NP-MRD: Showing NP-Card for 5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline (NP0259988)

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Record Information

Version

2.0

Created at

2022-09-08 02:01:37 UTC

Updated at

2022-09-08 02:01:37 UTC

NP-MRD ID

NP0259988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline

Description

Mollinedine belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine. 5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline is found in Mollinedia costaricensis. Mollinedine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 40  0  0  0  0  0  0  0  0999 V2000
   -0.2479   -2.5769    0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942   -2.6727    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251   -1.5464    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143   -1.6253   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763   -0.5064   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8432    0.7103   -0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618    0.7885   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -0.3243   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3229   -0.2638    0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3195    1.0819   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931    0.8759    0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3399    0.9659    1.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.7845    1.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5332    0.4983    0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0054    0.4051   -0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6355    0.5937   -0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0335    0.1124   -1.6210 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2365    0.2223   -0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8945    0.2668    0.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   -1.3731    0.3164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8323    1.6477   -0.7892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1090    1.1122   -0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8480   -0.2864   -0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478   -3.4703    0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1509   -3.6083    0.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1980   -2.5755   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9566    1.7331   -0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967    1.8211    0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    1.4522   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6653    1.1881    2.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1071    0.8569    2.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2420    0.5150   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7619    1.1235   -1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8813   -0.6933   -1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2587    1.2911    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9145    1.4764   -1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
 23  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  1 20  1  0
 16 11  1  0
 20  9  2  0
 15 14  1  0
  3  8  1  0
  5  6  2  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 18 33  1  0
 18 34  1  0
 16 32  1  0
  7 27  1  0
 22 35  1  0
 22 36  1  0
  4 26  1  0
  2 25  1  0
  1 24  1  0
M  END


  Mrv1533004251507092D          

 23 27  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -3.9674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9840   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 11 23  2  0  0  0  0
 15 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C(C1=CC=C2OCOC2=C1)C1=C2C=C3OCOC3=CC2=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C18H13NO4/c1-2-15-16(21-9-20-15)6-11(1)5-14-13-8-18-17(22-10-23-18)7-12(13)3-4-19-14/h1-4,6-8H,5,9-10H2

> <INCHI_KEY>
LLMXWLQPZZHFKK-UHFFFAOYSA-N

> <FORMULA>
C18H13NO4

> <MOLECULAR_WEIGHT>
307.305

> <EXACT_MASS>
307.084457903

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.24836647410706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2H-1,3-benzodioxol-5-yl)methyl]-2H-[1,3]dioxolo[4,5-g]isoquinoline

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
2.957227069666666

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.830953482018967

> <JCHEM_POLAR_SURFACE_AREA>
49.81

> <JCHEM_REFRACTIVITY>
81.1985

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(2H-1,3-benzodioxol-5-ylmethyl)-2H-[1,3]dioxolo[4,5-g]isoquinoline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.798  -7.406   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.703  -6.160   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.798  -4.914   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9    2                                                       
CONECT   11    1   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   11   15                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₃NO₄

Average Mass

307.3050 Da

Monoisotopic Mass

307.08446 Da

IUPAC Name

5-[(2H-1,3-benzodioxol-5-yl)methyl]-2H-[1,3]dioxolo[4,5-g]isoquinoline

Traditional Name

5-(2H-1,3-benzodioxol-5-ylmethyl)-2H-[1,3]dioxolo[4,5-g]isoquinoline

CAS Registry Number

Not Available

SMILES

C(C1=CC=C2OCOC2=C1)C1=C2C=C3OCOC3=CC2=CC=N1

InChI Identifier

InChI=1S/C18H13NO4/c1-2-15-16(21-9-20-15)6-11(1)5-14-13-8-18-17(22-10-23-18)7-12(13)3-4-19-14/h1-4,6-8H,5,9-10H2

InChI Key

LLMXWLQPZZHFKK-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

Species Name	Source	Reference
Mollinedia costaricensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Not Available

Direct Parent

Isoquinolines and derivatives

Alternative Parents

Substituents

Isoquinoline
Benzodioxole
Benzenoid
Pyridine
Heteroaromatic compound
Oxacycle
Azacycle
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	3.15	ALOGPS
logP	2.96	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	5.83	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	81.2 m³·mol⁻¹	ChemAxon
Polarizability	31.25 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

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

177772

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline (NP0259988)

MOL for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)

3D MOL for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)

3D SDF for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)

3D-SDF for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)

PDB for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)

3D PDB for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)

SMILES for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)

INCHI for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)

Structure for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)

3D Structure for NP0259988 (5-(2h-1,3-benzodioxol-5-ylmethyl)-2h-[1,3]dioxolo[4,5-g]isoquinoline)