NP-MRD: Showing NP-Card for (-)-Lupinine (NP0051279)

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Record Information

Version

2.0

Created at

2022-04-27 22:39:45 UTC

Updated at

2022-04-27 22:39:45 UTC

NP-MRD ID

NP0051279

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Lupinine

Description

Lupinine 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. (-)-Lupinine is found in Anabasis aphylla, Anarthrophyllum desideratum, Baptisia australis, Calpurnia aurea, Calpurnia aurea subsp. aurea , Lamprolobium fruticosum, Lamprolobium grandiflorum, Lupinus flavoculatus, Lupinus hirsutus , Lupinus hispanicus, Lupinus luteus , Lupinus mexicanus, Lupinus palmeri, Lupinus pilosus, Maackia hupehensis, Plagiocarpus axillaris, Sophora secundiflora, Virgilia divaricata and Xiphotheca elliptica. Lupinine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    0.4051    2.9305    0.8876 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3349    2.2134    0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843    0.7595    0.4878 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2684   -0.0638   -0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185   -1.5317   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7225   -1.8388    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3228   -1.1310    0.0218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466   -1.4561    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6451   -0.6010   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1194    0.2732   -1.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039    0.9187   -1.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1949    0.3191    0.1994 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2003    2.4217    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3426    2.5731    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1689    2.4094   -0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332    0.7197    1.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024    0.1263    0.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483    0.2604   -1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8094   -2.1260    0.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8932   -1.9461   -1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7950   -1.4791    1.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -2.9095    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8705   -2.5411    0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849   -1.1830    1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    0.0108    0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -1.2982   -0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    1.1054   -1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364   -0.2847   -2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283    0.6713   -1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8397    2.0269   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8520    0.6508    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  7 12  1  0
  3 12  1  0
 12 31  1  1
 11 29  1  0
 11 30  1  0
 10 27  1  0
 10 28  1  0
  9 25  1  0
  9 26  1  0
  8 23  1  0
  8 24  1  0
  6 21  1  0
  6 22  1  0
  5 19  1  0
  5 20  1  0
  4 17  1  0
  4 18  1  0
  3 16  1  1
  2 14  1  0
  2 15  1  0
  1 13  1  0
M  END

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      11.990  -1.984   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.334  -4.276   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.314  -5.827   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.998  -6.572   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      10.706  -5.816   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.370  -6.573   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.026  -5.820   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.026  -4.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.382  -3.513   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.294  -1.219   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.990  -3.524   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.717  -4.296   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      10.717  -2.756   0.000  0.00  0.00           H+0
CONECT    1   10   11                                                       
CONECT    2   11    3                                                       
CONECT    3    2    4                                                       
CONECT    4    5    3                                                       
CONECT    5   12    6    4                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    9    7                                                       
CONECT    9   12    8                                                       
CONECT   10    1                                                            
CONECT   11    1   12    2                                                  
CONECT   12    5   11    9   13                                             
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
1S-cis-Octahydro-2H-quinolizine-1-methanol	ChEBI

Chemical Formula

C₁₀H₁₉NO

Average Mass

169.2680 Da

Monoisotopic Mass

169.14666 Da

IUPAC Name

[(1R,9aR)-octahydro-1H-quinolizin-1-yl]methanol

Traditional Name

(-)-lupinine

CAS Registry Number

Not Available

SMILES

[H][C@]12CCCCN1CCC[C@H]2CO

InChI Identifier

InChI=1S/C10H19NO/c12-8-9-4-3-7-11-6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10+/m0/s1

InChI Key

HDVAWXXJVMJBAR-VHSXEESVSA-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
Anabasis aphylla	Plant	KNApSAcK
Anarthrophyllum desideratum	LOTUS Database	35616633
Baptisia australis	LOTUS Database	35616633
Calpurnia aurea	LOTUS Database	35616633
Calpurnia aurea subsp. aurea	Plant	KNApSAcK
Lamprolobium fruticosum	Plant	KNApSAcK
Lamprolobium grandiflorum	LOTUS Database	35616633
Lupinus flavoculatus	LOTUS Database	35616633
Lupinus hirsutus	Plant	KNApSAcK
Lupinus hispanicus	LOTUS Database	35616633
Lupinus luteus	Plant	KNApSAcK
Lupinus mexicanus	LOTUS Database	35616633
Lupinus palmeri	Plant	KNApSAcK
Lupinus pilosus	LOTUS Database	35616633
Maackia hupehensis	LOTUS Database	35616633
Plagiocarpus axillaris	LOTUS Database	35616633
Sophora secundiflora	LOTUS Database	35616633
Virgilia divaricata	LOTUS Database	35616633
Xiphotheca elliptica	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
Quinolizidine
Quinolizine
Piperidine
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

quinolizidine alkaloid (CHEBI:28012 )
Quinolizidine alkaloids (C10773 )

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	1.54	ALOGPS
logP	0.92	ChemAxon
logS	-0.5	ALOGPS
pKa (Strongest Acidic)	15.42	ChemAxon
pKa (Strongest Basic)	9.88	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.24 m³·mol⁻¹	ChemAxon
Polarizability	20.2 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00002226

Chemspider ID

Not Available

KEGG Compound ID

C10773

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lupinine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28012

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Lupinine (NP0051279)

MOL for NP0051279 ((-)-Lupinine)

3D MOL for NP0051279 ((-)-Lupinine)

3D SDF for NP0051279 ((-)-Lupinine)

3D-SDF for NP0051279 ((-)-Lupinine)

PDB for NP0051279 ((-)-Lupinine)

3D PDB for NP0051279 ((-)-Lupinine)

SMILES for NP0051279 ((-)-Lupinine)

INCHI for NP0051279 ((-)-Lupinine)

Structure for NP0051279 ((-)-Lupinine)

3D Structure for NP0051279 ((-)-Lupinine)