4-(2,3,4-trihydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)but-3-en-2-one

Details

• Internal ID: 14a008fd-4a5d-4f2f-b37c-afa57e2f40f1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 4-(2,3,4-trihydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)but-3-en-2-one
• SMILES (Canonical): CC(=O)C=CC1C2(CCCC(C2C(C(C1(C)O)O)O)(C)C)C
• SMILES (Isomeric): CC(=O)C=CC1C2(CCCC(C2C(C(C1(C)O)O)O)(C)C)C
• InChI: InChI=1S/C18H30O4/c1-11(19)7-8-12-17(4)10-6-9-16(2,3)14(17)13(20)15(21)18(12,5)22/h7-8,12-15,20-22H,6,9-10H2,1-5H3
• InChI Key: GUVJPXABQYFWPD-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₀O₄
• Molecular Weight: 310.40 g/mol
• Exact Mass: 310.21440943 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9618	96.18%
Caco-2	-	0.5223	52.23%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6389	63.89%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.8815	88.15%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7104	71.04%
P-glycoprotein inhibitior	-	0.8795	87.95%
P-glycoprotein substrate	-	0.8345	83.45%
CYP3A4 substrate	+	0.5810	58.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8939	89.39%
CYP3A4 inhibition	-	0.7836	78.36%
CYP2C9 inhibition	-	0.8177	81.77%
CYP2C19 inhibition	-	0.8678	86.78%
CYP2D6 inhibition	-	0.9315	93.15%
CYP1A2 inhibition	-	0.5747	57.47%
CYP2C8 inhibition	-	0.8591	85.91%
CYP inhibitory promiscuity	-	0.8786	87.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6519	65.19%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9842	98.42%
Skin irritation	+	0.5234	52.34%
Skin corrosion	-	0.9071	90.71%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6034	60.34%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5676	56.76%
skin sensitisation	-	0.5873	58.73%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5648	56.48%
Acute Oral Toxicity (c)	III	0.6922	69.22%
Estrogen receptor binding	+	0.7118	71.18%
Androgen receptor binding	-	0.6222	62.22%
Thyroid receptor binding	+	0.6028	60.28%
Glucocorticoid receptor binding	+	0.6648	66.48%
Aromatase binding	+	0.5457	54.57%
PPAR gamma	-	0.5860	58.60%
Honey bee toxicity	-	0.8834	88.34%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9854	98.54%

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	94.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.13%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.51%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.93%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	84.63%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.23%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.12%	89.00%
CHEMBL2581	P07339	Cathepsin D	82.57%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	82.33%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	81.79%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.30%	94.45%

Plants that contains it

• Stevia rebaudiana

Cross-Links

• PubChem: 73823950
• LOTUS: LTS0029484
• wikiData: Q105020640