Sparteine

Details

• Internal ID: 9767ca9a-770a-4bdc-b381-3a4938587d05
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Sparteine, lupanine, and related alkaloids
• IUPAC Name: (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
• SMILES (Canonical): C1CCN2CC3CC(C2C1)CN4C3CCCC4
• SMILES (Isomeric): C1CCN2C[C@@H]3C[C@H]([C@H]2C1)CN4[C@H]3CCCC4
• InChI: InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m0/s1
• InChI Key: SLRCCWJSBJZJBV-ZQDZILKHSA-N
• Popularity: 2,740 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₆N₂
• Molecular Weight: 234.38 g/mol
• Exact Mass: 234.209598838 g/mol
• Topological Polar Surface Area (TPSA): 6.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• (-)-Sparteine
• 90-39-1
• L-SPARTEINE
• lupinidine
• (-)-Lupinidine
• Genisteine Alkaloid
• Esparteina
• Lupinidin
• Spartein
• Sparteina
• Sparteinum
• Sparteine [INN]
• 6beta,7alpha,9alpha,11alpha-Pachycarpine
• 6-beta,7-alpha,9-alpha,11-alpha-Pachycarpine
• DTXSID4023591
• CHEBI:28827
• UNII-298897D62S
• EINECS 201-988-8
• DTXCID403591
• 298897D62S
• Sparteina [DCIT]
• (7S,7aR,14S,14aS)-Tetradecahydro-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocine
• [7S-(7alpha,7aalpha,14alpha,14abeta)]-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine
• 7,14-Methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-, (7S-(7alpha,7aalpha,14alpha,14abeta))-
• Sparteine, (-)-Isomer
• Sparteinum [INN-Latin]
• Esparteina [INN-Spanish]
• 7,14-Methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-
• spartein-
• Sparteine (-)
• (7S,7aR,14S,14aS)-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine
• (7S,7aS,14S,14aR)-dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine
• 7,14-METHANO-2H,6H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCINE, DODECAHYDRO-, (7S,7AR,14S,14AS)
• 7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine, dodecahydro-, [7S-(7alpha,7aalpha,14alpha,14abeta)]-
• SMR000059203
• Sparteine, (7S-(7alpha,7aalpha,14alpha,14abeta))-Isomer
• (-)sparteine
• C15-H26-N2
• CAS-90-39-1
• (-) sparteine
• NCGC00016346-01
• sparteine-(-)
• (7S,7aS,14S,14aR)-dodecahydro-7,14-methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine
• (7S-(7alpha,7aalpha,14alpha,14abeta))-dodecahydro-7,14-methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine
• Prestwick_426
• (+)-Spartein
• SPARTEINE [MI]
• Prestwick3_000618
• Sparteine (6CI,8CI)
• SPARTEINE [WHO-DD]
• SCHEMBL79043
• BSPBio_000556
• MLS000028889
• MLS002207055
• BPBio1_000612
• CHEMBL1908847
• C01BA04
• SLRCCWJSBJZJBV-ZQDZILKHSA-N
• HMS2096L18
• AMY25811
• Tox21_110386
• s9142
• AKOS016012217
• Tox21_110386_1
• CCG-266824
• CS-W012901
• DB06727
• HY-W012185
• (-)-Sparteine, >=98.0% (GC)
• NCGC00142614-01
• NCGC00181124-02
• 7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine, dodecahydro-, (7S,7aR,14S,14aS)-
• S-6998
• Q419552
• (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9739	97.39%
Caco-2	+	0.7475	74.75%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.4697	46.97%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.9744	97.44%
OATP1B3 inhibitior	+	0.9543	95.43%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.7129	71.29%
P-glycoprotein inhibitior	-	0.9419	94.19%
P-glycoprotein substrate	-	0.8851	88.51%
CYP3A4 substrate	-	0.7097	70.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.7046	70.46%
CYP3A4 inhibition	-	0.9518	95.18%
CYP2C9 inhibition	-	0.9576	95.76%
CYP2C19 inhibition	-	0.9576	95.76%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9888	98.88%
CYP inhibitory promiscuity	-	0.6629	66.29%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7110	71.10%
Eye corrosion	+	0.8805	88.05%
Eye irritation	+	0.9564	95.64%
Skin irritation	+	0.6936	69.36%
Skin corrosion	+	0.5839	58.39%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5218	52.18%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.8876	88.76%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.7778	77.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5753	57.53%
Acute Oral Toxicity (c)	III	0.8012	80.12%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.5392	53.92%
Thyroid receptor binding	-	0.6974	69.74%
Glucocorticoid receptor binding	-	0.7651	76.51%
Aromatase binding	-	0.8125	81.25%
PPAR gamma	-	0.8785	87.85%
Honey bee toxicity	-	0.9274	92.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.8000	80.00%
Fish aquatic toxicity	-	0.7834	78.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	316.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.88%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.02%	97.09%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	88.35%	94.78%
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	87.98%	97.98%
CHEMBL1978	P11511	Cytochrome P450 19A1	87.38%	91.76%
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	86.53%	95.61%
CHEMBL238	Q01959	Dopamine transporter	85.86%	95.88%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.48%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.92%	93.04%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	83.38%	98.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.87%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.58%	96.09%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	81.53%	91.43%
CHEMBL237	P41145	Kappa opioid receptor	81.53%	98.10%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.62%	86.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.42%	89.62%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.22%	99.18%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	80.21%	90.71%

Plants that contains it

• Adenocarpus hispanicus
• Ammodendron karelinii
• Ammopiptanthus mongolicus
• Anabasis aphylla
• Anagyris foetida
• Anarthrophyllum desideratum
• Aspalathus spinosa
• Baptisia alba
• Baptisia australis
• Bolusanthus speciosus
• Cadia purpurea
• Calobota saharae
• Caulophyllum robustum
• Chelidonium majus
• Cytisophyllum sessilifolium
• Cytisus scoparius
• Dermatophyllum secundiflorum
• Dicraeopetalum stipulare
• Genista acanthoclada
• Genista burdurensis
• Genista lobelii
• Genista lydia
• Genista majorica
• Hesperolaburnum platycarpum
• Lamprolobium fruticosum
• Leontice leontopetalum
• Liparia splendens
• Lupinus albus
• Lupinus angustifolius
• Lupinus arboreus
• Lupinus argenteus
• Lupinus hintonii
• Lupinus luteus
• Lupinus mutabilis
• Lupinus nanus
• Lupinus odoratus
• Lupinus pilosus
• Lupinus polyphyllus
• Lupinus pubescens
• Lupinus pusillus
• Lupinus sericeus
• Lupinus texensis
• Magnolia coco
• Ocimum basilicum
• Ormosia coarctata
• Ormosia macrocalyx
• Oxytropis ochrocephala
• Pearsonia aristata
• Pearsonia obovata
• Pinus hartwegii
• Plagiocarpus axillaris
• Podalyria sericea
• Polhillia brevicalyx
• Polhillia involucrata
• Prunus mahaleb
• Retama raetam
• Rothia hirsuta
• Sophora mollis
• Spartium junceum
• Thermopsis chinensis
• Thermopsis lanceolata

Cross-Links

• PubChem: 644020
• NPASS: NPC228980
• ChEMBL: CHEMBL1908847
• LOTUS: LTS0042917
• wikiData: Q419552