(3aS,4R,5Z,11aS)-4-hydroxy-6-methyl-3,10-dimethylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2,9-dione

Details

• Internal ID: 21bc677b-c73a-4675-bd7a-35cd7697fe89
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aS,4R,5Z,11aS)-4-hydroxy-6-methyl-3,10-dimethylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2,9-dione
• SMILES (Canonical): CC1=CC(C2C(CC(=C)C(=O)CC1)OC(=O)C2=C)O
• SMILES (Isomeric): C/C/1=C/[C@H]([C@H]2[C@H](CC(=C)C(=O)CC1)OC(=O)C2=C)O
• InChI: InChI=1S/C15H18O4/c1-8-4-5-11(16)9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h6,12-14,17H,2-5,7H2,1H3/b8-6-/t12-,13+,14+/m1/s1
• InChI Key: VHFDUPDINCLGLT-DSJGJMTKSA-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: 1.20
• Atomic LogP (AlogP): 1.70
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9810	98.10%
Caco-2	+	0.6054	60.54%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6351	63.51%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.9164	91.64%
OATP1B3 inhibitior	+	0.9267	92.67%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8919	89.19%
P-glycoprotein inhibitior	-	0.8866	88.66%
P-glycoprotein substrate	-	0.9307	93.07%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	-	0.8927	89.27%
CYP2C9 inhibition	-	0.9166	91.66%
CYP2C19 inhibition	-	0.8852	88.52%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	+	0.6591	65.91%
CYP2C8 inhibition	-	0.8759	87.59%
CYP inhibitory promiscuity	-	0.9642	96.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6059	60.59%
Eye corrosion	-	0.9250	92.50%
Eye irritation	+	0.5371	53.71%
Skin irritation	+	0.5312	53.12%
Skin corrosion	-	0.8873	88.73%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5777	57.77%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.7158	71.58%
skin sensitisation	-	0.7870	78.70%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.8018	80.18%
Acute Oral Toxicity (c)	III	0.4257	42.57%
Estrogen receptor binding	-	0.5663	56.63%
Androgen receptor binding	-	0.5618	56.18%
Thyroid receptor binding	-	0.6577	65.77%
Glucocorticoid receptor binding	+	0.5848	58.48%
Aromatase binding	-	0.7109	71.09%
PPAR gamma	-	0.5790	57.90%
Honey bee toxicity	-	0.8255	82.55%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9895	98.95%

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	93.85%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.56%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.36%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.32%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.84%	94.45%
CHEMBL2581	P07339	Cathepsin D	84.10%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.12%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.39%	100.00%

Plants that contains it

• Gonospermum revolutum
• Microliabum candidum
• Tanacetum argenteum
• Tanacetum aureum
• Tanacetum densum
• Tanacetum polycephalum
• Tanacetum praeteritum
• Tanacetum vulgare

Cross-Links

• PubChem: 102090479
• LOTUS: LTS0142101
• wikiData: Q104390077