[(3S,4aR,6aR,8S,10R,10aR,10bS)-8-acetyloxy-3-ethenyl-3,4a,7,7,10a-pentamethyl-5-oxo-1,2,6,6a,8,9,10,10b-octahydrobenzo[f]chromen-10-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 2ca2a009-effa-44c6-b1e9-3b2c23bc9842
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3S,4aR,6aR,8S,10R,10aR,10bS)-8-acetyloxy-3-ethenyl-3,4a,7,7,10a-pentamethyl-5-oxo-1,2,6,6a,8,9,10,10b-octahydrobenzo[f]chromen-10-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C(C2C1(C3CCC(OC3(C(=O)C2)C)(C)C=C)C)(C)C)OC(=O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C[C@@H](C([C@@H]2[C@@]1([C@@H]3CC[C@@](O[C@]3(C(=O)C2)C)(C)C=C)C)(C)C)OC(=O)C
• InChI: InChI=1S/C27H40O6/c1-10-16(3)23(30)32-22-15-21(31-17(4)28)24(5,6)19-14-20(29)27(9)18(26(19,22)8)12-13-25(7,11-2)33-27/h10-11,18-19,21-22H,2,12-15H2,1,3-9H3/b16-10-/t18-,19+,21-,22+,25+,26-,27+/m0/s1
• InChI Key: HXIYGSKVKLNHSK-FAESAKHDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₆
• Molecular Weight: 460.60 g/mol
• Exact Mass: 460.28248899 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.95
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	-	0.5561	55.61%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6928	69.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8740	87.40%
OATP1B3 inhibitior	+	0.8033	80.33%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9432	94.32%
P-glycoprotein inhibitior	+	0.7411	74.11%
P-glycoprotein substrate	-	0.7612	76.12%
CYP3A4 substrate	+	0.6863	68.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9049	90.49%
CYP3A4 inhibition	-	0.5958	59.58%
CYP2C9 inhibition	-	0.8757	87.57%
CYP2C19 inhibition	-	0.7480	74.80%
CYP2D6 inhibition	-	0.9337	93.37%
CYP1A2 inhibition	-	0.5882	58.82%
CYP2C8 inhibition	+	0.5638	56.38%
CYP inhibitory promiscuity	-	0.9073	90.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6437	64.37%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.8510	85.10%
Skin irritation	-	0.5247	52.47%
Skin corrosion	-	0.9010	90.10%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7774	77.74%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.6362	63.62%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7360	73.60%
Acute Oral Toxicity (c)	III	0.6515	65.15%
Estrogen receptor binding	+	0.8948	89.48%
Androgen receptor binding	+	0.5724	57.24%
Thyroid receptor binding	+	0.6982	69.82%
Glucocorticoid receptor binding	+	0.7695	76.95%
Aromatase binding	+	0.7648	76.48%
PPAR gamma	+	0.7226	72.26%
Honey bee toxicity	-	0.6457	64.57%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9893	98.93%

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	96.92%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	92.24%	94.75%
CHEMBL340	P08684	Cytochrome P450 3A4	92.21%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.68%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.51%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.90%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.40%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.33%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.42%	89.00%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	86.24%	98.99%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.63%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.21%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.60%	93.04%
CHEMBL2581	P07339	Cathepsin D	84.26%	98.95%
CHEMBL5408	Q9UHD2	Serine/threonine-protein kinase TBK1	82.17%	90.48%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.99%	94.00%
CHEMBL325	Q13547	Histone deacetylase 1	81.37%	95.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.97%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.61%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.60%	95.89%
CHEMBL3524	P56524	Histone deacetylase 4	80.38%	92.97%

Plants that contains it

• Helichrysum ambiguum

Cross-Links

• PubChem: 162995212
• LOTUS: LTS0132856
• wikiData: Q105035031