alpha-ISOSPARTEINE

Details

• Internal ID: 7de908aa-20bd-4790-af63-8f1641c665ad
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Sparteine, lupanine, and related alkaloids
• IUPAC Name: (1S,2R,9S,10R)-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-BYNSBNAKSA-N
• Popularity: 923 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

• alpha-Isosparteine
• Genisteine-alkaloid
• alpha-Sparteine
• alpha-Isospartein
• Isosparteine, alpha-
• 11-Isosparteine
• (-)-alpha-Isosparteine
• 6beta-sparteine
• 446-95-7
• UNII-94BIS8AH96
• l-alpha-isosparteine
• 94BIS8AH96
• EINECS 207-177-5
• NSC 366737
• CHEBI:81074
• (-)-Sparteine
• .alpha.-Isospartein
• .beta.-Isosparteine
• .alpha.-Isosparteine
• NSC-366737
• 7,14-METHANO-2H,6H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCINE, DODECAHYDRO-, (7S,7AR,14S,14AR)-
• 7,14-Methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-, (7S-(7alpha,7aalpha,14alpha,14aalpha))-
• C15-H26-N2
• (1S,2R,9S,10R)-7,15-diazatetracyclo(7.7.1.0(2,7).0(10,15))heptadecane
• (1S,2R,9S,10R)-7,15-diazatetracyclo[7.7.1.0(2,7).0(10,15)]heptadecane
• (7S,7aR,14S,14aR)-dodecahydro-2H,6H-7,14-methanodipyrido(1,2-a:1',2'-e)(1,5)diazocine
• (7S,7aR,14S,14aR)-dodecahydro-2H,6H-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocine
• C12CN3CCCCC3C(C2)CN4C1CCCC4
• CAS-90-39-1
• NCGC00016346-01
• (7S-(7alpha,7aalpha,14alpha,14aalpha))-Dodecahydro-7,14-methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine
• [7S-(7alpha,7aalpha,14alpha,14aalpha)]-dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine
• SCHEMBL5002193
• alpha-ISOSPARTEINE, (-)-
• CHEMBL1328708
• DTXSID601126235
• 7,14-METHANO-2H,6H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCINE, DODECAHYDRO-, (7S-(7.ALPHA.,7A.ALPHA.,14.ALPHA.,14A.ALPHA.))-
• 7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine, dodecahydro-, [7S-(7.alpha.,7a.beta.,14.alpha.,14a.beta.)]-
• SPARTEINE L-alpha-ISOSPARTEINE
• TNP00166
• AKOS015840978
• NCGC00017262-01
• SPARTEINE L-.ALPHA.-ISOSPARTEINE [MI]
• C17418
• Q27271670
• (1S,2R,9S,10R)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
• (7S,7aR,14S,14aR)-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine
• (7S-(7.ALPHA.,7A.ALPHA.,14.ALPHA.,14A.ALPHA.))-DODECAHYDRO-7,14-METHANO-2H,6H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCINE

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
CHEMBL289	P10635	Cytochrome P450 2D6	15848.9 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	316.2 nM; 316.2 nM	Potency; Potency	via CMAUP; 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

• Bolusanthus speciosus
• Brickellia cylindracea
• Calocephalus citreus
• Crotalaria medicaginea
• Cytisophyllum sessilifolium
• Cytisus scoparius
• Fritillaria stenanthera
• Genista majorica
• Genista pichisermolliana
• Hesperolaburnum platycarpum
• Kopsia teoi
• Lupinus excubitus
• Lupinus odoratus
• Monoon barnesii
• Ormosia cinerea
• Pearsonia grandifolia
• Pinalia floribunda
• Pinalia leucantha
• Plagiocarpus axillaris
• Rothia indica
• Rubus lambertianus
• Sidastrum burrerense
• Spartium junceum
• Stevia ovata
• Striga asiatica
• Ulex australis
• Virgilia divaricata
• Yucca gloriosa var. tristis

Cross-Links

• PubChem: 92759
• NPASS: NPC151004
• ChEMBL: CHEMBL1328708
• LOTUS: LTS0009315
• wikiData: Q27271670