NP-MRD: Showing NP-Card for 1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone (NP0327154)

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Record Information

Version

2.0

Created at

2022-09-12 09:27:07 UTC

Updated at

2022-09-12 09:27:07 UTC

NP-MRD ID

NP0327154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

Description

1-[25-(3,3-Dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]Pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethan-1-one belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole). 1-[25-(3,3-Dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]Pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethan-1-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161513452D          

 34 41  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004161513452D          

 34 41  0  0  0  0            999 V2000
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 28 29  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2NC3=CC=CC=C3C34CCN(C3N3CCC24C2=C(C=CC=C12)C3C1OC1(C)C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H32N4O2/c1-16(33)31-14-12-27-18-9-5-6-10-19(18)29-24-28(27)13-15-32(25(27)31)22(23-26(2,3)34-23)17-8-7-11-20(21(17)28)30(24)4/h5-11,22-25,29H,12-15H2,1-4H3

> <INCHI_KEY>
QKUUVGNHUMKUAN-UHFFFAOYSA-N

> <FORMULA>
C28H32N4O2

> <MOLECULAR_WEIGHT>
456.59

> <EXACT_MASS>
456.252526286

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.14085706273984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethan-1-one

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.0584611903333325

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.41075073337715

> <JCHEM_PKA_STRONGEST_BASIC>
6.089329968515567

> <JCHEM_POLAR_SURFACE_AREA>
51.35

> <JCHEM_REFRACTIVITY>
132.4407

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       6.411   0.666   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.138  -0.850   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.222  -2.001   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       8.278  -0.858   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.776  -1.285   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.245  -0.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.380  -1.863   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.046  -3.366   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.578  -3.829   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.442  -2.789   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.573  -4.119   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.154  -4.554   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.055  -5.822   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       9.733  -6.647   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       8.414  -5.733   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.862  -6.098   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.600  -6.703   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.272  -5.087   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.949  -3.606   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.423  -3.011   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.231  -4.105   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.915  -3.172   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.474  -1.635   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.541  -0.488   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.736  -1.543   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.183  -5.417   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.234  -6.630   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.019  -8.154   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.806  -7.205   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.433  -7.903   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.681  -6.154   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.696  -8.187   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.345  -8.925   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.011  -8.988   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   15   19                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   11   16                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    3   11   20                                             
CONECT   20   19   21   25                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    2   20                                                  
CONECT   26   21   16   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   27   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   14   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂N₄O₂

Average Mass

456.5900 Da

Monoisotopic Mass

456.25253 Da

IUPAC Name

1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethan-1-one

Traditional Name

1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

CAS Registry Number

Not Available

SMILES

CN1C2NC3=CC=CC=C3C34CCN(C3N3CCC24C2=C(C=CC=C12)C3C1OC1(C)C)C(C)=O

InChI Identifier

InChI=1S/C28H32N4O2/c1-16(33)31-14-12-27-18-9-5-6-10-19(18)29-24-28(27)13-15-32(25(27)31)22(23-26(2,3)34-23)17-8-7-11-20(21(17)28)30(24)4/h5-11,22-25,29H,12-15H2,1-4H3

InChI Key

QKUUVGNHUMKUAN-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Alpha carbolines

Alternative Parents

Substituents

Alpha-carboline
Aminoquinoline
Benzazepine
Tetrahydroquinoline
Naphthyridine
N-acylpyrrolidine
Dialkylarylamine
Azepine
Benzenoid
Piperidine
Tertiary carboxylic acid amide
Pyrrolidine
Acetamide
Carboxamide group
Azacycle
Oxacycle
Carboxylic acid derivative
Ether
Oxirane
Dialkyl ether
Amine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organic oxygen compound
Organooxygen 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	3.48	ALOGPS
logP	3.06	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	6.09	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.35 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.44 m³·mol⁻¹	ChemAxon
Polarizability	50.14 Å³	ChemAxon
Number of Rings	8	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

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

76461847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone (NP0327154)

MOL for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)

3D MOL for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)

3D SDF for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)

3D-SDF for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)

PDB for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)

3D PDB for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)

SMILES for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)

INCHI for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)

Structure for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)

3D Structure for NP0327154 (1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone)