NP-MRD: Showing NP-Card for Graveoline (NP0051227)

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Record Information

Version

2.0

Created at

2022-04-27 22:37:18 UTC

Updated at

2022-04-27 22:37:18 UTC

NP-MRD ID

NP0051227

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Graveoline

Description

Graveoline, also known as foliosine or rutamine, belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Graveoline is a moderately basic compound (based on its pKa). Outside of the human body, Graveoline has been detected, but not quantified in, herbs and spices. Graveoline is found in Haplophyllum dubium Eug.Kor., Haplophyllum foliosum Vved., Haplophyllum griffithianum, Haplophyllum perforatum, Lunasia amara, Ruta angustifolia , Ruta bracteosa, Ruta chalepensis , Ruta graveolens and Ruta graveolensis. This could make graveoline a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -0.5276    1.7676    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0295    0.4526    0.1122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -0.5549   -0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086   -0.3225   -0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.0964   -1.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0238    0.3460   -1.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8719    0.1654   -0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4035   -0.2515    0.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622   -0.5026    0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -0.3533    1.4322 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422   -0.0587    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2401    0.3245   -0.5641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7026   -1.8087   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0588   -2.0179   -0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5524   -3.1570   -0.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -0.9741   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -1.1580    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1083   -0.1380    0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5445    1.0904    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873    1.3263    0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3726    0.2770    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818    2.0066    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9799    2.5660   -0.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5572    1.7729    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0073    0.2385   -2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4365    0.6712   -2.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705   -0.8314    1.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3130   -0.9408    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2136    0.7896    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0344   -2.6061   -0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6412   -2.1468   -0.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1846   -0.2694    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2052    1.9133    0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7396    2.2873    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13  3  2  0
  3  4  1  0
  4  9  2  0
  9  8  1  0
  8  7  2  0
  7 12  1  0
 12 11  1  0
 11 10  1  0
  7  6  1  0
  6  5  2  0
  3  2  1  0
  5  4  1  0
 16 21  1  0
 10  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 20 34  1  0
 19 33  1  0
 18 32  1  0
 17 31  1  0
 13 30  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
  6 26  1  0
  5 25  1  0
M  END


  Mrv0541 05061307082D          

 21 24  0  0  0  0            999 V2000
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -3.8404    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
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  4  2  0  0  0  0
 13  5  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  2  0  0  0  0
 18  1  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  2  0  0  0  0
 20 10  1  0  0  0  0
 20 16  1  0  0  0  0
 21 10  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051227

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H13NO3/c1-18-13-5-3-2-4-12(13)15(19)9-14(18)11-6-7-16-17(8-11)21-10-20-16/h2-9H,10H2,1H3

> <INCHI_KEY>
COBBNRKBTCBWQP-UHFFFAOYSA-N

> <FORMULA>
C17H13NO3

> <MOLECULAR_WEIGHT>
279.29

> <EXACT_MASS>
279.089543287

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.59800509125454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-1-methyl-1,4-dihydroquinolin-4-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.7070003573333334

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.748291591651743

> <JCHEM_PKA_STRONGEST_BASIC>
2.0401098811238483

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
80.70349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
graveoline

> <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       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.592 -11.313   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259 -12.083   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.592  -9.773   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220  -5.923   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.259  -9.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.925  -9.773   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.259  -7.463   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -5.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590  -6.693   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.591  -9.003   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      11.592  -6.693   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.126  -4.677   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.126  -7.169   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3   13                                                       
CONECT    6    7   11                                                       
CONECT    7    6   16                                                       
CONECT    8   11   17                                                       
CONECT    9   14   15                                                       
CONECT   10   20   21                                                       
CONECT   11    6    8   14                                                  
CONECT   12    4   13   15                                                  
CONECT   13    5   12   18                                                  
CONECT   14    9   11   18                                                  
CONECT   15    9   12   19                                                  
CONECT   16    7   17   20                                                  
CONECT   17    8   16   21                                                  
CONECT   18    1   13   14                                                  
CONECT   19   15                                                            
CONECT   20   10   16                                                       
CONECT   21   10   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
1-Methyl-2-(3,4-methylenedioxyphenyl)-4(1H)-quinolinone	HMDB
2-(1,3-Benzodioxol-5-yl)-1-methyl-4(1H)-quinolinone, 9ci	HMDB
Alkaloid from ruta angustifolia plant	HMDB
Foliosine	HMDB
Graveolin	HMDB
Rutamine	HMDB

Chemical Formula

C₁₇H₁₃NO₃

Average Mass

279.2900 Da

Monoisotopic Mass

279.08954 Da

IUPAC Name

2-(2H-1,3-benzodioxol-5-yl)-1-methyl-1,4-dihydroquinolin-4-one

Traditional Name

graveoline

CAS Registry Number

Not Available

SMILES

CN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C17H13NO3/c1-18-13-5-3-2-4-12(13)15(19)9-14(18)11-6-7-16-17(8-11)21-10-20-16/h2-9H,10H2,1H3

InChI Key

COBBNRKBTCBWQP-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
Haplophyllum dubium Eug.Kor.	Plant	KNApSAcK
Haplophyllum foliosum Vved.	Plant	KNApSAcK
Haplophyllum griffithianum	LOTUS Database	35616633
Haplophyllum perforatum	Plant	KNApSAcK
Lunasia amara	LOTUS Database	35616633
Ruta angustifolia	Plant	KNApSAcK
Ruta bracteosa	Plant	KNApSAcK
Ruta chalepensis	Plant	KNApSAcK
Ruta graveolens	Plant	KNApSAcK
Ruta graveolensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
Dihydroquinoline
Benzodioxole
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Azacycle
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolines (CHEBI:5541 )
Quinoline alkaloids (C10689 )
Quinazoline alkaloids (C10689 )

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	2.6	ALOGPS
logP	2.71	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	16.75	ChemAxon
pKa (Strongest Basic)	2.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.7 m³·mol⁻¹	ChemAxon
Polarizability	29.6 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033480

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

353825

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Graveoline (NP0051227)

MOL for NP0051227 (Graveoline)

3D MOL for NP0051227 (Graveoline)

3D SDF for NP0051227 (Graveoline)

3D-SDF for NP0051227 (Graveoline)

PDB for NP0051227 (Graveoline)

3D PDB for NP0051227 (Graveoline)

SMILES for NP0051227 (Graveoline)

INCHI for NP0051227 (Graveoline)

Structure for NP0051227 (Graveoline)

3D Structure for NP0051227 (Graveoline)