(3As,6Z,10E,11aR)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylic acid

Details

• Internal ID: 9668d93e-73ee-45f6-9bec-ccc6afb9511b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,6Z,10E,11aR)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylic acid
• SMILES (Canonical): CC1=CC2C(CCC(=CCC1)C(=O)O)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@@H]2[C@@H](CC/C(=C/CC1)/C(=O)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H18O4/c1-9-4-3-5-11(14(16)17)6-7-12-10(2)15(18)19-13(12)8-9/h5,8,12-13H,2-4,6-7H2,1H3,(H,16,17)/b9-8+,11-5-/t12-,13+/m0/s1
• InChI Key: KZWCOWFKXMTBRH-ZWXOUNMOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Taraxinic acid
• 75911-33-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	+	0.6456	64.56%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7266	72.66%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9249	92.49%
OATP1B3 inhibitior	+	0.9155	91.55%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6821	68.21%
BSEP inhibitior	-	0.8847	88.47%
P-glycoprotein inhibitior	-	0.9098	90.98%
P-glycoprotein substrate	-	0.9352	93.52%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.5914	59.14%
CYP2D6 substrate	-	0.9150	91.50%
CYP3A4 inhibition	-	0.8715	87.15%
CYP2C9 inhibition	-	0.8492	84.92%
CYP2C19 inhibition	-	0.8125	81.25%
CYP2D6 inhibition	-	0.9023	90.23%
CYP1A2 inhibition	+	0.7110	71.10%
CYP2C8 inhibition	-	0.7299	72.99%
CYP inhibitory promiscuity	-	0.9421	94.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6196	61.96%
Eye corrosion	-	0.9199	91.99%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.5364	53.64%
Skin corrosion	-	0.9066	90.66%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7481	74.81%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.7463	74.63%
skin sensitisation	-	0.6984	69.84%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.5657	56.57%
Acute Oral Toxicity (c)	III	0.4795	47.95%
Estrogen receptor binding	-	0.5688	56.88%
Androgen receptor binding	+	0.5452	54.52%
Thyroid receptor binding	-	0.6862	68.62%
Glucocorticoid receptor binding	+	0.6156	61.56%
Aromatase binding	-	0.7626	76.26%
PPAR gamma	-	0.6097	60.97%
Honey bee toxicity	-	0.9046	90.46%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9963	99.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.06%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.01%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.69%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.17%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.83%	93.03%
CHEMBL4040	P28482	MAP kinase ERK2	84.44%	83.82%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.97%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.83%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.46%	97.25%

Plants that contains it

• Taraxacum mongolicum

Cross-Links

• PubChem: 9921439
• NPASS: NPC124025