24-Methylenecycloartanol, cis-ferulate

Details

• Internal ID: f00b0d79-5538-456b-9f8b-7d4e72521e7b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cycloartanols and derivatives
• IUPAC Name: [(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl] (Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(C)C(=C)CCC(C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)OC(=O)C=CC6=CC(=C(C=C6)O)OC)C)C
• SMILES (Isomeric): C[C@H](CCC(=C)C(C)C)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@H]2CC[C@@H]5[C@]3(C4)CC[C@@H](C5(C)C)OC(=O)/C=C\C6=CC(=C(C=C6)O)OC)C)C
• InChI: InChI=1S/C41H60O4/c1-26(2)27(3)10-11-28(4)30-18-20-39(8)34-16-15-33-37(5,6)35(19-21-40(33)25-41(34,40)23-22-38(30,39)7)45-36(43)17-13-29-12-14-31(42)32(24-29)44-9/h12-14,17,24,26,28,30,33-35,42H,3,10-11,15-16,18-23,25H2,1-2,4-9H3/b17-13-/t28-,30-,33+,34+,35+,38-,39+,40-,41+/m1/s1
• InChI Key: JBSUVXVGZSMGDJ-UQFIVECLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₀O₄
• Molecular Weight: 616.90 g/mol
• Exact Mass: 616.44916039 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 12.60
• Atomic LogP (AlogP): 10.39
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• 24-Methylenecycloartanol, cis-ferulate
• 24-Methylene-5alpha-cycloartan-3beta-ol (Z)-3-(3-methoxy-4-hydroxyphenyl)acrylat
• 9,19-Cyclolanostan-3-ol, 24-methylene-, 3-[(2Z)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate], (3.beta.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	-	0.8009	80.09%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7746	77.46%
OATP2B1 inhibitior	-	0.5702	57.02%
OATP1B1 inhibitior	+	0.8372	83.72%
OATP1B3 inhibitior	-	0.2146	21.46%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9692	96.92%
P-glycoprotein inhibitior	+	0.7748	77.48%
P-glycoprotein substrate	+	0.5814	58.14%
CYP3A4 substrate	+	0.6955	69.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8476	84.76%
CYP3A4 inhibition	-	0.5810	58.10%
CYP2C9 inhibition	-	0.5174	51.74%
CYP2C19 inhibition	+	0.5649	56.49%
CYP2D6 inhibition	-	0.9085	90.85%
CYP1A2 inhibition	-	0.5570	55.70%
CYP2C8 inhibition	+	0.8139	81.39%
CYP inhibitory promiscuity	-	0.7611	76.11%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9020	90.20%
Carcinogenicity (trinary)	Non-required	0.6705	67.05%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9210	92.10%
Skin irritation	-	0.6660	66.60%
Skin corrosion	-	0.9590	95.90%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6597	65.97%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6834	68.34%
skin sensitisation	-	0.7912	79.12%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.9346	93.46%
Acute Oral Toxicity (c)	IV	0.4673	46.73%
Estrogen receptor binding	+	0.7649	76.49%
Androgen receptor binding	+	0.8460	84.60%
Thyroid receptor binding	+	0.5535	55.35%
Glucocorticoid receptor binding	+	0.8234	82.34%
Aromatase binding	+	0.7102	71.02%
PPAR gamma	+	0.6857	68.57%
Honey bee toxicity	-	0.7219	72.19%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5245	52.45%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.85%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.59%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.47%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.00%	95.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	94.79%	90.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.11%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.25%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.81%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.92%	89.62%
CHEMBL2581	P07339	Cathepsin D	89.31%	98.95%
CHEMBL4208	P20618	Proteasome component C5	89.30%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.09%	96.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.81%	95.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.49%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.23%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.58%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.67%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.50%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.04%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	85.92%	91.19%
CHEMBL2535	P11166	Glucose transporter	84.98%	98.75%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	83.33%	94.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.19%	90.71%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.88%	91.03%
CHEMBL3194	P02766	Transthyretin	82.27%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.14%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.82%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.74%	91.07%

Plants that contains it

• Lycium chinense
• Oryza sativa

Cross-Links

• PubChem: 10793902
• NPASS: NPC47268