NP-MRD: Showing NP-Card for (7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene (NP0194944)

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Record Information

Version

2.0

Created at

2022-09-04 12:42:46 UTC

Updated at

2022-09-04 12:42:46 UTC

NP-MRD ID

NP0194944

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene

Description

Myrmicarin 215B, also known as myrmicarin, belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring. (7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene was first documented in 2006 (PMID: 20640170). Based on a literature review a small amount of articles have been published on Myrmicarin 215B (PMID: 19586059) (PMID: 19585010) (PMID: 17315932).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    4.5230   -1.4072   -1.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0740   -1.2407   -0.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5293   -0.2071   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1058   -0.0820   -0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4938    0.9999    0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641    2.1780    1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0141    3.4121    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8721    0.7663    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047   -0.3704   -0.1320 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938   -0.9311   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959   -2.2036   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769   -2.4742   -0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115   -1.0819   -0.4240 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1416   -0.7974    0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2694    0.6682    1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608    1.5111    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7218   -2.1023   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0698   -0.4478   -1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205   -1.9123   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209   -2.0002   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122    0.5421    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474    2.4328    2.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2329    2.0318    1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8303    4.3193    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8462    3.5184   -0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0873    3.2368   -0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136   -3.0626   -0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -2.0888   -2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2468   -3.1184   -1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5049   -2.9170    0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229   -0.7479   -1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8855   -1.4072    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1560   -1.1476    0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0090    1.1034    0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7822    0.7362    2.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263    2.4513    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482    1.8400    2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  8  2  0
  8 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
 10  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  4  5  1  0
  9  8  1  0
  9 13  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  6 22  1  0
  6 23  1  0
 16 36  1  0
 16 37  1  0
 15 34  1  0
 15 35  1  0
 14 32  1  0
 14 33  1  0
 13 31  1  6
 12 29  1  0
 12 30  1  0
 11 27  1  0
 11 28  1  0
  3 21  1  0
  2 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
M  END


  Mrv1652309042214422D          

 16 18  0  0  1  0            999 V2000
   -2.6391   -0.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8362   -0.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2705   -0.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4676   -0.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491   -1.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5883   -1.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2031   -2.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0161   -1.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627   -0.3807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1577    0.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473    0.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881    0.1574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2668   -0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4201   -0.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7948   -1.4638    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
  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
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  2  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  9  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C2CCC[C@@H]3CCC(N23)=C1\C=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C15H21N/c1-3-6-13-12(4-2)14-8-5-7-11-9-10-15(13)16(11)14/h3,6,11H,4-5,7-10H2,1-2H3/b6-3+/t11-/m1/s1

> <INCHI_KEY>
XHXBPJIMQMOKPK-ZXCPCRMDSA-N

> <FORMULA>
C15H21N

> <MOLECULAR_WEIGHT>
215.34

> <EXACT_MASS>
215.16739968

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.256612625162212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7R)-2-ethyl-3-[(1E)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0^{4,11}]undeca-1,3-diene

> <JCHEM_LOGP>
4.359570516333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
4.93

> <JCHEM_REFRACTIVITY>
70.8709

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(7R)-2-ethyl-3-[(1E)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0^{4,11}]undeca-1,3-diene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.926  -1.328   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.428  -1.682   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.372  -0.561   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.873  -0.915   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.278  -2.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.098  -3.639   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.379  -5.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.897  -2.224   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.610  -0.711   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.294   0.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.648   1.588   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.183   1.714   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.778   0.294   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.231  -0.215   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.518  -1.728   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.350  -2.732   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
Myrmicarin	MeSH
Myrmicarin 217	MeSH
Myrmicarin 215a	MeSH

Chemical Formula

C₁₅H₂₁N

Average Mass

215.3400 Da

Monoisotopic Mass

215.16740 Da

IUPAC Name

(7R)-2-ethyl-3-[(1E)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0^{4,11}]undeca-1,3-diene

Traditional Name

(7R)-2-ethyl-3-[(1E)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0^{4,11}]undeca-1,3-diene

CAS Registry Number

Not Available

SMILES

CCC1=C2CCC[C@@H]3CCC(N23)=C1\C=C\C

InChI Identifier

InChI=1S/C15H21N/c1-3-6-13-12(4-2)14-8-5-7-11-9-10-15(13)16(11)14/h3,6,11H,4-5,7-10H2,1-2H3/b6-3+/t11-/m1/s1

InChI Key

XHXBPJIMQMOKPK-ZXCPCRMDSA-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 pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizines

Sub Class

Not Available

Direct Parent

Pyrrolizines

Alternative Parents

Substituents

Pyrrolizine
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen 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	4.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	4.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.87 m³·mol⁻¹	ChemAxon
Polarizability	27.26 Å³	ChemAxon
Number of Rings	3	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

9370339

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11195270

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ondrus AE, Movassaghi M: Reversible dimerization of (+)-myrmicarin 215B. Org Lett. 2009 Jul 16;11(14):2960-3. doi: 10.1021/ol9008552. [PubMed:19586059 ]
Ondrus AE, Movassaghi M: Total synthesis and study of myrmicarin alkaloids. Chem Commun (Camb). 2009 Jul 28;(28):4151-65. doi: 10.1039/b903995n. Epub 2009 May 19. [PubMed:19585010 ]
Angle SR, Qian XL, Pletnev AA, Chinn J: General synthesis of pyrroloquinolizidines: synthesis of an unnatural homologue of the pyrroloindolizidine myrmicarin alkaloid 215B. J Org Chem. 2007 Mar 16;72(6):2015-20. doi: 10.1021/jo062262a. Epub 2007 Feb 22. [PubMed:17315932 ]
Ondrus AE, Movassaghi M: Dimerization of (+)-Myrmicarin 215B. A Potential Biomimetic Approach to Complex Myrmicarin Alkaloids. Tetrahedron. 2006 May 29;62(22):5287-5297. doi: 10.1016/j.tet.2006.01.108. [PubMed:20640170 ]
LOTUS database [Link]

Showing NP-Card for (7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene (NP0194944)

MOL for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)

3D MOL for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)

3D SDF for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)

3D-SDF for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)

PDB for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)

3D PDB for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)

SMILES for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)

INCHI for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)

Structure for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)

3D Structure for NP0194944 ((7r)-2-ethyl-3-[(1e)-prop-1-en-1-yl]-11-azatricyclo[5.3.1.0⁴,¹¹]undeca-1,3-diene)