NP-MRD: Showing NP-Card for (4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione (NP0044211)

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Record Information

Version

1.0

Created at

2021-12-17 00:26:08 UTC

Updated at

2021-12-17 00:26:08 UTC

NP-MRD ID

NP0044211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione

Description

CHEMBL2386533 belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. Based on a literature review very few articles have been published on CHEMBL2386533.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652312172101262D          

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M  END

     RDKit          3D

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M  END


  Mrv1652312172101262D          

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M  END
> <DATABASE_ID>
NP0044211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12NC(C)(C)C(=O)N1C1=CC=CC=C1[C@@]2(O)C[C@H]1N2C(=O)C3=CC=CC=C3N=C2C(NC1=O)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H27N5O4/c1-14(2)20-21-28-17-11-7-5-9-15(17)23(34)31(21)19(22(33)29-20)13-27(36)16-10-6-8-12-18(16)32-24(27)30-26(3,4)25(32)35/h5-12,19,24,30,36H,13H2,1-4H3,(H,29,33)/t19-,24-,27+/m1/s1

> <INCHI_KEY>
LCHQPVCRYDVSTJ-BRBPODBZSA-N

> <FORMULA>
C27H27N5O4

> <MOLECULAR_WEIGHT>
485.544

> <EXACT_MASS>
485.206304369

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31072451982562

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-4-{[(9S,9aR)-9-hydroxy-2,2-dimethyl-3-oxo-1H,2H,3H,9H,9aH-imidazo[1,2-a]indol-9-yl]methyl}-1-(propan-2-ylidene)-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
1.6321510883333332

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.99955931363467

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.122649207060043

> <JCHEM_PKA_STRONGEST_BASIC>
4.1177478257938915

> <JCHEM_POLAR_SURFACE_AREA>
114.34

> <JCHEM_REFRACTIVITY>
134.5948

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-{[(9S,9aR)-9-hydroxy-2,2-dimethyl-3-oxo-1H,9aH-imidazo[1,2-a]indol-9-yl]methyl}-1-(propan-2-ylidene)-2H,4H-pyrazino[2,1-b]quinazoline-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-DEC-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-DEC-21         0                                  
HETATM    1  H   UNK     0       4.434   0.395   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       3.279   1.413   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.605   2.197   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.269   3.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.798   3.877   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.252   5.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.735   3.845   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.951   5.171   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       2.124   2.432   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.798   1.648   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.671   2.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.805   1.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.469  -0.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.001  -0.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.134   0.145   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.700  -1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   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  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   16                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15    2   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   33                                                  
CONECT   20   19   21   30                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   20   31                                                  
CONECT   31   30   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   19   34                                                  
CONECT   34   33                                                            
CONECT   35   31   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₇H₂₇N₅O₄

Average Mass

485.5440 Da

Monoisotopic Mass

485.20630 Da

IUPAC Name

(4R)-4-{[(9S,9aR)-9-hydroxy-2,2-dimethyl-3-oxo-1H,2H,3H,9H,9aH-imidazo[1,2-a]indol-9-yl]methyl}-1-(propan-2-ylidene)-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

Traditional Name

(4R)-4-{[(9S,9aR)-9-hydroxy-2,2-dimethyl-3-oxo-1H,9aH-imidazo[1,2-a]indol-9-yl]methyl}-1-(propan-2-ylidene)-2H,4H-pyrazino[2,1-b]quinazoline-3,6-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12NC(C)(C)C(=O)N1C1=CC=CC=C1[C@@]2(O)C[C@H]1N2C(=O)C3=CC=CC=C3N=C2C(NC1=O)=C(C)C

InChI Identifier

InChI=1S/C27H27N5O4/c1-14(2)20-21-28-17-11-7-5-9-15(17)23(34)31(21)19(22(33)29-20)13-27(36)16-10-6-8-12-18(16)32-24(27)30-26(3,4)25(32)35/h5-12,19,24,30,36H,13H2,1-4H3,(H,29,33)/t19-,24-,27+/m1/s1

InChI Key

LCHQPVCRYDVSTJ-BRBPODBZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Quinazoline
Indole or derivatives
Pyrimidone
Imidazolidinone
Pyrimidine
Benzenoid
Tertiary carboxylic acid amide
Tertiary alcohol
Heteroaromatic compound
Imidazolidine
Secondary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Amine
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	1.32	ALOGPS
logP	1.63	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.12	ChemAxon
pKa (Strongest Basic)	4.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	134.59 m³·mol⁻¹	ChemAxon
Polarizability	51.31 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

30826831

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71725623

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione (NP0044211)

MOL for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)

3D MOL for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)

3D SDF for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)

3D-SDF for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)

PDB for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)

3D PDB for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)

SMILES for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)

INCHI for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)

Structure for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)

3D Structure for NP0044211 ((4R)‐4‐{[(9S,9aR)‐9‐hydroxy‐2,2‐dimethyl‐3‐oxo‐1H,2H,3H,9H,9aH‐imidazo[1,2‐a]indol‐9‐yl]methyl}‐1‐(propan‐2‐ylidene)‐1H,2H,3H,4H,6H‐pyrazino[2,1‐b]quinazoline‐3,6‐dione)