NP-MRD: Showing NP-Card for 5,6-Dehydro-alpha-isolupanine (NP0055101)

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Record Information

Version

2.0

Created at

2022-04-28 01:14:37 UTC

Updated at

2022-04-28 01:14:38 UTC

NP-MRD ID

NP0055101

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6-Dehydro-alpha-isolupanine

Description

5,6-Dehydrolupanine 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. 5,6-Dehydro-alpha-isolupanine is found in Castilleja spp., Caulophyllum thalictroides and Ulex europaeus. 5,6-Dehydro-alpha-isolupanine was first documented in 2005 (PMID: 16042152). Based on a literature review a small amount of articles have been published on 5,6-Dehydrolupanine (PMID: 16876210) (PMID: 25912242) (PMID: 19040102) (PMID: 17146716).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
   -3.0721    2.8822   -0.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0251    1.6342   -0.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1755    0.8427   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2234   -0.5514   -0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0058   -1.0796    0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -0.4198    0.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7301   -1.1232    1.0760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0922    0.1236    1.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2901    0.8455    0.4212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7089    1.8426    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9187    0.9722    0.1079 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817    0.5837    0.3114 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2973    0.9266   -1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7071    0.3868   -1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0118   -0.6011   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8512   -1.5517    0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795   -0.9003    0.4010 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4137   -1.5328    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1919    0.8575   -2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978    1.4185   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0627   -0.6278    0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5252   -1.2298   -1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0060   -2.1345    0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087   -1.8639    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532   -0.1501    2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8278    0.6127    2.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0158    0.2854   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    2.4687    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6076    2.5074   -0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3599    0.9237    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    2.0162   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6576    0.4598   -1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -0.0035   -2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3855    1.2583   -0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8567   -1.2343   -0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407   -0.1068    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452   -2.1430    1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7903   -2.3096   -0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337   -1.6805   -0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358   -2.6048    0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11  2  1  0
 17 12  1  0
 11  6  1  0
 18  7  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 12 30  1  1
 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  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
M  END


  Mrv1652304282203142D          

 18 21  0  0  1  0            999 V2000
    6.3404    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -0.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    1.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    2.6178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1646    1.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.6260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3281    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197    1.2094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9197    2.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    0.7969    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055101

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCC=C2[C@@H]3C[C@@H](CN12)[C@@H]1CCCCN1C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h5,11-13H,1-4,6-10H2/t11-,12+,13+/m1/s1

> <INCHI_KEY>
GSQQGCZVTAUICD-AGIUHOORSA-N

> <FORMULA>
C15H22N2O

> <MOLECULAR_WEIGHT>
246.354

> <EXACT_MASS>
246.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.79262830351783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
0.7436707089999994

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.628128143686018

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
72.9419

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e+01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

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      11.835   3.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.835   2.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.502   1.488   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.502  -0.052   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.168   2.258   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.168   3.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.502   4.568   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.079   4.886   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.774   2.835   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.539   1.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.079   1.169   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.450   2.258   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.450   3.798   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.539   4.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.116   4.568   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.783   3.798   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.783   2.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.116   1.488   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    8                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
5,6-Dehydro-lupanine	MeSH

Chemical Formula

C₁₅H₂₂N₂O

Average Mass

246.3540 Da

Monoisotopic Mass

246.17321 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O=C1CCC=C2[C@@H]3C[C@@H](CN12)[C@@H]1CCCCN1C3

InChI Identifier

InChI=1S/C15H22N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h5,11-13H,1-4,6-10H2/t11-,12+,13+/m1/s1

InChI Key

GSQQGCZVTAUICD-AGIUHOORSA-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
Castilleja spp.	Plant	KNApSAcK
Caulophyllum thalictroides	Plant	KNApSAcK
Ulex europaeus	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
Quinolizidine
Tetrahydropyridine
Piperidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic nitrogen compound
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	2.82	ALOGPS
logP	0.74	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	9.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.94 m³·mol⁻¹	ChemAxon
Polarizability	28.79 Å³	ChemAxon
Number of Rings	4	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

C00002219

Chemspider ID

391253

KEGG Compound ID

C10764

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Maximo P, Lourenco A, Tei A, Wink M: Chemotaxonomy of Portuguese Ulex: quinolizidine alkaloids as taxonomical markers. Phytochemistry. 2006 Sep;67(17):1943-9. doi: 10.1016/j.phytochem.2006.05.037. Epub 2006 Jul 28. [PubMed:16876210 ]
Green BT, Lee ST, Welch KD, Gardner DR, Stegelmeier BL, Davis TZ: The serum concentrations of lupine alkaloids in orally-dosed Holstein cattle. Res Vet Sci. 2015 Jun;100:239-44. doi: 10.1016/j.rvsc.2015.04.001. Epub 2015 Apr 13. [PubMed:25912242 ]
Perez-Lainez D, Garcia-Mateos R, San Miguel-Chavez R, Soto-Hernandez M, Rodriguez-Perez E, Kite G: Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev. Z Naturforsch C J Biosci. 2008 Sep-Oct;63(9-10):653-7. doi: 10.1515/znc-2008-9-1007. [PubMed:19040102 ]
Lee ST, Ralphs MH, Panter KE, Cook D, Gardner DR: Alkaloid profiles, concentration, and pools in velvet lupine (Lupinus leucophyllus) over the growing season. J Chem Ecol. 2007 Jan;33(1):75-84. doi: 10.1007/s10886-006-9211-z. Epub 2006 Dec 5. [PubMed:17146716 ]
Martins A, Wink M, Tei A, Brum-Bousquet M, Tillequin F, Rauter AP: A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry. Phytochem Anal. 2005 Jul-Aug;16(4):264-6. doi: 10.1002/pca.832. [PubMed:16042152 ]

Showing NP-Card for 5,6-Dehydro-alpha-isolupanine (NP0055101)

MOL for NP0055101 (5,6-Dehydro-alpha-isolupanine)

3D MOL for NP0055101 (5,6-Dehydro-alpha-isolupanine)

3D SDF for NP0055101 (5,6-Dehydro-alpha-isolupanine)

3D-SDF for NP0055101 (5,6-Dehydro-alpha-isolupanine)

PDB for NP0055101 (5,6-Dehydro-alpha-isolupanine)

3D PDB for NP0055101 (5,6-Dehydro-alpha-isolupanine)

SMILES for NP0055101 (5,6-Dehydro-alpha-isolupanine)

INCHI for NP0055101 (5,6-Dehydro-alpha-isolupanine)

Structure for NP0055101 (5,6-Dehydro-alpha-isolupanine)

3D Structure for NP0055101 (5,6-Dehydro-alpha-isolupanine)