(1R,9S,10S)-4-hydroxy-3-methoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6-triene-8,15-dione

Details

• Internal ID: b1952aea-5d8d-4ca5-b9af-4df097e3eea2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,9S,10S)-4-hydroxy-3-methoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6-triene-8,15-dione
• SMILES (Canonical): CC(C)C1=C(C(=C2C(=C1)C(=O)C3C4C2(CCCC4(C)C)C(=O)O3)OC)O
• SMILES (Isomeric): CC(C)C1=C(C(=C2C(=C1)C(=O)[C@@H]3[C@@H]4[C@@]2(CCCC4(C)C)C(=O)O3)OC)O
• InChI: InChI=1S/C21H26O5/c1-10(2)11-9-12-13(16(25-5)14(11)22)21-8-6-7-20(3,4)18(21)17(15(12)23)26-19(21)24/h9-10,17-18,22H,6-8H2,1-5H3/t17-,18+,21+/m1/s1
• InChI Key: FPXYVFQXMVNGKZ-LQWHRVPQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.17802393 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.71
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.7100	71.00%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7515	75.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8707	87.07%
OATP1B3 inhibitior	+	0.8808	88.08%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7867	78.67%
P-glycoprotein inhibitior	-	0.6560	65.60%
P-glycoprotein substrate	-	0.7330	73.30%
CYP3A4 substrate	+	0.6539	65.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8051	80.51%
CYP3A4 inhibition	-	0.6070	60.70%
CYP2C9 inhibition	-	0.5824	58.24%
CYP2C19 inhibition	-	0.7104	71.04%
CYP2D6 inhibition	-	0.9052	90.52%
CYP1A2 inhibition	+	0.5098	50.98%
CYP2C8 inhibition	-	0.6419	64.19%
CYP inhibitory promiscuity	-	0.9000	90.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5485	54.85%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.7509	75.09%
Skin irritation	-	0.7257	72.57%
Skin corrosion	-	0.9120	91.20%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8672	86.72%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5428	54.28%
skin sensitisation	-	0.8682	86.82%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8483	84.83%
Acute Oral Toxicity (c)	III	0.5192	51.92%
Estrogen receptor binding	+	0.7671	76.71%
Androgen receptor binding	+	0.6203	62.03%
Thyroid receptor binding	+	0.6997	69.97%
Glucocorticoid receptor binding	+	0.8772	87.72%
Aromatase binding	+	0.6142	61.42%
PPAR gamma	+	0.7830	78.30%
Honey bee toxicity	-	0.8670	86.70%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	98.99%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.68%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.39%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.98%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.92%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.24%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.96%	94.45%
CHEMBL2535	P11166	Glucose transporter	91.57%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.06%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.37%	96.77%
CHEMBL1937	Q92769	Histone deacetylase 2	90.31%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.95%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.90%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.59%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.48%	96.21%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.64%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.08%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.64%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.90%	97.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.89%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	83.75%	94.73%
CHEMBL5203	P33316	dUTP pyrophosphatase	81.99%	99.18%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.55%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.15%	91.07%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	80.91%	97.88%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.84%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	80.82%	91.19%

Plants that contains it

• Salvia officinalis

Cross-Links

• PubChem: 163033760
• LOTUS: LTS0268835
• wikiData: Q104999456