NP-MRD: Showing NP-Card for (1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate (NP0296352)

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Record Information

Version

2.0

Created at

2022-09-10 05:52:42 UTC

Updated at

2022-09-10 05:52:42 UTC

NP-MRD ID

NP0296352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate

Description

[(1S,5R,9aR)-5-oxo-octahydro-1H-5λ⁵-quinolizin-1-yl]methyl acetate belongs to the class of organic compounds known as lupinine-type alkaloids. These are lupin alkaloids with a structure based on the lupinine skeleton, which is a bicyclic compound consisting of a quinolizidine. (1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate is found in Lupinus cosentinii and Lupinus pilosus. Based on a literature review very few articles have been published on [(1S,5R,9aR)-5-oxo-octahydro-1H-5λ⁵-quinolizin-1-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    3.7561    2.0914   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0499    0.8038   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8555    0.3237   -1.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5549    0.0389    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910   -1.1691    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -1.1102   -0.1748 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0961   -2.5538   -0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -2.6384   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7021   -1.3100   -1.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853   -0.3251   -0.1779 N   0  0  2  0  0  4  0  0  0  0  0  0
   -2.7331   -0.6311    0.6223 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.9985    0.9479   -0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    2.0396    0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020    1.7869    1.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0455    1.0910    0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -0.3103    0.5325 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6768    2.6890   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    2.6330    0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394    1.8319    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5540   -1.9939    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801   -1.5067    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -0.7166   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0934   -2.8640    0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438   -3.1750   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545   -3.3850   -1.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0333   -2.9523    0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7797   -1.3717   -1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -0.9704   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2091    1.1978   -1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354    0.7889   -1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9840    3.0091   -0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    2.0453    0.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    1.0134    2.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0608    2.6990    1.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2964    1.6724   -0.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6939    1.1158    1.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -0.8351    1.5202 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  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16  6  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  1
M  CHG  2  10   1  11  -1
M  END


  Mrv1652309102207522D          

 16 17  0  0  1  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  3  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  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  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
  6 16  1  0  0  0  0
 10 16  1  0  0  0  0
M  CHG  2  10   1  11  -1
M  END
> <DATABASE_ID>
NP0296352

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1CCC[N@+]2([O-])CCCC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO3/c1-10(14)16-9-11-5-4-8-13(15)7-3-2-6-12(11)13/h11-12H,2-9H2,1H3/t11-,12-,13-/m1/s1

> <INCHI_KEY>
JPUKLZZPUHNSLJ-JHJVBQTASA-N

> <FORMULA>
C12H21NO3

> <MOLECULAR_WEIGHT>
227.304

> <EXACT_MASS>
227.15214354

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
24.97158588675386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,9aR)-1-[(acetyloxy)methyl]-decahydroquinolizin-5-ium-5-olate

> <JCHEM_LOGP>
0.237269962666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.8676920640786188

> <JCHEM_POLAR_SURFACE_AREA>
49.36

> <JCHEM_REFRACTIVITY>
61.440200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,9aR)-1-[(acetyloxy)methyl]-octahydro-1H-quinolizin-5-ium-5-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+1
HETATM   11  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
[(1S,5R,9AR)-5-oxo-octahydro-1H-5-quinolizin-1-yl]methyl acetic acid	Generator

Chemical Formula

C₁₂H₂₁NO₃

Average Mass

227.3040 Da

Monoisotopic Mass

227.15214 Da

IUPAC Name

(1S,5R,9aR)-1-[(acetyloxy)methyl]-decahydroquinolizin-5-ium-5-olate

Traditional Name

(1S,5R,9aR)-1-[(acetyloxy)methyl]-octahydro-1H-quinolizin-5-ium-5-olate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1CCC[N@+]2([O-])CCCC[C@H]12

InChI Identifier

InChI=1S/C12H21NO3/c1-10(14)16-9-11-5-4-8-13(15)7-3-2-6-12(11)13/h11-12H,2-9H2,1H3/t11-,12-,13-/m1/s1

InChI Key

JPUKLZZPUHNSLJ-JHJVBQTASA-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
Lupinus cosentinii	LOTUS Database	35616633
Lupinus pilosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lupinine-type alkaloids. These are lupin alkaloids with a structure based on the lupinine skeleton, which is a bicyclic compound consisting of a quinolizidine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Lupinine-type alkaloids

Direct Parent

Lupinine-type alkaloids

Alternative Parents

Substituents

Lupinine
Quinolizine
Quinolizidine
Piperidine
Trialkyl amine oxide
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Monocarboxylic acid or derivatives
Carboxylic acid derivative
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	0.24	ChemAxon
pKa (Strongest Basic)	3.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.44 m³·mol⁻¹	ChemAxon
Polarizability	24.97 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

163195235

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate (NP0296352)

MOL for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)

3D MOL for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)

3D SDF for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)

3D-SDF for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)

PDB for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)

3D PDB for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)

SMILES for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)

INCHI for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)

Structure for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)

3D Structure for NP0296352 ((1s,5r,9ar)-1-[(acetyloxy)methyl]-octahydro-1h-quinolizin-5-ium-5-olate)