[(1R,5R,6R,8R,8aR)-1-hydroxy-3,8-dimethyl-2-oxo-5-prop-1-en-2-yl-4,5,6,7,8,8a-hexahydro-1H-azulen-6-yl] 3-methylbutanoate

Details

• Internal ID: 21e2ef4c-93f3-4016-8a98-6c58af92b736
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: [(1R,5R,6R,8R,8aR)-1-hydroxy-3,8-dimethyl-2-oxo-5-prop-1-en-2-yl-4,5,6,7,8,8a-hexahydro-1H-azulen-6-yl] 3-methylbutanoate
• SMILES (Canonical): CC1CC(C(CC2=C(C(=O)C(C12)O)C)C(=C)C)OC(=O)CC(C)C
• SMILES (Isomeric): C[C@@H]1C[C@H]([C@H](CC2=C(C(=O)[C@@H]([C@H]12)O)C)C(=C)C)OC(=O)CC(C)C
• InChI: InChI=1S/C20H30O4/c1-10(2)7-17(21)24-16-8-12(5)18-15(9-14(16)11(3)4)13(6)19(22)20(18)23/h10,12,14,16,18,20,23H,3,7-9H2,1-2,4-6H3/t12-,14-,16-,18-,20-/m1/s1
• InChI Key: VOHXZWFGTMZFIP-VMVFICBVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.44
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9813	98.13%
Caco-2	+	0.5625	56.25%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7567	75.67%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.9035	90.35%
OATP1B3 inhibitior	+	0.8201	82.01%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5735	57.35%
P-glycoprotein inhibitior	-	0.6478	64.78%
P-glycoprotein substrate	-	0.5067	50.67%
CYP3A4 substrate	+	0.5868	58.68%
CYP2C9 substrate	-	0.7791	77.91%
CYP2D6 substrate	-	0.8952	89.52%
CYP3A4 inhibition	-	0.5252	52.52%
CYP2C9 inhibition	-	0.7489	74.89%
CYP2C19 inhibition	-	0.7813	78.13%
CYP2D6 inhibition	-	0.9111	91.11%
CYP1A2 inhibition	-	0.6965	69.65%
CYP2C8 inhibition	-	0.8859	88.59%
CYP inhibitory promiscuity	-	0.9214	92.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9117	91.17%
Carcinogenicity (trinary)	Non-required	0.6855	68.55%
Eye corrosion	-	0.9786	97.86%
Eye irritation	-	0.7863	78.63%
Skin irritation	-	0.5877	58.77%
Skin corrosion	-	0.9599	95.99%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5479	54.79%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6658	66.58%
skin sensitisation	-	0.6703	67.03%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6115	61.15%
Acute Oral Toxicity (c)	III	0.4792	47.92%
Estrogen receptor binding	+	0.5741	57.41%
Androgen receptor binding	+	0.5320	53.20%
Thyroid receptor binding	+	0.5260	52.60%
Glucocorticoid receptor binding	-	0.5255	52.55%
Aromatase binding	-	0.6990	69.90%
PPAR gamma	-	0.6896	68.96%
Honey bee toxicity	-	0.7983	79.83%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	96.90%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.70%	98.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	93.69%	96.47%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.07%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	87.54%	91.19%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.54%	97.21%
CHEMBL221	P23219	Cyclooxygenase-1	84.71%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.35%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.17%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.47%	93.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.09%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.07%	99.17%

Plants that contains it

• Moscharia pinnatifida

Cross-Links

• PubChem: 15143878
• LOTUS: LTS0038471
• wikiData: Q105290189