[(2R,4R,8S,9S,10R,11R)-10-acetyloxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 3-methylbutanoate

Details

• Internal ID: 9293c556-ebfc-43fe-a153-4465664967a0
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(2R,4R,8S,9S,10R,11R)-10-acetyloxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 3-methylbutanoate
• SMILES (Canonical): CC1CC2C(C(C(C3(C(=O)C=C1O3)C)OC(=O)C)OC(=O)CC(C)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@@H]([C@@H]([C@H]([C@@]3(C(=O)C=C1O3)C)OC(=O)C)OC(=O)CC(C)C)C(=C)C(=O)O2
• InChI: InChI=1S/C22H28O8/c1-10(2)7-17(25)29-19-18-12(4)21(26)28-15(18)8-11(3)14-9-16(24)22(6,30-14)20(19)27-13(5)23/h9-11,15,18-20H,4,7-8H2,1-3,5-6H3/t11-,15-,18+,19+,20-,22+/m1/s1
• InChI Key: JFZFRJGWYGAVDA-IIMRBXPBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₈
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.17841785 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.26
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	+	0.5104	51.04%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6739	67.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8240	82.40%
OATP1B3 inhibitior	-	0.2510	25.10%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5110	51.10%
P-glycoprotein inhibitior	+	0.7842	78.42%
P-glycoprotein substrate	-	0.5311	53.11%
CYP3A4 substrate	+	0.6460	64.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8960	89.60%
CYP3A4 inhibition	-	0.5204	52.04%
CYP2C9 inhibition	-	0.8216	82.16%
CYP2C19 inhibition	-	0.8013	80.13%
CYP2D6 inhibition	-	0.9238	92.38%
CYP1A2 inhibition	-	0.8033	80.33%
CYP2C8 inhibition	-	0.6406	64.06%
CYP inhibitory promiscuity	-	0.7664	76.64%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8243	82.43%
Carcinogenicity (trinary)	Non-required	0.3906	39.06%
Eye corrosion	-	0.9533	95.33%
Eye irritation	-	0.8358	83.58%
Skin irritation	-	0.6824	68.24%
Skin corrosion	-	0.9193	91.93%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5169	51.69%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6336	63.36%
skin sensitisation	+	0.4765	47.65%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5364	53.64%
Acute Oral Toxicity (c)	III	0.5113	51.13%
Estrogen receptor binding	+	0.8346	83.46%
Androgen receptor binding	+	0.7085	70.85%
Thyroid receptor binding	+	0.5536	55.36%
Glucocorticoid receptor binding	+	0.7989	79.89%
Aromatase binding	+	0.5597	55.97%
PPAR gamma	+	0.7308	73.08%
Honey bee toxicity	-	0.7004	70.04%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9673	96.73%

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	98.60%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.62%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.52%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.28%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.18%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.95%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	93.95%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	88.64%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.23%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.08%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.26%	95.50%
CHEMBL299	P17252	Protein kinase C alpha	83.57%	98.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.21%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.62%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.45%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.11%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	81.38%	91.19%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	80.95%	88.42%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.87%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.00%	93.56%

Plants that contains it

• Neurolaena lobata
• Neurolaena macrocephala
• Neurolaena oaxacana

Cross-Links

• PubChem: 101035409
• LOTUS: LTS0058506
• wikiData: Q105127130