NP-MRD: Showing NP-Card for Preskimmianine (NP0068523)

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Record Information

Version

2.0

Created at

2022-04-28 13:47:56 UTC

Updated at

2022-04-28 13:47:56 UTC

NP-MRD ID

NP0068523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Preskimmianine

Description

4,7,8-Trimethoxy-3-(3-methylbut-2-en-1-yl)quinolin-2-ol belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Preskimmianine is found in Acronychia oligophylebia, Boronia bowmanii, Boronia pinnata, Citrus grandis , Dictaminus albus, Dictaminus angustifolius, Dictaminus dasycarpus, Dictamnus albus L. , Dictamnus angustifolius, Dictamnus dasycarpus and Orixa japonica . 4,7,8-Trimethoxy-3-(3-methylbut-2-en-1-yl)quinolin-2-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -5.8804    1.2310    1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0407    0.9184   -0.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6862    0.6732    0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2006    0.7424    1.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8660    0.5001    1.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959    0.1874    0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -0.0428    1.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8117    0.0273    2.3449 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800   -1.1782    3.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136   -0.3621    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -0.6058    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375    0.4989    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577    0.2766   -0.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8087   -1.0669   -1.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4820    1.3814   -1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6772   -0.4171   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.6966   -2.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6335   -0.1841   -1.5202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5061    0.1232   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326    0.3595   -0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3430    0.2963   -2.0965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8758   -0.8636   -2.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9568    1.1554    0.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7409    0.5501    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7423    2.2919    1.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8116    0.9831    2.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847    0.5567    2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8413   -2.0624    2.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1483   -1.2106    3.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6860   -1.1811    3.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0110   -1.5597   -0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -0.7398    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989    1.5138    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0528   -1.7232   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7504   -1.0834   -1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9700   -1.5328   -1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8885    1.7590   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3390    1.0268   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9664    2.2471   -1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939   -0.2407   -2.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9057   -0.6179   -3.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9580   -1.6688   -1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2099   -1.1641   -3.5256 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 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 10  7  2  0
  7  8  1  0
  8  9  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
  7  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 18 40  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
M  END


  Mrv1533004241506032D          

 22 23  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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
    2.1434   -1.2375    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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 13 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(NC(=O)C(CC=C(C)C)=C2OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO4/c1-10(2)6-7-12-15(21-4)11-8-9-13(20-3)16(22-5)14(11)18-17(12)19/h6,8-9H,7H2,1-5H3,(H,18,19)

> <INCHI_KEY>
OAEZQCLAAGSHHA-UHFFFAOYSA-N

> <FORMULA>
C17H21NO4

> <MOLECULAR_WEIGHT>
303.358

> <EXACT_MASS>
303.14705816

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.73507030570454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7,8-trimethoxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydroquinolin-2-one

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.2517763999999993

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.432544803603895

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3776550938395813

> <JCHEM_POLAR_SURFACE_AREA>
56.790000000000006

> <JCHEM_REFRACTIVITY>
88.4078

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7,8-trimethoxy-3-(3-methylbut-2-en-1-yl)-1H-quinolin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    3   13                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₁NO₄

Average Mass

303.3580 Da

Monoisotopic Mass

303.14706 Da

IUPAC Name

4,7,8-trimethoxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydroquinolin-2-one

Traditional Name

4,7,8-trimethoxy-3-(3-methylbut-2-en-1-yl)-1H-quinolin-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(NC(=O)C(CC=C(C)C)=C2OC)=C1OC

InChI Identifier

InChI=1S/C17H21NO4/c1-10(2)6-7-12-15(21-4)11-8-9-13(20-3)16(22-5)14(11)18-17(12)19/h6,8-9H,7H2,1-5H3,(H,18,19)

InChI Key

OAEZQCLAAGSHHA-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
Acronychia oligophylebia	Plant	KNApSAcK
Boronia bowmanii	Plant	KNApSAcK
Boronia pinnata	Plant	KNApSAcK
Citrus maxima	Plant	KNApSAcK
Dictaminus albus	-	KNApSAcK
Dictaminus angustifolius	-	KNApSAcK
Dictaminus dasycarpus	-	KNApSAcK
Dictamnus albus	Plant	KNApSAcK
Dictamnus angustifolius	Plant	KNApSAcK
Dictamnus dasycarpus	Plant	KNApSAcK
Orixa japonica	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
Anisole
Phenol ether
Alkyl aryl ether
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous ester
Lactam
Azacycle
Ether
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
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	2.48	ALOGPS
logP	2.25	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.43	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.79 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.41 m³·mol⁻¹	ChemAxon
Polarizability	32.74 Å³	ChemAxon
Number of Rings	2	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

12305721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Preskimmianine (NP0068523)

MOL for NP0068523 (Preskimmianine)

3D MOL for NP0068523 (Preskimmianine)

3D SDF for NP0068523 (Preskimmianine)

3D-SDF for NP0068523 (Preskimmianine)

PDB for NP0068523 (Preskimmianine)

3D PDB for NP0068523 (Preskimmianine)

SMILES for NP0068523 (Preskimmianine)

INCHI for NP0068523 (Preskimmianine)

Structure for NP0068523 (Preskimmianine)

3D Structure for NP0068523 (Preskimmianine)