(S)-Cheilanthifoline

Details

• Internal ID: a0724a04-5740-47c0-a888-33855854568f
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13S)-17-methoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-16-ol
• SMILES (Canonical): COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O
• SMILES (Isomeric): COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O
• InChI: InChI=1S/C19H19NO4/c1-22-18-7-12-4-5-20-9-14-11(2-3-17-19(14)24-10-23-17)6-15(20)13(12)8-16(18)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1
• InChI Key: FVXCQULKSPVRPK-HNNXBMFYSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.40 g/mol
• Exact Mass: 325.13140809 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• (13S)-17-methoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-16-ol
• (6aS)-6,6a,11,14-Tetrahydro-8-methoxy-12H-benzo[a]-1,3-benzodioxolo[4,5-g]quinolizim-9-ol
• (6aS)-9-methoxy-6,11,12,14-tetrahydro-2H,6aH-[1,3]dioxolo[4,5-h]isoquino[2,1-b]isoquinolin-8-ol
• C05174
• SCHEMBL18890976
• CHEBI:16233
• DTXSID70964044
• E87180
• Q15410880
• (6aS)-6, 6a, 11,14-tetrahydro-8-methoxy-12H-benzo[a]-1,3-benzodioxolo[4, 5-g]quinolizim-9-ol
• 9-Methoxy-6,11,12,14-tetrahydro-2H,6aH-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9544	95.44%
Caco-2	+	0.8554	85.54%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6412	64.12%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.9279	92.79%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.7715	77.15%
P-glycoprotein inhibitior	-	0.6655	66.55%
P-glycoprotein substrate	-	0.5496	54.96%
CYP3A4 substrate	+	0.6035	60.35%
CYP2C9 substrate	-	0.6106	61.06%
CYP2D6 substrate	+	0.6924	69.24%
CYP3A4 inhibition	+	0.7410	74.10%
CYP2C9 inhibition	-	0.8981	89.81%
CYP2C19 inhibition	+	0.8837	88.37%
CYP2D6 inhibition	+	0.9215	92.15%
CYP1A2 inhibition	+	0.9179	91.79%
CYP2C8 inhibition	-	0.6137	61.37%
CYP inhibitory promiscuity	+	0.6463	64.63%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5360	53.60%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9593	95.93%
Skin irritation	-	0.7659	76.59%
Skin corrosion	-	0.9470	94.70%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6656	66.56%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8581	85.81%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5069	50.69%
Acute Oral Toxicity (c)	III	0.5990	59.90%
Estrogen receptor binding	+	0.6483	64.83%
Androgen receptor binding	-	0.4817	48.17%
Thyroid receptor binding	+	0.5257	52.57%
Glucocorticoid receptor binding	+	0.6414	64.14%
Aromatase binding	-	0.6527	65.27%
PPAR gamma	+	0.6609	66.09%
Honey bee toxicity	-	0.8090	80.90%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6451	64.51%
Fish aquatic toxicity	+	0.6778	67.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.68%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.24%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.85%	94.45%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	93.69%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.56%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.19%	86.33%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	92.68%	82.67%
CHEMBL217	P14416	Dopamine D2 receptor	91.91%	95.62%
CHEMBL2581	P07339	Cathepsin D	91.26%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.04%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.70%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.52%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.13%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	89.70%	88.48%
CHEMBL2056	P21728	Dopamine D1 receptor	88.18%	91.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.48%	95.89%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	87.10%	96.86%
CHEMBL2535	P11166	Glucose transporter	86.61%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.60%	92.62%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.59%	82.38%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	86.56%	90.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.36%	96.77%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.43%	95.78%
CHEMBL4208	P20618	Proteasome component C5	82.04%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.44%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.30%	100.00%
CHEMBL261	P00915	Carbonic anhydrase I	80.81%	96.76%
CHEMBL5747	Q92793	CREB-binding protein	80.78%	95.12%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.13%	89.05%

Plants that contains it

• Angelica dahurica
• Artabotrys maingayi
• Corydalis calliantha
• Corydalis cheilanthifolia
• Corydalis heterocarpa
• Corydalis ophiocarpa
• Corydalis scouleri
• Corydalis stricta
• Corydalis ternata
• Diospyros ebenum
• Fumaria parviflora
• Fumaria vaillantii
• Lappula squarrosa
• Ligularia sagitta
• Mezzettia parviflora
• Papaver arenarium
• Piper methysticum
• Psacalium peltatum
• Senna spectabilis
• Stachys plumosa
• Symphytum officinale
• Thuja plicata
• Ulex parviflorus subsp. airensis
• Vepris heterophylla

Cross-Links

• PubChem: 440582
• NPASS: NPC42824
• LOTUS: LTS0064487
• wikiData: Q15410880