NP-MRD: Showing NP-Card for (-)-Isocorypalmine (NP0138612)

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Record Information

Version

2.0

Created at

2022-06-29 17:37:35 UTC

Updated at

2022-06-29 17:37:35 UTC

NP-MRD ID

NP0138612

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Isocorypalmine

Description

(S)-tetrahydrocolumbamine, also known as isocorypalmine, 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 (S)-tetrahydrocolumbamine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (-)-Isocorypalmine is found in Annickia chlorantha, Bocconia frutescens, Corydalis cava, Corydalis heterocarpa, Pseudofumaria lutea, Corydalis nobilis, Corydalis ophiocarpa, Corydalis saxicola, Corydalis solida, Corydalis turtschaninovii, Corydalis yanhusuo, Glaucium fimbrilligerum, Hydrastis canadensis, Liriodendron tulipifera, Pseudofumaria alba and Thalictrum dioicum. (-)-Isocorypalmine was first documented in 2015 (PMID: 26297140). Based on a literature review a small amount of articles have been published on (S)-tetrahydrocolumbamine (PMID: 30573738) (PMID: 29915609) (PMID: 26977585) (PMID: 26943262).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292219372D          

 25 28  0  0  1  0            999 V2000
   -2.1604   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203   -3.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9705   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -4.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -4.3914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009   -2.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -1.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -4.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.4827    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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  1  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 21  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
   -6.8381   -0.1498   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0248    0.9536    0.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6681    0.7253    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1048   -0.5273    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7600   -0.7577    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9775    0.3251    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5360    1.5789    0.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848    1.8125    0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4154    3.0982    0.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5276    0.0781    0.8177 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2659    1.3561    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025    1.1226    0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7211    1.8032    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0459    1.5177    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3607    0.5532   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710    0.2585   -0.4456 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7059    0.9754    0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315   -0.1388   -0.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -1.1079   -1.7033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7687   -2.4361   -1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601    0.1729   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9209   -0.5392   -1.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034   -0.9057   -0.0248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7442   -2.0459   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1521   -2.1164    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9161    0.1754   -0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7577   -0.9774    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5780   -0.5535   -1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7390   -1.3821   -0.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321    2.4497    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4069    3.2387    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4529   -0.3279    1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430    2.1028    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1616    1.8183    1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5166    2.5526    1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8800    2.0290    1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6881    0.6063   -0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5578    2.0493    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5718    0.8049    1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899   -2.8276   -1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947   -3.0940   -1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5715   -2.5379   -0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653   -1.4308   -1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4229    0.1297   -1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -2.9886   -0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872   -2.1572   -1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8230   -2.6965   -0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1946   -2.5896    1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25  5  1  0
  5  4  2  0
 21 18  1  0
 18 19  1  0
 19 20  1  0
 18 15  2  0
 15 16  1  0
 16 17  1  0
 15 14  1  0
 14 13  2  0
  4  3  1  0
  5  6  1  0
 23 10  1  0
 13 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  9 31  1  0
  7 30  1  0
 10 32  1  1
 11 33  1  0
 11 34  1  0
 22 43  1  0
 22 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
  4 29  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 14 36  1  0
 13 35  1  0
M  END


  Mrv1652306292219372D          

 25 28  0  0  1  0            999 V2000
   -2.1604   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203   -3.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9705   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -4.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -4.3914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009   -2.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -1.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -4.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.4827    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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  1  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 21  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138612

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(OC)=C(OC)C=C4

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m0/s1

> <INCHI_KEY>
KDFKJOFJHSVROC-INIZCTEOSA-N

> <FORMULA>
C20H23NO4

> <MOLECULAR_WEIGHT>
341.407

> <EXACT_MASS>
341.162708225

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.035373031406046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
3.0020806643333335

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.116461714349075

> <JCHEM_PKA_STRONGEST_BASIC>
5.095023742610015

> <JCHEM_POLAR_SURFACE_AREA>
51.16000000000001

> <JCHEM_REFRACTIVITY>
96.87320000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrahydrocolumbamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.033  -5.578   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.024  -6.742   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.512  -6.451   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.504  -7.615   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.008  -7.324   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.512  -5.869   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.024  -5.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.033  -6.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.545  -6.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.049  -4.996   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.561  -4.705   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.569  -5.869   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.065  -7.324   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.553  -7.615   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.049  -9.070   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.537  -9.361   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.529  -8.197   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.016  -8.488   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.082  -5.578   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.586  -4.123   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.065  -3.250   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.504  -4.705   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.008  -4.996   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.008  -9.070   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000 -10.234   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17    5                                                       
CONECT   19   12   20                                                       
CONECT   20   19                                                            
CONECT   21   11                                                            
CONECT   22    6   23                                                       
CONECT   23   22    3                                                       
CONECT   24    4   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
(13AS)-5,8,13,13a-tetrahydro-3,9,10-trimethoxy-6H-dibenzo[a,g]quinolizin-2-ol	ChEBI
5,8,13,13a-Tetrahydrocolumbamine	ChEBI
Isocorypalmine	ChEBI
Tetrahydro-columbamine	MeSH
Tetrahydrocolumbamine	MeSH

Chemical Formula

C₂₀H₂₃NO₄

Average Mass

341.4070 Da

Monoisotopic Mass

341.16271 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

483-34-1

SMILES

COC1=C(O)C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(OC)=C(OC)C=C4

InChI Identifier

InChI=1S/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m0/s1

InChI Key

KDFKJOFJHSVROC-INIZCTEOSA-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
Annickia chlorantha	LOTUS Database	35616633
Bocconia frutescens	LOTUS Database	35616633
Corydalis cava	LOTUS Database	35616633
Corydalis heterocarpa	LOTUS Database	35616633
Corydalis lutea	LOTUS Database	35616633
Corydalis nobilis	LOTUS Database	35616633
Corydalis ophiocarpa	LOTUS Database	35616633
Corydalis saxicola	LOTUS Database	35616633
Corydalis solida	LOTUS Database	35616633
Corydalis turtschaninovii	LOTUS Database	35616633
Corydalis yanhusuo	LOTUS Database	35616633
Glaucium fimbrilligerum	LOTUS Database	35616633
Hydrastis canadensis	LOTUS Database	35616633
Liriodendron tulipifera	LOTUS Database	35616633
Pseudofumaria alba	LOTUS Database	35616633
Thalictrum dioicum	LOTUS Database	35616633

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
1-hydroxy-2-unsubstituted benzenoid
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:17772 )
berberine alkaloid (CHEBI:17772 )
Isoquinoline alkaloids (C04118 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025632

Chemspider ID

389213

KEGG Compound ID

C04118

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440229

PDB ID

Not Available

ChEBI ID

17772

Good Scents ID

Not Available

References

General References

Chang L, Hagel JM, Facchini PJ: Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum. Plant Physiol. 2015 Oct;169(2):1127-40. doi: 10.1104/pp.15.01240. Epub 2015 Aug 21. [PubMed:26297140 ]
Huang P, Liu W, Xu M, Jiang R, Xia L, Wang P, Li H, Tang Z, Zheng Q, Zeng J: Modulation of benzylisoquinoline alkaloid biosynthesis by overexpression berberine bridge enzyme in Macleaya cordata. Sci Rep. 2018 Dec 20;8(1):17988. doi: 10.1038/s41598-018-36211-8. [PubMed:30573738 ]
He SM, Liang YL, Cong K, Chen G, Zhao X, Zhao QM, Zhang JJ, Wang X, Dong Y, Yang JL, Zhang GH, Qian ZL, Fan W, Yang SC: Identification and Characterization of Genes Involved in Benzylisoquinoline Alkaloid Biosynthesis in Coptis Species. Front Plant Sci. 2018 Jun 4;9:731. doi: 10.3389/fpls.2018.00731. eCollection 2018. [PubMed:29915609 ]
Yang XH, Cheng XL, Qin B, Cai ZY, Cai X, Liu S, Wang Q, Qin Y: Ultra-high performance liquid chromatography coupled with quadrupole/time of flight mass spectrometry based chemical profiling approach for the holistic quality control of complex Kang-Jing formula preparations. J Pharm Biomed Anal. 2016 May 30;124:319-336. doi: 10.1016/j.jpba.2016.03.012. Epub 2016 Mar 6. [PubMed:26977585 ]
Xiaowen L, Ling T, Yunfei L, Guoxiang S, Dailin Y, Herry S: Simultaneous determination of seven alkaloids in rat plasma by UFLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cerebralcare Granule. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Apr 1;1017-1018:28-35. doi: 10.1016/j.jchromb.2016.01.062. Epub 2016 Feb 26. [PubMed:26943262 ]

Showing NP-Card for (-)-Isocorypalmine (NP0138612)

MOL for NP0138612 ((-)-Isocorypalmine)

3D MOL for NP0138612 ((-)-Isocorypalmine)

3D SDF for NP0138612 ((-)-Isocorypalmine)

3D-SDF for NP0138612 ((-)-Isocorypalmine)

PDB for NP0138612 ((-)-Isocorypalmine)

3D PDB for NP0138612 ((-)-Isocorypalmine)

SMILES for NP0138612 ((-)-Isocorypalmine)

INCHI for NP0138612 ((-)-Isocorypalmine)

Structure for NP0138612 ((-)-Isocorypalmine)

3D Structure for NP0138612 ((-)-Isocorypalmine)