NP-MRD: Showing NP-Card for (+)-Homochelidonine (NP0069947)

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Record Information

Version

2.0

Created at

2022-04-28 15:14:41 UTC

Updated at

2022-04-28 15:14:41 UTC

NP-MRD ID

NP0069947

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Homochelidonine

Description

Homochelidonine belongs to the class of organic compounds known as hexahydrobenzophenanthridine alkaloids. These are alkaloids containing a hexahydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a hexahydrophenanthridine moiety. (+)-Homochelidonine is found in Chelidonium majus and Eschscholzia californica. (+)-Homochelidonine was first documented in 2008 (PMID: 18200643). Based on a literature review a small amount of articles have been published on Homochelidonine (PMID: 29527613) (PMID: 26969379) (PMID: 23676491) (PMID: 21213973).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217142D          

 27 31  0  0  1  0            999 V2000
    5.0722    0.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2760    0.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6856    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8914    1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876    0.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -0.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934    0.2828    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3029    0.8590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5067    1.6584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3009    1.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163    2.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087    0.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049   -0.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953   -0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896   -0.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2800   -1.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107   -0.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798    0.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240    0.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740   -0.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4644    0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -1.1864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4873   -1.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    1.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4043    0.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7696   -0.2878    0.0000 O   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  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  1  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 27  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
    5.8103    0.8494    1.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0083    0.8419    0.4681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525    0.2787    0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695   -0.3284    1.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8920   -0.8991    1.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802   -0.8595    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801   -0.2520   -0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0270    0.3131   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057    0.8951   -1.9305 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2358    0.0484   -2.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9797   -0.2045   -2.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209    0.2982   -1.6353 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1472    1.5196   -0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9905   -0.7354   -0.8709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2862   -0.2584   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9376    0.8622   -0.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1566    1.2574   -0.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7672    0.5482    0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1290   -0.5812    1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9259   -0.9381    0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2364   -2.1583    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187   -1.6897    1.4694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8741   -0.5678    2.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675   -1.4512    0.1238 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9703    1.1626    0.9830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2826    2.0581   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    2.3110   -0.6410 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2456    1.2691    2.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7085    1.4584    1.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0728   -0.1863    1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064   -0.3752    2.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -1.3754    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8322    0.6181   -3.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5556   -0.6809   -3.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9597   -0.5927   -2.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3851    0.5522   -2.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8816   -1.1797   -2.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7515    1.5764    0.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9161    1.5723   -0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2963    2.4179   -1.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2803   -1.4900   -1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4819    1.4319   -1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6210   -1.1264    1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407   -2.5153    2.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1926   -2.9020    0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -2.4849    1.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7954   -0.3726    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512   -2.5123   -0.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9748    1.5666   -0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6736    3.0104    0.3394 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
  9 10  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 24  1  0
 24 22  1  0
 22 23  1  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 27  1  0
 27 26  1  0
 26 25  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 11  1  0
  4  3  1  0
 14 24  1  0
 11  7  1  0
 15 20  1  0
 25 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
  5 32  1  0
  4 31  1  0
 24 48  1  6
 22 46  1  1
 23 47  1  0
 21 44  1  0
 21 45  1  0
 19 43  1  0
 26 49  1  0
 26 50  1  0
 16 42  1  0
 14 41  1  6
 13 38  1  0
 13 39  1  0
 13 40  1  0
 11 36  1  0
 11 37  1  0
M  END


  Mrv1652304282217142D          

 27 31  0  0  1  0            999 V2000
    5.0722    0.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2760    0.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6856    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8914    1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876    0.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -0.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934    0.2828    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3029    0.8590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5067    1.6584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3009    1.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163    2.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087    0.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049   -0.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953   -0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896   -0.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2800   -1.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107   -0.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798    0.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240    0.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740   -0.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4644    0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -1.1864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4873   -1.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    1.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4043    0.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7696   -0.2878    0.0000 O   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  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  1  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069947

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C(C=C1)[C@H]1[C@@H](O)CC3=CC4=C(OCO4)C=C3[C@H]1N(C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C21H23NO5/c1-22-9-14-12(4-5-16(24-2)21(14)25-3)19-15(23)6-11-7-17-18(27-10-26-17)8-13(11)20(19)22/h4-5,7-8,15,19-20,23H,6,9-10H2,1-3H3/t15-,19-,20+/m0/s1

> <INCHI_KEY>
MADYLZJCRKUBIK-RYGJVYDSSA-N

> <FORMULA>
C21H23NO5

> <MOLECULAR_WEIGHT>
369.417

> <EXACT_MASS>
369.157622845

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.67921742436663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,13R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-2,4(8),9,14(19),15,17-hexaen-12-ol

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.1161687259999997

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.648492033522825

> <JCHEM_PKA_STRONGEST_BASIC>
5.614243206186422

> <JCHEM_POLAR_SURFACE_AREA>
60.390000000000015

> <JCHEM_REFRACTIVITY>
100.16770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,13R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-2,4(8),9,14(19),15,17-hexaen-12-ol

> <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       9.468   0.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.849   1.778   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.746   2.854   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.264   2.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.883   0.945   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.986  -0.131   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.401   0.528   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.299   1.603   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.679   3.096   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.162   3.512   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.577   4.171   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.816   1.187   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.436  -0.306   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.538  -1.381   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.021  -0.964   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.123  -2.040   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.953  -0.722   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.149   0.353   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.232   1.846   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.714   2.262   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.631  -0.063   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.734   1.012   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.573  -2.215   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.910  -2.631   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.385   1.877   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.955   0.446   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.770  -0.537   0.000  0.00  0.00           O+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8   13   20                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14    7   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18   23                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   12                                                       
CONECT   21   18   22                                                       
CONECT   22   21                                                            
CONECT   23   17   24                                                       
CONECT   24   23                                                            
CONECT   25    2   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    1                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
(+/-)-homochelidonine	Kegg
Norchelidonine	MeSH

Chemical Formula

C₂₁H₂₃NO₅

Average Mass

369.4170 Da

Monoisotopic Mass

369.15762 Da

IUPAC Name

(1S,12S,13R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-2,4(8),9,14(19),15,17-hexaen-12-ol

Traditional Name

(1S,12S,13R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-2,4(8),9,14(19),15,17-hexaen-12-ol

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(C=C1)[C@H]1[C@@H](O)CC3=CC4=C(OCO4)C=C3[C@H]1N(C)C2

InChI Identifier

InChI=1S/C21H23NO5/c1-22-9-14-12(4-5-16(24-2)21(14)25-3)19-15(23)6-11-7-17-18(27-10-26-17)8-13(11)20(19)22/h4-5,7-8,15,19-20,23H,6,9-10H2,1-3H3/t15-,19-,20+/m0/s1

InChI Key

MADYLZJCRKUBIK-RYGJVYDSSA-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
Chelidonium majus	Plant	KNApSAcK
Eschscholzia californica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexahydrobenzophenanthridine alkaloids. These are alkaloids containing a hexahydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a hexahydrophenanthridine moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Hexahydrobenzophenanthridine alkaloids

Direct Parent

Hexahydrobenzophenanthridine alkaloids

Alternative Parents

Substituents

Hexahydrobenzophenanthridine alkaloid skeleton
Benzoquinoline
Phenanthridine
Quinoline
Tetrahydroisoquinoline
Tetralin
Benzodioxole
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Ether
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzophenanthridine alkaloid (CHEBI:31025 )

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	2.14	ALOGPS
logP	2.12	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.65	ChemAxon
pKa (Strongest Basic)	5.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.17 m³·mol⁻¹	ChemAxon
Polarizability	39.68 Å³	ChemAxon
Number of Rings	5	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

C00028351

Chemspider ID

144306

KEGG Compound ID

C12257

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164609

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fleming MJ, McManus HA, Rudolph A, Chan WH, Ruiz J, Dockendorff C, Lautens M: Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a Pd II-catalyzed ring-opening strategy. Chemistry. 2008;14(7):2112-24. doi: 10.1002/chem.200701775. [PubMed:18200643 ]
Li RQ, He Y, Ding Y, Ang CK, Tian JS, Loh TP: Formal synthesis of chelamidine alkaloids and their derivatives. Chem Commun (Camb). 2018 Mar 28;54(25):3150-3153. doi: 10.1039/c7cc09875h. Epub 2018 Mar 12. [PubMed:29527613 ]
Havelek R, Seifrtova M, Kralovec K, Krocova E, Tejkalova V, Novotny I, Cahlikova L, Safratova M, Opletal L, Bilkova Z, Vavrova J, Rezacova M: Comparative cytotoxicity of chelidonine and homochelidonine, the dimethoxy analogues isolated from Chelidonium majus L. (Papaveraceae), against human leukemic and lung carcinoma cells. Phytomedicine. 2016 Mar 15;23(3):253-66. doi: 10.1016/j.phymed.2016.01.001. Epub 2016 Jan 22. [PubMed:26969379 ]
Bozhadze AD, Vachnadze VIu, Dzhokhadze MS, Berashvili DT, Bakuridze AD: [Study on the separation process of pharmacological active total alkaloids from Chelidonium majus L. growing in Georgia]. Georgian Med News. 2013 Apr;(217):61-5. [PubMed:23676491 ]
Cahlikova L, Opletal L, Kurfurst M, Macakova K, Kulhankova A, Hostalkova A: Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). Nat Prod Commun. 2010 Nov;5(11):1751-4. [PubMed:21213973 ]

Showing NP-Card for (+)-Homochelidonine (NP0069947)

MOL for NP0069947 ((+)-Homochelidonine)

3D MOL for NP0069947 ((+)-Homochelidonine)

3D SDF for NP0069947 ((+)-Homochelidonine)

3D-SDF for NP0069947 ((+)-Homochelidonine)

PDB for NP0069947 ((+)-Homochelidonine)

3D PDB for NP0069947 ((+)-Homochelidonine)

SMILES for NP0069947 ((+)-Homochelidonine)

INCHI for NP0069947 ((+)-Homochelidonine)

Structure for NP0069947 ((+)-Homochelidonine)

3D Structure for NP0069947 ((+)-Homochelidonine)