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Lupanine
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | O=C1CCC[C@H]2N1C[C@@H]1C[C@H]2CN2[C@H]1CCCC2 |
|---|---|
| InChI | InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13-,14+/m0/s1 |
| InChIKey | JYIJIIVLEOETIQ-XDQVBPFNSA-N |
| Formula | C15H24N2O |
| HBA | 2 |
| HBD | 0 |
| MW | 248.37 |
| Rotatable Bonds | 0 |
| TPSA | 23.55 |
| LogP | 1.87 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 248.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Dicraeopetalum stipulare | Leguminosae/Fabaceae | Plantae | 149649 |
Showing of synonyms
Lupanine
Lupanin
D-Lupanine
2-Oxosparteine
Lupanine d-form
(+)-2-Oxosparteine
Spartein-2-one
Lupanine, D-
UNII-183KU7535A
CHEBI:28193
183KU7535A
LUPANINE, (+)-
(7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol[1,2-a:1',2'-e][1,5]diazocin-11-one
7,14-METHANO-2H,11H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCIN-11-ONE, DODECAHYDRO-, (7S,7AR,14S,14AS)-
(7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol(1,2-a:1',2'-e)(1,5)diazocin-11-one
550-90-3
(+)-Lupanine
Lupanine, (+/-)-
(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one
9K48888N9P
4356-43-8
UNII-9K48888N9P
15-Oxosparteine
DL-LUPANINE
(+/-)-LUPANINE
(RAC)-2-OXOSPARTEINE
LUPANINE D-FORM [MI]
SCHEMBL564463
LUPANINE DL-FORM [MI]
CHEMBL459396
(+/-)-2-OXOSPARTEINE
JYIJIIVLEOETIQ-XDQVBPFNSA-N
DTXSID001023908
HY-N3359
AKOS040760061
AT20203
FL65068
DA-49111
CS-0023989
NS00094225
AE-508/21133018
Q27103558
(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0?,?.0??,??]heptadecan-6-one
7,14-METHANO-2H,11H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCIN-11-ONE, DODECAHYDRO-, (7R,7AS,14R,14AR)-REL-
Pubchem:
91471
Cas:
550-90-3
Gnps:
CCMSLIB00010127351
Zinc:
ZINC000005133852
Chebi:
28193
Nmrshiftdb2:
60019625
Metabolights:
MTBLC28193
Chembl:
CHEMBL459396
CPRiL:
11354
SMILES: C1CCC(=O)N(C1C23)CC(C2)C4N(C3)CCCC4
Level: 0
Mol. Weight: 248.37 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.06
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.84
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.31
- Plasma Protein Binding
- 35.85
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.44
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -1.71
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.55
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.11
- 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
- 3.13
- Rat (Acute)
- 2.8
- Rat (Chronic Oral)
- 1.35
- Fathead Minnow
- 3.52
- 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
- 368.49
- Hydration Free Energy
- -5.28
- Log(D) at pH=7.4
- 0.01
- Log(P)
- 1.21
- Log S
- -1.47
- Log(Vapor Pressure)
- -6.67
- Melting Point
- 97.16
- pKa Acid
- 9.42
- pKa Basic
- 9.14
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7837 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7837 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7771 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7771 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7648 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7648 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7623 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7623 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7600 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7600 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 3 | 0.7579 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 3 | 0.7579 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7524 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7524 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7513 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7513 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7508 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7508 |
| Retinoic acid receptor RXR-alpha | P28700 | RXRA_MOUSE | Mus musculus | 3 | 0.7447 |
| Retinoic acid receptor RXR-alpha | P28700 | RXRA_MOUSE | Mus musculus | 3 | 0.7447 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7434 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7434 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7389 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7389 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7340 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7340 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7327 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7327 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7327 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7327 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7322 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7322 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7303 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7303 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7112 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7112 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7032 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7032 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7022 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7022 |