NP-MRD: Showing NP-Card for Chelilutine (NP0023965)

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Record Information

Version

2.0

Created at

2021-04-21 17:21:28 UTC

Updated at

2021-08-10 02:03:31 UTC

NP-MRD ID

NP0023965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chelilutine

Provided By

JEOL Database JEOL Logo

Description

Chelilutine belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety. Chelilutine can be extracted and purified from the dried roots of Sanguinaria canadensis (also known asbloodroot plant) as well as from the California poppy (Eschscholzia californica Cham.) (PMID:8229008 ; PMID: 1822177 ). Chelilutine has also been reported to be found in five other plant species belonging to the family Papaveraceae (Dicranostigma lactucoides, Chelidonium majus, Macleaya cordata, Macleaya microcarpa (Maxim) and Stylophorum lasiocarpum) (PMID:17367981 ). As with other dihydrobenzophenanthridine alkaloids, chelilutine exhibits strong binding to DNA (PMID: 19183968 ). Antiproliferative activities for chelilutine against three tumour (HeLa; HL-60; A-2780) and two normal (V-79; LEP) cell lines have also been detected(PMID: 20138138 ). Chelilutine is an efficient inducer of apoptosis.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306102103383D          

 50 54  0  0  0  0            999 V2000
    1.2458   -1.0180   -4.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -0.9862   -4.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775   -1.1874   -3.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2603   -1.3671   -2.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758   -1.5320   -0.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412   -1.6521    0.1909 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9376   -0.3628    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6644   -1.5806   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063   -1.3374   -1.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631   -1.1822   -2.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -0.9487   -4.0442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0259   -2.1508   -4.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9942   -1.2563   -1.4842 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5718   -2.5411   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3293   -0.7541   -0.1547 N   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.3001   -2.2818    5.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7559   -0.2065   -4.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4 33  1  0  0  0  0
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  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 14 41  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
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   -4.3968    0.7007   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3204   -2.7211    2.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5560   -2.1220    4.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  2  0
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M  END

  Mrv1652306102103383D          

 50 54  0  0  0  0            999 V2000
    1.2458   -1.0180   -4.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -0.9862   -4.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4089    1.1565   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0691    1.1181   -0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6851   -2.9235    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -3.2506    3.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305   -3.0207    5.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2704   -0.7885    1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7968   -0.8708    5.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3369   -2.4623    5.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  8  1  0  0  0  0
 24 23  1  0  0  0  0
  4  3  2  0  0  0  0
 19 18  2  0  0  0  0
 17 26  2  0  0  0  0
  9 13  1  0  0  0  0
 21 20  2  0  0  0  0
 20 19  1  0  0  0  0
 23 29  1  0  0  0  0
 13 15  1  0  0  0  0
 27 24  1  0  0  0  0
  3 10  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 17  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
 10 11  1  0  0  0  0
 10  9  2  0  0  0  0
 29 28  1  0  0  0  0
 27 28  1  0  0  0  0
 11 12  1  0  0  0  0
 21 26  1  0  0  0  0
  9  8  1  0  0  0  0
  5  6  1  0  0  0  0
 26 25  1  0  0  0  0
  6  7  1  0  0  0  0
  8  5  2  0  0  0  0
  2  1  1  0  0  0  0
 25 24  2  0  0  0  0
 13 14  1  0  0  0  0
  4 33  1  0  0  0  0
 13 40  1  0  0  0  0
 25 48  1  0  0  0  0
 19 45  1  0  0  0  0
 20 46  1  0  0  0  0
 22 47  1  0  0  0  0
 16 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 28 49  1  0  0  0  0
 28 50  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 14 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])N(C2=C3C([H])=C4OC([H])([H])OC4=C([H])C3=C([H])C([H])=C2C2=C(OC([H])([H])[H])C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C12)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H21NO6/c1-23-20-12(6-5-11-7-14-15(8-13(11)20)29-10-28-14)18-16(25-2)9-17(26-3)21(27-4)19(18)22(23)24/h5-9,22,24H,10H2,1-4H3/t22-/m1/s1

> <INCHI_KEY>
FZCQRBWAPLJNQK-UHFFFAOYSA-N

> <FORMULA>
C22H21NO6

> <MOLECULAR_WEIGHT>
395.411

> <EXACT_MASS>
395.1368874

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
42.07200287784789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(20R)-15,17,18-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaen-20-ol

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.2552148236666656

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.52732705655323

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8803471454636176

> <JCHEM_POLAR_SURFACE_AREA>
69.62

> <JCHEM_REFRACTIVITY>
106.81400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Chelilutine

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
    1.2458   -1.0180   -4.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -0.9862   -4.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775   -1.1874   -3.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2603   -1.3671   -2.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758   -1.5320   -0.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412   -1.6521    0.1909 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9376   -0.3628    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6644   -1.5806   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063   -1.3374   -1.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631   -1.1822   -2.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -0.9487   -4.0442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0259   -2.1508   -4.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9942   -1.2563   -1.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5718   -2.5411   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3293   -0.7541   -0.1547 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3968    0.7007   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6564   -1.3982    0.9178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150   -1.8322    0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6851   -2.5155    1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -2.7211    2.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6293   -2.2851    3.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2504   -2.5231    4.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5560   -2.1220    4.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2530   -1.5101    3.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6778   -1.2579    2.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3292   -1.6260    2.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5285   -1.2057    3.9706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5525   -1.7010    5.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3001   -2.2818    5.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7559   -0.2065   -4.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030   -0.8657   -5.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6709   -1.9923   -4.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401   -1.3701   -2.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0366    0.1378    1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175   -0.5056    1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    0.2665   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441   -2.3964   -5.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8611   -1.9787   -5.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2901   -2.9940   -4.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4704   -0.6155   -2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1573   -2.5613   -0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7844    1.0108    0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4089    1.1565   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0691    1.1181   -0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6851   -2.9235    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -3.2506    3.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305   -3.0207    5.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2704   -0.7885    1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7968   -0.8708    5.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3369   -2.4623    5.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  8  1  0
 24 23  1  0
  4  3  2  0
 19 18  2  0
 17 26  2  0
  9 13  1  0
 21 20  2  0
 20 19  1  0
 23 29  1  0
 13 15  1  0
 27 24  1  0
  3 10  1  0
 21 22  1  0
 22 23  2  0
 15 17  1  0
 15 16  1  0
 17 18  1  0
  3  2  1  0
  5  4  1  0
 10 11  1  0
 10  9  2  0
 29 28  1  0
 27 28  1  0
 11 12  1  0
 21 26  1  0
  9  8  1  0
  5  6  1  0
 26 25  1  0
  6  7  1  0
  8  5  2  0
  2  1  1  0
 25 24  2  0
 13 14  1  0
  4 33  1  0
 13 40  1  0
 25 48  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 28 49  1  0
 28 50  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 14 41  1  0
M  END

HEADER    PROTEIN                                 10-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUN-21         0                                  
HETATM    1  C   UNK     0       1.246  -1.018  -4.739  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.154  -0.986  -4.497  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.578  -1.187  -3.210  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.260  -1.367  -2.114  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.276  -1.532  -0.827  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.641  -1.652   0.191  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.938  -0.363   0.734  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.664  -1.581  -0.595  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.506  -1.337  -1.706  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.963  -1.182  -2.996  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.824  -0.949  -4.044  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.026  -2.151  -4.792  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.994  -1.256  -1.484  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.572  -2.541  -1.607  0.00  0.00           O+0
HETATM   15  N   UNK     0      -4.329  -0.754  -0.155  0.00  0.00           N+0
HETATM   16  C   UNK     0      -4.397   0.701  -0.019  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.656  -1.398   0.918  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.315  -1.832   0.720  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.685  -2.515   1.770  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.320  -2.721   2.997  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.629  -2.285   3.211  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.250  -2.523   4.450  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.556  -2.122   4.619  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.253  -1.510   3.611  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.678  -1.258   2.384  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.329  -1.626   2.158  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.529  -1.206   3.971  0.00  0.00           O+0
HETATM   28  C   UNK     0      -7.553  -1.701   5.325  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.300  -2.282   5.745  0.00  0.00           O+0
HETATM   30  H   UNK     0       1.756  -0.207  -4.209  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.403  -0.866  -5.811  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.671  -1.992  -4.476  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.340  -1.370  -2.215  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.037   0.138   1.105  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.617  -0.506   1.579  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.444   0.267  -0.006  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.144  -2.396  -5.391  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.861  -1.979  -5.477  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.290  -2.994  -4.144  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.470  -0.616  -2.234  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.157  -2.561  -0.831  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.784   1.011   0.957  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.409   1.157  -0.153  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.069   1.118  -0.777  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.685  -2.924   1.649  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.779  -3.251   3.778  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.731  -3.021   5.262  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.270  -0.789   1.606  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.797  -0.871   5.998  0.00  0.00           H+0
HETATM   50  H   UNK     0      -8.337  -2.462   5.407  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1                                                       
CONECT    3    4   10    2                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   34   35   36                                             
CONECT    8   18    9    5                                                  
CONECT    9   13   10    8                                                  
CONECT   10    3   11    9                                                  
CONECT   11   10   12                                                       
CONECT   12   11   37   38   39                                             
CONECT   13    9   15   14   40                                             
CONECT   14   13   41                                                       
CONECT   15   13   17   16                                                  
CONECT   16   15   42   43   44                                             
CONECT   17   26   15   18                                                  
CONECT   18    8   19   17                                                  
CONECT   19   18   20   45                                                  
CONECT   20   21   19   46                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   47                                                  
CONECT   23   24   29   22                                                  
CONECT   24   23   27   25                                                  
CONECT   25   26   24   48                                                  
CONECT   26   17   21   25                                                  
CONECT   27   24   28                                                       
CONECT   28   29   27   49   50                                             
CONECT   29   23   28                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   16                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   22                                                            
CONECT   48   25                                                            
CONECT   49   28                                                            
CONECT   50   28                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  108    0
END

RDKit          3D

50 54  0  0  0  0  0  0  0  0999 V2000
    1.2458   -1.0180   -4.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -0.9862   -4.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775   -1.1874   -3.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2603   -1.3671   -2.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758   -1.5320   -0.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412   -1.6521    0.1909 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9376   -0.3628    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6644   -1.5806   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063   -1.3374   -1.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631   -1.1822   -2.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -0.9487   -4.0442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0259   -2.1508   -4.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9942   -1.2563   -1.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5718   -2.5411   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3293   -0.7541   -0.1547 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3968    0.7007   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6564   -1.3982    0.9178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150   -1.8322    0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6851   -2.5155    1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -2.7211    2.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6293   -2.2851    3.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2504   -2.5231    4.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5560   -2.1220    4.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2530   -1.5101    3.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6778   -1.2579    2.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3292   -1.6260    2.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5285   -1.2057    3.9706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5525   -1.7010    5.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3001   -2.2818    5.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7559   -0.2065   -4.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030   -0.8657   -5.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6709   -1.9923   -4.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401   -1.3701   -2.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0366    0.1378    1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175   -0.5056    1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    0.2665   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441   -2.3964   -5.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8611   -1.9787   -5.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2901   -2.9940   -4.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4704   -0.6155   -2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1573   -2.5613   -0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7844    1.0108    0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4089    1.1565   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0691    1.1181   -0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6851   -2.9235    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -3.2506    3.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305   -3.0207    5.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2704   -0.7885    1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7968   -0.8708    5.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3369   -2.4623    5.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  8  1  0
 24 23  1  0
  4  3  2  0
 19 18  2  0
 17 26  2  0
  9 13  1  0
 21 20  2  0
 20 19  1  0
 23 29  1  0
 13 15  1  0
 27 24  1  0
  3 10  1  0
 21 22  1  0
 22 23  2  0
 15 17  1  0
 15 16  1  0
 17 18  1  0
  3  2  1  0
  5  4  1  0
 10 11  1  0
 10  9  2  0
 29 28  1  0
 27 28  1  0
 11 12  1  0
 21 26  1  0
  9  8  1  0
  5  6  1  0
 26 25  1  0
  6  7  1  0
  8  5  2  0
  2  1  1  0
 25 24  2  0
 13 14  1  0
  4 33  1  0
 13 40  1  0
 25 48  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 28 49  1  0
 28 50  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 14 41  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁NO₆

Average Mass

395.4110 Da

Monoisotopic Mass

395.13689 Da

IUPAC Name

(20R)-15,17,18-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaen-20-ol

Traditional Name

Chelilutine

CAS Registry Number

55950-32-8

SMILES

COC1=CC(OC)=C2C3=CC=C4C=C5OCOC5=CC4=C3N(C)C(O)C2=C1OC

InChI Identifier

InChI=1S/C22H21NO6/c1-23-20-12(6-5-11-7-14-15(8-13(11)20)29-10-28-14)18-16(25-2)9-17(26-3)21(27-4)19(18)22(23)24/h5-9,22,24H,10H2,1-4H3

InChI Key

FZCQRBWAPLJNQK-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chelidonium majus	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Dicranostigma lactucoides	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Eschscholzia californica	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Macleaya cordata	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Macleaya microcarpa	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Pteridophyllum racemosum Sieb.et Zuce.	Plant	KNApSAcK
Sanguinaria canadensis	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Stylophorum lasiocarpum	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)

Chemical Taxonomy

Classification

Not classified

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	3.04	ALOGPS
logP	3.26	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.53	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.81 m³·mol⁻¹	ChemAxon
Polarizability	42.07 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

Not Available

Chemspider ID

10228987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21599905

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bambagiotti-Alberti M, Pinzauti S, Moneti G, Gratteri P, Coran SA, Vincieri FF: Characterization of Sanguinaria canadensis L. fluid extract by FAB mass spectrometry. J Pharm Biomed Anal. 1991;9(10-12):1083-7. doi: 10.1016/0731-7085(91)80048-e. [PubMed:1822177 ]
Suchomelova J, Bochorakova H, Paulova H, Musil P, Taborska E: HPLC quantification of seven quaternary benzo[c]phenanthridine alkaloids in six species of the family Papaveraceae. J Pharm Biomed Anal. 2007 May 9;44(1):283-7. doi: 10.1016/j.jpba.2007.02.005. Epub 2007 Feb 13. [PubMed:17367981 ]
Slunska Z, Gelnarova E, Hammerova J, Taborska E, Slaninova I: Effect of quaternary benzo[c]phenanthridine alkaloids sanguilutine and chelilutine on normal and cancer cells. Toxicol In Vitro. 2010 Apr;24(3):697-706. doi: 10.1016/j.tiv.2010.01.012. Epub 2010 Feb 4. [PubMed:20138138 ]
Urbanova J, Lubal P, Slaninova I, Taborska E, Taborsky P: Fluorescence properties of selected benzo[c]phenantridine alkaloids and studies of their interaction with CT DNA. Anal Bioanal Chem. 2009 Jun;394(4):997-1002. doi: 10.1007/s00216-009-2601-7. Epub 2009 Jan 30. [PubMed:19183968 ]
Pavlína Sečkářová, Radek Marek, Jiří Dostál, Roger Dommisse, Eddy L. Esmans (2002). Pavlína Sečkářová, Radek Marek, Jiří Dostál, Roger Dommisse, Eddy L. Esmans. Structural studies of benzophenanthridine alkaloid free bases by NMR spectroscopy. Magn. Reson. Chem. 40(2), 147-152. Magnetic Resonance in Chemistry.
JEOL [Link]

Showing NP-Card for Chelilutine (NP0023965)

MOL for NP0023965 (Chelilutine)

3D MOL for NP0023965 (Chelilutine)

3D SDF for NP0023965 (Chelilutine)

3D-SDF for NP0023965 (Chelilutine)

PDB for NP0023965 (Chelilutine)

3D PDB for NP0023965 (Chelilutine)

SMILES for NP0023965 (Chelilutine)

INCHI for NP0023965 (Chelilutine)

Structure for NP0023965 (Chelilutine)

3D Structure for NP0023965 (Chelilutine)