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Securinine
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Ketone
- Subclass: Alpha,Beta-Unsaturated Ketone
| Canonical Smiles | O=C1C=C2[C@@]3(O1)C[C@@H](C=C2)N1[C@@H]3CCCC1 |
|---|---|
| InChI | InChI=1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1 |
| InChIKey | SWZMSZQQJRKFBP-WZRBSPASSA-N |
| Formula | C13H15NO2 |
| HBA | 3 |
| HBD | 0 |
| MW | 217.27 |
| Rotatable Bonds | 0 |
| TPSA | 29.54 |
| LogP | 1.41 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 217.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Margaritaria discoidea | Euphorbiaceae | Plantae | 319151 |
Showing of synonyms
Securinine
Securinan-11-one
Securinina
Securinin
Securininum
Securinine, (-)-
L-Securinine
(6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one
UNII-G4VS580P5E
G4VS580P5E
DTXSID7045944
NSC 107413
NSC-107413
(6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro(2,3-c)pyrido(1,2-a)azepin-2(6H)-one
DTXCID5025944
2-Oxo-2,6,9,10,11,11a-hexahydro-8H-6,11b-methanofuro(2,3-c)pyrido(1,2-a)azepin
6,10-METHANOPYRIDO(1,2-A)AZEPINE-gamma9(6H),alpha-ACETIC ACID,1,2,3,4,10,10A-HEXAHYDRO-10-HYDROXY-, gamma-LACTONE
5610-40-2
(-)-Securinine
Securinine [INN]
CHEBI:9079
Rel-(6S,11AR,11bS)-6,8,9,10,11,11a-hexahydro-2H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2-one
(-)-Securinin
Securininum [INN-Latin]
Securinina [INN-Spanish]
Securinine?
NSC107413
(a?-Securinine
NCGC00095172-01
CAS-5610-40-2
SECURININE [MI]
Spectrum2_000669
Spectrum3_001977
UPCMLD-DP039
SECURININE [WHO-DD]
(-)-Securinine (Standard)
BSPBio_003577
MLS006011461
SCHEMBL892754
SPECTRUM1505334
SPBio_000737
CHEMBL303062
Securinine, >=98% (HPLC)
UPCMLD-DP039:001
HY-N2079R
KBio3_002957
HMS1922D22
HMS3886H20
Pharmakon1600-01505334
ALBB-020907
HY-N2079
Tox21_111468
CCG-40031
MFCD03225476
NSC758972
STK256368
AKOS000265560
FS27810
NSC-758972
(1S,8S,14R)-2-oxa-9-azatetracyclo[6.6.1.0<1,5>.0<9,14>]pentadeca-4,6-dien-3-on e
Rac-(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.0~1,11~.0~2,7~]pentadeca-9,11-dien-13-one
NCGC00017322-02
NCGC00017322-03
NCGC00017322-04
NCGC00017322-05
NCGC00142506-01
NCGC00142506-03
NCGC00142506-04
BS-17623
SMR000542846
SBI-0207079.P001
DB-179323
CS-0018584
S9249
AB00643342_02
EN300-19767685
Q4413415
BRD-K49071277-001-02-1
BRD-K49071277-001-03-9
BRD-K49071277-001-04-7
(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one
(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.0^{1,11}.0^{2,7}]pentadeca-9,11-dien-13-one
(6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro[2,3-c]-pyrido[1,2-a]azepin-2(6H)-one
1,2,3,4,10,10a-Hexahydro-10-hydroxy-6 ,10-methanopyrido [1,2-a]azepine-9(6H),a-acetic Acid ?-Lactone
6,10-METHANOPYRIDO(1,2-A)AZEPINE-.GAMMA.9(6H),.ALPHA.-ACETIC ACID,1,2,3,4,10,10A-HEXAHYDRO-10-HYDROXY-, .GAMMA.-LACTONE
8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, 9,10,11,11a-tetrahydro-, (6S,11aR,11bS)-
REL-(6R,11AS,11BR)-9,10,11,11A-TETRAHYDRO-8H-6,11B-METHANOFURO[2,3-C]PYRIDO[1,2-A]AZEPIN-2(6H)-ONE
Pubchem:
442872
Cas:
5610-40-2
Gnps:
CCMSLIB00004690949
Zinc:
ZINC000019701765
Kegg Ligand:
C10614
Chebi:
9079
Nmrshiftdb2:
60078069
Chembl:
CHEMBL303062
Comptox:
DTXSID7045944
CPRiL:
53665
SMILES: O=C(O1)C=C(C123)C=CC(C3)N4C2CCCC4
Level: 0
Mol. Weight: 217.27 g/mol
Antimalarial
Absorption
- Caco-2 (logPapp)
- -5.1
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.650
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.34
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.350
- Plasma Protein Binding
- 31.14
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- 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
- 9.620
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.600
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.070
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.350
- Micronucleos
- Toxic
- 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
- 1.460
- Rat (Acute)
- 2.550
- Rat (Chronic Oral)
- 1.670
- Fathead Minnow
- 3.780
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 317.130
- Hydration Free Energy
- -7.070
- Log(D) at pH=7.4
- 1.120
- Log(P)
- 0.88
- Log S
- -1.59
- Log(Vapor Pressure)
- -4.76
- Melting Point
- 116.37
- pKa Acid
- 7.99
- pKa Basic
- 7.64
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8014 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8014 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7726 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7726 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7709 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7709 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7644 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7644 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7538 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7538 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7506 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7506 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7501 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7501 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7460 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7460 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7453 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7453 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7428 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7428 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7396 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7396 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7369 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7369 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7356 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7356 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7337 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7337 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7328 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7328 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7314 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7314 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7307 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7307 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7289 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7289 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 2 | 0.7245 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 2 | 0.7245 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7200 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7200 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7182 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7182 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7147 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7147 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7131 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7131 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7128 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7128 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7068 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7068 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7065 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7065 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7051 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7051 |