NP-MRD: Showing NP-Card for (1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione (NP0255233)

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Record Information

Version

2.0

Created at

2022-09-07 19:39:16 UTC

Updated at

2022-09-07 19:39:16 UTC

NP-MRD ID

NP0255233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione

Description

Fumiquinazoline N 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 a small amount of articles have been published on Fumiquinazoline N.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221392D          

 39 45  0  0  1  0            999 V2000
    3.8862   -5.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2238   -4.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4667   -5.3021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -4.8821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1377   -5.4277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4654   -6.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3596   -5.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072221392D          

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 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 26 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 29 39  1  0  0  0  0
 21 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@@H](C[C@]2(O)[C@@H]3N(C(=O)C4(CC4)N3C(C)=O)C3=CC=CC=C23)N2C(=O)C3=CC=CC=C3N=C2[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H27N5O6/c1-15(34)33-24-28(39,17-9-5-7-11-19(17)32(24)25(37)27(33)12-13-27)14-20-22(36)30(3)26(2,38)23-29-18-10-6-4-8-16(18)21(35)31(20)23/h4-11,20,24,38-39H,12-14H2,1-3H3/t20-,24-,26-,28-/m1/s1

> <INCHI_KEY>
GGABVSOOPZYWQV-VLVNZMPXSA-N

> <FORMULA>
C28H27N5O6

> <MOLECULAR_WEIGHT>
529.553

> <EXACT_MASS>
529.196133609

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
53.108618111867266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R)-4-{[(9'R,9'aS)-1'-acetyl-9'-hydroxy-3'-oxo-1',3',9',9'a-tetrahydrospiro[cyclopropane-1,2'-imidazo[1,2-a]indole]-9'-yl]methyl}-1-hydroxy-1,2-dimethyl-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

> <JCHEM_LOGP>
0.19158768199999943

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.92809843271301

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.884701267742805

> <JCHEM_PKA_STRONGEST_BASIC>
1.7354647235024285

> <JCHEM_POLAR_SURFACE_AREA>
134.06

> <JCHEM_REFRACTIVITY>
138.43470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R)-4-[(9'R,9'aS)-1'-acetyl-9'-hydroxy-3'-oxo-9'aH-spiro[cyclopropane-1,2'-imidazo[1,2-a]indole]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4H-pyrazino[2,1-b]quinazoline-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.254 -10.204   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.018  -9.286   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.195  -7.756   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.605  -9.897   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.279  -9.113   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.124 -10.132   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.735 -11.545   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.951 -12.871   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.269 -11.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.728 -11.891   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.573 -12.910   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.798  -9.348   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.671  -9.808   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.805  -8.766   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.469  -7.263   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.001  -6.803   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.134  -7.845   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.700  -6.160   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.011  -1.130   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.991  -1.130   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   39  N   UNK     0       5.335  -4.620   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    4   10   11                                             
CONECT   10    9   11                                                       
CONECT   11   10    9                                                       
CONECT   12    6   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17    5   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   39                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31   37                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   29   21                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₇N₅O₆

Average Mass

529.5530 Da

Monoisotopic Mass

529.19613 Da

IUPAC Name

(1R,4R)-4-{[(9'R,9'aS)-1'-acetyl-9'-hydroxy-3'-oxo-1',3',9',9'a-tetrahydrospiro[cyclopropane-1,2'-imidazo[1,2-a]indole]-9'-yl]methyl}-1-hydroxy-1,2-dimethyl-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

Traditional Name

(1R,4R)-4-[(9'R,9'aS)-1'-acetyl-9'-hydroxy-3'-oxo-9'aH-spiro[cyclopropane-1,2'-imidazo[1,2-a]indole]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4H-pyrazino[2,1-b]quinazoline-3,6-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@@H](C[C@]2(O)[C@@H]3N(C(=O)C4(CC4)N3C(C)=O)C3=CC=CC=C23)N2C(=O)C3=CC=CC=C3N=C2[C@@]1(C)O

InChI Identifier

InChI=1S/C28H27N5O6/c1-15(34)33-24-28(39,17-9-5-7-11-19(17)32(24)25(37)27(33)12-13-27)14-20-22(36)30(3)26(2,38)23-29-18-10-6-4-8-16(18)21(35)31(20)23/h4-11,20,24,38-39H,12-14H2,1-3H3/t20-,24-,26-,28-/m1/s1

InChI Key

GGABVSOOPZYWQV-VLVNZMPXSA-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

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
Imidazolidine
Heteroaromatic compound
Tertiary alcohol
Tertiary carboxylic acid amide
Acetamide
Lactam
Carboxamide group
Carboxylic acid derivative
Alkanolamine
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
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	0.19	ChemAxon
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	1.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	134.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	138.43 m³·mol⁻¹	ChemAxon
Polarizability	53.11 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

29215537

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71605143

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione (NP0255233)

MOL for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)

3D MOL for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)

3D SDF for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)

3D-SDF for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)

PDB for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)

3D PDB for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)

SMILES for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)

INCHI for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)

Structure for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)

3D Structure for NP0255233 ((1r,4r)-4-[(9'r,9'as)-1'-acetyl-9'-hydroxy-3'-oxo-9'ah-spiro[cyclopropane-1,2'-imidazo[1,2-a]indol]-9'-ylmethyl]-1-hydroxy-1,2-dimethyl-4h-pyrazino[2,1-b]quinazoline-3,6-dione)