NP-MRD: Showing NP-Card for Cassameridin (NP0067939)

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Record Information

Version

2.0

Created at

2022-04-28 12:46:48 UTC

Updated at

2022-04-28 12:46:48 UTC

NP-MRD ID

NP0067939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cassameridin

Description

Cassameridine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Cassameridine is a strong basic compound (based on its pKa). Cassameridin is found in Cassytha filiformis , Lindera megaphylla and Stephania tetrandra S.Moore . An oxoaporphine alkaloid that is 7H-dibenzoquinolin-7-one which is substituted by methylenedioxy grups at the 1,2 and 9,10 positions.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 38  0  0  0  0  0  0  0  0999 V2000
   -0.3715    3.7349   -0.0698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0246    2.5235   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0671    1.5241   -0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3952    1.8666   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3973    0.9053   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769   -0.4224   -0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7225   -0.7944   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420    0.1638   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752   -0.2289    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0177   -1.5630    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708   -1.9043    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3826   -0.9705    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9921    0.3499    0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569    1.3598    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911    2.6876    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031    3.0685    0.0061 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489    2.0883    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750    0.7503    0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177   -3.2917    0.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837   -3.7615   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868   -2.7449    0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2572   -1.1265   -0.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3338   -0.2464    0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7862    0.9863   -0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6472    2.9148   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -1.8477    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -1.2210    0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844    1.0245    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3776    3.4486    0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957   -3.8275   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -4.7248    0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4315   -0.2119    1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2701   -0.5094   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 22  1  0
 22 23  1  0
 23 24  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 18  2  0
 18 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10 21  1  0
 21 20  1  0
 20 19  1  0
 17  2  1  0
 19 11  1  0
  8  3  1  0
 10  9  1  0
 24  5  1  0
 17 18  1  0
  4 25  1  0
 23 32  1  0
 23 33  1  0
  7 26  1  0
 14 28  1  0
 15 29  1  0
 12 27  1  0
 20 30  1  0
 20 31  1  0
M  END


  Mrv1533004241506452D          

 24 29  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 O   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
    2.8579    0.8250    0.0000 C   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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5564    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    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
    2.8579    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565   -1.7895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209   -2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005   -2.4570    0.0000 O   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 C   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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    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
    1.4289    0.8250    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
  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  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  2  0  0  0  0
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C2=CC3=C(OCO3)C=C2C2=C3C(C=CN=C13)=CC1=C2OCO1

> <INCHI_IDENTIFIER>
InChI=1S/C18H9NO5/c20-17-10-5-12-11(21-6-22-12)4-9(10)15-14-8(1-2-19-16(14)17)3-13-18(15)24-7-23-13/h1-5H,6-7H2

> <INCHI_KEY>
ANNPRBPTCAXMQI-UHFFFAOYSA-N

> <FORMULA>
C18H9NO5

> <MOLECULAR_WEIGHT>
319.272

> <EXACT_MASS>
319.048072394

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
31.482640103532383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,12,14,16,18(22)-octaen-11-one

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
2.5106999900000004

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.4701198885053093

> <JCHEM_POLAR_SURFACE_AREA>
66.88000000000001

> <JCHEM_REFRACTIVITY>
81.1668

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,12,14,16,18(22)-octaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.467   2.016   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.372   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.467  -0.476   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.145  -3.340   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.519  -4.747   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.988  -4.586   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   11                                                  
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   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2   24                                                  
CONECT   24   23   12   19                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Value	Source
Cassameridin	ChEBI

Chemical Formula

C₁₈H₉NO₅

Average Mass

319.2720 Da

Monoisotopic Mass

319.04807 Da

IUPAC Name

5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,12,14,16,18(22)-octaen-11-one

Traditional Name

5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,12,14,16,18(22)-octaen-11-one

CAS Registry Number

Not Available

SMILES

O=C1C2=CC3=C(OCO3)C=C2C2=C3C(C=CN=C13)=CC1=C2OCO1

InChI Identifier

InChI=1S/C18H9NO5/c20-17-10-5-12-11(21-6-22-12)4-9(10)15-14-8(1-2-19-16(14)17)3-13-18(15)24-7-23-13/h1-5H,6-7H2

InChI Key

ANNPRBPTCAXMQI-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, 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
Cassytha filiformis	Plant	KNApSAcK
Lindera megaphylla	Plant	KNApSAcK
Stephania tetrandra	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Isoquinoline
Naphthalene
Quinoline
Benzodioxole
Aryl ketone
Pyridine
Benzenoid
Heteroaromatic compound
Ketone
Oxacycle
Acetal
Azacycle
Organoheterocyclic compound
Aldehyde
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
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	2.01	ALOGPS
logP	2.51	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	3.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.88 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.17 m³·mol⁻¹	ChemAxon
Polarizability	31.48 Å³	ChemAxon
Number of Rings	6	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

C00025782

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

Not Available

PDB ID

Not Available

ChEBI ID

132894

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cassameridin (NP0067939)

MOL for NP0067939 (Cassameridin)

3D MOL for NP0067939 (Cassameridin)

3D SDF for NP0067939 (Cassameridin)

3D-SDF for NP0067939 (Cassameridin)

PDB for NP0067939 (Cassameridin)

3D PDB for NP0067939 (Cassameridin)

SMILES for NP0067939 (Cassameridin)

INCHI for NP0067939 (Cassameridin)

Structure for NP0067939 (Cassameridin)

3D Structure for NP0067939 (Cassameridin)