NP-MRD: Showing NP-Card for Bruceolline C (NP0069653)

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Record Information

Version

2.0

Created at

2022-04-28 15:01:33 UTC

Updated at

2022-04-28 15:01:33 UTC

NP-MRD ID

NP0069653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bruceolline C

Description

12-Hydroxy-8,11-dimethoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]Hexadeca-3,5(16),6,8,10(15),11,13-heptaen-2-one belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. Bruceolline C is found in Brucea mollis and Brucea mollis var. tonkinensis. 12-Hydroxy-8,11-dimethoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]Hexadeca-3,5(16),6,8,10(15),11,13-heptaen-2-one is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
    3.2720   -0.4960   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3684   -0.4272    1.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2499   -1.2359    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452   -2.5875    1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5407   -3.0615    1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2362   -3.3995    1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490   -2.9083    0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0372   -1.5785    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836   -0.7343    0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2996    0.5345   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3041    1.7763   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6056    1.9703    0.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903    3.1839    0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807    2.8157   -0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7821    2.6718   -0.9081 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3839    1.4802   -0.8575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7135    1.2814   -1.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1535   -0.0196   -1.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3367   -1.0558   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7861   -2.2208   -0.5185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481   -0.8240   -0.2771 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6184    0.4326   -0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -0.0996   -1.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858    0.0931    0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360   -1.5243   -0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108   -2.4295    1.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441   -4.4412    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7843   -3.5737    0.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4046    3.0493    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653    3.7752   -0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612    3.8585    1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820    3.8044   -0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3139    2.1009   -1.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884   -0.2108   -1.3652 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
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21  8  1  0
  8  9  2  0
  9 10  1  0
 10 22  2  0
  9  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
 10 11  1  0
 22 16  1  0
 22 21  1  0
  7  8  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 18 34  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
M  END


  Mrv1533005011512452D          

 22 25  0  0  0  0            999 V2000
    1.5629   -1.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1150   -0.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0531    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981    1.3377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    2.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    3.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    3.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4058    3.5696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246    2.2642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5961    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1481   -0.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342   -0.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 12 20  2  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
  6 22  1  0  0  0  0
 11 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CN=C2C=CC(=O)N3C4=C(C1=C23)C(OC)=C(O)C=C4

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O4/c1-21-11-7-17-8-3-6-12(20)18-9-4-5-10(19)16(22-2)13(9)14(11)15(8)18/h3-7,19H,1-2H3

> <INCHI_KEY>
DGEILRLBRKVUDN-UHFFFAOYSA-N

> <FORMULA>
C16H12N2O4

> <MOLECULAR_WEIGHT>
296.282

> <EXACT_MASS>
296.079706874

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.360856660781735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-hydroxy-8,11-dimethoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
1.1939617849999997

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.897928193679565

> <JCHEM_PKA_STRONGEST_BASIC>
4.460924633993919

> <JCHEM_POLAR_SURFACE_AREA>
73.58

> <JCHEM_REFRACTIVITY>
79.404

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxy-8,11-dimethoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-15         0                                  
HETATM    1  C   UNK     0       2.918  -1.897   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.948  -0.752   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.472   0.712   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.966   1.032   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.490   2.497   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.520   3.641   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.459   5.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.705   6.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.112   5.758   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.357   6.663   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       5.273   4.226   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.518   3.321   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.025   3.641   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.055   2.497   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.579   1.032   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.610  -0.112   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.073   0.712   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.597  -0.752   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.091  -1.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.043   1.857   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.503   1.857   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.027   3.321   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   22                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   12   21                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21    6   11                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂N₂O₄

Average Mass

296.2820 Da

Monoisotopic Mass

296.07971 Da

IUPAC Name

12-hydroxy-8,11-dimethoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

Traditional Name

12-hydroxy-8,11-dimethoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CN=C2C=CC(=O)N3C4=C(C1=C23)C(OC)=C(O)C=C4

InChI Identifier

InChI=1S/C16H12N2O4/c1-21-11-7-17-8-3-6-12(20)18-9-4-5-10(19)16(22-2)13(9)14(11)15(8)18/h3-7,19H,1-2H3

InChI Key

DGEILRLBRKVUDN-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
Brucea mollis	LOTUS Database	35616633
Brucea mollis var. tonkinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Indolonaphthyridine alkaloids

Sub Class

Not Available

Direct Parent

Indolonaphthyridine alkaloids

Alternative Parents

Substituents

Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Diazanaphthalene
Hydroxyindole
Naphthyridine
Indole
Indole or derivatives
Indolizine
Pyrrolopyridine
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Lactam
Azacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen 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	2.29	ALOGPS
logP	1.19	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.9	ChemAxon
pKa (Strongest Basic)	4.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.4 m³·mol⁻¹	ChemAxon
Polarizability	29.36 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Bruceolline C (NP0069653)

MOL for NP0069653 (Bruceolline C)

3D MOL for NP0069653 (Bruceolline C)

3D SDF for NP0069653 (Bruceolline C)

3D-SDF for NP0069653 (Bruceolline C)

PDB for NP0069653 (Bruceolline C)

3D PDB for NP0069653 (Bruceolline C)

SMILES for NP0069653 (Bruceolline C)

INCHI for NP0069653 (Bruceolline C)

Structure for NP0069653 (Bruceolline C)

3D Structure for NP0069653 (Bruceolline C)