2-[(3aR,4S,5R,6S,8aS)-4,6,8a-trihydroxy-3-methyl-8-methylidene-1,3a,4,5,6,7-hexahydroazulen-5-yl]prop-2-enoic acid

Details

• Internal ID: e032d3d3-3418-4749-b0b8-dca030177d47
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: 2-[(3aR,4S,5R,6S,8aS)-4,6,8a-trihydroxy-3-methyl-8-methylidene-1,3a,4,5,6,7-hexahydroazulen-5-yl]prop-2-enoic acid
• SMILES (Canonical): CC1=CCC2(C1C(C(C(CC2=C)O)C(=C)C(=O)O)O)O
• SMILES (Isomeric): CC1=CC[C@@]2([C@H]1[C@H]([C@@H]([C@H](CC2=C)O)C(=C)C(=O)O)O)O
• 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/h4,10-13,16-17,20H,2-3,5-6H2,1H3,(H,18,19)/t10-,11+,12+,13-,15+/m0/s1
• InChI Key: KKQHLFPBXNSIAB-IHWVXMPCSA-N
• Popularity: 0 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: -0.50
• 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	+	0.9712	97.12%
Caco-2	-	0.8376	83.76%
Blood Brain Barrier	-	0.5473	54.73%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5113	51.13%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9276	92.76%
OATP1B3 inhibitior	+	0.9242	92.42%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9588	95.88%
BSEP inhibitior	-	0.9163	91.63%
P-glycoprotein inhibitior	-	0.9101	91.01%
P-glycoprotein substrate	-	0.7932	79.32%
CYP3A4 substrate	+	0.5681	56.81%
CYP2C9 substrate	-	0.6230	62.30%
CYP2D6 substrate	-	0.8848	88.48%
CYP3A4 inhibition	-	0.8933	89.33%
CYP2C9 inhibition	-	0.8530	85.30%
CYP2C19 inhibition	-	0.8130	81.30%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	-	0.7390	73.90%
CYP2C8 inhibition	-	0.8648	86.48%
CYP inhibitory promiscuity	-	0.9503	95.03%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9425	94.25%
Carcinogenicity (trinary)	Non-required	0.5584	55.84%
Eye corrosion	-	0.9808	98.08%
Eye irritation	-	0.8668	86.68%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8648	86.48%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6271	62.71%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.6845	68.45%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6334	63.34%
Acute Oral Toxicity (c)	III	0.4282	42.82%
Estrogen receptor binding	-	0.5531	55.31%
Androgen receptor binding	+	0.5477	54.77%
Thyroid receptor binding	-	0.5094	50.94%
Glucocorticoid receptor binding	+	0.6219	62.19%
Aromatase binding	-	0.6499	64.99%
PPAR gamma	-	0.5913	59.13%
Honey bee toxicity	-	0.9156	91.56%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9680	96.80%

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	92.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.89%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.81%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.52%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.69%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.20%	89.00%
CHEMBL4208	P20618	Proteasome component C5	80.88%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.67%	97.25%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.17%	95.50%

Plants that contains it

• Achillea coarctata

Cross-Links

• PubChem: 162956201
• LOTUS: LTS0178871
• wikiData: Q105142315