NP-MRD: Showing NP-Card for 1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine (NP0337918)

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Record Information

Version

2.0

Created at

2024-09-11 13:02:21 UTC

Updated at

2024-09-11 13:02:21 UTC

NP-MRD ID

NP0337918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine

Description

1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. 1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine is a very strong basic compound (based on its pKa). Outside of the human body, 1,2-dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine has been detected, but not quantified in, fruits and herbs and spices. This could make 1,2-dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061312222D          

 26 30  0  0  0  0            999 V2000
    2.3765    1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633    0.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4645    1.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0154   -2.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212   -2.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327   -1.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -1.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4001   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1188   -0.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    0.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -1.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2232   -1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174   -1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347   -0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9905   -1.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867   -0.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194   -0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6078   -0.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252   -0.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040    0.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1595   -0.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214    0.7739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138   -1.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4840   -0.1247    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
 11  1  1  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  2  0  0  0  0
 15  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 18 17  2  0  0  0  0
 19 11  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  2  0  0  0  0
 21 19  1  0  0  0  0
 22 11  1  0  0  0  0
 22 20  2  0  0  0  0
 23  2  1  0  0  0  0
 23 16  1  0  0  0  0
 24  3  1  0  0  0  0
 24 21  1  0  0  0  0
 25 10  1  0  0  0  0
 25 17  1  0  0  0  0
 26 10  1  0  0  0  0
 26 18  1  0  0  0  0
M  END


  Mrv0541 05061312222D          

 26 30  0  0  0  0            999 V2000
    2.3765    1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633    0.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4645    1.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0154   -2.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212   -2.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327   -1.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -1.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4001   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1188   -0.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    0.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -1.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2232   -1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174   -1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347   -0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9905   -1.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867   -0.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194   -0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6078   -0.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252   -0.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040    0.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1595   -0.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214    0.7739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138   -1.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4840   -0.1247    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
 11  1  1  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  2  0  0  0  0
 15  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 18 17  2  0  0  0  0
 19 11  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  2  0  0  0  0
 21 19  1  0  0  0  0
 22 11  1  0  0  0  0
 22 20  2  0  0  0  0
 23  2  1  0  0  0  0
 23 16  1  0  0  0  0
 24  3  1  0  0  0  0
 24 21  1  0  0  0  0
 25 10  1  0  0  0  0
 25 17  1  0  0  0  0
 26 10  1  0  0  0  0
 26 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C(C)N=C3C4=CC5=C(OCO5)C=C4C=CC3=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H17NO4/c1-11-19-13(6-7-16(23-2)21(19)24-3)14-5-4-12-8-17-18(26-10-25-17)9-15(12)20(14)22-11/h4-9H,10H2,1-3H3

> <INCHI_KEY>
FYDZPRHXTQYOIW-UHFFFAOYSA-N

> <FORMULA>
C21H17NO4

> <MOLECULAR_WEIGHT>
347.364

> <EXACT_MASS>
347.115758037

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.782967668293004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
3.549115089999999

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.393561537557147

> <JCHEM_POLAR_SURFACE_AREA>
49.81

> <JCHEM_REFRACTIVITY>
96.16449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.51e-03 g/l

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

> <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       4.436   1.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.678   0.786   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.734   2.740   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.495  -4.282   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.013  -3.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.048  -3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.565  -2.616   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.080  -3.624   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.319  -0.639   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.288  -1.216   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.872   0.611   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.597  -3.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.150  -1.957   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.632  -2.373   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.217  -1.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.185  -1.123   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.182  -2.548   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.802  -1.056   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.770  -0.464   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.735  -1.298   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.287  -0.048   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.354   0.195   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0      -0.298  -0.707   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.907   1.445   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      12.719  -2.647   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      12.103  -0.233   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    5   12                                                       
CONECT    5    4   14                                                       
CONECT    6    7   13                                                       
CONECT    7    6   16                                                       
CONECT    8   12   17                                                       
CONECT    9   15   18                                                       
CONECT   10   25   26                                                       
CONECT   11    1   19   22                                                  
CONECT   12    4    8   15                                                  
CONECT   13    6   14   19                                                  
CONECT   14    5   13   20                                                  
CONECT   15    9   12   20                                                  
CONECT   16    7   21   23                                                  
CONECT   17    8   18   25                                                  
CONECT   18    9   17   26                                                  
CONECT   19   11   13   21                                                  
CONECT   20   14   15   22                                                  
CONECT   21   16   19   24                                                  
CONECT   22   11   20                                                       
CONECT   23    2   16                                                       
CONECT   24    3   21                                                       
CONECT   25   10   17                                                       
CONECT   26   10   18                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine, 9ci	HMDB

Chemical Formula

C₂₁H₁₇NO₄

Average Mass

347.3640 Da

Monoisotopic Mass

347.11576 Da

IUPAC Name

17,18-dimethoxy-20-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaene

Traditional Name

17,18-dimethoxy-20-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaene

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(C)N=C3C4=CC5=C(OCO5)C=C4C=CC3=C2C=C1

InChI Identifier

InChI=1S/C21H17NO4/c1-11-19-13(6-7-16(23-2)21(19)24-3)14-5-4-12-8-17-18(26-10-25-17)9-15(12)20(14)22-11/h4-9H,10H2,1-3H3

InChI Key

FYDZPRHXTQYOIW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Isoquinoline
Naphthalene
Benzodioxole
Anisole
Alkyl aryl ether
Methylpyridine
Pyridine
Benzenoid
Heteroaromatic compound
Oxacycle
Acetal
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.45	ALOGPS
logP	3.55	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	5.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.81 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.16 m³·mol⁻¹	ChemAxon
Polarizability	37.78 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

HMDB0041063

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020938

KNApSAcK ID

Not Available

Chemspider ID

30777530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101673185

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine (NP0337918)

MOL for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)

3D MOL for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)

3D SDF for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)

3D-SDF for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)

PDB for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)

3D PDB for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)

SMILES for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)

INCHI for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)

Structure for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)

3D Structure for NP0337918 (1,2-Dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]phenanthridine)