NP-MRD: Showing NP-Card for (+)-Epilupinine-N-oxide (NP0055084)

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Record Information

Version

2.0

Created at

2022-04-28 01:13:51 UTC

Updated at

2022-04-28 01:13:51 UTC

NP-MRD ID

NP0055084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Epilupinine-N-oxide

Description

(1S,9aR)-Octahydro-4H-quinolizine-1-methanol 5-oxide 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. (+)-Epilupinine-N-oxide is found in Lupinus angustifolius, Lupinus hirsutus , Lupinus pilosus and Lupinus varius . Based on a literature review very few articles have been published on (1S,9aR)-Octahydro-4H-quinolizine-1-methanol 5-oxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -1.5595    1.4866   -1.3740 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.8166    1.0685   -0.3118 N   0  0  1  0  0  4  0  0  0  0  0  0
   -1.6010    0.8969    0.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333   -0.2534    0.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0451   -1.4945    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0283   -1.3242   -0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367   -0.1368   -0.7246 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0359   -0.3290    0.1981 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5913   -1.7171    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -1.7302    1.0526 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.6018   -0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668    1.8789   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478    2.1055   -0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085    0.8689    1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1760    1.8596    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    0.0989    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7891   -0.4492    1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483   -2.1714    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9442   -2.0432   -0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774   -2.2214   -0.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5664   -1.2994   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730    0.0761   -1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8465   -0.0333    1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8762   -2.4457    0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -2.0680   -0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5335   -2.0132    0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438    0.1229   -1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235    0.7442    0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346    1.9482   -1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329    2.7183   -0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    3.0870   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    2.1676    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13  2  1  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  2  1  0
 10 26  1  0
  9 24  1  0
  9 25  1  0
  8 23  1  1
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  6
M  CHG  2   1  -1   2   1
M  END


  Mrv1652304282203132D          

 13 14  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  1  7  1  0  0  0  0
  6  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
  4 11  1  0  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1CCCN2(=O)CCCC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C10H19NO2/c12-8-9-4-3-7-11(13)6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10-,11?/m1/s1

> <INCHI_KEY>
DPDAZDMDSXQXJW-DIOIDXFWSA-N

> <FORMULA>
C10H19NO2

> <MOLECULAR_WEIGHT>
185.267

> <EXACT_MASS>
185.141578856

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
20.98006662609571

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9aR)-1-(hydroxymethyl)-octahydro-1H-5lambda5-quinolizin-5-one

> <ALOGPS_LOGP>
-0.73

> <JCHEM_LOGP>
-0.20385544766666613

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.405101383665244

> <JCHEM_PKA_STRONGEST_BASIC>
2.5319624610336895

> <JCHEM_POLAR_SURFACE_AREA>
47.11

> <JCHEM_REFRACTIVITY>
52.288700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9aR)-1-(hydroxymethyl)-octahydro-1H-5lambda5-quinolizin-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   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  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6   11                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    4                                                       
CONECT   12    8   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₉NO₂

Average Mass

185.2670 Da

Monoisotopic Mass

185.14158 Da

IUPAC Name

(1S,9aR)-1-(hydroxymethyl)-octahydro-1H-5lambda5-quinolizin-5-one

Traditional Name

(1S,9aR)-1-(hydroxymethyl)-octahydro-1H-5lambda5-quinolizin-5-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1CCCN2(=O)CCCC[C@H]12

InChI Identifier

InChI=1S/C10H19NO2/c12-8-9-4-3-7-11(13)6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10-,11?/m1/s1

InChI Key

DPDAZDMDSXQXJW-DIOIDXFWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 angustifolius	LOTUS Database	35616633
Lupinus hirsutus	Plant	KNApSAcK
Lupinus pilosus	LOTUS Database	35616633
Lupinus varius	Plant	KNApSAcK

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
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Primary alcohol
Organooxygen compound
Organonitrogen compound
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	-0.73	ALOGPS
logP	-0.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	2.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.11 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	52.29 m³·mol⁻¹	ChemAxon
Polarizability	20.98 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

15144020

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Epilupinine-N-oxide (NP0055084)

MOL for NP0055084 ((+)-Epilupinine-N-oxide)

3D MOL for NP0055084 ((+)-Epilupinine-N-oxide)

3D SDF for NP0055084 ((+)-Epilupinine-N-oxide)

3D-SDF for NP0055084 ((+)-Epilupinine-N-oxide)

PDB for NP0055084 ((+)-Epilupinine-N-oxide)

3D PDB for NP0055084 ((+)-Epilupinine-N-oxide)

SMILES for NP0055084 ((+)-Epilupinine-N-oxide)

INCHI for NP0055084 ((+)-Epilupinine-N-oxide)

Structure for NP0055084 ((+)-Epilupinine-N-oxide)

3D Structure for NP0055084 ((+)-Epilupinine-N-oxide)