NP-MRD: Showing NP-Card for (-)-O-Methylthaicanine (NP0067551)

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Record Information

Version

2.0

Created at

2022-04-28 12:25:01 UTC

Updated at

2022-04-28 12:25:01 UTC

NP-MRD ID

NP0067551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-O-Methylthaicanine

Description

(12BS)-3,4,9,10,11-pentamethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene 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. (-)-O-Methylthaicanine is found in Parabaena sagittata and Parabaena sagittata Miers. Based on a literature review very few articles have been published on (12bS)-3,4,9,10,11-pentamethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214252D          

 28 31  0  0  1  0            999 V2000
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    7.0951   -1.3133   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1290   -0.6782    0.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7920   -0.5933   -0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3461   -1.1339   -1.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0140   -1.0279   -1.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098   -0.3839   -0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5700    0.1422    0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322    0.0419    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3689    0.5902    1.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8211    1.9163    1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6838    0.8374    1.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386    0.4069    1.0314 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536   -0.8812    1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -1.4926    1.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0812   -0.5754    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5161    0.4563   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2911    1.3219   -1.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6769    1.1934   -1.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4699    2.0681   -1.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782    3.1251   -2.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375    0.1629   -0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6150    0.0168   -0.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5070    0.6227    0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4572   -0.7110    0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0162   -1.7439    0.9786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2198   -3.0442    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0434    0.5982   -0.3496 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6794   -0.2853   -1.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6265   -2.2816   -1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0263   -1.5113   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3491   -0.7448   -1.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0241   -1.6302   -2.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5935   -1.4309   -2.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846    2.6456    2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484    2.2444    1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4172    1.9644    2.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7063    1.9475    1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    0.6835    2.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -1.6125    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0541   -0.7778    2.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0186   -2.4447    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7960   -1.8522    1.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655    2.1373   -1.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6487    3.6322   -3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4557    3.9033   -1.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0886    2.7582   -3.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4627    0.0420    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1126    0.6354    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6891    1.6627    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2508   -3.5824    0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6880   -2.9836   -0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9027   -3.5744    1.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357    1.6611   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -1.2833   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.1561   -2.3356 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 28  1  0
 28 27  1  0
 27 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 12 11  1  0
 11  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8  3  1  0
  7  6  1  0
 16 27  1  0
 24 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
 28 54  1  0
 28 55  1  0
 27 53  1  6
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 11 37  1  0
 11 38  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
M  END


  Mrv1652304282214252D          

 28 31  0  0  1  0            999 V2000
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C[C@@H]3N(CCC4=C3C=C(OC)C(OC)=C4OC)CC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO5/c1-24-18-7-6-13-10-17-15-11-19(25-2)22(28-5)21(27-4)14(15)8-9-23(17)12-16(13)20(18)26-3/h6-7,11,17H,8-10,12H2,1-5H3/t17-/m0/s1

> <INCHI_KEY>
ODXIINJWIDRSBL-KRWDZBQOSA-N

> <FORMULA>
C22H27NO5

> <MOLECULAR_WEIGHT>
385.46

> <EXACT_MASS>
385.188922973

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.73681280452196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12bS)-3,4,9,10,11-pentamethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.990303454666666

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.10497249799023

> <JCHEM_POLAR_SURFACE_AREA>
49.39

> <JCHEM_REFRACTIVITY>
107.81869999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12bS)-3,4,9,10,11-pentamethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.862   2.807   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.342   3.680   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.179   4.553   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.691   0.188   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.699   1.352   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.326  -2.140   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.187  -2.431   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.399   3.680   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.391   4.844   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.919   2.807   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   27                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21                                                            
CONECT   23   16   24                                                       
CONECT   24   23                                                            
CONECT   25    3   26                                                       
CONECT   26   25                                                            
CONECT   27    2   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇NO₅

Average Mass

385.4600 Da

Monoisotopic Mass

385.18892 Da

IUPAC Name

(12bS)-3,4,9,10,11-pentamethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

Traditional Name

(12bS)-3,4,9,10,11-pentamethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C[C@@H]3N(CCC4=C3C=C(OC)C(OC)=C4OC)CC2=C1OC

InChI Identifier

InChI=1S/C22H27NO5/c1-24-18-7-6-13-10-17-15-11-19(25-2)22(28-5)21(27-4)14(15)8-9-23(17)12-16(13)20(18)26-3/h6-7,11,17H,8-10,12H2,1-5H3/t17-/m0/s1

InChI Key

ODXIINJWIDRSBL-KRWDZBQOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Parabaena sagittata	LOTUS Database	35616633
Parabaena sagittata Miers	Plant	KNApSAcK

Chemical Taxonomy

Description

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

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	2.94	ALOGPS
logP	2.99	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.82 m³·mol⁻¹	ChemAxon
Polarizability	41.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

14487606

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-O-Methylthaicanine (NP0067551)

MOL for NP0067551 ((-)-O-Methylthaicanine)

3D MOL for NP0067551 ((-)-O-Methylthaicanine)

3D SDF for NP0067551 ((-)-O-Methylthaicanine)

3D-SDF for NP0067551 ((-)-O-Methylthaicanine)

PDB for NP0067551 ((-)-O-Methylthaicanine)

3D PDB for NP0067551 ((-)-O-Methylthaicanine)

SMILES for NP0067551 ((-)-O-Methylthaicanine)

INCHI for NP0067551 ((-)-O-Methylthaicanine)

Structure for NP0067551 ((-)-O-Methylthaicanine)

3D Structure for NP0067551 ((-)-O-Methylthaicanine)