularia, Berberis thunbergii, Cocculus laurifolius, Corydalis cava, Corydalis solida, Corydalis turtschaninovii, Corydalis yanhusuo, Croton draconoides, Croton hemiargyreus, Croton lechleri, Cryptocarya chinensis, Dicentra formosa, Eschscholzia californica, Fissistigma oldhamii, Glaucium corniculatum, Glaucium flavum, Glaucium leiocarpum, Hedycarya angustifolia, Hypecoum procumbens, Liriodendron tulipifera, Litsea wightiana, Magnolia obovata, Berberis repens, Neolitsea parvigemma, Ocotea macrophylla, Ocotea velloziana, Papaver pilosum, Phoenicanthus obliquus, Platycapnos saxicola, Platycapnos spicata, Platycapnos tenuiloba, Pseudofumaria alba, Annona mucosa, Sarcocapnos baetica, Sarcocapnos crassifolia, Sarcocapnos enneaphylla, Thalictrum baicalense, Thalictrum flavum, Thalictrum foetidum, Thalictrum hernandezii, Thalictrum ichangense, Thalictrum minus, Xylopia parviflora and Zanthoxylum ailanthoides. (9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene was first documented in 2019 (PMID: 30849504). Based on a literature review a small amount of articles have been published on (S)-glaucine (PMID: 30216681) (PMID: 35799063) (PMID: 35672295).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092211422D          

 26 29  0  0  1  0            999 V2000
    5.7158    0.0000    0.0000 C   0  0  0  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
    4.2868    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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  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
    1.4289    3.3000    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  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
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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
    0.0000    0.8250    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  2  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    3.9325   -4.2086   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1436   -2.8582    0.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0512   -1.9877    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7919   -2.4439   -0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290   -1.5755   -0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237   -0.2423   -0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1650    0.2429    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447   -0.6570    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5252   -0.2353    0.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7200    1.1341    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396    0.6313    0.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574    1.9878    0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1193    2.6516    0.3485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7632    3.2488   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1915    2.8098    0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9817    4.1737    0.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0390    5.1059    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376    2.2659    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158    0.8990   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125    0.0829   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6682   -1.3961   -0.0410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5977   -2.1242   -0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9938   -1.8344   -0.4187 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -3.2352   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -1.0710    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9652    0.3242   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8371   -4.8019    0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0865   -4.5921    0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7086   -4.3610   -1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6318   -3.5091   -0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    1.2208    0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415    1.4029    1.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303    1.7132    0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7689    1.3743    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    4.1576   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.5234   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8653    2.4615   -1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8450    4.8428   -0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826    5.1366    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258    6.1000    0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3159    2.9032    0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6006   -1.7371    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6219   -3.1846   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575   -2.0994   -1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026   -3.6423    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -3.7798   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2153   -3.4347    0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5788   -1.0068    1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9529   -1.5651    0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1266    0.2243   -1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7591    0.9645    0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
  8  3  1  0
 20 11  1  0
 22  5  1  0
 26 19  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  1
 22 43  1  0
 22 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
M  END


  Mrv1652309092211422D          

 26 29  0  0  1  0            999 V2000
    5.7158    0.0000    0.0000 C   0  0  0  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
    4.2868    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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  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
    1.4289    3.3000    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  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
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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
    0.0000    0.8250    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  2  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0282751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)C1=C(OC)C(OC)=CC3=C1[C@H](C2)N(C)CC3

> <INCHI_IDENTIFIER>
InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1

> <INCHI_KEY>
RUZIUYOSRDWYQF-HNNXBMFYSA-N

> <FORMULA>
C21H25NO4

> <MOLECULAR_WEIGHT>
355.434

> <EXACT_MASS>
355.178358289

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.881998168457685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,13(17),14-hexaene

> <JCHEM_LOGP>
3.0707269650000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.012719476367068

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
101.87909999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,13(17),14-hexaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   20                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   11   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21    5                                                       
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
1,2,9,10-Tetramethoxy-6a-alpha-aporphine	ChEBI
Boldine dimethyl ether	ChEBI
D-Glaucine	ChEBI
Glaucine	ChEBI
S-(+)-Glaucine	ChEBI
Tusidil	Kegg
1,2,9,10-Tetramethoxy-6a-a-aporphine	Generator
1,2,9,10-Tetramethoxy-6a-α-aporphine	Generator
Glaucine hydrobromide, (+-)-isomer	MeSH
Glaucine hydrobromide, (R)-isomer	MeSH
Glaucine hydrobromide, (S)-isomer	MeSH
Glaucine hydroiodide, (R)-isomer	MeSH
Glaucine phosphate, (S)-isomer	MeSH
Glaucine tartrate (1:1), (S)-isomer	MeSH
Glaucine tartrate, (+-)-isomer	MeSH
Glaucine hydrochloride, (R)-isomer	MeSH
Glaucine hydroiodide, (S)-isomer	MeSH
Glaucine mesylate, (+-)-isomer	MeSH
Glaucine phosphate (2:3), (S)-isomer	MeSH
Glaucine phosphate (5:8), (+-)-isomer	MeSH
Glaucine tartrate (1:1), (+-)-isomer	MeSH
Glaucine, (R)-isomer	MeSH
Tussiglaucin	MeSH
Glaucine acetate, (+-)-isomer	MeSH
Glaucine hydrochloride, (+-)-isomer	MeSH
Glaucine maleate, (+-)-isomer	MeSH
Glaucine phosphate (2:3), (+-)-isomer	MeSH
Glaucine phosphate (2:3), (R)-isomer	MeSH
Glaucine sulphate, (+-)-isomer	MeSH
Glaucine tartrate (1:1), (R)-isomer	MeSH
Glaucine tartrate, (R)-isomer	MeSH
Glaucine tartrate, (S)-isomer	MeSH
Glaucine, (S)-isomer	MeSH
Glaucine citrate, (+-)-isomer	MeSH
Glaucine hydrochloride, (S)-isomer	MeSH
Glaucine phosphate	MeSH
Glaucine phosphate (5:7), (+-)-isomer	MeSH
Glaucine tosylate, (R)-isomer	MeSH

Chemical Formula

C₂₁H₂₅NO₄

Average Mass

355.4340 Da

Monoisotopic Mass

355.17836 Da

IUPAC Name

(9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,13(17),14-hexaene

Traditional Name

(9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,13(17),14-hexaene

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)C1=C(OC)C(OC)=CC3=C1[C@H](C2)N(C)CC3

InChI Identifier

InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1

InChI Key

RUZIUYOSRDWYQF-HNNXBMFYSA-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
Annona purpurea	LOTUS Database	35616633
Annona reticulata	LOTUS Database	35616633
Berberis cretica	LOTUS Database	35616633
Berberis heteropoda	LOTUS Database	35616633
Berberis integerrima	LOTUS Database	35616633
Berberis nummularia	LOTUS Database	35616633
Berberis thunbergii	LOTUS Database	35616633
Cocculus laurifolius	LOTUS Database	35616633
Corydalis cava	LOTUS Database	35616633
Corydalis solida	LOTUS Database	35616633
Corydalis turtschaninovii	LOTUS Database	35616633
Corydalis yanhusuo	LOTUS Database	35616633
Croton draconoides	LOTUS Database	35616633
Croton hemiargyreus	LOTUS Database	35616633
Croton lechleri	LOTUS Database	35616633
Cryptocarya chinensis	LOTUS Database	35616633
Dicentra formosa	LOTUS Database	35616633
Eschscholzia californica	LOTUS Database	35616633
Fissistigma oldhamii	LOTUS Database	35616633
Glaucium corniculatum	LOTUS Database	35616633
Glaucium flavum	LOTUS Database	35616633
Glaucium leiocarpum	LOTUS Database	35616633
Hedycarya angustifolia	LOTUS Database	35616633
Hypecoum procumbens	LOTUS Database	35616633
Liriodendron tulipifera	LOTUS Database	35616633
Litsea wightiana	LOTUS Database	35616633
Magnolia obovata	LOTUS Database	35616633
Mahonia repens	LOTUS Database	35616633
Neolitsea parvigemma	LOTUS Database	35616633
Ocotea macrophylla	LOTUS Database	35616633
Ocotea velloziana	LOTUS Database	35616633
Papaver pilosum	LOTUS Database	35616633
Phoenicanthus obliquus	LOTUS Database	35616633
Platycapnos saxicola	LOTUS Database	35616633
Platycapnos spicata	LOTUS Database	35616633
Platycapnos tenuiloba	LOTUS Database	35616633
Pseudofumaria alba	LOTUS Database	35616633
Rollinia mucosa	LOTUS Database	35616633
Sarcocapnos baetica	LOTUS Database	35616633
Sarcocapnos crassifolia	LOTUS Database	35616633
Sarcocapnos enneaphylla	LOTUS Database	35616633
Thalictrum baicalense	LOTUS Database	35616633
Thalictrum flavum	LOTUS Database	35616633
Thalictrum foetidum	LOTUS Database	35616633
Thalictrum hernandezii	LOTUS Database	35616633
Thalictrum ichangense	LOTUS Database	35616633
Thalictrum minus	LOTUS Database	35616633
Xylopia parviflora	LOTUS Database	35616633
Zanthoxylum ailanthoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Ether
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid (CHEBI:5373 )
Isoquinoline alkaloids (C09446 )

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	3.07	ChemAxon
pKa (Strongest Basic)	7.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.88 m³·mol⁻¹	ChemAxon
Polarizability	39.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001861

Chemspider ID

15883

KEGG Compound ID

C09446

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16754

PDB ID

Not Available

ChEBI ID

5373

Good Scents ID

rw1736571

References

General References

Garcia Diaz J, Tuenter E, Escalona Arranz JC, Llaurado Maury G, Cos P, Pieters L: Antimicrobial activity of leaf extracts and isolated constituents of Croton linearis. J Ethnopharmacol. 2019 May 23;236:250-257. doi: 10.1016/j.jep.2019.01.049. Epub 2019 Mar 5. [PubMed:30849504 ]
Heng HL, Chee CF, Thy CK, Tee JT, Chin SP, Herr DR, Buckle MJC, Paterson IC, Doughty SW, Abd Rahman N, Chung LY: In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5-HT(2) and alpha(1) receptors. Chem Biol Drug Des. 2019 Feb;93(2):132-138. doi: 10.1111/cbdd.13390. Epub 2018 Oct 3. [PubMed:30216681 ]
d'Oelsnitz S, Kim W, Burkholder NT, Javanmardi K, Thyer R, Zhang Y, Alper HS, Ellington AD: Using fungible biosensors to evolve improved alkaloid biosyntheses. Nat Chem Biol. 2022 Sep;18(9):981-989. doi: 10.1038/s41589-022-01072-w. Epub 2022 Jul 7. [PubMed:35799063 ]
Catania T, Li Y, Winzer T, Harvey D, Meade F, Caridi A, Leech A, Larson TR, Ning Z, Chang J, Van de Peer Y, Graham IA: A functionally conserved STORR gene fusion in Papaver species that diverged 16.8 million years ago. Nat Commun. 2022 Jun 7;13(1):3150. doi: 10.1038/s41467-022-30856-w. [PubMed:35672295 ]
LOTUS database [Link]

Showing NP-Card for (9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene (NP0282751)

MOL for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)

3D MOL for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)

3D SDF for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)

3D-SDF for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)

PDB for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)

3D PDB for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)

SMILES for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)

INCHI for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)

Structure for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)

3D Structure for NP0282751 ((9s)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene)