NP-MRD: Showing NP-Card for (1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate (NP0236278)

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Record Information

Version

2.0

Created at

2022-09-06 19:08:04 UTC

Updated at

2022-09-06 19:08:04 UTC

NP-MRD ID

NP0236278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate

Description

Bao gong teng A 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,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate is found in Erycibe obtusifolia. (1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate was first documented in 2006 (PMID: 16402833). Based on a literature review very few articles have been published on Bao gong teng A (PMID: 21107467).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    4.3371    0.7463   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931    0.2581   -0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1051   -0.1914   -2.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943    0.2796   -0.2451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678   -0.1504   -0.7236 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1779   -1.2304    0.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242   -0.4503    1.2538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5229    0.9577    0.8669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4608    0.8293   -0.5777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7132    0.1637   -1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7128   -0.1366   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1157   -0.7853    1.1802 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6914   -0.1503    2.3023 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631    0.0813   -0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356    0.6569    0.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740    1.7886   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.5431   -1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4009   -2.0044   -0.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0374   -1.7311    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -0.6210    2.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3491    1.4956    1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    1.7654   -1.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4831   -0.7868   -1.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294    0.8084   -1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5042   -0.7706   -0.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274    0.8366    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064   -1.8604    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0517    0.7445    2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  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
  9  5  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  6
  6 18  1  0
  6 19  1  0
  7 20  1  1
  8 21  1  0
  9 22  1  6
 10 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  1
 13 28  1  0
M  END


  Mrv1652309062221082D          

 13 14  0  0  1  0            999 V2000
   -1.3889    2.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    1.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0360    2.1395    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  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
    0.8044    1.0085    0.0000 C   0  0  2  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
    1.9666    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1231   -1.3067    0.0000 O   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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  8  1  6  0  0  0
  5  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
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0236278

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H15NO3/c1-5(11)13-9-4-7-8(12)3-2-6(9)10-7/h6-10,12H,2-4H2,1H3/t6-,7-,8+,9+/m1/s1

> <INCHI_KEY>
FSXBMHMVOFJROW-HXFLIBJXSA-N

> <FORMULA>
C9H15NO3

> <MOLECULAR_WEIGHT>
185.223

> <EXACT_MASS>
185.105193347

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
19.012913674677723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,6S)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate

> <JCHEM_LOGP>
-0.5986565429999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.596265845891622

> <JCHEM_PKA_STRONGEST_BASIC>
9.569223605793352

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
45.547700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,6S)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.593   3.794   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.205   3.126   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.067   3.994   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.090   1.591   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.297   0.922   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.297  -0.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.501  -1.578   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.934   0.152   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.501   1.883   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.003   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.671   0.152   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.003  -1.235   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.963  -2.439   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
Bao gong teng a, 3,5-dinitrobenzoate salt	MeSH
Baogongteng a	MeSH
Erycibe alkaloid II	MeSH
Bao gong teng a benzoate, (exo,exo)-(-)-isomer	MeSH

Chemical Formula

C₉H₁₅NO₃

Average Mass

185.2230 Da

Monoisotopic Mass

185.10519 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H15NO3/c1-5(11)13-9-4-7-8(12)3-2-6(9)10-7/h6-10,12H,2-4H2,1H3/t6-,7-,8+,9+/m1/s1

InChI Key

FSXBMHMVOFJROW-HXFLIBJXSA-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
Erycibe obtusifolia	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
Pyrrolidine
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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

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

137623

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156282

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin GJ, Zheng X, Huang PQ: A new method for the construction of the hydroxylated tropane skeleton: enantioselective synthesis of (-)-Bao Gong Teng A. Chem Commun (Camb). 2011 Feb 7;47(5):1545-7. doi: 10.1039/c0cc04371k. Epub 2010 Nov 25. [PubMed:21107467 ]
Zhang Y, Liebeskind LS: Organometallic enantiomeric scaffolding: organometallic chirons. Total synthesis of (-)-Bao Gong Teng A by a molybdenum-mediated [5 + 2] cycloaddition. J Am Chem Soc. 2006 Jan 18;128(2):465-72. doi: 10.1021/ja055623x. [PubMed:16402833 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate (NP0236278)

MOL for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)

3D MOL for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)

3D SDF for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)

3D-SDF for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)

PDB for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)

3D PDB for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)

SMILES for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)

INCHI for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)

Structure for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)

3D Structure for NP0236278 ((1r,2s,5r,6s)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl acetate)