NP-MRD: Showing NP-Card for (3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one (NP0189362)

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Record Information

Version

2.0

Created at

2022-09-04 05:50:13 UTC

Updated at

2022-09-04 05:50:14 UTC

NP-MRD ID

NP0189362

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one

Description

BDBM86021 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. (3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one is found in Skimmia laureola. Based on a literature review very few articles have been published on BDBM86021.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.2744   -1.9693   -1.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1731   -1.2757   -0.6090 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9319   -1.7800   -0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012   -2.8760   -1.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767   -1.1394   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254    0.0558    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2391    0.5837    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985    1.7795    1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813    2.2832    1.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7813    1.6080    0.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117    0.4133    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3465   -0.1046    0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1721    0.6598    0.8522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930    0.5942    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904    0.8531    1.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4120    1.7616   -0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -0.6897   -0.5779 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7864   -1.2683   -0.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141   -1.6923   -0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9423   -2.8466   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356   -2.4253   -0.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0180   -1.4479   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5263    2.2977    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8085    3.2219    1.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788    2.0508    1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4442   -0.1374   -0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4573    0.4403    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5272    1.9255    1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569    0.3462    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001    2.2864   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213    2.5110   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022    1.3913   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758   -0.4881   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -2.1802    0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4988   -2.3631   -1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119   -2.3794    0.4155 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
  3  5  1  0
  5  6  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  2  1  0
 19  5  1  0
 12  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  6
 18 34  1  0
 19 35  1  0
 19 36  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
M  END


  Mrv1652309042207502D          

 19 21  0  0  1  0            999 V2000
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   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
    1.5395    0.4125    0.0000 C   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
    2.7770   -0.3020    0.0000 O   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
    3.4587   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  2 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  5 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0189362

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)C2=C(OC(C)(C)[C@@H](O)C2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H17NO3/c1-15(2)12(17)8-10-13(19-15)9-6-4-5-7-11(9)16(3)14(10)18/h4-7,12,17H,8H2,1-3H3/t12-/m0/s1

> <INCHI_KEY>
DWGJDUGVGKBCGA-LBPRGKRZSA-N

> <FORMULA>
C15H17NO3

> <MOLECULAR_WEIGHT>
259.305

> <EXACT_MASS>
259.120843411

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.67471520355901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-hydroxy-2,2,6-trimethyl-2H,3H,4H,5H,6H-pyrano[3,2-c]quinolin-5-one

> <JCHEM_LOGP>
0.8093232580000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.896725733928008

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9802603061419403

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
72.6836

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-hydroxy-2,2,6-trimethyl-3H,4H-pyrano[3,2-c]quinolin-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.874   3.437   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.171  -1.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   19                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7    2                                                  
CONECT   13    6   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    5                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₇NO₃

Average Mass

259.3050 Da

Monoisotopic Mass

259.12084 Da

IUPAC Name

(3S)-3-hydroxy-2,2,6-trimethyl-2H,3H,4H,5H,6H-pyrano[3,2-c]quinolin-5-one

Traditional Name

(3S)-3-hydroxy-2,2,6-trimethyl-3H,4H-pyrano[3,2-c]quinolin-5-one

CAS Registry Number

Not Available

SMILES

CN1C(=O)C2=C(OC(C)(C)[C@@H](O)C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C15H17NO3/c1-15(2)12(17)8-10-13(19-15)9-6-4-5-7-11(9)16(3)14(10)18/h4-7,12,17H,8H2,1-3H3/t12-/m0/s1

InChI Key

DWGJDUGVGKBCGA-LBPRGKRZSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Skimmia laureola	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
Dihydroquinolone
Dihydroquinoline
Pyranopyridine
Alkyl aryl ether
Pyridinone
Pyran
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous ester
Lactam
Secondary alcohol
Oxacycle
Ether
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxide
Organic oxygen compound
Organic nitrogen 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	0.81	ChemAxon
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-0.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.68 m³·mol⁻¹	ChemAxon
Polarizability	27.67 Å³	ChemAxon
Number of Rings	3	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

34948384

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57340431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one (NP0189362)

MOL for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)

3D MOL for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)

3D SDF for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)

3D-SDF for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)

PDB for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)

3D PDB for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)

SMILES for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)

INCHI for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)

Structure for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)

3D Structure for NP0189362 ((3s)-3-hydroxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one)