NP-MRD: Showing NP-Card for Arborine (NP0051199)

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Record Information

Version

2.0

Created at

2022-04-27 22:36:17 UTC

Updated at

2022-04-27 22:36:17 UTC

NP-MRD ID

NP0051199

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arborine

Description

Arborine, also known as glycosine, belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. Arborine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Arborine has been detected, but not quantified in, herbs and spices. Arborine is found in Glycosmis arborea, Glycosmis bilocularis, Glycosmis cochinchinensis, Glycosmis pentaphylla , Ruta graveolens and Zanthoxylum budrunga . This could make arborine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.6996   -1.6855    1.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8307   -0.8676   -0.1142 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -0.6544   -0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5444   -1.2157   -0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446   -0.3183   -0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686    0.6441   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0259    1.5098   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2049    1.4638    1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4972    0.5205    1.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6282   -0.3577    1.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379    0.1198   -2.0416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080    0.6987   -2.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043    1.4278   -3.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2780    0.5006   -1.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5049    1.0894   -1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5322    0.8772   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3393    0.0852    0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1061   -0.4834    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0348   -0.2963   -0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5425   -2.4431    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -1.0323    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2082   -2.3026    1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307   -2.2144   -0.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9511   -1.3521   -1.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.6895   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5807    2.2549   -0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8938    2.1634    1.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5876    0.4275    3.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -1.1036    1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5892    1.6970   -2.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5093    1.3271   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1755   -0.0798    0.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9943   -1.0895    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  3 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv0541 05061305102D          

 19 21  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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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   -1.6500    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
    2.8579   -2.4750    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
    0.7145   -1.2375    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
    1.4289    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   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18  1  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051199

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(CC2=CC=CC=C2)=NC(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H14N2O/c1-18-14-10-6-5-9-13(14)16(19)17-15(18)11-12-7-3-2-4-8-12/h2-10H,11H2,1H3

> <INCHI_KEY>
XVPZRKIQCKKYNE-UHFFFAOYSA-N

> <FORMULA>
C16H14N2O

> <MOLECULAR_WEIGHT>
250.2952

> <EXACT_MASS>
250.11061308

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.97070379863004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-benzyl-1-methyl-1,4-dihydroquinazolin-4-one

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.4969905236666667

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.40267183346111757

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
75.9132

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arborin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+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  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    3   12                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   14                                                       
CONECT   11   12   15                                                       
CONECT   12    7    8   11                                                  
CONECT   13    9   14   16                                                  
CONECT   14   10   13   18                                                  
CONECT   15   11   17   18                                                  
CONECT   16   13   17   19                                                  
CONECT   17   15   16                                                       
CONECT   18    1   14   15                                                  
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Glycosine	Kegg
1-Methyl-2-(phenylmethyl)-4(1H)-quinazolinone	HMDB
2-Benzyl-1-methyl-4(1H)-quinazolinone	HMDB
4(1H)-Quinazolinone, 1-methyl-2-(phenylmethyl)- (9ci)	HMDB
4(1H)-Quinazolinone, 2-benzyl-1-methyl- (8ci)	HMDB
Arborin	HMDB

Chemical Formula

C₁₆H₁₄N₂O

Average Mass

250.2952 Da

Monoisotopic Mass

250.11061 Da

IUPAC Name

2-benzyl-1-methyl-1,4-dihydroquinazolin-4-one

Traditional Name

arborin

CAS Registry Number

Not Available

SMILES

CN1C(CC2=CC=CC=C2)=NC(=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C16H14N2O/c1-18-14-10-6-5-9-13(14)16(19)17-15(18)11-12-7-3-2-4-8-12/h2-10H,11H2,1H3

InChI Key

XVPZRKIQCKKYNE-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
Glycosmis arborea	Plant	KNApSAcK
Glycosmis bilocularis	Plant	KNApSAcK
Glycosmis cochinchinensis	Plant	KNApSAcK
Glycosmis pentaphylla	Plant	KNApSAcK
Ruta graveolens	Plant	KNApSAcK
Zanthoxylum budrunga	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolines

Alternative Parents

Substituents

Quinazoline
Pyrimidone
Monocyclic benzene moiety
Pyrimidine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinazolines (CHEBI:2803 )
Quinazoline alkaloids (C10642 )

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	2.7	ALOGPS
logP	2.5	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-0.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.91 m³·mol⁻¹	ChemAxon
Polarizability	26.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon