NP-MRD: Showing NP-Card for daibucarboline (NP0190043)

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Record Information

Version

2.0

Created at

2022-09-04 06:38:35 UTC

Updated at

2022-09-04 06:38:35 UTC

NP-MRD ID

NP0190043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

daibucarboline

Description

Daibucarboline B belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. daibucarboline was first documented in 2011 (PMID: 22148193). Based on a literature review very few articles have been published on Daibucarboline B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
   -1.8002    4.7353   -1.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597    3.6209   -0.8697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7719    2.4242   -0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    1.3493   -0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8002    0.1540   -0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4900    0.0469   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1385   -1.2342   -0.3332 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -1.9161    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -3.2266    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5911   -3.6295    1.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628   -2.7771    1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8928   -3.2090    1.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640   -1.4780    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2535   -1.0649    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1970    1.1469   -1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5784    1.0375   -1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291    1.3687   -2.6964 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5946    0.5461   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4728    0.6391    0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4632    0.1554    1.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5876   -0.4286    1.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5640   -0.9087    1.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6987   -0.5156   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7278   -0.0409   -1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5148    2.2704   -1.1570 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602    4.4754   -1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7765    5.5129   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3166    5.2028   -2.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4977    1.3993    0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7986   -1.6130   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5356   -3.9144    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7567   -4.6539    1.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5815   -3.5700    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3058   -0.7950    0.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927    1.0937    1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857    0.2643    2.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4145   -1.3467    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6036   -0.9872   -0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8787   -0.1339   -2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8 14  2  0
 14 13  1  0
 13 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  6 15  1  0
 15 25  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 25  3  1  0
 24 18  1  0
 14  5  1  0
  9  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
 13 34  1  0
 12 33  1  0
 10 32  1  0
  9 31  1  0
 19 35  1  0
 20 36  1  0
 22 37  1  0
 23 38  1  0
 24 39  1  0
M  END


  Mrv1652309042208382D          

 25 28  0  0  0  0            999 V2000
    5.0645    1.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703   -1.3283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113   -1.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3662   -2.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8142   -3.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0072   -2.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -3.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7523   -2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3043   -1.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  2  0  0  0  0
  5 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 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
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 15 25  2  0  0  0  0
  3 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(NC3=C2C=C(O)C=C3)C(=N1)C(=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H14N2O4/c1-25-16-9-14-13-8-12(23)6-7-15(13)20-17(14)18(21-16)19(24)10-2-4-11(22)5-3-10/h2-9,20,22-23H,1H3

> <INCHI_KEY>
PLWQOMURVJHKRD-UHFFFAOYSA-N

> <FORMULA>
C19H14N2O4

> <MOLECULAR_WEIGHT>
334.331

> <EXACT_MASS>
334.095356939

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
35.170928008259594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-hydroxybenzoyl)-3-methoxy-9H-pyrido[3,4-b]indol-6-ol

> <JCHEM_LOGP>
3.548072246333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.051383135392618

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.677682914063246

> <JCHEM_PKA_STRONGEST_BASIC>
0.7773783812196147

> <JCHEM_POLAR_SURFACE_AREA>
95.44

> <JCHEM_REFRACTIVITY>
92.25730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
daibucarboline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       9.454   2.739   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.947   3.059   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.727   3.059   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.344  -2.479   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.808  -3.304   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.284  -4.768   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.253  -5.913   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.747  -5.593   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.716  -6.737   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.271  -4.128   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.301  -2.984   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       7.393   0.450   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8    5                                                  
CONECT   15    6   16   25                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   15    3                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄N₂O₄

Average Mass

334.3310 Da

Monoisotopic Mass

334.09536 Da

IUPAC Name

1-(4-hydroxybenzoyl)-3-methoxy-9H-pyrido[3,4-b]indol-6-ol

Traditional Name

daibucarboline

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(NC3=C2C=C(O)C=C3)C(=N1)C(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C19H14N2O4/c1-25-16-9-14-13-8-12(23)6-7-15(13)20-17(14)18(21-16)19(24)10-2-4-11(22)5-3-10/h2-9,20,22-23H,1H3

InChI Key

PLWQOMURVJHKRD-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Aryl-phenylketone
Hydroxyindole
Indole
Indole or derivatives
Pyridine carboxylic acid or derivatives
Benzoyl
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Pyridine
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous amide
Pyrrole
Ketone
Azacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

harmala alkaloid (CHEBI:69068 )

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	3.55	ChemAxon
pKa (Strongest Acidic)	7.68	ChemAxon
pKa (Strongest Basic)	0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.26 m³·mol⁻¹	ChemAxon
Polarizability	35.17 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

35518214

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56925485

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wong SL, Chang HS, Wang GJ, Chiang MY, Huang HY, Chen CH, Tsai SC, Lin CH, Chen IS: Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity. J Nat Prod. 2011 Dec 27;74(12):2489-96. doi: 10.1021/np100874f. Epub 2011 Dec 7. [PubMed:22148193 ]
LOTUS database [Link]

Showing NP-Card for daibucarboline (NP0190043)

MOL for NP0190043 (daibucarboline)

3D MOL for NP0190043 (daibucarboline)

3D SDF for NP0190043 (daibucarboline)

3D-SDF for NP0190043 (daibucarboline)

PDB for NP0190043 (daibucarboline)

3D PDB for NP0190043 (daibucarboline)

SMILES for NP0190043 (daibucarboline)

INCHI for NP0190043 (daibucarboline)

Structure for NP0190043 (daibucarboline)

3D Structure for NP0190043 (daibucarboline)