(3S,3aR,4S,5E,9Z,11aR)-4-hydroxy-3,6-dimethyl-2-oxo-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-10-carboxylic acid

Details

• Internal ID: 2a5edd72-6a1a-40f6-9e36-9f0b4b312b26
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aR,4S,5E,9Z,11aR)-4-hydroxy-3,6-dimethyl-2-oxo-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-10-carboxylic acid
• SMILES (Canonical): CC1C2C(CC(=CCCC(=CC2O)C)C(=O)O)OC1=O
• SMILES (Isomeric): C[C@H]1[C@H]2[C@@H](C/C(=C/CC/C(=C/[C@@H]2O)/C)/C(=O)O)OC1=O
• InChI: InChI=1S/C15H20O5/c1-8-4-3-5-10(14(17)18)7-12-13(11(16)6-8)9(2)15(19)20-12/h5-6,9,11-13,16H,3-4,7H2,1-2H3,(H,17,18)/b8-6+,10-5-/t9-,11-,12+,13+/m0/s1
• InChI Key: NNWUEKCWSKTUCA-BJGCBDFLSA-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: 1.30
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9763	97.63%
Caco-2	+	0.5663	56.63%
Blood Brain Barrier	+	0.5855	58.55%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7631	76.31%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9328	93.28%
OATP1B3 inhibitior	+	0.9291	92.91%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	-	0.8740	87.40%
P-glycoprotein inhibitior	-	0.9351	93.51%
P-glycoprotein substrate	-	0.9113	91.13%
CYP3A4 substrate	-	0.5069	50.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9019	90.19%
CYP3A4 inhibition	-	0.6784	67.84%
CYP2C9 inhibition	-	0.9074	90.74%
CYP2C19 inhibition	-	0.9012	90.12%
CYP2D6 inhibition	-	0.9312	93.12%
CYP1A2 inhibition	+	0.6521	65.21%
CYP2C8 inhibition	-	0.8839	88.39%
CYP inhibitory promiscuity	-	0.9467	94.67%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5938	59.38%
Eye corrosion	-	0.9755	97.55%
Eye irritation	-	0.8927	89.27%
Skin irritation	-	0.5307	53.07%
Skin corrosion	-	0.9055	90.55%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6986	69.86%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5746	57.46%
skin sensitisation	-	0.8156	81.56%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.7184	71.84%
Acute Oral Toxicity (c)	II	0.4848	48.48%
Estrogen receptor binding	-	0.8350	83.50%
Androgen receptor binding	-	0.5693	56.93%
Thyroid receptor binding	-	0.7021	70.21%
Glucocorticoid receptor binding	-	0.5783	57.83%
Aromatase binding	-	0.8655	86.55%
PPAR gamma	-	0.7256	72.56%
Honey bee toxicity	-	0.8861	88.61%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7718	77.18%
Fish aquatic toxicity	+	0.9867	98.67%

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	92.80%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.31%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.53%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.61%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.58%	91.11%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	85.07%	86.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.79%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.58%	89.00%

Plants that contains it

• Schkuhria schkuhrioides

Cross-Links

• PubChem: 163105234
• LOTUS: LTS0194018
• wikiData: Q105182355