NP-MRD: Showing NP-Card for (1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate (NP0313784)

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Record Information

Version

2.0

Created at

2022-09-11 11:32:37 UTC

Updated at

2022-09-11 11:32:37 UTC

NP-MRD ID

NP0313784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate

Description

3Alpha-hydroxy-6beta-tigloyloxytropane 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. (1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate is found in Schizanthus hookeri and Schizanthus pinnatus. (1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate was first documented in 2010 (PMID: 20189614). Based on a literature review very few articles have been published on 3alpha-hydroxy-6beta-tigloyloxytropane.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    5.7459   -0.2819   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3855   -0.8470   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020   -0.0971   -0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545    1.3745   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9913   -0.6889    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805   -1.9447    0.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8348    0.0598    0.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -0.5761    0.3902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1911    0.0356    1.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376    0.9414    0.8622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5256    0.1773    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032   -1.0422   -0.0210 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6571   -2.1772    0.8098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3473   -1.2204   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2751   -0.1932   -0.8189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6946    1.0942   -0.4069 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427    1.9741   -1.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1651    0.1664    0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4182   -1.1261   -0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7616    0.4568   -1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2303   -1.9212   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497    1.8640   -0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    1.5942   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9787    1.7393    0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -1.6639    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520    0.7405    2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6608   -0.7323    2.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4039    1.8582    1.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    0.9006    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8020   -0.0690    1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4378   -1.0451   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7827   -2.5591    1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6481   -1.2799   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8630   -2.2230   -0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6871   -0.1203   -1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171    1.9237   -1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192    1.8769   -2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0438    3.0312   -0.9871 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
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15  8  1  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 10 28  1  1
 11 29  1  0
 11 30  1  0
 12 31  1  6
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  6
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  END


  Mrv1652309112213322D          

 17 18  0  0  1  0            999 V2000
   -2.8139    1.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706    1.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6905    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656    0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -0.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    0.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.4941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1593   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -0.8453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    0.0816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7916    0.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.0085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0361    0.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.3366    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  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  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
 10 16  1  6  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313784

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO3/c1-4-8(2)13(16)17-12-6-9-5-10(15)7-11(12)14(9)3/h4,9-12,15H,5-7H2,1-3H3/b8-4+/t9-,10-,11+,12-/m0/s1

> <INCHI_KEY>
FSTVJNLNEVDORU-MFCSVHNESA-N

> <FORMULA>
C13H21NO3

> <MOLECULAR_WEIGHT>
239.315

> <EXACT_MASS>
239.15214354

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.07141956297884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
1.0988002866666662

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.155868065063736

> <JCHEM_PKA_STRONGEST_BASIC>
8.108257473672776

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
65.7415

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.253   3.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.865   2.927   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.750   1.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.022   0.524   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.362   0.723   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.247  -0.813   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.090   1.591   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.297   0.922   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.297  -0.618   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.501  -1.578   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.003  -1.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.671   0.152   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.211   0.152   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.003   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.501   1.883   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.934   0.152   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.399   0.628   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
3a-Hydroxy-6b-tigloyloxytropane	Generator
3Α-hydroxy-6β-tigloyloxytropane	Generator

Chemical Formula

C₁₃H₂₁NO₃

Average Mass

239.3150 Da

Monoisotopic Mass

239.15214 Da

IUPAC Name

(1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1S,3S,5R,6S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H21NO3/c1-4-8(2)13(16)17-12-6-9-5-10(15)7-11(12)14(9)3/h4,9-12,15H,5-7H2,1-3H3/b8-4+/t9-,10-,11+,12-/m0/s1

InChI Key

FSTVJNLNEVDORU-MFCSVHNESA-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
Schizanthus hookeri	LOTUS Database	35616633
Schizanthus pinnatus	LOTUS Database	35616633

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
Cyclic alcohol
Pyrrolidine
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
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	1.1	ChemAxon
pKa (Strongest Acidic)	15.16	ChemAxon
pKa (Strongest Basic)	8.11	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.74 m³·mol⁻¹	ChemAxon
Polarizability	26.07 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

129649783

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Reina M, Burgueno-Tapia E, Bucio MA, Joseph-Nathan P: Absolute configuration of tropane alkaloids from Schizanthus species by vibrational circular dichroism. Phytochemistry. 2010 May;71(7):810-5. doi: 10.1016/j.phytochem.2010.02.004. Epub 2010 Feb 26. [PubMed:20189614 ]
LOTUS database [Link]

Showing NP-Card for (1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate (NP0313784)

MOL for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)

PDB for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)

Structure for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0313784 ((1s,3s,5r,6s)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl (2e)-2-methylbut-2-enoate)