(1S,11aS)-1-hydroxy-4-(hydroxymethyl)-8,8,11a-trimethyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7,7a,9,10,11-hexahydro-1H-naphtho[1,2-e][2]benzofuran-3-one

Details

• Internal ID: 3fcf24b5-deaf-497e-87d2-972ee5ad037b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1S,11aS)-1-hydroxy-4-(hydroxymethyl)-8,8,11a-trimethyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7,7a,9,10,11-hexahydro-1H-naphtho[1,2-e][2]benzofuran-3-one
• SMILES (Canonical): CC1(CCCC2(C1CCC3=C2C4=C(C(=C3OC5C(C(C(C(O5)CO)O)O)O)CO)C(=O)OC4O)C)C
• SMILES (Isomeric): C[C@]12CCCC(C1CCC3=C2C4=C(C(=C3O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)CO)C(=O)O[C@@H]4O)(C)C
• InChI: InChI=1S/C26H36O10/c1-25(2)7-4-8-26(3)14(25)6-5-11-17(26)16-15(22(32)36-23(16)33)12(9-27)21(11)35-24-20(31)19(30)18(29)13(10-28)34-24/h13-14,18-20,23-24,27-31,33H,4-10H2,1-3H3/t13-,14?,18-,19+,20-,23+,24+,26+/m1/s1
• InChI Key: OEPKOXUBUIKMNC-WMBLXUSHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₀
• Molecular Weight: 508.60 g/mol
• Exact Mass: 508.23084734 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.55
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7767	77.67%
Caco-2	-	0.8083	80.83%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8332	83.32%
OATP2B1 inhibitior	-	0.7173	71.73%
OATP1B1 inhibitior	+	0.8452	84.52%
OATP1B3 inhibitior	+	0.8808	88.08%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.5819	58.19%
P-glycoprotein inhibitior	-	0.5445	54.45%
P-glycoprotein substrate	-	0.7538	75.38%
CYP3A4 substrate	+	0.6972	69.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8657	86.57%
CYP3A4 inhibition	-	0.8805	88.05%
CYP2C9 inhibition	-	0.8375	83.75%
CYP2C19 inhibition	-	0.8086	80.86%
CYP2D6 inhibition	-	0.9307	93.07%
CYP1A2 inhibition	-	0.7632	76.32%
CYP2C8 inhibition	+	0.5397	53.97%
CYP inhibitory promiscuity	-	0.8772	87.72%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6245	62.45%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9239	92.39%
Skin irritation	-	0.7648	76.48%
Skin corrosion	-	0.9527	95.27%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5269	52.69%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7140	71.40%
skin sensitisation	-	0.9291	92.91%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7360	73.60%
Acute Oral Toxicity (c)	III	0.4353	43.53%
Estrogen receptor binding	+	0.6753	67.53%
Androgen receptor binding	+	0.6104	61.04%
Thyroid receptor binding	-	0.5954	59.54%
Glucocorticoid receptor binding	+	0.7006	70.06%
Aromatase binding	+	0.7418	74.18%
PPAR gamma	+	0.6027	60.27%
Honey bee toxicity	-	0.8082	80.82%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9778	97.78%

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	97.94%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.13%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.79%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.54%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.62%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.63%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.11%	96.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.04%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.19%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.44%	100.00%
CHEMBL220	P22303	Acetylcholinesterase	88.05%	94.45%
CHEMBL2083	P15090	Fatty acid binding protein adipocyte	87.99%	95.71%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.79%	90.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.87%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.59%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.36%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.25%	99.23%
CHEMBL4072	P07858	Cathepsin B	83.63%	93.67%
CHEMBL1937	Q92769	Histone deacetylase 2	83.23%	94.75%
CHEMBL237	P41145	Kappa opioid receptor	81.95%	98.10%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.62%	94.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.56%	96.37%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.87%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.53%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.13%	97.14%

Plants that contains it

• Betonica officinalis

Cross-Links

• PubChem: 101998021
• LOTUS: LTS0166648
• wikiData: Q105190453