NP-MRD: Showing NP-Card for (3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one (NP0272604)

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Record Information

Version

2.0

Created at

2022-09-08 19:16:52 UTC

Updated at

2022-09-08 19:16:52 UTC

NP-MRD ID

NP0272604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one

Description

Quinolactacin A1 belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline. (3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one is found in Penicillium spathulatum. Based on a literature review very few articles have been published on Quinolactacin A1.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.7004    0.6542   -2.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7956    1.0545   -0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5658    0.0105    0.4332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7286    0.5709    1.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5224   -1.0039    0.2694 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8629   -1.7863   -0.9276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058   -1.9035   -1.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607   -2.5935   -2.9399 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -1.2032   -1.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1361   -0.6572    0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    0.0304    0.6740 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213    0.5324    1.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1076    0.1943    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0360    0.9251    0.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3175    1.1002    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6355    0.5386   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7172   -0.1836   -1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4499   -0.3571   -1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923   -1.0641   -1.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145   -1.5652   -2.8291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6572    0.6867   -2.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092    1.4245   -2.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1760   -0.3278   -2.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8143    1.4924   -0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1082    1.9321   -0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453   -0.6210    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1734    1.5104    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8037    0.8513    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5255   -0.2268    2.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634   -1.7529    1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087   -3.2046   -3.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1570   -0.2064    2.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222    1.5664    2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493    0.4358    2.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8286    1.3952    1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    1.6780    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557    0.6993   -1.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9644   -0.6261   -2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 18 13  1  0
 19  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  6
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  1
  8 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END


  Mrv1652309082221162D          

 20 22  0  0  1  0            999 V2000
    4.9594   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.0396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3454   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.1434   -0.4125    0.0000 N   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
    1.4289   -0.0000    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.8250    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
    2.1434    2.0625    0.0000 O   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  1  6  0  0  0
  5  3  1  6  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
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0272604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@H]1N=C(O)C2=C1N(C)C1=CC=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O2/c1-4-9(2)13-14-12(16(20)17-13)15(19)10-7-5-6-8-11(10)18(14)3/h5-9,13H,4H2,1-3H3,(H,17,20)/t9-,13+/m0/s1

> <INCHI_KEY>
FLHQAMWKNPOTDV-TVQRCGJNSA-N

> <FORMULA>
C16H18N2O2

> <MOLECULAR_WEIGHT>
270.332

> <EXACT_MASS>
270.136827828

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.66261559217273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-[(2S)-butan-2-yl]-1-hydroxy-4-methyl-3H,4H,9H-pyrrolo[3,4-b]quinolin-9-one

> <JCHEM_LOGP>
3.0318217406666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.381637909478503

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.593328377248957

> <JCHEM_PKA_STRONGEST_BASIC>
2.007168944867545

> <JCHEM_POLAR_SURFACE_AREA>
52.900000000000006

> <JCHEM_REFRACTIVITY>
79.6853

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(2S)-butan-2-yl]-1-hydroxy-4-methyl-3H-pyrrolo[3,4-b]quinolin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.257  -3.725   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.782  -2.261   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.275  -1.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.245  -3.085   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.799  -0.476   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       7.705   0.770   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.275   3.481   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    9   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈N₂O₂

Average Mass

270.3320 Da

Monoisotopic Mass

270.13683 Da

IUPAC Name

(3R)-3-[(2S)-butan-2-yl]-1-hydroxy-4-methyl-3H,4H,9H-pyrrolo[3,4-b]quinolin-9-one

Traditional Name

(3R)-3-[(2S)-butan-2-yl]-1-hydroxy-4-methyl-3H-pyrrolo[3,4-b]quinolin-9-one

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H]1N=C(O)C2=C1N(C)C1=CC=CC=C1C2=O

InChI Identifier

InChI=1S/C16H18N2O2/c1-4-9(2)13-14-12(16(20)17-13)15(19)10-7-5-6-8-11(10)18(14)3/h5-9,13H,4H2,1-3H3,(H,17,20)/t9-,13+/m0/s1

InChI Key

FLHQAMWKNPOTDV-TVQRCGJNSA-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
Penicillium spathulatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Pyrroloquinolines

Direct Parent

Pyrroloquinolines

Alternative Parents

Substituents

Pyrroloquinoline
Dihydroquinolone
Dihydroquinoline
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Secondary carboxylic acid amide
Lactam
Carboxamide group
Carboxylic acid derivative
Azacycle
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
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	3.03	ChemAxon
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	2.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.69 m³·mol⁻¹	ChemAxon
Polarizability	29.66 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

C00015977

Chemspider ID

21431252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26202199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one (NP0272604)

MOL for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)

3D MOL for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)

3D SDF for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)

3D-SDF for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)

PDB for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)

3D PDB for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)

SMILES for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)

INCHI for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)

Structure for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)

3D Structure for NP0272604 ((3r)-3-[(2s)-butan-2-yl]-1-hydroxy-4-methyl-3h-pyrrolo[3,4-b]quinolin-9-one)