NP-MRD: Showing NP-Card for (1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one (NP0242289)

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Record Information

Version

2.0

Created at

2022-09-07 02:34:51 UTC

Updated at

2022-09-07 02:34:51 UTC

NP-MRD ID

NP0242289

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one

Description

58845-84-4 Belongs to the class of organic compounds known as leontidine-type alkaloids. These are lupin alkaloids with a structure based on the leontidine skeleton, a tetracyclic compound containing fused piperidine, pyridine, and pyrrolidine rings. (1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one is found in Camoensia scandens. Based on a literature review very few articles have been published on 58845-84-4.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    2.9133    1.9367   -1.8998 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463    1.0920   -1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8493    0.6096   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4234    0.4887    1.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9767    0.0968    1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5156   -0.5521    0.2513 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2087   -1.2463    0.3034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1905   -1.4768   -1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274   -0.1878   -1.6532 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3064    0.8951   -1.4577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862    0.4827   -0.7562 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9510    0.2039   -0.8719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9911   -0.8489   -0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8119   -0.3430    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8676    0.6362    1.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689    0.4505    0.4906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -0.6005    1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157   -0.3716   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7239    1.2941   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962    1.3881    1.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0350   -0.3409    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8873   -0.5272    2.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    1.0729    1.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3156   -1.2894   -0.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3880   -2.2777    0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7486   -1.7099   -1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413   -2.3442   -1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0132   -0.2119   -2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1073    1.7612   -0.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051    1.3367   -2.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    1.1192   -1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6496   -1.8442   -0.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6513   -0.9349   -1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7292    0.1351    0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0309   -1.1526    1.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2615    1.6595    0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381    0.4910    2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5716   -1.3919    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -0.2116    2.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 11  2  1  0
 16 12  1  0
 11  6  1  0
 17  7  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  6
  7 25  1  1
  8 26  1  0
  8 27  1  0
  9 28  1  6
 10 29  1  0
 10 30  1  0
 12 31  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv1652309072204342D          

 17 20  0  0  1  0            999 V2000
    5.8334   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8334   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5479    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5479    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8334    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5356    1.4084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3721    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7106   -0.5834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5356   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3426   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3426    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7106    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  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  1  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  6 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  1  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242289

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCC[C@H]2[C@@H]3C[C@H](CN12)[C@H]1CCCN1C3

> <INCHI_IDENTIFIER>
InChI=1S/C14H22N2O/c17-14-5-1-3-13-10-7-11(9-16(13)14)12-4-2-6-15(12)8-10/h10-13H,1-9H2/t10-,11-,12-,13+/m1/s1

> <INCHI_KEY>
ZALYGVJIPDSPLI-LPWJVIDDSA-N

> <FORMULA>
C14H22N2O

> <MOLECULAR_WEIGHT>
234.343

> <EXACT_MASS>
234.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.20859850475229

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,9R,10R)-7,14-diazatetracyclo[7.6.1.0^{2,7}.0^{10,14}]hexadecan-6-one

> <JCHEM_LOGP>
0.631358646999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.776377624704413

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
66.84750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,9R,10R)-7,14-diazatetracyclo[7.6.1.0^{2,7}.0^{10,14}]hexadecan-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      10.889  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.889  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.223   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.223   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.889   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.555   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.466   2.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.161   0.578   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.926  -1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.466  -1.089   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.555   0.000   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.838   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.373  -0.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.468   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.373   2.016   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.838   1.540   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.926   2.629   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2    6                                                  
CONECT   12    9   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16    7                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₂N₂O

Average Mass

234.3430 Da

Monoisotopic Mass

234.17321 Da

IUPAC Name

(1R,2S,9R,10R)-7,14-diazatetracyclo[7.6.1.0^{2,7}.0^{10,14}]hexadecan-6-one

Traditional Name

(1R,2S,9R,10R)-7,14-diazatetracyclo[7.6.1.0^{2,7}.0^{10,14}]hexadecan-6-one

CAS Registry Number

Not Available

SMILES

O=C1CCC[C@H]2[C@@H]3C[C@H](CN12)[C@H]1CCCN1C3

InChI Identifier

InChI=1S/C14H22N2O/c17-14-5-1-3-13-10-7-11(9-16(13)14)12-4-2-6-15(12)8-10/h10-13H,1-9H2/t10-,11-,12-,13+/m1/s1

InChI Key

ZALYGVJIPDSPLI-LPWJVIDDSA-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
Camoensia scandens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leontidine-type alkaloids. These are lupin alkaloids with a structure based on the leontidine skeleton, a tetracyclic compound containing fused piperidine, pyridine, and pyrrolidine rings.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Leontidine-type alkaloids

Direct Parent

Leontidine-type alkaloids

Alternative Parents

Substituents

Leontidine alkaloid skeleton
Quinolizidinone
Quinolizidine
Indolizidine
Delta-lactam
Piperidinone
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Amino acid or derivatives
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Amine
Organopnictogen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.63	ChemAxon
pKa (Strongest Basic)	10.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.85 m³·mol⁻¹	ChemAxon
Polarizability	26.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00007781

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

15060885

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one (NP0242289)

MOL for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)

3D MOL for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)

3D SDF for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)

3D-SDF for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)

PDB for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)

3D PDB for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)

SMILES for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)

INCHI for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)

Structure for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)

3D Structure for NP0242289 ((1r,2s,9r,10r)-7,14-diazatetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁴]hexadecan-6-one)