NP-MRD: Showing NP-Card for Gravacridonol (NP0083541)

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Record Information

Version

2.0

Created at

2022-04-29 04:33:15 UTC

Updated at

2022-04-29 04:33:15 UTC

NP-MRD ID

NP0083541

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gravacridonol

Description

Gravacridonol 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. Gravacridonol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Gravacridonol has been detected, but not quantified in, herbs and spices. Gravacridonol is found in Ruta bracteosa, Ruta callus cultures, Ruta chalepensis , Ruta graveolens , Ruta macrophylla and Thamnosma montana. This could make gravacridonol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    4.8609    0.1071    1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1884   -0.0060    0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    0.4011   -0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2848    1.4399   -1.3704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -0.5134    0.4872 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7528    0.4535   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6243   -0.4801   -0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -1.7731   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3639   -2.9035   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943   -2.7761   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198   -3.9025   -0.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5522   -1.5200   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9194   -1.4259   -0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187   -2.4677   -0.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818   -0.2129    0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8484   -0.1208    0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4867    1.0922    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7151    2.1993    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3146    2.1430    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6897    0.9249    0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3282    0.8462    0.0511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151    2.0328    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7447   -0.3639   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5514   -1.6436   -0.2764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664    0.4695    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -0.1880    2.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1269   -0.4463   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9601    0.7720   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5876    1.6652   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5198   -0.7356    1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1637    0.7499   -1.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191    1.2120    0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -3.9130   -0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -4.8027   -0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5020   -1.0068    0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5844    1.1303    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1815    3.1675    0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7550    3.0506    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996    2.8477   -0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2179    2.4642    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421    2.0332   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  2  0
 13 12  1  0
 12 23  2  0
 23  7  1  0
  7  8  2  0
  8 24  1  0
 24  5  1  0
  5  6  1  0
  5  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 23 21  1  0
  6  7  1  0
 15 20  1  0
 10 12  1  0
 22 39  1  0
 22 40  1  0
 22 41  1  0
 19 38  1  0
 18 37  1  0
 17 36  1  0
 16 35  1  0
  5 30  1  1
  6 31  1  0
  6 32  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  9 33  1  0
 11 34  1  0
M  END


  Mrv0541 05061311232D          

 24 27  0  0  0  0            999 V2000
    0.7972    2.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5210    2.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1879    1.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9384    2.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6317    0.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1326    2.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0010    2.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1019    0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606    3.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836    2.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8259    1.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4086    1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5764    1.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929    2.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524    0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4639    0.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144    1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2697    0.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7706    2.0041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513    4.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1573   -0.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5193   -0.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1010    1.3033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
 10  1  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 12  7  1  0  0  0  0
 13  6  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  2  0  0  0  0
 19 11  1  0  0  0  0
 19 17  1  0  0  0  0
 20  2  1  0  0  0  0
 20 13  1  0  0  0  0
 20 18  1  0  0  0  0
 21  9  1  0  0  0  0
 22 14  1  0  0  0  0
 23 19  2  0  0  0  0
 24 15  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083541

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC(C1)C(=C)CO)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NO4/c1-10(9-21)15-7-12-16(24-15)8-14(22)17-18(12)20(2)13-6-4-3-5-11(13)19(17)23/h3-6,8,15,21-22H,1,7,9H2,2H3

> <INCHI_KEY>
LTIJMFZBJZDNOD-UHFFFAOYSA-N

> <FORMULA>
C19H17NO4

> <MOLECULAR_WEIGHT>
323.3426

> <EXACT_MASS>
323.115758037

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
34.320214219859366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(3-hydroxyprop-1-en-2-yl)-11-methyl-1H,2H,6H,11H-furo[2,3-c]acridin-6-one

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
3.1052138056666667

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.100544837889938

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.273969670529072

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7548245273645504

> <JCHEM_POLAR_SURFACE_AREA>
70

> <JCHEM_REFRACTIVITY>
90.60169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2-(3-hydroxyprop-1-en-2-yl)-11-methyl-1H,2H-furo[2,3-c]acridin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.488   4.536   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.439   5.209   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.417   2.749   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.952   4.217   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.379   1.612   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.448   4.548   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.602   4.273   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.790   0.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.286   6.506   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.956   5.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.875   1.943   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.363   2.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.409   3.411   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.294  -0.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.093   3.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.324   1.797   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.333   1.136   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.867   2.604   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.837   0.805   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.905   3.741   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       2.149   7.544   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.760  -1.469   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.303  -0.662   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.922   2.433   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   13                                                       
CONECT    7   12   15                                                       
CONECT    8   14   16                                                       
CONECT    9   10   21                                                       
CONECT   10    1    9   15                                                  
CONECT   11    5   13   19                                                  
CONECT   12    7   16   18                                                  
CONECT   13    6   11   20                                                  
CONECT   14    8   17   22                                                  
CONECT   15    7   10   24                                                  
CONECT   16    8   12   24                                                  
CONECT   17   14   18   19                                                  
CONECT   18   12   17   20                                                  
CONECT   19   11   17   23                                                  
CONECT   20    2   13   18                                                  
CONECT   21    9                                                            
CONECT   22   14                                                            
CONECT   23   19                                                            
CONECT   24   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₇NO₄

Average Mass

323.3426 Da

Monoisotopic Mass

323.11576 Da

IUPAC Name

5-hydroxy-2-(3-hydroxyprop-1-en-2-yl)-11-methyl-1H,2H,6H,11H-furo[2,3-c]acridin-6-one

Traditional Name

5-hydroxy-2-(3-hydroxyprop-1-en-2-yl)-11-methyl-1H,2H-furo[2,3-c]acridin-6-one

CAS Registry Number

Not Available

SMILES

CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC(C1)C(=C)CO)C=C2O

InChI Identifier

InChI=1S/C19H17NO4/c1-10(9-21)15-7-12-16(24-15)8-14(22)17-18(12)20(2)13-6-4-3-5-11(13)19(17)23/h3-6,8,15,21-22H,1,7,9H2,2H3

InChI Key

LTIJMFZBJZDNOD-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
Ruta bracteosa	Plant	KNApSAcK
Ruta callus cultures	Plant	KNApSAcK
Ruta chalepensis	Plant	KNApSAcK
Ruta graveolens	Plant	KNApSAcK
Ruta macrophylla	Plant	KNApSAcK
Thamnosma montana	Plant	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
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Vinylogous amide
Vinylogous acid
Heteroaromatic compound
Oxacycle
Azacycle
Ether
Alcohol
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
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	2.14	ALOGPS
logP	3.11	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.6 m³·mol⁻¹	ChemAxon
Polarizability	34.32 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

HMDB0039756

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019404

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

14805775

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gravacridonol (NP0083541)

MOL for NP0083541 (Gravacridonol)

3D MOL for NP0083541 (Gravacridonol)

3D SDF for NP0083541 (Gravacridonol)

3D-SDF for NP0083541 (Gravacridonol)

PDB for NP0083541 (Gravacridonol)

3D PDB for NP0083541 (Gravacridonol)

SMILES for NP0083541 (Gravacridonol)

INCHI for NP0083541 (Gravacridonol)

Structure for NP0083541 (Gravacridonol)

3D Structure for NP0083541 (Gravacridonol)