(1R,8S,10S)-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2(7),5-diene-3,4-dione

Details

• Internal ID: 035b1493-bb76-4d20-bc9f-66e3c32185b9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,8S,10S)-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2(7),5-diene-3,4-dione
• SMILES (Canonical): CC(C)C1=CC2=C(C(=O)C1=O)C34CCCC(C3CC2OC4)(C)C
• SMILES (Isomeric): CC(C)C1=CC2=C(C(=O)C1=O)[C@@]34CCCC([C@@H]3C[C@@H]2OC4)(C)C
• InChI: InChI=1S/C20H26O3/c1-11(2)12-8-13-14-9-15-19(3,4)6-5-7-20(15,10-23-14)16(13)18(22)17(12)21/h8,11,14-15H,5-7,9-10H2,1-4H3/t14-,15-,20+/m0/s1
• InChI Key: MCRKHQBQOAINHY-AUSJPIAWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.40 g/mol
• Exact Mass: 314.18819469 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.63
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.8324	83.24%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8560	85.60%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.9102	91.02%
OATP1B3 inhibitior	+	0.9805	98.05%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.5835	58.35%
P-glycoprotein inhibitior	-	0.6030	60.30%
P-glycoprotein substrate	-	0.8137	81.37%
CYP3A4 substrate	+	0.6136	61.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8434	84.34%
CYP3A4 inhibition	-	0.8396	83.96%
CYP2C9 inhibition	-	0.8367	83.67%
CYP2C19 inhibition	-	0.7895	78.95%
CYP2D6 inhibition	-	0.8966	89.66%
CYP1A2 inhibition	-	0.7319	73.19%
CYP2C8 inhibition	-	0.7961	79.61%
CYP inhibitory promiscuity	-	0.8721	87.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5863	58.63%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8972	89.72%
Skin irritation	-	0.6324	63.24%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.5954	59.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4805	48.05%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5839	58.39%
skin sensitisation	-	0.6572	65.72%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5670	56.70%
Acute Oral Toxicity (c)	III	0.6448	64.48%
Estrogen receptor binding	+	0.7042	70.42%
Androgen receptor binding	+	0.6056	60.56%
Thyroid receptor binding	+	0.7057	70.57%
Glucocorticoid receptor binding	+	0.7124	71.24%
Aromatase binding	-	0.6150	61.50%
PPAR gamma	+	0.7762	77.62%
Honey bee toxicity	-	0.7051	70.51%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9792	97.92%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1782	P14324	Farnesyl diphosphate synthase	230 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.51%	97.25%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	94.08%	96.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.64%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.56%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.27%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	92.96%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.90%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.55%	90.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.37%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.65%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.09%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.49%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.65%	99.23%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.35%	95.71%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.12%	90.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.24%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.02%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	81.70%	95.93%

Plants that contains it

• Amentotaxus yunnanensis
• Artemisia siversiana
• Deguelia hatschbachii
• Delphinium cyphoplectrum
• Dioscorea communis
• Euphorbia retusa
• Hemionitis artax
• Salvia przewalskii
• Stauntonia obovatifoliola
• Uvaria klaineana
• Vicia sativa

Cross-Links

• PubChem: 102280560
• NPASS: NPC267076
• LOTUS: LTS0068676
• wikiData: Q105161387