NP-MRD: Showing NP-Card for (-)-Cytisine (NP0051271)

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Record Information

Version

2.0

Created at

2022-04-27 22:39:12 UTC

Updated at

2026-02-17 20:01:15 UTC

NP-MRD ID

NP0051271

Natural Product DOI

https://doi.org/10.57994/7446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cytisine

Description

CYTISINE, also known as tabex or tsitizin, belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one. (-)-Cytisine is found in Anagyris spp., Baptisia australis, Baptisia spp., Baptisia tinctoria R.Br. , Bolusanthus speciosus, Bolusanthus specious, Chamaecytisus eriocarpus, Cladrastis amurensis, Clathrotropis glaucophylla, Corydalis yanhusuo , Cuscuta platyloba, Cytisus canariensis, Cytisus monspessulanus L., Cytisus spp., Euchresta formosana, Euchresta horsfieldii , Genista germanica, Genista libanotica, Genista spp., Genista tinctoria , Laburnum alpinum x wateri, Cytisus laburnum L., Maackia tashiroi, Petteria ramentacea, Piptanthus concolor, Piptanthus nepalensis, Sophora alopecuroides L., Sophora chrysophylla, Sophora davidii, Sophora griffithii Stocks., Sophora japonica L. , Sophora macrophylla, Sophora pachycarpa, Sophora pachycarpa Schrenk., Sophora secundiflora , Sophora speciosa, Sophora spp., Sophora tomentosa , Sophora tonkinensis, Sophora viciifolia, Spartium junceum , Spondias mangifera, Styphnolobium japonicum, Templetonia retusa, Thermopsis alterniflora Rgl.et Schmalh., Thermopsis lanceolata R.Br., Thermopsis rhombifolia, Thermopsis spp., Ulex airensis, Ulex australis, Ulex densus, Ulex europaeus , Ulex minor, Ulex parviflorus, Ulex jussiaei, Vexibia pachycarpa and Viscum cruciatum . (-)-Cytisine was first documented in 2021 (PMID: 34933632). Based on a literature review a small amount of articles have been published on CYTISINE (PMID: 35396127) (PMID: 35049904) (PMID: 34984943) (PMID: 34982029).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200392D          

 14 16  0  0  1  0            999 V2000
    4.1130    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722    0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4891   -0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483   -1.0845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7469    0.0986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6877    0.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3708    1.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0641    1.4615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9797    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3840   -0.5842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2069   -0.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -0.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    0.7787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2412    1.4024    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  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  6  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  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C=CC=C2[C@@H]3CNC[C@@H](C3)CN12

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m1/s1

> <INCHI_KEY>
ANJTVLIZGCUXLD-BDAKNGLRSA-N

> <FORMULA>
C11H14N2O

> <MOLECULAR_WEIGHT>
190.246

> <EXACT_MASS>
190.110613079

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.33726999714097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9R)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
-0.27985360699999995

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.823392598653696

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
56.9283

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9R)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-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       7.678   1.911   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.788   0.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.513  -0.488   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.623  -2.024   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.128   0.184   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.017   1.720   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.292   2.584   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.853   2.728   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.696   0.660   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.583  -1.091   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.120  -0.980   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.419  -0.083   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.309   1.454   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.317   2.618   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                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-11-norcytisine	MeSH
Tabex	MeSH
Tsitizin	MeSH
Citizine	MeSH
Cystisin	MeSH
Cytisine dihydrochloride, trihydrate	MeSH
Cytisine hydrochloride	MeSH
Cytisine hydrochloride, hydrate	MeSH
Cytisine tetrahydrochloride, trihydrate	MeSH
Cytiton	MeSH

Chemical Formula

C₁₁H₁₄N₂O

Average Mass

190.2460 Da

Monoisotopic Mass

190.11061 Da

IUPAC Name

(1S,9R)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

Traditional Name

(1S,9R)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

CAS Registry Number

Not Available

SMILES

O=C1C=CC=C2[C@@H]3CNC[C@@H](C3)CN12

InChI Identifier

InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m1/s1

InChI Key

ANJTVLIZGCUXLD-BDAKNGLRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.31, Dimethylsulfoxide-d6, simulated)	[email protected]	Not Available	Not Available	2026-02-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.052, Dimethylsulfoxide-d6, simulated)	[email protected]	Not Available	Not Available	2026-02-17	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anagyris spp.	Plant	KNApSAcK
Baptisia australis	Plant	KNApSAcK
Baptisia spp.	Plant	KNApSAcK
Baptisia tinctoria R.Br.	Plant	KNApSAcK
Bolusanthus speciosus	LOTUS Database	35616633
Bolusanthus specious	Plant	KNApSAcK
Chamaecytisus eriocarpus	Plant	KNApSAcK
Cladrastis amurensis	Plant	KNApSAcK
Clathrotropis glaucophylla	Plant	KNApSAcK
Corydalis yanhusuo	Plant	KNApSAcK
Cuscuta platyloba	Plant	KNApSAcK
Cytisus canariensis	Plant	KNApSAcK
Cytisus monspessulanus L.	Plant	KNApSAcK
Cytisus spp.	Plant	KNApSAcK
Euchresta formosana	Plant	KNApSAcK
Euchresta horsfieldii	Plant	KNApSAcK
Genista germanica	Plant	KNApSAcK
Genista libanotica	Plant	KNApSAcK
Genista spp.	Plant	KNApSAcK
Genista tinctoria	Plant	KNApSAcK
Laburnum alpinum x wateri	Plant	KNApSAcK
Laburnum anagyroides		Not Available
Laburnum anagyroides	Plant	KNApSAcK
Maackia tashiroi	Plant	KNApSAcK
Petteria ramentacea	Plant	KNApSAcK
Piptanthus concolor	Plant	KNApSAcK
Piptanthus nepalensis	Plant	KNApSAcK
Sophora alopecuroides	Plant	KNApSAcK
Sophora chrysophylla	Plant	KNApSAcK
Sophora davidii	LOTUS Database	35616633
Sophora griffithii Stocks.	Plant	KNApSAcK
Sophora japonica L.	Plant	KNApSAcK
Sophora macrophylla	Plant	KNApSAcK
Sophora pachycarpa	LOTUS Database	35616633
Sophora pachycarpa Schrenk.	Plant	KNApSAcK
Sophora secundiflora	Plant	KNApSAcK
Sophora speciosa	Plant	KNApSAcK
Sophora spp.	Plant	KNApSAcK
Sophora tomentosa	Plant	KNApSAcK
Sophora tonkinensis	Plant	KNApSAcK
Sophora viciifolia	Plant	KNApSAcK
Spartium junceum	Plant	KNApSAcK
Spondias mangifera	Plant	KNApSAcK
Styphnolobium japonicum	LOTUS Database	35616633
Templetonia retusa	Plant	KNApSAcK
Thermopsis alterniflora Rgl.et Schmalh.	Plant	KNApSAcK
Thermopsis lanceolata	Plant	KNApSAcK
Thermopsis rhombifolia	Plant	KNApSAcK
Thermopsis spp.	Plant	KNApSAcK
Ulex airensis	Plant	KNApSAcK
Ulex australis	Plant	KNApSAcK
Ulex densus	Plant	KNApSAcK
Ulex europaeus	Plant	KNApSAcK
Ulex minor	Plant	KNApSAcK
Ulex parviflorus	LOTUS Database	35616633
Ulex parviflorus subsp. jussiaei	Plant	KNApSAcK
Vexibia pachycarpa	Plant	KNApSAcK
Viscum cruciatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Cytisine and derivatives

Direct Parent

Cytisine and derivatives

Alternative Parents

Substituents

Cytisine
Aralkylamine
Pyridinone
Piperidine
Pyridine
Heteroaromatic compound
Lactam
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Amine
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.06	ALOGPS
logP	-0.28	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	9.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.93 m³·mol⁻¹	ChemAxon
Polarizability	20.34 Å³	ChemAxon
Number of Rings	3	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

C00002216

Chemspider ID

595434

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

683511

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Meng C, Wang Y, Chen S, Li M, Yuan C, Yin X: Discovery, Topo I inhibitory activity and mechanism evaluation of two novel cytisine-type alkaloid dimers from the seeds of Sophora alopecuroides L. Bioorg Med Chem. 2022 May 1;61:116723. doi: 10.1016/j.bmc.2022.116723. Epub 2022 Mar 26. [PubMed:35396127 ]
Kem WR, Andrud K, Bruno G, Xing H, Soti F, Talley TT, Taylor P: Interactions of Nereistoxin and Its Analogs with Vertebrate Nicotinic Acetylcholine Receptors and Molluscan ACh Binding Proteins. Mar Drugs. 2022 Jan 4;20(1). pii: md20010049. doi: 10.3390/md20010049. [PubMed:35049904 ]
Zhang P, Zou JB, An Q, Yi P, Yuan CM, Huang LJ, Gu W, Hu ZX, Hao XJ: Two new cytisine-type alkaloids from the seeds of Thermopsis lanceolata. J Asian Nat Prod Res. 2022 Jan 5:1-9. doi: 10.1080/10286020.2021.2020759. [PubMed:34984943 ]
Nichols AL, Blumenfeld Z, Fan C, Luebbert L, Blom AEM, Cohen BN, Marvin JS, Borden PM, Kim CH, Muthusamy AK, Shivange AV, Knox HJ, Campello HR, Wang JH, Dougherty DA, Looger LL, Gallagher T, Rees DC, Lester HA: Fluorescence activation mechanism and imaging of drug permeation with new sensors for smoking-cessation ligands. Elife. 2022 Jan 4;11. pii: 74648. doi: 10.7554/eLife.74648. [PubMed:34982029 ]
Zhang L, Zheng L, Wang Q, Pana Z, Zhang X, Huang M, Xu H, Ni L: Cytisine-like alkaloids from the seeds of Ormosia hosiei Hemsl. et Wils. Nat Prod Res. 2021 Dec 22:1-7. doi: 10.1080/14786419.2021.2005591. [PubMed:34933632 ]
DOI: 10.1016/j.molstruc.2010.10.036

Showing NP-Card for (-)-Cytisine (NP0051271)

MOL for NP0051271 ((-)-Cytisine)

3D MOL for NP0051271 ((-)-Cytisine)

3D SDF for NP0051271 ((-)-Cytisine)

3D-SDF for NP0051271 ((-)-Cytisine)

PDB for NP0051271 ((-)-Cytisine)

3D PDB for NP0051271 ((-)-Cytisine)

SMILES for NP0051271 ((-)-Cytisine)

INCHI for NP0051271 ((-)-Cytisine)

Structure for NP0051271 ((-)-Cytisine)

3D Structure for NP0051271 ((-)-Cytisine)