(1S,8R,10S)-3,6-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one

Details

• Internal ID: 57bfdc41-d9bb-40f6-ad70-677c2c99935b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1S,8R,10S)-3,6-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
• SMILES (Canonical): CC(C)C1=CC(=C2C(=C1O)C3CC4C2(CCCC4(C)C)C(=O)O3)O
• SMILES (Isomeric): CC(C)C1=CC(=C2C(=C1O)[C@H]3C[C@@H]4[C@]2(CCCC4(C)C)C(=O)O3)O
• InChI: InChI=1S/C20H26O4/c1-10(2)11-8-12(21)16-15(17(11)22)13-9-14-19(3,4)6-5-7-20(14,16)18(23)24-13/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14+,20+/m1/s1
• InChI Key: MCMQSPNBTJWIEO-CKNLXJGOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.29
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9639	96.39%
Caco-2	+	0.6508	65.08%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8052	80.52%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8904	89.04%
OATP1B3 inhibitior	+	0.9590	95.90%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5911	59.11%
P-glycoprotein inhibitior	-	0.8198	81.98%
P-glycoprotein substrate	-	0.8185	81.85%
CYP3A4 substrate	+	0.6216	62.16%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.7197	71.97%
CYP3A4 inhibition	-	0.8217	82.17%
CYP2C9 inhibition	-	0.8636	86.36%
CYP2C19 inhibition	-	0.8521	85.21%
CYP2D6 inhibition	-	0.9315	93.15%
CYP1A2 inhibition	+	0.7073	70.73%
CYP2C8 inhibition	-	0.7690	76.90%
CYP inhibitory promiscuity	-	0.9357	93.57%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7227	72.27%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.8294	82.94%
Skin irritation	-	0.6248	62.48%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8185	81.85%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5072	50.72%
skin sensitisation	-	0.8701	87.01%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.8882	88.82%
Acute Oral Toxicity (c)	III	0.6160	61.60%
Estrogen receptor binding	+	0.6860	68.60%
Androgen receptor binding	+	0.6450	64.50%
Thyroid receptor binding	+	0.6910	69.10%
Glucocorticoid receptor binding	+	0.8862	88.62%
Aromatase binding	-	0.5218	52.18%
PPAR gamma	+	0.8156	81.56%
Honey bee toxicity	-	0.8603	86.03%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9916	99.16%

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	98.77%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.14%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.12%	96.38%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.46%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.98%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.08%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.94%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.35%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.07%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.70%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.42%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.80%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.58%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.21%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.85%	95.89%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.01%	85.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.61%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.49%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.49%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.60%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	83.02%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.01%	96.21%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.63%	93.04%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.78%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.15%	94.00%

Plants that contains it

• Salvia lanigera

Cross-Links

• PubChem: 162894695
• LOTUS: LTS0026355
• wikiData: Q105161297