NP-MRD: Showing NP-Card for (1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate (NP0259274)

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Record Information

Version

2.0

Created at

2022-09-08 01:05:16 UTC

Updated at

2022-09-08 01:05:17 UTC

NP-MRD ID

NP0259274

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1R)-1-{3-[(4'S,9R,9aR)-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}-2-methylpropyl acetate belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Based on a literature review very few articles have been published on (1R)-1-{3-[(4'S,9R,9aR)-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}-2-methylpropyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082203052D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309082203052D          

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    2.7942   -0.5840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0117    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3055   -0.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3620   -0.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  6 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 35  1  6  0  0  0
 29 37  1  0  0  0  0
 19 37  1  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259274

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](OC(C)=O)C1=NC2=CC=CC=C2C(=O)N1[C@H]1C[C@]2(OC1=O)[C@H]1N(O)C(C)(C)C(=O)N1C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C29H30N4O7/c1-15(2)22(39-16(3)34)23-30-19-12-8-6-10-17(19)24(35)31(23)21-14-29(40-25(21)36)18-11-7-9-13-20(18)32-26(29)33(38)28(4,5)27(32)37/h6-13,15,21-22,26,38H,14H2,1-5H3/t21-,22+,26+,29+/m0/s1

> <INCHI_KEY>
CYNVLFGDEQQUPE-YPMWMNAPSA-N

> <FORMULA>
C29H30N4O7

> <MOLECULAR_WEIGHT>
546.58

> <EXACT_MASS>
546.211449322

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.94189108181258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-1-{3-[(4'S,9R,9aR)-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}-2-methylpropyl acetate

> <JCHEM_LOGP>
2.722268284666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.751657049544775

> <JCHEM_PKA_STRONGEST_BASIC>
1.5918849627725982

> <JCHEM_POLAR_SURFACE_AREA>
129.05

> <JCHEM_REFRACTIVITY>
142.18220000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

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

> <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      13.958   0.307   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.424   0.437   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.544  -0.826   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.770   1.832   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.236   1.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.582   3.357   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      10.462   4.620   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.808   6.014   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.689   7.278   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.035   8.672   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.500   8.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.620   7.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.274   6.145   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.393   4.882   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.859   5.012   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       8.047   3.487   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       7.167   2.224   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.671   0.769   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.444  -0.161   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.180   0.720   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.627   2.194   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.697   3.421   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.707  -1.041   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.207  -0.691   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.260  -1.815   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.813  -3.289   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.313  -3.639   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.260  -2.515   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       5.720  -2.545   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       4.493  -3.475   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.523  -5.014   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.229  -2.594   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.486  -3.943   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.810  -1.996   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       3.676  -1.121   0.000  0.00  0.00           N+0
HETATM   36  O   UNK     0       2.746   0.107   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.216  -1.090   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.355   0.699   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.037  -0.097   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.009  -0.695   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    6   17                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23   37                                             
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21                                                            
CONECT   23   19   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   37                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   29   19                                                  
CONECT   38    5   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1R)-1-{3-[(4's,9R,9ar)-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}-2-methylpropyl acetic acid	Generator

Chemical Formula

C₂₉H₃₀N₄O₇

Average Mass

546.5800 Da

Monoisotopic Mass

546.21145 Da

IUPAC Name

(1R)-1-{3-[(4'S,9R,9aR)-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}-2-methylpropyl acetate

Traditional Name

(1R)-1-{3-[(4'S,9R,9aR)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9aH-spiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](OC(C)=O)C1=NC2=CC=CC=C2C(=O)N1[C@H]1C[C@]2(OC1=O)[C@H]1N(O)C(C)(C)C(=O)N1C1=CC=CC=C21

InChI Identifier

InChI=1S/C29H30N4O7/c1-15(2)22(39-16(3)34)23-30-19-12-8-6-10-17(19)24(35)31(23)21-14-29(40-25(21)36)18-11-7-9-13-20(18)32-26(29)33(38)28(4,5)27(32)37/h6-13,15,21-22,26,38H,14H2,1-5H3/t21-,22+,26+,29+/m0/s1

InChI Key

CYNVLFGDEQQUPE-YPMWMNAPSA-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 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	2.72	ChemAxon
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	5	ChemAxon
Refractivity	142.18 m³·mol⁻¹	ChemAxon
Polarizability	55.94 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

139266809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate (NP0259274)

MOL for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)

3D MOL for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)

3D SDF for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)

3D-SDF for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)

PDB for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)

3D PDB for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)

SMILES for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)

INCHI for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)

Structure for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)

3D Structure for NP0259274 ((1r)-1-{3-[(4's,9r,9ar)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9ah-spiro[imidazo[1,2-a]indole-9,2'-oxolan]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate)