NP-MRD: Showing NP-Card for (1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one (NP0303236)

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Record Information

Version

2.0

Created at

2022-09-10 17:25:41 UTC

Updated at

2022-09-10 17:25:41 UTC

NP-MRD ID

NP0303236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one

Description

Leontine, also known as allomatrine, belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton. (1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one is found in Gymnospermium darwasicum. (1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one was first documented in 2012 (PMID: 22702382). Based on a literature review very few articles have been published on Leontine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
    2.9998   -2.9153    0.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8335   -1.6809    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9638   -0.8442   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8376    0.5047    0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515    1.1218   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4024    0.3572    0.4189 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1329    0.9159   -0.1503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1060    2.3114    0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848    2.6741    0.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3068    1.8020   -0.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151    0.4586   -0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826   -0.2655   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0662   -1.7261    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8887   -2.1906   -0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773   -1.3406   -0.5133 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4205   -1.9737    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588   -1.0532    0.2612 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -0.0144    0.1926 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8242   -0.7213   -1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9272   -1.3396   -0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7263    0.3037    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7222    1.1309    0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    1.0664   -1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4767    2.1808    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284    0.6685    1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2475    0.9341   -1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3489    2.5001    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800    3.0284   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0492    2.4954    1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7399    3.7274    0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7151    1.9244   -1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3382    2.1061   -0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8764    0.0788    0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083   -0.1473   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8903   -1.9893    1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9445   -2.3301   -0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884   -2.2368   -1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -3.2191   -0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318   -1.1028   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -2.0556    1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6429   -2.9453   -0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492   -0.1990    1.2855 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
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 17  2  1  0
 17  6  1  0
 18  7  1  0
 18 11  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  6
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  6
 16 40  1  0
 16 41  1  0
 18 42  1  1
M  END


  Mrv1652309102219252D          

 18 21  0  0  1  0            999 V2000
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  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  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
  6 17  1  1  0  0  0
 15 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 11  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0303236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCC[C@H]2[C@@H]3CCCN4CCC[C@H](CN12)[C@@H]34

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15+/m1/s1

> <INCHI_KEY>
ZSBXGIUJOOQZMP-OSFYFWSMSA-N

> <FORMULA>
C15H24N2O

> <MOLECULAR_WEIGHT>
248.37

> <EXACT_MASS>
248.188863401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.167220565829115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,9R,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-6-one

> <JCHEM_LOGP>
1.0759273119999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.75220211509645

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
71.4485

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,9R,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    2    6                                                  
CONECT   18   15    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
Allomatrine	MeSH

Chemical Formula

C₁₅H₂₄N₂O

Average Mass

248.3700 Da

Monoisotopic Mass

248.18886 Da

IUPAC Name

(1S,2S,9R,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-6-one

Traditional Name

(1S,2S,9R,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-6-one

CAS Registry Number

Not Available

SMILES

O=C1CCC[C@H]2[C@@H]3CCCN4CCC[C@H](CN12)[C@@H]34

InChI Identifier

InChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15+/m1/s1

InChI Key

ZSBXGIUJOOQZMP-OSFYFWSMSA-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
Gymnospermium darwasicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Matrine alkaloids

Direct Parent

Matrine alkaloids

Alternative Parents

Substituents

Matrine
Quinolizidinone
Diazanaphthalene
Naphthyridine
Quinolizidine
Delta-lactam
Piperidinone
Piperidine
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Amine
Carbonyl group
Organopnictogen compound
Organic oxide
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	1.08	ChemAxon
pKa (Strongest Basic)	9.75	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	71.45 m³·mol⁻¹	ChemAxon
Polarizability	29.17 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

Not Available

Chemspider ID

418302

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leontine

METLIN ID

Not Available

PubChem Compound

476484

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mayer V: Lesbian classics in Germany? A film historical analysis of Madchen in Uniform (1931 and 1958). J Lesbian Stud. 2012;16(3):340-53. doi: 10.1080/10894160.2012.673933. [PubMed:22702382 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one (NP0303236)

MOL for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)

3D MOL for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)

3D SDF for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)

3D-SDF for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)

PDB for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)

3D PDB for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)

SMILES for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)

INCHI for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)

Structure for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)

3D Structure for NP0303236 ((1s,2s,9r,17s)-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one)