[(3aS,4R,6E,9R,10Z,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate

Details

• Internal ID: ad5b6469-498d-41d8-911f-99cf7796185b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4R,6E,9R,10Z,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate
• SMILES (Canonical): CC1=CCC(C(=CC2C(C(C1)OC(=O)C)C(=C)C(=O)O2)C)O
• SMILES (Isomeric): C/C/1=C\C[C@H](/C(=C\[C@@H]2[C@H]([C@@H](C1)OC(=O)C)C(=C)C(=O)O2)/C)O
• InChI: InChI=1S/C17H22O5/c1-9-5-6-13(19)10(2)8-15-16(11(3)17(20)22-15)14(7-9)21-12(4)18/h5,8,13-16,19H,3,6-7H2,1-2,4H3/b9-5+,10-8-/t13-,14-,15-,16+/m1/s1
• InChI Key: OHKKKYNMSVNOFP-XBJKLAMHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.06
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.7711	77.11%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5241	52.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9237	92.37%
OATP1B3 inhibitior	+	0.9016	90.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9238	92.38%
P-glycoprotein inhibitior	-	0.8106	81.06%
P-glycoprotein substrate	-	0.7784	77.84%
CYP3A4 substrate	+	0.5969	59.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	-	0.5823	58.23%
CYP2C9 inhibition	-	0.9036	90.36%
CYP2C19 inhibition	-	0.8885	88.85%
CYP2D6 inhibition	-	0.9602	96.02%
CYP1A2 inhibition	-	0.6241	62.41%
CYP2C8 inhibition	-	0.7855	78.55%
CYP inhibitory promiscuity	-	0.9540	95.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5539	55.39%
Eye corrosion	-	0.9602	96.02%
Eye irritation	-	0.6836	68.36%
Skin irritation	-	0.5470	54.70%
Skin corrosion	-	0.9274	92.74%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5656	56.56%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.7159	71.59%
skin sensitisation	-	0.7304	73.04%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7322	73.22%
Acute Oral Toxicity (c)	II	0.3758	37.58%
Estrogen receptor binding	-	0.6183	61.83%
Androgen receptor binding	-	0.6493	64.93%
Thyroid receptor binding	-	0.6007	60.07%
Glucocorticoid receptor binding	+	0.6487	64.87%
Aromatase binding	-	0.7223	72.23%
PPAR gamma	-	0.5994	59.94%
Honey bee toxicity	-	0.7041	70.41%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9854	98.54%

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	93.98%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.15%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.12%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.15%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.55%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.32%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	81.92%	91.19%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.72%	93.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.05%	96.09%

Plants that contains it

• Ambrosia confertiflora

Cross-Links

• PubChem: 163186657
• LOTUS: LTS0199632
• wikiData: Q105192125