1alpha,6alpha,8alpha-trihydroxy-5alpha,7betaH-guaia-3,9,11(13)-trien-12-oic acid

Details

• Internal ID: 373500f5-4c8d-46c8-8d03-a3e41e06b1c7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: 2-[(3aR,4S,5R,6S,8aS)-4,6,8a-trihydroxy-3,8-dimethyl-3a,4,5,6-tetrahydro-1H-azulen-5-yl]prop-2-enoic acid
• InChI: InChI=1S/C15H20O5/c1-7-4-5-15(20)8(2)6-10(16)11(9(3)14(18)19)13(17)12(7)15/h4,6,10-13,16-17,20H,3,5H2,1-2H3,(H,18,19)/t10-,11+,12+,13-,15+/m0/s1
• InChI Key: PURFAWWKECSNFN-IHWVXMPCSA-N
• Popularity: 2 references 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): 98.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9659	96.59%
Caco-2	-	0.6601	66.01%
Blood Brain Barrier	+	0.5777	57.77%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Lysosomes	0.5302	53.02%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9260	92.60%
OATP1B3 inhibitior	+	0.9334	93.34%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9088	90.88%
BSEP inhibitior	-	0.9205	92.05%
P-glycoprotein inhibitior	-	0.9355	93.55%
P-glycoprotein substrate	-	0.8316	83.16%
CYP3A4 substrate	+	0.5612	56.12%
CYP2C9 substrate	-	0.6230	62.30%
CYP2D6 substrate	-	0.8848	88.48%
CYP3A4 inhibition	-	0.8170	81.70%
CYP2C9 inhibition	-	0.8743	87.43%
CYP2C19 inhibition	-	0.8515	85.15%
CYP2D6 inhibition	-	0.9236	92.36%
CYP1A2 inhibition	-	0.7771	77.71%
CYP2C8 inhibition	-	0.8204	82.04%
CYP inhibitory promiscuity	-	0.9259	92.59%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9225	92.25%
Carcinogenicity (trinary)	Non-required	0.5780	57.80%
Eye corrosion	-	0.9799	97.99%
Eye irritation	-	0.9030	90.30%
Skin irritation	+	0.5417	54.17%
Skin corrosion	-	0.8432	84.32%
Ames mutagenesis	-	0.5654	56.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7081	70.81%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.6238	62.38%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6320	63.20%
Acute Oral Toxicity (c)	III	0.3542	35.42%
Estrogen receptor binding	-	0.6596	65.96%
Androgen receptor binding	-	0.5779	57.79%
Thyroid receptor binding	-	0.5620	56.20%
Glucocorticoid receptor binding	-	0.5185	51.85%
Aromatase binding	-	0.6042	60.42%
PPAR gamma	+	0.6283	62.83%
Honey bee toxicity	-	0.8995	89.95%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9307	93.07%

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	91.26%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.33%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.19%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.40%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.63%	97.25%
CHEMBL4208	P20618	Proteasome component C5	83.76%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.70%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.06%	89.00%

Plants that contains it

• Achillea coarctata

Cross-Links

• PubChem: 162817346
• LOTUS: LTS0211859
• wikiData: Q105215236