NP-MRD: Showing NP-Card for {17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid (NP0214293)

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Record Information

Version

2.0

Created at

2022-09-05 13:33:12 UTC

Updated at

2022-09-05 13:33:12 UTC

NP-MRD ID

NP0214293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid

Description

8-Carboxymethyldihydrochelerythrine 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. 8-Carboxymethyldihydrochelerythrine is a moderately basic compound (based on its pKa). Outside of the human body, 8-carboxymethyldihydrochelerythrine has been detected, but not quantified in, fruits and herbs and spices. This could make 8-carboxymethyldihydrochelerythrine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061304522D          

 30 34  0  0  0  0            999 V2000
    1.8511    1.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5067    1.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316    2.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8720   -1.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -0.8334    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
   -1.3049   -0.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2567   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8491    0.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    2.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9754    0.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4624   -0.4804    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
    0.8740   -0.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2586    0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664    1.5649    0.0000 C   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
    3.8471   -0.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    0.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    2.9405    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
    1.4644    0.5422    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
    1.2606    1.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493    3.7400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6473    2.7173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3029    0.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220    2.0114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6704   -0.1807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3406    1.1128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  6  1  0  0  0  0
 14  5  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 18  2  0  0  0  0
 20 10  1  0  0  0  0
 21 13  2  0  0  0  0
 21 16  1  0  0  0  0
 22 14  2  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 23 21  1  0  0  0  0
 24  1  1  0  0  0  0
 24 16  1  0  0  0  0
 24 22  1  0  0  0  0
 25 20  2  0  0  0  0
 26 20  1  0  0  0  0
 27  2  1  0  0  0  0
 27 17  1  0  0  0  0
 28  3  1  0  0  0  0
 28 23  1  0  0  0  0
 29 11  1  0  0  0  0
 29 18  1  0  0  0  0
 30 11  1  0  0  0  0
 30 19  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -6.0392   -2.0715   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2553   -0.9115   -0.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880   -1.0323   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3049   -2.2769   -0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402   -2.4498   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1400   -1.3225   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965   -0.0673   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0416    0.0788   -0.3329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6860    1.3101   -0.4045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1840    2.0009    0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739    1.1357    0.1224 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7500    1.2167    1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0588    2.3915    2.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3025    2.3735    2.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410    3.5664    2.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    0.9581   -0.4273 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0223    1.9991   -1.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855   -0.3008   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2955   -1.4633   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134   -2.6969   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2822   -2.7948   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0641   -1.6684   -0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4371   -1.7590   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2116   -0.6250   -0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159    0.6023   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2211    0.7364   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4631   -0.3925   -0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940    1.5703   -0.4663 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8884    0.9532   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6049   -0.4165   -0.3562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1256   -1.8664   -0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8121   -2.7973    0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8602   -2.6314   -1.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8916   -3.1796   -0.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016   -3.4131   -0.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894    2.3855    0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1502    1.3145    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    2.8948    0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4039    2.0169   -0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418    1.3359    2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169    0.2897    2.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118    4.0154    2.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0969    2.2698   -1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1661    2.9812   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    1.6811   -2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621   -3.6084    0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463   -3.7744   -0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946   -2.7615   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8553    1.7132   -0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4162    1.3549    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4195    1.1350   -1.4046 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 19  1  0
 19 18  2  0
 18 16  1  0
 16 17  1  0
 16 11  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 18 27  1  0
 27 26  2  0
 26 25  1  0
 25 24  2  0
 24 30  1  0
 30 29  1  0
 29 28  1  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
  4  3  1  0
 20 19  1  0
 11  7  1  0
 22 27  1  0
 28 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
  5 35  1  0
  4 34  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 11 39  1  6
 12 40  1  0
 12 41  1  0
 15 42  1  0
 26 49  1  0
 29 50  1  0
 29 51  1  0
 23 48  1  0
 21 47  1  0
 20 46  1  0
M  END


  Mrv0541 05061304522D          

 30 34  0  0  0  0            999 V2000
    1.8511    1.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5067    1.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316    2.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8720   -1.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -0.8334    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
   -1.3049   -0.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2567   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8491    0.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    2.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9754    0.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4624   -0.4804    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
    0.8740   -0.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2586    0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664    1.5649    0.0000 C   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
    3.8471   -0.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    0.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    2.9405    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
    1.4644    0.5422    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
    1.2606    1.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493    3.7400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6473    2.7173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3029    0.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220    2.0114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6704   -0.1807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3406    1.1128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  6  1  0  0  0  0
 14  5  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 18  2  0  0  0  0
 20 10  1  0  0  0  0
 21 13  2  0  0  0  0
 21 16  1  0  0  0  0
 22 14  2  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 23 21  1  0  0  0  0
 24  1  1  0  0  0  0
 24 16  1  0  0  0  0
 24 22  1  0  0  0  0
 25 20  2  0  0  0  0
 26 20  1  0  0  0  0
 27  2  1  0  0  0  0
 27 17  1  0  0  0  0
 28  3  1  0  0  0  0
 28 23  1  0  0  0  0
 29 11  1  0  0  0  0
 29 18  1  0  0  0  0
 30 11  1  0  0  0  0
 30 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C(C=C1)C1=C(N(C)C2CC(O)=O)C2=CC3=C(OCO3)C=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H21NO6/c1-24-16(10-20(25)26)21-13(6-7-17(27-2)23(21)28-3)14-5-4-12-8-18-19(30-11-29-18)9-15(12)22(14)24/h4-9,16H,10-11H2,1-3H3,(H,25,26)

> <INCHI_KEY>
OZWQDEDYZWNLMM-UHFFFAOYSA-N

> <FORMULA>
C23H21NO6

> <MOLECULAR_WEIGHT>
407.4159

> <EXACT_MASS>
407.136887409

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
42.78196026331686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-yl}acetic acid

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
3.551873145666666

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.951210506812898

> <JCHEM_PKA_STRONGEST_BASIC>
1.5578331473126743

> <JCHEM_POLAR_SURFACE_AREA>
77.46000000000002

> <JCHEM_REFRACTIVITY>
109.77509999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-yl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.455   3.580   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.679   3.096   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.992   4.830   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.494  -1.972   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.012  -1.556   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.953  -0.722   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.436  -0.306   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.079  -1.314   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.318   1.671   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.490   4.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.287   1.094   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.596  -0.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.149   0.353   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.631  -0.063   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.216   0.595   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.871   2.921   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.816   1.187   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.181  -0.238   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.801   1.254   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.592   5.489   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.231   1.846   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.734   1.012   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.714   2.262   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       2.353   2.505   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       1.212   6.981   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.075   5.072   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.299   1.603   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.094   3.755   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.718  -0.337   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.102   2.077   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   27                                                            
CONECT    3   28                                                            
CONECT    4    5   12                                                       
CONECT    5    4   14                                                       
CONECT    6    7   13                                                       
CONECT    7    6   17                                                       
CONECT    8   12   18                                                       
CONECT    9   15   19                                                       
CONECT   10   16   20                                                       
CONECT   11   29   30                                                       
CONECT   12    4    8   15                                                  
CONECT   13    6   14   21                                                  
CONECT   14    5   13   22                                                  
CONECT   15    9   12   22                                                  
CONECT   16   10   21   24                                                  
CONECT   17    7   23   27                                                  
CONECT   18    8   19   29                                                  
CONECT   19    9   18   30                                                  
CONECT   20   10   25   26                                                  
CONECT   21   13   16   23                                                  
CONECT   22   14   15   24                                                  
CONECT   23   17   21   28                                                  
CONECT   24    1   16   22                                                  
CONECT   25   20                                                            
CONECT   26   20                                                            
CONECT   27    2   17                                                       
CONECT   28    3   23                                                       
CONECT   29   11   18                                                       
CONECT   30   11   19                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
2-{17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-yl}acetate	Generator

Chemical Formula

C₂₃H₂₁NO₆

Average Mass

407.4159 Da

Monoisotopic Mass

407.13689 Da

IUPAC Name

2-{17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-yl}acetic acid

Traditional Name

{17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-yl}acetic acid

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(C=C1)C1=C(N(C)C2CC(O)=O)C2=CC3=C(OCO3)C=C2C=C1

InChI Identifier

InChI=1S/C23H21NO6/c1-24-16(10-20(25)26)21-13(6-7-17(27-2)23(21)28-3)14-5-4-12-8-18-19(30-11-29-18)9-15(12)22(14)24/h4-9,16H,10-11H2,1-3H3,(H,25,26)

InChI Key

OZWQDEDYZWNLMM-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Dihydrobenzophenanthridine alkaloids

Direct Parent

Dihydrobenzophenanthridine alkaloids

Alternative Parents

Not Available

Substituents

Not Available

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	3.52	ALOGPS
logP	3.55	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	1.56	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.78 m³·mol⁻¹	ChemAxon
Polarizability	42.78 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

HMDB0029832

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001047

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

13946324

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid (NP0214293)

MOL for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)

3D MOL for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)

3D SDF for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)

3D-SDF for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)

PDB for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)

3D PDB for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)

SMILES for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)

INCHI for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)

Structure for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)

3D Structure for NP0214293 ({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}acetic acid)