[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2E,4E)-5-[(1R,3R,7S,8S,9R)-7-acetyloxy-3-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoate

Details

• Internal ID: cc421b41-553f-4ee0-90e0-33b3472a1ed5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2E,4E)-5-[(1R,3R,7S,8S,9R)-7-acetyloxy-3-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoate
• SMILES (Canonical): CC1=CCC2(C3CCC2(CC1O)C(=O)OC3(C)C=CC=C(C)C(=O)OC4C(C(C(C(O4)CO)O)O)O)OC(=O)C
• SMILES (Isomeric): CC1=CC[C@@]2([C@H]3CC[C@]2(C[C@H]1O)C(=O)O[C@]3(C)/C=C/C=C(\C)/C(=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC(=O)C
• InChI: InChI=1S/C28H38O12/c1-14-7-11-28(39-16(3)30)19-8-10-27(28,12-17(14)31)25(36)40-26(19,4)9-5-6-15(2)23(35)38-24-22(34)21(33)20(32)18(13-29)37-24/h5-7,9,17-22,24,29,31-34H,8,10-13H2,1-4H3/b9-5+,15-6+/t17-,18-,19+,20-,21+,22-,24+,26-,27+,28+/m1/s1
• InChI Key: BKRBXZYJRMXVNW-PZUIDARMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₁₂
• Molecular Weight: 566.60 g/mol
• Exact Mass: 566.23632664 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.05
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7210	72.10%
Caco-2	-	0.8517	85.17%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7707	77.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8294	82.94%
OATP1B3 inhibitior	+	0.9214	92.14%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7048	70.48%
BSEP inhibitior	+	0.7528	75.28%
P-glycoprotein inhibitior	+	0.6460	64.60%
P-glycoprotein substrate	-	0.6823	68.23%
CYP3A4 substrate	+	0.7018	70.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8846	88.46%
CYP3A4 inhibition	-	0.9222	92.22%
CYP2C9 inhibition	-	0.8635	86.35%
CYP2C19 inhibition	-	0.9258	92.58%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.8953	89.53%
CYP2C8 inhibition	+	0.5784	57.84%
CYP inhibitory promiscuity	-	0.9592	95.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6945	69.45%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9280	92.80%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6479	64.79%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6669	66.69%
skin sensitisation	-	0.9108	91.08%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5266	52.66%
Acute Oral Toxicity (c)	I	0.4684	46.84%
Estrogen receptor binding	+	0.7681	76.81%
Androgen receptor binding	+	0.6688	66.88%
Thyroid receptor binding	+	0.5504	55.04%
Glucocorticoid receptor binding	+	0.7494	74.94%
Aromatase binding	+	0.6398	63.98%
PPAR gamma	+	0.5955	59.55%
Honey bee toxicity	-	0.7350	73.50%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9216	92.16%

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	97.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.90%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.23%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.91%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.92%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.56%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.16%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.11%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.14%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.71%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	85.32%	94.73%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.11%	94.80%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.52%	94.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.24%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.19%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	83.18%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.12%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.91%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.89%	93.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.70%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.09%	99.23%

Plants that contains it

• Pseudolarix amabilis

Cross-Links

• PubChem: 44421306
• LOTUS: LTS0082146
• wikiData: Q104937738