NP-MRD: Showing NP-Card for Flindersine (NP0051221)

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Record Information

Version

2.0

Created at

2022-04-27 22:37:06 UTC

Updated at

2022-04-27 22:37:06 UTC

NP-MRD ID

NP0051221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Flindersine

Description

Flindersine belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Flindersine is found in Atalantia roxburghiana, Flindersia australis, Geijera balansae, Geijera parviflora, Glycosmis citrifolia, Glycosmis parviflora, Haplophyllum acutifolium , Haplophyllum bucharicum, Haplophyllum canaliculatum, Haplophyllum glabrinum, Haplophyllum mytifolium, Haplophyllum perforatum, Haplophyllum sieversii, Haplophyllum suaveolens, Haplophyllum thesioides, Haplophyllum tuberculatum, Haplophyllum tuberculatum (Forssk.) Al Juss. , Helietta apiculata, Hortia colombiana, Micromelum minutum , Neoraputia paraensis, Zanthoxylum arnottianum, Zanthoxylum beecheyanum, Zanthoxylum chalybeum, Zanthoxylum coco, Zanthoxylum nitidum, Zanthoxylum simulans and Zanthoxylum zanthoxyloides. Flindersine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -2.9904    0.5792    1.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715    0.1198    0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9458    0.8182   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815   -1.3418   -0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3388   -2.1428   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0111   -1.5763   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1248   -0.2072   -0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3812    0.4056    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4790    1.7769    0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7241    2.3554    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8203    1.5475    0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    0.1840   -0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735   -0.4303   -0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480   -1.7636   -0.1810 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1374   -2.3674   -0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -3.6321   -0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681    0.6142    0.0756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6911   -0.2273    1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5147    1.5291    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2029    0.7549    2.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4089    0.4761   -2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175    0.6196   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6871    1.8976   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3818   -1.8113   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698   -3.2158   -0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192    2.4257    0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190    3.4304    0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8003    1.9974    0.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930   -0.4536   -0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -2.3621   -0.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 17  1  0
 17  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  4  2  1  0
  8 13  1  0
  8  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  5 25  1  0
  4 24  1  0
 14 30  1  0
 12 29  1  0
 11 28  1  0
 10 27  1  0
  9 26  1  0
M  END


  Mrv1533004251507042D          

 17 19  0  0  0  0            999 V2000
    3.4587    1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772    1.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    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
  2  4  1  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  2  0  0  0  0
  2  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  5 17  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=C(C=C1)C(=O)NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C14H13NO2/c1-14(2)8-7-10-12(17-14)9-5-3-4-6-11(9)15-13(10)16/h3-8H,1-2H3,(H,15,16)

> <INCHI_KEY>
PXNMNABLQWUMCX-UHFFFAOYSA-N

> <FORMULA>
C14H13NO2

> <MOLECULAR_WEIGHT>
227.263

> <EXACT_MASS>
227.094628663

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.293408110002524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-dimethyl-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
1.8141465996666666

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.612782495627084

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5127194528741659

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
69.16880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flindersine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       6.456   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.171   2.630   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       2.874  -1.897   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    8                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2                                                       
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    5   12                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₃NO₂

Average Mass

227.2630 Da

Monoisotopic Mass

227.09463 Da

IUPAC Name

2,2-dimethyl-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

Traditional Name

flindersine

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C(C=C1)C(=O)NC1=CC=CC=C21

InChI Identifier

InChI=1S/C14H13NO2/c1-14(2)8-7-10-12(17-14)9-5-3-4-6-11(9)15-13(10)16/h3-8H,1-2H3,(H,15,16)

InChI Key

PXNMNABLQWUMCX-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
Atalantia roxburghiana	Plant	KNApSAcK
Flindersia australis	Plant	KNApSAcK
Geijera balansae	Plant	KNApSAcK
Geijera parviflora	Plant	KNApSAcK
Glycosmis citrifolia	Plant	KNApSAcK
Glycosmis parviflora	Plant	KNApSAcK
Haplophyllum acutifolium	Plant	KNApSAcK
Haplophyllum bucharicum	LOTUS Database	35616633
Haplophyllum canaliculatum	Plant	KNApSAcK
Haplophyllum glabrinum	Plant	KNApSAcK
Haplophyllum mytifolium	Plant	KNApSAcK
Haplophyllum perforatum	Plant	KNApSAcK
Haplophyllum sieversii	Plant	KNApSAcK
Haplophyllum suaveolens	Plant	KNApSAcK
Haplophyllum thesioides	Plant	KNApSAcK
Haplophyllum tuberculatum	LOTUS Database	35616633
Haplophyllum tuberculatum (Forssk.) Al Juss.	Plant	KNApSAcK
Helietta apiculata	LOTUS Database	35616633
Hortia colombiana	Plant	KNApSAcK
Micromelum minutum	Plant	KNApSAcK
Neoraputia paraensis	Plant	KNApSAcK
Zanthoxylum arnottianum	Plant	KNApSAcK
Zanthoxylum beecheyanum	Plant	KNApSAcK
Zanthoxylum chalybeum	LOTUS Database	35616633
Zanthoxylum coco	Plant	KNApSAcK
Zanthoxylum nitidum	LOTUS Database	35616633
Zanthoxylum simulans	Plant	KNApSAcK
Zanthoxylum zanthoxyloides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Pyranoquinolines

Alternative Parents

Substituents

Pyranoquinoline
Pyranopyridine
Alkyl aryl ether
Hydroxypyridine
Benzenoid
Pyridine
Pyran
Heteroaromatic compound
Ether
Oxacycle
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:5094 )
oxacycle (CHEBI:5094 )
organonitrogen heterocyclic compound (CHEBI:5094 )
Quinoline alkaloids (C10679 )

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	2.58	ALOGPS
logP	1.81	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.61	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.17 m³·mol⁻¹	ChemAxon
Polarizability	24.29 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002162

Chemspider ID

Not Available

KEGG Compound ID

C10679

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68230

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Flindersine (NP0051221)

MOL for NP0051221 (Flindersine)

3D MOL for NP0051221 (Flindersine)

3D SDF for NP0051221 (Flindersine)

3D-SDF for NP0051221 (Flindersine)

PDB for NP0051221 (Flindersine)

3D PDB for NP0051221 (Flindersine)

SMILES for NP0051221 (Flindersine)

INCHI for NP0051221 (Flindersine)

Structure for NP0051221 (Flindersine)

3D Structure for NP0051221 (Flindersine)