NP-MRD: Showing NP-Card for (1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate (NP0284163)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 11:44:37 UTC

Updated at

2022-09-09 11:44:37 UTC

NP-MRD ID

NP0284163

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate

Description

Meteloidine 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. (1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate is found in Datura inoxia. (1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate was first documented in 1984 (PMID: 17340258). Based on a literature review very few articles have been published on Meteloidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    5.5428   -0.4810    1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1049   -0.2615    0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6546    0.8066    0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6487    1.8191   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2126    0.9787   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079    2.0027   -0.7481 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788    0.0563    0.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1170    0.1804    0.0160 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8861    0.2719    1.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2868   -0.2116    1.2219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1279    0.7713    0.4237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4832    0.5888    0.6373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496    0.3829   -0.9996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9048    0.3476   -1.7529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0963   -0.9920   -0.8766 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6005   -0.8827   -0.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4030   -1.4470    0.4778 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7010   -2.0240    0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6624   -1.5668    1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1339   -0.2717    0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9028    0.0701    1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3462   -0.9839    1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871    1.9219    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    2.7727   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1274    1.3928   -1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2343    1.1610   -0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141   -0.2368    2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9154    1.3528    1.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6730   -0.3225    2.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7866    1.7935    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8563    1.1908    1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0675    1.1264   -1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8332   -0.4117   -2.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5224   -1.6281   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2270   -0.6525   -1.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1734   -1.8635   -0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876   -1.7134    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2836   -1.8978   -0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5707   -3.1400    0.6381 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
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 16  8  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  8 26  1  6
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  1
 12 31  1  0
 13 32  1  6
 14 33  1  0
 15 34  1  6
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
M  END


  Mrv1652309092213442D          

 18 19  0  0  1  0            999 V2000
    6.0880   -0.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630   -0.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505   -0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130   -0.7926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2374    1.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2374   -0.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5690    0.6363    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
  7  8  1  0  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  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 15 17  1  1  0  0  0
 10 17  1  1  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284163

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)OC1C[C@H]2[C@H](O)[C@H](O)[C@@H](C1)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO4/c1-4-7(2)13(17)18-8-5-9-11(15)12(16)10(6-8)14(9)3/h4,8-12,15-16H,5-6H2,1-3H3/b7-4+/t8?,9-,10+,11-,12+

> <INCHI_KEY>
YZFJTFVPCWEPND-LTDHHRLMSA-N

> <FORMULA>
C13H21NO4

> <MOLECULAR_WEIGHT>
255.314

> <EXACT_MASS>
255.14705816

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.27649486674818

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,6S,7R)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
0.40850560566666594

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.682309392686701

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.258814755519662

> <JCHEM_PKA_STRONGEST_BASIC>
8.337608012852519

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
66.8386

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,6S,7R)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      11.364  -1.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.824  -1.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.054  -0.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.824   1.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.514  -0.146   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.744  -1.480   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.744   1.188   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.204   1.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.536   2.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.035   2.918   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.831   1.958   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.443   2.626   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.831   0.418   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.443  -0.250   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.035  -0.542   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.536  -0.200   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.602   1.188   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       1.062   1.188   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   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15    8                                                       
CONECT   17   15   10   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₁NO₄

Average Mass

255.3140 Da

Monoisotopic Mass

255.14706 Da

IUPAC Name

(1R,5S,6S,7R)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1R,5S,6S,7R)-6,7-dihydroxy-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)OC1C[C@H]2[C@H](O)[C@H](O)[C@@H](C1)N2C

InChI Identifier

InChI=1S/C13H21NO4/c1-4-7(2)13(17)18-8-5-9-11(15)12(16)10(6-8)14(9)3/h4,8-12,15-16H,5-6H2,1-3H3/b7-4+/t8?,9-,10+,11-,12+

InChI Key

YZFJTFVPCWEPND-LTDHHRLMSA-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
Datura inoxia	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
1,2-aminoalcohol
1,2-diol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Carbonyl group
Organopnictogen compound
Organic oxide
Alcohol
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	0.41	ChemAxon
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	8.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.84 m³·mol⁻¹	ChemAxon
Polarizability	27.28 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

C00002296

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Meteloidine

METLIN ID

Not Available

PubChem Compound

12312780

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

El Imam YM, Evans WC: Tropane alkaloids of species of anthocercis, cyphanthera and crenidium. Planta Med. 1984 Feb;50(1):86-7. doi: 10.1055/s-2007-969628. [PubMed:17340258 ]
LOTUS database [Link]

Showing NP-Card for (1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate (NP0284163)

MOL for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

PDB for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

Structure for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0284163 ((1r,5s,6s,7r)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enoate)