(1S,3R,4R,5R,7R,8R,10R,11R)-4,10-dihydroxy-5,8-dimethyl-9-methylidene-12-oxatetracyclo[6.4.0.01,11.03,7]dodecane-5-carboxylic acid

Details

• Internal ID: dba1fc0e-1f28-492e-9c95-e43c065facf7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1S,3R,4R,5R,7R,8R,10R,11R)-4,10-dihydroxy-5,8-dimethyl-9-methylidene-12-oxatetracyclo[6.4.0.01,11.03,7]dodecane-5-carboxylic acid
• SMILES (Canonical): CC1(CC2C(C1O)CC34C2(C(=C)C(C3O4)O)C)C(=O)O
• SMILES (Isomeric): C[C@]1(C[C@@H]2[C@H]([C@H]1O)C[C@]34[C@]2(C(=C)[C@H]([C@H]3O4)O)C)C(=O)O
• InChI: InChI=1S/C15H20O5/c1-6-9(16)11-15(20-11)4-7-8(14(6,15)3)5-13(2,10(7)17)12(18)19/h7-11,16-17H,1,4-5H2,2-3H3,(H,18,19)/t7-,8-,9-,10-,11-,13-,14+,15-/m1/s1
• InChI Key: WAKQWLLYKSZRIA-LFLQLQHVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 90.30 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.55
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9293	92.93%
Caco-2	-	0.6610	66.10%
Blood Brain Barrier	-	0.5723	57.23%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5988	59.88%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.8932	89.32%
OATP1B3 inhibitior	+	0.9356	93.56%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8977	89.77%
P-glycoprotein inhibitior	-	0.9329	93.29%
P-glycoprotein substrate	-	0.7789	77.89%
CYP3A4 substrate	+	0.5718	57.18%
CYP2C9 substrate	-	0.8149	81.49%
CYP2D6 substrate	-	0.8385	83.85%
CYP3A4 inhibition	-	0.7308	73.08%
CYP2C9 inhibition	-	0.8642	86.42%
CYP2C19 inhibition	-	0.8378	83.78%
CYP2D6 inhibition	-	0.9315	93.15%
CYP1A2 inhibition	-	0.6403	64.03%
CYP2C8 inhibition	-	0.8183	81.83%
CYP inhibitory promiscuity	-	0.9221	92.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6332	63.32%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.8855	88.55%
Skin irritation	-	0.5463	54.63%
Skin corrosion	-	0.9104	91.04%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.8422	84.22%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5409	54.09%
skin sensitisation	-	0.7445	74.45%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7516	75.16%
Acute Oral Toxicity (c)	III	0.3223	32.23%
Estrogen receptor binding	+	0.8970	89.70%
Androgen receptor binding	+	0.5903	59.03%
Thyroid receptor binding	+	0.5944	59.44%
Glucocorticoid receptor binding	+	0.6341	63.41%
Aromatase binding	-	0.5183	51.83%
PPAR gamma	+	0.5694	56.94%
Honey bee toxicity	-	0.8632	86.32%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.40%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.49%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.31%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.30%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.97%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.57%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.87%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.45%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.77%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.32%	97.25%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162964041
• LOTUS: LTS0175553
• wikiData: Q105300293