NP-MRD: Showing NP-Card for n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid (NP0218040)

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Record Information

Version

2.0

Created at

2022-09-05 18:34:37 UTC

Updated at

2022-09-05 18:34:37 UTC

NP-MRD ID

NP0218040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid

Description

N-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]Trideca-2,4-dien-11-yl}methyl)ethanimidic acid belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one. n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid is found in Maackia hupehensis. N-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]Trideca-2,4-dien-11-yl}methyl)ethanimidic acid is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004151516432D          

 19 21  0  0  0  0            999 V2000
    7.7283    2.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1187    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2954    0.6905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3325    1.7463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7229    1.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367    1.4403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667    2.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360    2.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1662    1.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828    0.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049    0.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9521    1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2752    0.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283    1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584    1.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353    2.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654    3.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    2.0935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4140    2.7242    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)NCN1CC2CC(C1)C1=CC=CC(=O)N1C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H19N3O2/c1-10(18)15-9-16-6-11-5-12(8-16)13-3-2-4-14(19)17(13)7-11/h2-4,11-12H,5-9H2,1H3,(H,15,18)

> <INCHI_KEY>
FRRVGRCLXTXJOB-UHFFFAOYSA-N

> <FORMULA>
C14H19N3O2

> <MOLECULAR_WEIGHT>
261.325

> <EXACT_MASS>
261.147726864

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.790004546142313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)acetamide

> <ALOGPS_LOGP>
0.64

> <JCHEM_LOGP>
-0.7648419330000005

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.861462162033568

> <JCHEM_PKA_STRONGEST_BASIC>
6.647272405713796

> <JCHEM_POLAR_SURFACE_AREA>
52.650000000000006

> <JCHEM_REFRACTIVITY>
74.42609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      14.426   3.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.288   2.793   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.618   1.289   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      11.821   3.260   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      10.683   2.222   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       9.215   2.689   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.085   4.223   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.907   5.216   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.777   3.146   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.688   1.381   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.222   1.511   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.511   2.373   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.247   1.493   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.853   2.147   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.722   3.682   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.986   4.562   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.855   6.096   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       5.380   3.908   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       6.373   5.085   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                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    6                                                       
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18    8                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
N-({6-oxo-7,11-diazatricyclo[7.3.1.0,]trideca-2,4-dien-11-yl}methyl)ethanimidate	Generator
N-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidate	Generator

Chemical Formula

C₁₄H₁₉N₃O₂

Average Mass

261.3250 Da

Monoisotopic Mass

261.14773 Da

IUPAC Name

N-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)acetamide

Traditional Name

N-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)acetamide

CAS Registry Number

Not Available

SMILES

CC(=O)NCN1CC2CC(C1)C1=CC=CC(=O)N1C2

InChI Identifier

InChI=1S/C14H19N3O2/c1-10(18)15-9-16-6-11-5-12(8-16)13-3-2-4-14(19)17(13)7-11/h2-4,11-12H,5-9H2,1H3,(H,15,18)

InChI Key

FRRVGRCLXTXJOB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Maackia hupehensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Cytisine and derivatives

Direct Parent

Cytisine and derivatives

Alternative Parents

Substituents

Cytisine
Pyridinone
Piperidine
Pyridine
Heteroaromatic compound
Lactam
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Azacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen 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	0.64	ALOGPS
logP	-0.76	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	6.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.65 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.43 m³·mol⁻¹	ChemAxon
Polarizability	27.79 Å³	ChemAxon
Number of Rings	3	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

73201090

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid (NP0218040)

MOL for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)

3D MOL for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)

3D SDF for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)

3D-SDF for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)

PDB for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)

3D PDB for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)

SMILES for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)

INCHI for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)

Structure for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)

3D Structure for NP0218040 (n-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)ethanimidic acid)