NP-MRD: Showing NP-Card for Tigloidine (NP0051333)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:43:14 UTC

Updated at

2022-04-27 22:43:14 UTC

NP-MRD ID

NP0051333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tigloidine

Description

(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]Octan-3-yl (2E)-2-methylbut-2-enoate belongs to the class of organic compounds known as tropane alkaloids. Tigloidine is found in Brugmansia sanguinea, Cyphomandra betaceae, Datura innoxia , Datura metel , Datura stramonium, Duboisia myoporoides , Mandragora turcomanica, Mandragora turcomanica Mizger, Nierembergia hippomanica, Nierembergia linariifolia, Physalis alkekengi and Physalis peruviana . These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane (1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]Octan-3-yl (2E)-2-methylbut-2-enoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    5.8017    0.3282    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4456    0.5775    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    0.1062   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -0.6464   -1.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475    0.3114    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8861    0.9536    1.4604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351   -0.1570   -0.2553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893    0.0411    0.2040 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1121    0.8749   -0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6270    0.8301   -0.5865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8600    1.2573    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7397   -0.0204    1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5358   -1.1085    0.5524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0256   -1.3001    0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0064   -0.5602   -0.6802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4187   -0.7407   -0.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5720    0.3472    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0476    1.1641   -0.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8365   -0.6198   -0.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3348    1.1393    1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6827   -0.8960   -1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -1.6273   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3279   -0.0696   -2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318    0.6203    1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561    1.9037   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9598    0.4316   -1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1148    1.4766   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313    1.9698    1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8315    1.7740    0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6648   -0.2018    2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9047   -0.0170    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367   -2.0196    0.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880   -1.8105    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9066   -1.8628   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6270   -1.8246   -0.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0440   -0.2060   -0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6319   -0.4182   -1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  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
 13 15  1  0
 15 16  1  0
 14  8  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  4 21  1  0
  4 22  1  0
  4 23  1  0
  8 24  1  1
  9 25  1  0
  9 26  1  0
 10 27  1  6
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  1
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  END


  Mrv1652309272006312D          

 16 17  0  0  0  0            999 V2000
 9995.6218 9999.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4601 9999.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1037 9998.4262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8180 9998.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5341 9998.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2483 9998.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9624 9998.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5341 9997.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8180 9999.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3903 9998.8537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8859 9998.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1949 9999.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0610 9998.1887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7084 9999.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5369 9998.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.446210000.0018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 10  3  1  1  0  0  0
 16  2  1  1  0  0  0
 13  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051333

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@H]1C[C@@H]2CC[C@H](C1)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO2/c1-4-9(2)13(15)16-12-7-10-5-6-11(8-12)14(10)3/h4,10-12H,5-8H2,1-3H3/b9-4+/t10-,11+,12-

> <INCHI_KEY>
UVHGSMZRSVGWDJ-WJKWMCMVSA-N

> <FORMULA>
C13H21NO2

> <MOLECULAR_WEIGHT>
223.316

> <EXACT_MASS>
223.15722892

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.400710940154212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.2464978996666662

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.420340195976381

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
64.42360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8658.4948665.497   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8661.9268664.892   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0    8664.9948663.729   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8666.3278664.500   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8667.6648663.729   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.9978664.500   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.3308663.729   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.6648662.189   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8666.3278666.041   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8663.6628664.527   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.7208663.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.2978666.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.1818663.286   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.5228665.981   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.2028664.475   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8661.9008666.670   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1   16   13                                                  
CONECT    3    4   10                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4                                                            
CONECT   10   11   12    3                                                  
CONECT   11   10   13                                                       
CONECT   12   10   16                                                       
CONECT   13   11   15    2                                                  
CONECT   14   15   16                                                       
CONECT   15   13   14                                                       
CONECT   16   12   14    2                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(1R,3R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoic acid	Generator
3beta-Tigloyloxytropane	PhytoBank
3β-Tigloyloxytropane	PhytoBank
Tigloidin	PhytoBank
Tigloyl pseudotropine	PhytoBank
Tiglylpseudotropine	PhytoBank
Tiglyssin	PhytoBank

Chemical Formula

C₁₃H₂₁NO₂

Average Mass

223.3160 Da

Monoisotopic Mass

223.15723 Da

IUPAC Name

(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@H]1C[C@@H]2CC[C@H](C1)N2C

InChI Identifier

InChI=1S/C13H21NO2/c1-4-9(2)13(15)16-12-7-10-5-6-11(8-12)14(10)3/h4,10-12H,5-8H2,1-3H3/b9-4+/t10-,11+,12-

InChI Key

UVHGSMZRSVGWDJ-WJKWMCMVSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Brugmansia sanguinea	LOTUS Database	35616633
Cyphomandra betaceae	Plant	KNApSAcK
Datura inoxia	Plant	KNApSAcK
Datura metel	Plant	KNApSAcK
Datura stramonium	LOTUS Database	35616633
Duboisia myoporoides	Plant	KNApSAcK
Mandragora turcomanica	LOTUS Database	35616633
Mandragora turcomanica Mizger	Plant	KNApSAcK
Nierembergia hippomanica	LOTUS Database	35616633
Nierembergia linariifolia	LOTUS Database	35616633
Physalis alkekengi	Plant	KNApSAcK
Physalis peruviana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tropane alkaloid
Fatty acid ester
Piperidine
N-alkylpyrrolidine
Fatty acyl
Pyrrolidine
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
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	2.41	ALOGPS
logP	2.25	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	9.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.42 m³·mol⁻¹	ChemAxon
Polarizability	25.4 Å³	ChemAxon
Number of Rings	2	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

16736065

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tigloidine (NP0051333)

MOL for NP0051333 (Tigloidine)

3D MOL for NP0051333 (Tigloidine)

3D SDF for NP0051333 (Tigloidine)

3D-SDF for NP0051333 (Tigloidine)

PDB for NP0051333 (Tigloidine)

3D PDB for NP0051333 (Tigloidine)

SMILES for NP0051333 (Tigloidine)

INCHI for NP0051333 (Tigloidine)

Structure for NP0051333 (Tigloidine)

3D Structure for NP0051333 (Tigloidine)