NP-MRD: Showing NP-Card for (1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol (NP0256536)

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Record Information

Version

2.0

Created at

2022-09-07 21:24:20 UTC

Updated at

2022-09-07 21:24:20 UTC

NP-MRD ID

NP0256536

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol

Description

(1R,2S,3R,4S,5R,6R)-8-azabicyclo[3.2.1]Octane-1,2,3,4,6-pentol belongs to the class of organic compounds known as tropane alkaloids. (1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol is found in Duboisia leichhardtii, Ipomoea carnea and Ipomoea violacea. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane (1R,2S,3R,4S,5R,6R)-8-azabicyclo[3.2.1]Octane-1,2,3,4,6-pentol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09041212542D          

 18 19  0  0  0  0            999 V2000
    0.1197   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9893   -0.5417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6113   -0.9304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5824   -0.0348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927   -2.1626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990   -0.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8092   -1.8896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6655    0.0268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2255   -0.6651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4378   -2.0334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8706    0.2456    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247    0.2667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8357   -0.9360    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3677   -0.6011    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  1  0  0  0  0
  2  9  1  6  0  0  0
  4 10  1  6  0  0  0
  5 11  1  1  0  0  0
  6 12  1  1  0  0  0
  7 13  1  1  0  0  0
  2 14  1  1  0  0  0
  3 15  1  6  0  0  0
  4 16  1  1  0  0  0
  5 17  1  6  0  0  0
  6 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0256536

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(O)C[C@]2(O)N[C@@]1([H])[C@]([H])(O)[C@@]([H])(O)[C@]2([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO5/c9-2-1-7(13)6(12)5(11)4(10)3(2)8-7/h2-6,8-13H,1H2/t2-,3-,4+,5-,6+,7-/m1/s1

> <INCHI_KEY>
GGOJRYWHKVYFQK-XQCVOTFFSA-N

> <FORMULA>
C7H13NO5

> <MOLECULAR_WEIGHT>
191.1818

> <EXACT_MASS>
191.079372531

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
17.53256421241298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3R,4S,5R,6R)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol

> <ALOGPS_LOGP>
-2.28

> <JCHEM_LOGP>
-2.8571149069999997

> <ALOGPS_LOGS>
0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.012332754598756

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.074419668656592

> <JCHEM_PKA_STRONGEST_BASIC>
7.923207715514753

> <JCHEM_POLAR_SURFACE_AREA>
113.18

> <JCHEM_REFRACTIVITY>
39.86489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,4S,5R,6R)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1    3    9   14                                             
CONECT    3    2    4    8   15                                             
CONECT    4    3    5   10   16                                             
CONECT    5    4    6   11   17                                             
CONECT    6    5    7   12   18                                             
CONECT    7    1    6    8   13                                             
CONECT    8    3    7                                                       
CONECT    9    2                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    2                                                            
CONECT   15    3                                                            
CONECT   16    4                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₇H₁₃NO₅

Average Mass

191.1818 Da

Monoisotopic Mass

191.07937 Da

IUPAC Name

(1R,2S,3R,4S,5R,6R)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol

Traditional Name

(1R,2S,3R,4S,5R,6R)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)C[C@]2(O)N[C@@]1([H])[C@]([H])(O)[C@@]([H])(O)[C@]2([H])O

InChI Identifier

InChI=1S/C7H13NO5/c9-2-1-7(13)6(12)5(11)4(10)3(2)8-7/h2-6,8-13H,1H2/t2-,3-,4+,5-,6+,7-/m1/s1

InChI Key

GGOJRYWHKVYFQK-XQCVOTFFSA-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
Duboisia leichhardtii	LOTUS Database	35616633
Ipomoea carnea	LOTUS Database	35616633
Ipomoea violacea	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
Piperidine
Cyclic alcohol
Pyrrolidine
Hemiaminal
Secondary alcohol
Alkanolamine
Secondary aliphatic amine
Polyol
Azacycle
Secondary amine
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Alcohol
Hydrocarbon derivative
Amine
Organic nitrogen compound
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	-2.3	ALOGPS
logP	-2.9	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	12.07	ChemAxon
pKa (Strongest Basic)	7.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	113.18 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	39.86 m³·mol⁻¹	ChemAxon
Polarizability	17.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

10081256

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol (NP0256536)

MOL for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)

3D MOL for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)

3D SDF for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)

3D-SDF for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)

PDB for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)

3D PDB for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)

SMILES for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)

INCHI for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)

Structure for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)

3D Structure for NP0256536 ((1r,2s,3r,4s,5r,6r)-8-azabicyclo[3.2.1]octane-1,2,3,4,6-pentol)