(3aR,4R,8R,11aS)-4,8-dihydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,11,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: a7dbc075-e0b2-4645-8ce5-f49bdb3b344e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aR,4R,8R,11aS)-4,8-dihydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,11,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC(C=C(CC2C(C(C1)O)C(=C)C(=O)O2)C)O
• SMILES (Isomeric): CC1=C[C@H](C=C(C[C@H]2[C@@H]([C@@H](C1)O)C(=C)C(=O)O2)C)O
• InChI: InChI=1S/C15H20O4/c1-8-4-11(16)5-9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h4-5,11-14,16-17H,3,6-7H2,1-2H3/t11-,12-,13+,14-/m1/s1
• InChI Key: DUDNGOIZUFKVBJ-YIYPIFLZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9807	98.07%
Caco-2	+	0.7387	73.87%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4982	49.82%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.9166	91.66%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9416	94.16%
P-glycoprotein inhibitior	-	0.8684	86.84%
P-glycoprotein substrate	-	0.8978	89.78%
CYP3A4 substrate	-	0.5337	53.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.7987	79.87%
CYP2C9 inhibition	-	0.9098	90.98%
CYP2C19 inhibition	-	0.8432	84.32%
CYP2D6 inhibition	-	0.9328	93.28%
CYP1A2 inhibition	-	0.7779	77.79%
CYP2C8 inhibition	-	0.9494	94.94%
CYP inhibitory promiscuity	-	0.8909	89.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5151	51.51%
Eye corrosion	-	0.9564	95.64%
Eye irritation	-	0.6787	67.87%
Skin irritation	-	0.6054	60.54%
Skin corrosion	-	0.9094	90.94%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6047	60.47%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.7274	72.74%
skin sensitisation	-	0.7072	70.72%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6632	66.32%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6961	69.61%
Acute Oral Toxicity (c)	II	0.3364	33.64%
Estrogen receptor binding	-	0.6016	60.16%
Androgen receptor binding	-	0.4914	49.14%
Thyroid receptor binding	-	0.4892	48.92%
Glucocorticoid receptor binding	-	0.4867	48.67%
Aromatase binding	-	0.7432	74.32%
PPAR gamma	-	0.5872	58.72%
Honey bee toxicity	-	0.8288	82.88%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9448	94.48%

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	92.06%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.24%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.78%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.71%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.72%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.62%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.51%	93.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.15%	94.00%
CHEMBL2581	P07339	Cathepsin D	81.94%	98.95%

Plants that contains it

• Calostephane divaricata

Cross-Links

• PubChem: 162990900
• LOTUS: LTS0155387
• wikiData: Q104989176