methyl (2E,4E)-5-[(1R,4S,7S,8S,9R)-7-acetyloxy-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate

Details

• Internal ID: 32626d17-129d-43fe-9953-ff738dbb2005
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: methyl (2E,4E)-5-[(1R,4S,7S,8S,9R)-7-acetyloxy-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate
• SMILES (Canonical): CC(=CC=CC1(C2CCC3(C2(CCC(C=C3)(C)O)OC(=O)C)C(=O)O1)C)C(=O)OC
• SMILES (Isomeric): C/C(=C\C=C\[C@@]1([C@@H]2CC[C@@]3([C@@]2(CC[C@](C=C3)(C)O)OC(=O)C)C(=O)O1)C)/C(=O)OC
• InChI: InChI=1S/C23H30O7/c1-15(18(25)28-5)7-6-9-21(4)17-8-10-22(19(26)30-21)13-11-20(3,27)12-14-23(17,22)29-16(2)24/h6-7,9,11,13,17,27H,8,10,12,14H2,1-5H3/b9-6+,15-7+/t17-,20+,21+,22-,23-/m0/s1
• InChI Key: WYIMJLOGLKUJNQ-LSHKRLLPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₀O₇
• Molecular Weight: 418.50 g/mol
• Exact Mass: 418.19915329 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	-	0.5839	58.39%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6813	68.13%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8694	86.94%
OATP1B3 inhibitior	+	0.9428	94.28%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8271	82.71%
BSEP inhibitior	+	0.8889	88.89%
P-glycoprotein inhibitior	+	0.6226	62.26%
P-glycoprotein substrate	-	0.7682	76.82%
CYP3A4 substrate	+	0.6717	67.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9107	91.07%
CYP3A4 inhibition	-	0.8627	86.27%
CYP2C9 inhibition	-	0.8246	82.46%
CYP2C19 inhibition	-	0.8938	89.38%
CYP2D6 inhibition	-	0.9611	96.11%
CYP1A2 inhibition	-	0.6851	68.51%
CYP2C8 inhibition	-	0.5601	56.01%
CYP inhibitory promiscuity	-	0.9820	98.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6816	68.16%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9209	92.09%
Skin irritation	-	0.5654	56.54%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4944	49.44%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5709	57.09%
skin sensitisation	-	0.8122	81.22%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.8158	81.58%
Acute Oral Toxicity (c)	II	0.6702	67.02%
Estrogen receptor binding	+	0.8352	83.52%
Androgen receptor binding	+	0.6437	64.37%
Thyroid receptor binding	+	0.7215	72.15%
Glucocorticoid receptor binding	+	0.7557	75.57%
Aromatase binding	+	0.7264	72.64%
PPAR gamma	+	0.5410	54.10%
Honey bee toxicity	-	0.7814	78.14%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9129	91.29%

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	98.08%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.81%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.43%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.48%	96.09%
CHEMBL4072	P07858	Cathepsin B	90.24%	93.67%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	90.00%	85.30%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.19%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	88.50%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.67%	99.23%
CHEMBL2581	P07339	Cathepsin D	85.83%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.95%	89.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.69%	92.88%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.50%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.29%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.82%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.80%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.68%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.74%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.67%	100.00%
CHEMBL5028	O14672	ADAM10	81.39%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.82%	91.19%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.14%	94.80%

Plants that contains it

• Pseudolarix amabilis

Cross-Links

• PubChem: 163189488
• LOTUS: LTS0218066
• wikiData: Q105322235