6-Formyl-5'-hydroxy-5,5-dimethyl-8'-methylidene-1',9'-dioxohexahydro-1'H,3'H-spiro[cyclohexane-1,4'-[2]oxa[7,9a]methanocyclohepta[c]pyran]-2-yl acetate

Details

• Internal ID: 8d3da187-40cf-4713-8175-058612da7eb9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (3'-formyl-7-hydroxy-4',4'-dimethyl-10-methylidene-2,11-dioxospiro[3-oxatricyclo[7.2.1.01,6]dodecane-5,2'-cyclohexane]-1'-yl) acetate
• SMILES (Canonical): CC(=O)OC1CCC(C(C12COC(=O)C34C2C(CC(C3)C(=C)C4=O)O)C=O)(C)C
• SMILES (Isomeric): CC(=O)OC1CCC(C(C12COC(=O)C34C2C(CC(C3)C(=C)C4=O)O)C=O)(C)C
• InChI: InChI=1S/C22H28O7/c1-11-13-7-14(25)17-21(8-13,18(11)26)19(27)28-10-22(17)15(9-23)20(3,4)6-5-16(22)29-12(2)24/h9,13-17,25H,1,5-8,10H2,2-4H3
• InChI Key: ORDKVFHKMGUXSQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.18350323 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• DTXSID00942113
• (3'-Formyl-7-hydroxy-4',4'-dimethyl-10-methylidene-2,11-dioxospiro[3-oxatricyclo[7.2.1.01,6]dodecane-5,2'-cyclohexane]-1'-yl) acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9704	97.04%
Caco-2	-	0.5352	53.52%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7671	76.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7969	79.69%
OATP1B3 inhibitior	+	0.9102	91.02%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.6493	64.93%
P-glycoprotein inhibitior	-	0.5968	59.68%
P-glycoprotein substrate	-	0.5784	57.84%
CYP3A4 substrate	+	0.6901	69.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8764	87.64%
CYP3A4 inhibition	-	0.7255	72.55%
CYP2C9 inhibition	-	0.6732	67.32%
CYP2C19 inhibition	-	0.8083	80.83%
CYP2D6 inhibition	-	0.9445	94.45%
CYP1A2 inhibition	-	0.5808	58.08%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9417	94.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6739	67.39%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9293	92.93%
Skin irritation	+	0.5345	53.45%
Skin corrosion	-	0.9338	93.38%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6611	66.11%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5427	54.27%
skin sensitisation	-	0.8067	80.67%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.8410	84.10%
Acute Oral Toxicity (c)	III	0.3847	38.47%
Estrogen receptor binding	+	0.8395	83.95%
Androgen receptor binding	+	0.6651	66.51%
Thyroid receptor binding	+	0.5930	59.30%
Glucocorticoid receptor binding	+	0.7038	70.38%
Aromatase binding	+	0.5688	56.88%
PPAR gamma	+	0.6699	66.99%
Honey bee toxicity	-	0.7568	75.68%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5498	54.98%
Fish aquatic toxicity	+	0.9939	99.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.09%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.33%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.78%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.15%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.58%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	90.69%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.16%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	89.70%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.56%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.91%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.84%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.30%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.09%	82.69%
CHEMBL2581	P07339	Cathepsin D	84.91%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.34%	91.07%
CHEMBL1871	P10275	Androgen Receptor	84.01%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.68%	93.04%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.60%	89.50%
CHEMBL5255	O00206	Toll-like receptor 4	83.40%	92.50%
CHEMBL1902	P62942	FK506-binding protein 1A	83.11%	97.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.84%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.12%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.86%	92.94%
CHEMBL284	P27487	Dipeptidyl peptidase IV	81.60%	95.69%
CHEMBL1937	Q92769	Histone deacetylase 2	81.18%	94.75%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.94%	94.33%
CHEMBL5028	O14672	ADAM10	80.60%	97.50%

Plants that contains it

• Isodon rubescens
• Isodon trichocarpus

Cross-Links

• PubChem: 177797
• LOTUS: LTS0087621
• wikiData: Q82919085