NP-MRD: Showing NP-Card for hydroxylupanine (NP0281981)

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Record Information

Version

2.0

Created at

2022-09-09 08:38:03 UTC

Updated at

2022-09-09 08:38:03 UTC

NP-MRD ID

NP0281981

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hydroxylupanine

Description

Hydroxylupanine belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. hydroxylupanine is found in Cadia purpurea, Calpurnia aurea, Castilleja miniata, Cytisus scoparius, Genista obtusiramea, Leontice leontopetalum, Lupinus albus, Lupinus angustifolius, Lupinus gibertianus, Lupinus hintonii, Lupinus lanatus, Lupinus mexicanus, Lupinus mutabilis, Lupinus pilosus, Lupinus polyphyllus, Lupinus pubescens, Lupinus sericeus, Lupinus shockleyi, Pearsonia cajanifolia, Petteria ramentacea, Rothia indica and Thermopsis montana. hydroxylupanine was first documented in 2020 (PMID: 35087995). Based on a literature review a small amount of articles have been published on Hydroxylupanine (PMID: 35011535) (PMID: 32875217) (PMID: 35566183) (PMID: 33276190).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    2.4801    2.9163   -1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6994    1.8689   -0.9667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0886    1.3506   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2115   -0.0394   -0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8851   -0.7779   -0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9534    0.0338    0.4489 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7764   -0.7271    0.9416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2244    0.3026    1.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581    1.0366    0.2707 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3377    1.8380   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287    1.2382   -0.2714 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887    0.0968   -0.7409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8533    0.3748   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5813    0.0851    0.3602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9578    0.2492    0.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3141   -1.3077    0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2291   -2.0116    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -1.2518   -0.4137 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1467   -1.6346   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176    2.0604   -0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449    1.3562   -2.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5698   -0.0275    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9549   -0.6595   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450   -0.7985   -1.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250   -1.7791   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5631    0.3269    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659   -1.3537    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866   -0.1438    2.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3448    1.0332    2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618    1.7432    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077    2.0579   -1.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4064    2.8599    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028    0.2992   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0678    1.4088   -1.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2328   -0.3270   -1.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137    0.8337    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4674    0.4963    0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2419   -1.9478    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0754   -1.3095    1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835   -2.6105   -0.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8188   -2.8042    0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590   -1.6547   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1205   -2.7007    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 12 18  1  0
  6  7  1  0
  2 11  1  0
 15 37  1  0
 14 36  1  1
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
  7 27  1  1
  8 28  1  0
  8 29  1  0
  9 30  1  1
 10 31  1  0
 10 32  1  0
  6 26  1  1
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 20  1  0
  3 21  1  0
 12 33  1  6
 13 34  1  0
 13 35  1  0
M  END


  Mrv1652309092210382D          

 19 22  0  0  1  0            999 V2000
    6.1269   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8290    1.4084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6655    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -0.5834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8290   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7062   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2773   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  6 11  1  1  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  6  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281981

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CCN2C[C@@H]3C[C@@H](CN4[C@@H]3CCCC4=O)[C@@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2/t10-,11-,12-,13+,14-/m0/s1

> <INCHI_KEY>
JVYKIBAJVKEZSQ-YHQUGGNUSA-N

> <FORMULA>
C15H24N2O2

> <MOLECULAR_WEIGHT>
264.369

> <EXACT_MASS>
264.183778021

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.84124620919227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,9S,10S,12S)-12-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

> <JCHEM_LOGP>
-0.4563792270000015

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.16945581161129

> <JCHEM_PKA_STRONGEST_BASIC>
9.234808806424699

> <JCHEM_POLAR_SURFACE_AREA>
43.78000000000001

> <JCHEM_REFRACTIVITY>
73.03079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,9S,10S,12S)-12-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0      11.437  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.437  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.770   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.770   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.437   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.103   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.014   2.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.709   0.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.474  -1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.014  -1.089   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      10.103  -0.000   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.385  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.052  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.718   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.384  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.718   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.052   2.310   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       6.385   1.540   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       7.474   2.629   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2    6                                                  
CONECT   12    9   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18    7                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
13-Hydroxy-lupanine	MeSH
13-Hydroxylupanine	MeSH
13-Hydroxylupanine hydrochloride	MeSH
13alpha-Hydroxylupanine	MeSH

Chemical Formula

C₁₅H₂₄N₂O₂

Average Mass

264.3690 Da

Monoisotopic Mass

264.18378 Da

IUPAC Name

(1S,2R,9S,10S,12S)-12-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

Traditional Name

(1S,2R,9S,10S,12S)-12-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

CAS Registry Number

Not Available

SMILES

O[C@H]1CCN2C[C@@H]3C[C@@H](CN4[C@@H]3CCCC4=O)[C@@H]2C1

InChI Identifier

InChI=1S/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2/t10-,11-,12-,13+,14-/m0/s1

InChI Key

JVYKIBAJVKEZSQ-YHQUGGNUSA-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
Cadia purpurea	LOTUS Database	35616633
Calpurnia aurea	LOTUS Database	35616633
Castilleja miniata	LOTUS Database	35616633
Cytisus scoparius	LOTUS Database	35616633
Genista obtusiramea	LOTUS Database	35616633
Leontice leontopetalum	LOTUS Database	35616633
Lupinus albus	LOTUS Database	35616633
Lupinus angustifolius	LOTUS Database	35616633
Lupinus gibertianus	LOTUS Database	35616633
Lupinus hintonii	LOTUS Database	35616633
Lupinus lanatus	LOTUS Database	35616633
Lupinus mexicanus	LOTUS Database	35616633
Lupinus mutabilis	LOTUS Database	35616633
Lupinus pilosus	LOTUS Database	35616633
Lupinus polyphyllus	LOTUS Database	35616633
Lupinus pubescens	LOTUS Database	35616633
Lupinus sericeus	LOTUS Database	35616633
Lupinus shockleyi	LOTUS Database	35616633
Pearsonia cajanifolia	LOTUS Database	35616633
Petteria ramentacea	LOTUS Database	35616633
Rothia indica	LOTUS Database	35616633
Thermopsis montana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Sparteine, lupanine, and related alkaloids

Direct Parent

Sparteine, lupanine, and related alkaloids

Alternative Parents

Substituents

Sparteine-lupanine skeleton
Quinolizidinone
Quinolizidine
Delta-lactam
Piperidinone
Piperidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
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	-0.46	ChemAxon
pKa (Strongest Acidic)	15.17	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.03 m³·mol⁻¹	ChemAxon
Polarizability	28.84 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00002221

Chemspider ID

66121

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73404

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kushnareva AV, Shelengsmall a, Cyrillic TV, Perchuk IN, Egorova GP, Malyshev LL, Kerv YA, Shavarda AL, Vishnyakova MA: Selection of an optimal method for screening the collection of narrow-leaved lupine held by the Vavilov Institute for the qualitative and quantitative composition of seed alkaloids. Vavilovskii Zhurnal Genet Selektsii. 2020 Dec;24(8):829-835. doi: 10.18699/VJ20.680. [PubMed:35087995 ]
Cely-Veloza W, Quiroga D, Coy-Barrera E: Quinolizidine-Based Variations and Antifungal Activity of Eight Lupinus Species Grown under Greenhouse Conditions. Molecules. 2022 Jan 4;27(1). pii: molecules27010305. doi: 10.3390/molecules27010305. [PubMed:35011535 ]
Hwang IM, Lee HW, Lee HM, Yang JS, Seo HY, Chung YJ, Kim SH: Rapid and Simultaneous Quantification of Five Quinolizidine Alkaloids in Lupinus angustifolius L. and Its Processed Foods by UPLC-MS/MS. ACS Omega. 2020 Aug 10;5(33):20825-20830. doi: 10.1021/acsomega.0c01929. eCollection 2020 Aug 25. [PubMed:32875217 ]
Bernal FA, Coy-Barrera E: Composition and Antifungal Activity of the Alkaloidal Fraction of Lupinus mirabilis Leaves: A Biochemometrics-Based Exploration. Molecules. 2022 Apr 29;27(9):2832. doi: 10.3390/molecules27092832. [PubMed:35566183 ]
Wang X, Li F, Chen Z, Yang B, Komatsu S, Zhou S: Proteomic analysis reveals the effects of melatonin on soybean root tips under flooding stress. J Proteomics. 2021 Feb 10;232:104064. doi: 10.1016/j.jprot.2020.104064. Epub 2020 Dec 1. [PubMed:33276190 ]
LOTUS database [Link]

Showing NP-Card for hydroxylupanine (NP0281981)

MOL for NP0281981 (hydroxylupanine)

3D MOL for NP0281981 (hydroxylupanine)

3D SDF for NP0281981 (hydroxylupanine)

3D-SDF for NP0281981 (hydroxylupanine)

PDB for NP0281981 (hydroxylupanine)

3D PDB for NP0281981 (hydroxylupanine)

SMILES for NP0281981 (hydroxylupanine)

INCHI for NP0281981 (hydroxylupanine)

Structure for NP0281981 (hydroxylupanine)

3D Structure for NP0281981 (hydroxylupanine)