[(1S,2R,3R,4S,5S,6R)-3-acetyloxy-2,6-dihydroxy-5-[(Z)-2-methylbut-2-enoyl]oxy-4-(2-methylbut-2-enoyloxy)cyclohexyl] 2-methylbut-2-enoate

Details

• Internal ID: d6605bca-1386-455c-a33a-df77c1a9e20b
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: [(1S,2R,3R,4S,5S,6R)-3-acetyloxy-2,6-dihydroxy-5-[(Z)-2-methylbut-2-enoyl]oxy-4-(2-methylbut-2-enoyloxy)cyclohexyl] 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(C(C(C1O)OC(=O)C(=CC)C)OC(=O)C(=CC)C)OC(=O)C)O
• SMILES (Isomeric): CC=C(C)C(=O)O[C@H]1[C@H]([C@H]([C@@H]([C@H]([C@@H]1O)OC(=O)/C(=C\C)/C)OC(=O)C(=CC)C)OC(=O)C)O
• InChI: InChI=1S/C23H32O10/c1-8-11(4)21(27)31-17-15(25)18(30-14(7)24)20(33-23(29)13(6)10-3)19(16(17)26)32-22(28)12(5)9-2/h8-10,15-20,25-26H,1-7H3/b11-8?,12-9-,13-10?/t15-,16-,17+,18-,19+,20+/m1/s1
• InChI Key: ODTBYXFKNHAVFE-IPAZESSSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₂O₁₀
• Molecular Weight: 468.50 g/mol
• Exact Mass: 468.19954721 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9009	90.09%
Caco-2	-	0.6506	65.06%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7922	79.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9205	92.05%
OATP1B3 inhibitior	+	0.9345	93.45%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5126	51.26%
P-glycoprotein inhibitior	+	0.7053	70.53%
P-glycoprotein substrate	-	0.9726	97.26%
CYP3A4 substrate	-	0.5382	53.82%
CYP2C9 substrate	-	0.5954	59.54%
CYP2D6 substrate	-	0.8999	89.99%
CYP3A4 inhibition	-	0.9049	90.49%
CYP2C9 inhibition	-	0.8134	81.34%
CYP2C19 inhibition	-	0.8308	83.08%
CYP2D6 inhibition	-	0.8893	88.93%
CYP1A2 inhibition	-	0.9375	93.75%
CYP2C8 inhibition	-	0.9773	97.73%
CYP inhibitory promiscuity	-	0.8686	86.86%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7447	74.47%
Carcinogenicity (trinary)	Non-required	0.5580	55.80%
Eye corrosion	-	0.9583	95.83%
Eye irritation	-	0.7820	78.20%
Skin irritation	-	0.6002	60.02%
Skin corrosion	-	0.9572	95.72%
Ames mutagenesis	-	0.6737	67.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3906	39.06%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.6179	61.79%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.7298	72.98%
Acute Oral Toxicity (c)	IV	0.4771	47.71%
Estrogen receptor binding	+	0.5809	58.09%
Androgen receptor binding	-	0.7294	72.94%
Thyroid receptor binding	+	0.5336	53.36%
Glucocorticoid receptor binding	-	0.5437	54.37%
Aromatase binding	-	0.7647	76.47%
PPAR gamma	-	0.5184	51.84%
Honey bee toxicity	-	0.6712	67.12%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7655	76.55%
Fish aquatic toxicity	+	0.9405	94.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.01%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.76%	91.11%
CHEMBL2581	P07339	Cathepsin D	82.32%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	81.65%	91.19%

Plants that contains it

• Inula cappa

Cross-Links

• PubChem: 162818868
• LOTUS: LTS0125870
• wikiData: Q105190022