NP-MRD: Showing NP-Card for 1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate (NP0303778)

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Record Information

Version

2.0

Created at

2022-09-10 18:25:03 UTC

Updated at

2022-09-10 18:25:03 UTC

NP-MRD ID

NP0303778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate

Description

1-(3-{1-Hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl}-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl acetate belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. 1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate is found in Penicillium aethiopicum. 1-(3-{1-Hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl}-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl acetate is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251506052D          

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M  END

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M  END


  Mrv1533004251506052D          

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 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 24 32  1  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
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 20 38  1  0  0  0  0
 33 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(OC(C)=O)C1=NC2=CC=CC=C2C(=O)N1C1CC2(OC1=O)C1N(O)C(C)(C)C(=O)N1C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C27H26N4O7/c1-14(37-15(2)32)21-28-18-11-7-5-9-16(18)22(33)29(21)20-13-27(38-23(20)34)17-10-6-8-12-19(17)30-24(27)31(36)26(3,4)25(30)35/h5-12,14,20,24,36H,13H2,1-4H3

> <INCHI_KEY>
NWBIHDXUFYUNGB-UHFFFAOYSA-N

> <FORMULA>
C27H26N4O7

> <MOLECULAR_WEIGHT>
518.526

> <EXACT_MASS>
518.180149193

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
52.27598297225601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazolidino[1,2-a]indole-9,2'-oxolane]-4'-yl}-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl acetate

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.8347730633333335

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.751657049544772

> <JCHEM_PKA_STRONGEST_BASIC>
1.5859505556397067

> <JCHEM_POLAR_SURFACE_AREA>
129.05

> <JCHEM_REFRACTIVITY>
133.1866

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9aH-spiro[imidazolidino[1,2-a]indole-9,2'-oxolane]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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       6.593   3.518   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.523   4.746   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.051   4.555   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.980   5.783   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.382   7.202   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.508   5.592   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.924   6.165   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       7.854   7.393   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.255   8.812   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.185  10.040   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.586  11.459   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.058  11.650   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.129  10.422   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.727   9.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.798   7.775   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.270   7.966   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       5.396   6.356   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.467   5.129   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.913   3.655   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.650   2.774   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.422   3.704   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.927   5.159   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.046   6.422   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.878   1.845   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       6.417   1.814   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0       7.347   3.042   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.864   0.341   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.283   0.939   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.608  -1.008   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.601  -0.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.571  -2.079   0.000  0.00  0.00           O+0
HETATM   32  N   UNK     0       4.373   0.390   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.833   0.420   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.781  -0.704   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.281  -0.354   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.166   1.120   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.887   2.244   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.387   1.894   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    7   18                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   24   38                                             
CONECT   21   20   22                                                       
CONECT   22   21   18   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25   32                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   24   33                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   20   33                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl}-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl acetic acid	Generator

Chemical Formula

C₂₇H₂₆N₄O₇

Average Mass

518.5260 Da

Monoisotopic Mass

518.18015 Da

IUPAC Name

1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazolidino[1,2-a]indole-9,2'-oxolane]-4'-yl}-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl acetate

Traditional Name

1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9aH-spiro[imidazolidino[1,2-a]indole-9,2'-oxolane]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate

CAS Registry Number

Not Available

SMILES

CC(OC(C)=O)C1=NC2=CC=CC=C2C(=O)N1C1CC2(OC1=O)C1N(O)C(C)(C)C(=O)N1C1=CC=CC=C21

InChI Identifier

InChI=1S/C27H26N4O7/c1-14(37-15(2)32)21-28-18-11-7-5-9-16(18)22(33)29(21)20-13-27(38-23(20)34)17-10-6-8-12-19(17)30-24(27)31(36)26(3,4)25(30)35/h5-12,14,20,24,36H,13H2,1-4H3

InChI Key

NWBIHDXUFYUNGB-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, 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 aethiopicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Diazanaphthalene
Quinazoline
Indole or derivatives
Pyrimidone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Imidazolidinone
Pyrimidine
Benzenoid
Imidazolidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Tetrahydrofuran
Carboxamide group
Lactone
Lactam
Carboxylic acid ester
Azacycle
Oxacycle
Organoheterocyclic compound
N-organohydroxylamine
Organooxygen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organonitrogen 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	1.88	ALOGPS
logP	1.83	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	129.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.19 m³·mol⁻¹	ChemAxon
Polarizability	52.28 Å³	ChemAxon
Number of Rings	6	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85384242

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate (NP0303778)

MOL for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)

3D MOL for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)

3D SDF for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)

3D-SDF for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)

PDB for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)

3D PDB for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)

SMILES for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)

INCHI for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)

Structure for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)

3D Structure for NP0303778 (1-(3-{1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl}-4-oxoquinazolin-2-yl)ethyl acetate)