NP-MRD: Showing NP-Card for Tryptoquivaline I (NP0066216)

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Record Information

Version

2.0

Created at

2022-04-28 10:22:57 UTC

Updated at

2022-04-28 10:22:58 UTC

NP-MRD ID

NP0066216

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tryptoquivaline I

Description

(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-4'-[2-(2-methylpropanoyl)-4-oxo-3,4-dihydroquinazolin-3-yl]-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Tryptoquivaline I is found in Aspergillus fumigatus. Based on a literature review very few articles have been published on (4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-4'-[2-(2-methylpropanoyl)-4-oxo-3,4-dihydroquinazolin-3-yl]-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212232D          

 37 42  0  0  1  0            999 V2000
   -2.0283   -2.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9421   -1.5438    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


  Mrv1652304282212232D          

 37 42  0  0  1  0            999 V2000
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 32 36  1  0  0  0  0
 31 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)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=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H26N4O6/c1-14(2)20(32)21-28-17-11-7-5-9-15(17)22(33)29(21)19-13-27(37-23(19)34)16-10-6-8-12-18(16)30-24(27)31(36)26(3,4)25(30)35/h5-12,14,19,24,36H,13H2,1-4H3/t19-,24+,27+/m1/s1

> <INCHI_KEY>
YLDPIHLIWYLZID-WMEMMNBJSA-N

> <FORMULA>
C27H26N4O6

> <MOLECULAR_WEIGHT>
502.527

> <EXACT_MASS>
502.185234573

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.392087697905346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-4'-[2-(2-methylpropanoyl)-4-oxo-3,4-dihydroquinazolin-3-yl]-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
3.1748732496666667

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.751655910321837

> <JCHEM_PKA_STRONGEST_BASIC>
0.9676185784571731

> <JCHEM_POLAR_SURFACE_AREA>
119.82000000000001

> <JCHEM_REFRACTIVITY>
132.3864

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-4'-[2-(2-methylpropanoyl)-4-oxoquinazolin-3-yl]-9aH-spiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -3.786  -4.413   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.193  -5.040   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.439  -4.134   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.278  -2.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.871  -1.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.625  -2.882   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.032  -6.571   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -3.526  -6.891   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.756  -5.558   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.986  -4.224   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.479  -4.544   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.665  -3.514   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.318  -6.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.725  -6.702   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.015  -6.846   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.349  -6.076   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.349  -4.536   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.683  -6.846   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.683  -8.386   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.349  -9.156   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.015  -8.386   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.318  -9.156   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.652  -8.386   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.318 -10.696   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.652 -11.466   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.015 -11.466   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.016  -9.156   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.350  -8.386   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.350  -6.846   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.016  -6.076   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -3.365  -8.423   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      -4.772  -9.049   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.002 -10.383   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.802  -7.905   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -7.334  -8.066   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.018  -9.955   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.031  -9.193   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8   34                                                  
CONECT    8    7    9   31                                                  
CONECT    9    8    1   10   14                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   30                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   19   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   18                                                       
CONECT   31    8   32   37                                                  
CONECT   32   31   33   34   36                                             
CONECT   33   32                                                            
CONECT   34   32    7   35                                                  
CONECT   35   34                                                            
CONECT   36   32                                                            
CONECT   37   31                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₆N₄O₆

Average Mass

502.5270 Da

Monoisotopic Mass

502.18523 Da

IUPAC Name

(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-4'-[2-(2-methylpropanoyl)-4-oxo-3,4-dihydroquinazolin-3-yl]-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

Traditional Name

(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-4'-[2-(2-methylpropanoyl)-4-oxoquinazolin-3-yl]-9aH-spiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

CAS Registry Number

Not Available

SMILES

CC(C)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=C2C=CC=C1

InChI Identifier

InChI=1S/C27H26N4O6/c1-14(2)20(32)21-28-17-11-7-5-9-15(17)22(33)29(21)19-13-27(37-23(19)34)16-10-6-8-12-18(16)30-24(27)31(36)26(3,4)25(30)35/h5-12,14,19,24,36H,13H2,1-4H3/t19-,24+,27+/m1/s1

InChI Key

YLDPIHLIWYLZID-WMEMMNBJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspergillus fumigatus	Fungi	KNApSAcK

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
Aryl alkyl ketone
Aryl ketone
Pyrimidone
Benzenoid
Pyrimidine
Imidazolidinone
Gamma butyrolactone
Heteroaromatic compound
Tetrahydrofuran
Tertiary carboxylic acid amide
Imidazolidine
Lactone
Lactam
Ketone
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
N-organohydroxylamine
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	2.23	ALOGPS
logP	3.17	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	0.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	119.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	132.39 m³·mol⁻¹	ChemAxon
Polarizability	51.39 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

162949927

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tryptoquivaline I (NP0066216)

MOL for NP0066216 (Tryptoquivaline I)

3D MOL for NP0066216 (Tryptoquivaline I)

3D SDF for NP0066216 (Tryptoquivaline I)

3D-SDF for NP0066216 (Tryptoquivaline I)

PDB for NP0066216 (Tryptoquivaline I)

3D PDB for NP0066216 (Tryptoquivaline I)

SMILES for NP0066216 (Tryptoquivaline I)

INCHI for NP0066216 (Tryptoquivaline I)

Structure for NP0066216 (Tryptoquivaline I)

3D Structure for NP0066216 (Tryptoquivaline I)