3-(8-Hydroxy-6,8-dimethyl-3-methylidene-2-oxo-3a,4,5,8a-tetrahydrocyclohepta[b]furan-7-yl)propanoic acid

Details

• Internal ID: 84909d16-42c6-4426-bab3-6e27a4c86d94
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 3-(8-hydroxy-6,8-dimethyl-3-methylidene-2-oxo-3a,4,5,8a-tetrahydrocyclohepta[b]furan-7-yl)propanoic acid
• SMILES (Canonical): CC1=C(C(C2C(CC1)C(=C)C(=O)O2)(C)O)CCC(=O)O
• SMILES (Isomeric): CC1=C(C(C2C(CC1)C(=C)C(=O)O2)(C)O)CCC(=O)O
• InChI: InChI=1S/C15H20O5/c1-8-4-5-10-9(2)14(18)20-13(10)15(3,19)11(8)6-7-12(16)17/h10,13,19H,2,4-7H2,1,3H3,(H,16,17)
• InChI Key: PPUVIGSDWLRHCY-UHFFFAOYSA-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): 83.80 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.81
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

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	+	0.5658	56.58%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6821	68.21%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.8626	86.26%
OATP1B3 inhibitior	+	0.9337	93.37%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7092	70.92%
BSEP inhibitior	-	0.9149	91.49%
P-glycoprotein inhibitior	-	0.8410	84.10%
P-glycoprotein substrate	-	0.8479	84.79%
CYP3A4 substrate	+	0.5783	57.83%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8964	89.64%
CYP3A4 inhibition	-	0.6010	60.10%
CYP2C9 inhibition	-	0.7881	78.81%
CYP2C19 inhibition	-	0.7651	76.51%
CYP2D6 inhibition	-	0.9320	93.20%
CYP1A2 inhibition	-	0.5744	57.44%
CYP2C8 inhibition	-	0.8084	80.84%
CYP inhibitory promiscuity	-	0.9456	94.56%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6013	60.13%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.6053	60.53%
Skin irritation	+	0.5532	55.32%
Skin corrosion	-	0.9034	90.34%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7010	70.10%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.7968	79.68%
skin sensitisation	-	0.7955	79.55%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6680	66.80%
Acute Oral Toxicity (c)	III	0.3764	37.64%
Estrogen receptor binding	+	0.6523	65.23%
Androgen receptor binding	+	0.5428	54.28%
Thyroid receptor binding	-	0.6469	64.69%
Glucocorticoid receptor binding	+	0.5983	59.83%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5107	51.07%
Honey bee toxicity	-	0.9331	93.31%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9898	98.98%

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	95.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.81%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	91.18%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.14%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.60%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.85%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.05%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	86.79%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.71%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.20%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	83.76%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.43%	94.45%

Plants that contains it

• Ambrosia tenuifolia

Cross-Links

• PubChem: 72746098
• LOTUS: LTS0220889
• wikiData: Q105213051