[(1S,2S,4aR,8aR)-1-hydroxy-1,4a-dimethyl-6-oxo-7-propan-2-ylidene-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: daa6ff9c-af89-469b-a7e4-512883d0fc4e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2S,4aR,8aR)-1-hydroxy-1,4a-dimethyl-6-oxo-7-propan-2-ylidene-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2(CC(=O)C(=C(C)C)CC2C1(C)O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CC[C@@]2(CC(=O)C(=C(C)C)C[C@H]2[C@]1(C)O)C
• InChI: InChI=1S/C20H30O4/c1-7-13(4)18(22)24-17-8-9-19(5)11-15(21)14(12(2)3)10-16(19)20(17,6)23/h7,16-17,23H,8-11H2,1-6H3/b13-7-/t16-,17+,19-,20+/m1/s1
• InChI Key: KNSVBXYIPSLXCS-KQSOIWLMSA-N
• Popularity: 0 references 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): 3.73
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9893	98.93%
Caco-2	+	0.8002	80.02%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8940	89.40%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.9078	90.78%
OATP1B3 inhibitior	-	0.3297	32.97%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.6071	60.71%
BSEP inhibitior	+	0.5553	55.53%
P-glycoprotein inhibitior	-	0.6453	64.53%
P-glycoprotein substrate	-	0.8380	83.80%
CYP3A4 substrate	+	0.6446	64.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9177	91.77%
CYP3A4 inhibition	-	0.7604	76.04%
CYP2C9 inhibition	-	0.8733	87.33%
CYP2C19 inhibition	-	0.8475	84.75%
CYP2D6 inhibition	-	0.9454	94.54%
CYP1A2 inhibition	-	0.7654	76.54%
CYP2C8 inhibition	-	0.8701	87.01%
CYP inhibitory promiscuity	-	0.9387	93.87%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6539	65.39%
Eye corrosion	-	0.9938	99.38%
Eye irritation	-	0.8579	85.79%
Skin irritation	+	0.5862	58.62%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4205	42.05%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5291	52.91%
skin sensitisation	-	0.5461	54.61%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6961	69.61%
Acute Oral Toxicity (c)	III	0.6185	61.85%
Estrogen receptor binding	+	0.7683	76.83%
Androgen receptor binding	-	0.5679	56.79%
Thyroid receptor binding	+	0.5724	57.24%
Glucocorticoid receptor binding	+	0.5998	59.98%
Aromatase binding	-	0.6282	62.82%
PPAR gamma	+	0.6646	66.46%
Honey bee toxicity	-	0.7939	79.39%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.41%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.48%	94.45%
CHEMBL284	P27487	Dipeptidyl peptidase IV	92.31%	95.69%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	91.98%	85.30%
CHEMBL2581	P07339	Cathepsin D	90.68%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.62%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	88.17%	91.19%
CHEMBL1937	Q92769	Histone deacetylase 2	88.08%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.02%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.01%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.01%	93.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.99%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.27%	99.23%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	85.27%	80.96%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.65%	93.04%
CHEMBL217	P14416	Dopamine D2 receptor	84.44%	95.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.25%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.39%	100.00%
CHEMBL325	Q13547	Histone deacetylase 1	82.25%	95.92%
CHEMBL4040	P28482	MAP kinase ERK2	82.14%	83.82%
CHEMBL299	P17252	Protein kinase C alpha	81.78%	98.03%
CHEMBL1902	P62942	FK506-binding protein 1A	81.20%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.13%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.09%	93.03%

Plants that contains it

• Neurolaena lobata

Cross-Links

• PubChem: 162911243
• LOTUS: LTS0141622
• wikiData: Q105143558