NP-MRD: Showing NP-Card for Cusculine (NP0083506)

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Record Information

Version

2.0

Created at

2022-04-29 04:31:57 UTC

Updated at

2022-04-29 04:31:57 UTC

NP-MRD ID

NP0083506

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cusculine

Description

Cusculine belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Cusculine is found in Angostura paniculata. Based on a literature review very few articles have been published on Cusculine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
   -3.7712    3.3297   -0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0750    1.9826   -0.5772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0311    1.1120   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    1.5407   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6692    0.6804   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6122    1.0923   -0.0912 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    0.2429    0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9512    0.6981    0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2131    2.0044   -0.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4326    2.5035   -1.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9729   -0.2184    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2944    0.1925    0.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3086   -0.7416    0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6925   -1.5316    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -1.9821    0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -1.0747    0.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0626   -1.4827    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1674   -2.6982    0.7767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871   -0.6285    0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835   -1.0992    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009   -2.4058    0.5652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334   -2.7830    1.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197   -0.2027   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6430   -0.5915    0.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2061   -1.0708   -1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952    3.8356   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9856    3.4287   -1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3717    3.8530    0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752    2.5853   -0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368    2.0818   -0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936    2.6539   -1.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178    1.8053   -2.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662    3.4528   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1570   -1.6016   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1309   -1.1682    1.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3136   -0.3120    0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4842   -2.2591    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1703   -3.0226    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414   -3.7953    2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -2.1001    2.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940   -2.6569    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1327   -1.6482   -1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3891   -0.2337   -1.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859   -1.7672   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 23  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
  7 16  1  0
  5 19  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 22 39  1  0
 22 40  1  0
 22 41  1  0
 25 42  1  0
 25 43  1  0
 25 44  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
M  END


  Mrv1652304292206312D          

 25 27  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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -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
    3.5724   -1.2375    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   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
    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
   -0.7145   -0.4125    0.0000 O   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
    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 O   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   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  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  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  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
  2 25  1  0  0  0  0
 14 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083506

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=O)C3=C(OC)C(OC)=C(OC)C=C3NC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO6/c1-21-11-7-6-9-14(16(11)23-3)19-10-8-12(22-2)17(24-4)18(25-5)13(10)15(9)20/h6-8H,1-5H3,(H,19,20)

> <INCHI_KEY>
CCYFNSHESGHUKB-UHFFFAOYSA-N

> <FORMULA>
C18H19NO6

> <MOLECULAR_WEIGHT>
345.351

> <EXACT_MASS>
345.121237336

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.79796249139859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,3,5,6-pentamethoxy-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
3.4109224843333332

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.722839470719208

> <JCHEM_PKA_STRONGEST_BASIC>
-3.430953065503844

> <JCHEM_POLAR_SURFACE_AREA>
75.25000000000001

> <JCHEM_REFRACTIVITY>
91.37769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,3,5,6-pentamethoxy-10H-acridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         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  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9    3   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22    2   14                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO₆

Average Mass

345.3510 Da

Monoisotopic Mass

345.12124 Da

IUPAC Name

1,2,3,5,6-pentamethoxy-9,10-dihydroacridin-9-one

Traditional Name

1,2,3,5,6-pentamethoxy-10H-acridin-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=O)C3=C(OC)C(OC)=C(OC)C=C3NC2=C1OC

InChI Identifier

InChI=1S/C18H19NO6/c1-21-11-7-6-9-14(16(11)23-3)19-10-8-12(22-2)17(24-4)18(25-5)13(10)15(9)20/h6-8H,1-5H3,(H,19,20)

InChI Key

CCYFNSHESGHUKB-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
Angostura paniculata	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Dihydroquinolone
Dihydroquinoline
Anisole
Phenol ether
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Vinylogous ester
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
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	2.88	ALOGPS
logP	3.41	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	15.72	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	75.25 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	91.38 m³·mol⁻¹	ChemAxon
Polarizability	35.8 Å³	ChemAxon
Number of Rings	3	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

C00052252

Chemspider ID

24716979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44584644

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cusculine (NP0083506)

MOL for NP0083506 (Cusculine)

3D MOL for NP0083506 (Cusculine)

3D SDF for NP0083506 (Cusculine)

3D-SDF for NP0083506 (Cusculine)

PDB for NP0083506 (Cusculine)

3D PDB for NP0083506 (Cusculine)

SMILES for NP0083506 (Cusculine)

INCHI for NP0083506 (Cusculine)

Structure for NP0083506 (Cusculine)

3D Structure for NP0083506 (Cusculine)