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Sparteine
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Quinolizidine Alkaloid
| Canonical Smiles | C1CC[C@@H]2N(C1)C[C@@H]1C[C@H]2CN2[C@@H]1CCCC2 |
|---|---|
| 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 |
| InChIKey | SLRCCWJSBJZJBV-ZQDZILKHSA-N |
| Formula | C15H26N2 |
| HBA | 2 |
| HBD | 0 |
| MW | 234.39 |
| Rotatable Bonds | 0 |
| TPSA | 6.48 |
| LogP | 2.35 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 1.0 |
| Exact Mass | 234.21 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Dicraeopetalum stipulare | Leguminosae/Fabaceae | Plantae | 149649 |
| 2 | Lupinus atlanticus | Leguminosae/Fabaceae | Plantae | 53218 |
| 3 | Lupinus digitatus | Leguminosae/Fabaceae | Plantae | 53225 |
| 4 | Lupinus palaestinus | Leguminosae/Fabaceae | Plantae | 61117 |
| 5 | Lupinus tassilicus | Leguminosae/Fabaceae | Plantae | 925616 |
Showing of synonyms
Sparteine
90-39-1
L-SPARTEINE
Lupinidine
Esparteina
Genisteine Alkaloid
Sparteina
Sparteinum
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
[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))-
7,14-Methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-
(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)]-
Sparteine, (-)-Isomer
(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
C01BA04
Sparteine, (7S-(7alpha,7aalpha,14alpha,14abeta))-Isomer
201-988-8
(-)-Sparteine
(-)-Lupinidine
Lupinidin
Spartein
Sparteine [INN]
(7S,7aR,14S,14aS)-Tetradecahydro-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocine
Sparteine (-)
(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
SMR000059203
Sparteina [DCIT]
Sparteinum [INN-Latin]
Esparteina [INN-Spanish]
(-)sparteine
CAS-90-39-1
(-) sparteine
NCGC00016346-01
Sparteine-(-)
Prestwick_426
SPARTEINE [MI]
Prestwick3_000618
Sparteine (6CI,8CI)
SPARTEINE [WHO-DD]
(-)-Sparteine (Standard)
SCHEMBL79043
BSPBio_000556
7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine, dodecahydro-, (7S,7aR,14S,14aS)-
MLS000028889
MLS002207055
BPBio1_000612
CHEMBL1908847
HMS2096L18
HY-W012185R
Tox21_110386
MSK168091
S9142
AKOS016012217
Tox21_110386_1
CCG-266824
CS-W012901
DB06727
HY-W012185
(-)-Sparteine, >=98.0% (GC)
NCGC00142614-01
NCGC00181124-02
1ST168091
NS00008083
A11625
Q419552
(7S,7aR,14S,14aS)-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine
- Asres K, Tei A, et al. (1997). Quinolizidine alkaloids from the east-african legume Dicraeopetalum stipulare harms.. Biochemical Systematics and Ecology,1997,25(4),305-308. [View] [PubMed]
- Ainouche A, Greinwald R, et al. (1996). Seed Alkaloid Composition of Lupinus tassilicus Maire (Fabaceae: Genisteae) and Comparison with its Related Rough Seeded Lupin Species. Biochemical Systematics and Ecology, 1996, 24(5), 405-414. [View]
Pubchem:
644020
Cas:
90-39-1
Gnps:
CCMSLIB00005768026
Zinc:
ZINC000001408502
Chebi:
28827
Nmrshiftdb2:
60025425
Metabolights:
MTBLC28827
Chembl:
CHEMBL1908847
Drugbank:
DB06727
CPRiL:
10604
SMILES: C1CCCN(C1C23)CC(C2)C4N(C3)CCCC4
Level: 0
Mol. Weight: 234.39 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.1
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.79
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.7
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.31
- Plasma Protein Binding
- 33.11
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 15.36
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -1.15
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.92
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.81
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 3.7
- Rat (Acute)
- 3.04
- Rat (Chronic Oral)
- 1.51
- Fathead Minnow
- 3.47
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 320.61
- Hydration Free Energy
- -3.68
- Log(D) at pH=7.4
- 0.29
- Log(P)
- 2.2
- Log S
- -1.6
- Log(Vapor Pressure)
- -4.06
- Melting Point
- 43.65
- pKa Acid
- 10.6
- pKa Basic
- 11.27
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.8390 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.8390 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7638 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7638 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7365 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7365 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7214 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7214 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7054 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7054 |