Senkirkine

Details

• Internal ID: 476419df-ae92-449a-b50e-07667b48e69a
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1R,4Z,6R,7R,11Z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione
• SMILES (Canonical): CC=C1CC(C(C(=O)OCC2=CCN(CCC(C2=O)OC1=O)C)(C)O)C
• SMILES (Isomeric): C/C=C\1/C[C@H]([C@@](C(=O)OC/C/2=C/CN(CC[C@H](C2=O)OC1=O)C)(C)O)C
• InChI: InChI=1S/C19H27NO6/c1-5-13-10-12(2)19(3,24)18(23)25-11-14-6-8-20(4)9-7-15(16(14)21)26-17(13)22/h5-6,12,15,24H,7-11H2,1-4H3/b13-5-,14-6-/t12-,15-,19-/m1/s1
• InChI Key: HPDHKHMHQGCNPE-QLJRNOHWSA-N
• Popularity: 30 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₇NO₆
• Molecular Weight: 365.40 g/mol
• Exact Mass: 365.18383758 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.01
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• SENKIRKIN
• Renardin
• 2318-18-5
• UNII-X65P7V4LVJ
• X65P7V4LVJ
• NSC-89945
• Renardine
• Senkarkane
• CCRIS 557
• HSDB 3536
• Renardine (neutral)
• Senkirkine (neutral)
• CHEBI:9111
• CHEMBL470059
• DTXSID4021266
• (1R,4Z,6R,7R,11Z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione
• 12-Hydroxy-4-methyl-4,8-secosenecionan-8,11,16-trione
• SENKIRKINE (IARC)
• SENKIRKINE [IARC]
• Renardine (neutral) (VAN)
• trans-15-Ethylidene-12-beta-hydroxy-4,12-alpha,13-beta-trimethyl 8-oxo-4,8 secosenec-1-enine
• Senkirkine (neutral) (VAN)
• 2,12-Dihydroxy-4-methyl-11,16-dioxosenecionanium
• 4,8-Secosenecionan-8,11,16-trione, 12-hydroxy-4-methyl-
• (1R,4Z,6R,7R)-4-ETHYLIDENE-7-HYDROXY-6,7,14-TRIMETHYL-2,9-DIOXA-14-AZABICYCLO(9.5.1)HEPTADEC-11-ENE-3,8,17-TRIONE
• 2,9-DIOXA-14-AZABICYCLO(9.5.1)HEPTADEC-11-ENE-3,8,17-TRIONE, 4-ETHYLIDENE-7-HYDROXY-6,7,14-TRIMETHYL-, (1R,4Z,6R,7R)-
• AC1NQZ0B
• Senecionanium, 8,12-dihydroxy-4-methyl-11,16-dioxo-
• C19H27NO6
• C19-H27-N-O6
• Senkirkine, analytical standard
• DTXCID701266
• Senkirkine 100 microg/mL in Water
• MFCD01684247
• HY-122509
• CS-0085930
• Q27108274
• trans-15-ethylidene-12-beta-hydroxy-4,12-alpha,13-beta-trimethyl-8-oxp-4,8-secosenec-1-enine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8373	83.73%
Caco-2	+	0.7339	73.39%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5549	55.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.9269	92.69%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6521	65.21%
BSEP inhibitior	-	0.4560	45.60%
P-glycoprotein inhibitior	-	0.6111	61.11%
P-glycoprotein substrate	-	0.5588	55.88%
CYP3A4 substrate	+	0.6380	63.80%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8369	83.69%
CYP3A4 inhibition	-	0.8314	83.14%
CYP2C9 inhibition	-	0.8981	89.81%
CYP2C19 inhibition	-	0.9017	90.17%
CYP2D6 inhibition	-	0.9443	94.43%
CYP1A2 inhibition	-	0.8447	84.47%
CYP2C8 inhibition	-	0.9006	90.06%
CYP inhibitory promiscuity	-	0.9964	99.64%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7000	70.00%
Carcinogenicity (trinary)	Danger	0.7525	75.25%
Eye corrosion	-	0.9789	97.89%
Eye irritation	-	0.9801	98.01%
Skin irritation	-	0.7254	72.54%
Skin corrosion	-	0.9151	91.51%
Ames mutagenesis	+	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5434	54.34%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8214	82.14%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.7588	75.88%
Acute Oral Toxicity (c)	III	0.4445	44.45%
Estrogen receptor binding	-	0.6512	65.12%
Androgen receptor binding	-	0.5930	59.30%
Thyroid receptor binding	-	0.6378	63.78%
Glucocorticoid receptor binding	+	0.5892	58.92%
Aromatase binding	-	0.5988	59.88%
PPAR gamma	-	0.6661	66.61%
Honey bee toxicity	-	0.8510	85.10%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.6825	68.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.73%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.04%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.07%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.67%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.39%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.70%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.90%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.07%	93.40%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.87%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.58%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.38%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.20%	97.14%

Plants that contains it

• Acacia paradoxa
• Adonis sutchuenensis
• Astragalus ernestii
• Berneuxia thibetica
• Bongardia chrysogonum
• Chersodoma jodopappa
• Crotalaria laburnifolia
• Eragrostis curvula
• Fritillaria meleagris
• Gynura elliptica
• Isophysis tasmanica
• Jacobaea vulgaris
• Matricaria discoidea
• Metasequoia glyptostroboides
• Packera candidissima
• Packera glabella
• Petasites hybridus
• Petasites japonicus
• Petasites pyrenaicus
• Petasites spurius
• Philenoptera laxiflora
• Pittocaulon filare
• Pittocaulon praecox
• Plantago lundborgii
• Senecio almeidae
• Senecio deferens
• Senecio gallicus
• Senecio inaequidens
• Senecio neaei
• Senecio scandens
• Senecio tenuifolius
• Senecio varicosus
• Senecio vernalis
• Sideritis arborescens
• Solanum pseudoquina
• Telanthophora grandifolia
• Tephroseris integrifolia
• Triadica sebifera
• Tussilago farfara

Cross-Links

• PubChem: 5281752
• NPASS: NPC195435
• LOTUS: LTS0193348
• wikiData: Q27108274