(3aR,4S,6E,10E,11aR)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 8646a27f-06b3-4313-bdf3-c692e325dea0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aR,4S,6E,10E,11aR)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CCCC(=CC2C(C(C1)O)C(=C)C(=O)O2)CO
• SMILES (Isomeric): C/C/1=C\CC/C(=C\[C@@H]2[C@@H]([C@H](C1)O)C(=C)C(=O)O2)/CO
• InChI: InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-13-14(12(17)6-9)10(2)15(18)19-13/h4,7,12-14,16-17H,2-3,5-6,8H2,1H3/b9-4+,11-7+/t12-,13+,14+/m0/s1
• InChI Key: BLDTUWFMPJJRPR-SOTOPDJXSA-N
• Popularity: 0 references 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: 0.60
• Atomic LogP (AlogP): 1.49
• 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	+	0.9824	98.24%
Caco-2	+	0.6166	61.66%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6352	63.52%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9272	92.72%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6281	62.81%
BSEP inhibitior	-	0.9417	94.17%
P-glycoprotein inhibitior	-	0.8820	88.20%
P-glycoprotein substrate	-	0.8439	84.39%
CYP3A4 substrate	+	0.5255	52.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
CYP3A4 inhibition	-	0.6986	69.86%
CYP2C9 inhibition	-	0.9170	91.70%
CYP2C19 inhibition	-	0.8656	86.56%
CYP2D6 inhibition	-	0.9204	92.04%
CYP1A2 inhibition	-	0.6072	60.72%
CYP2C8 inhibition	-	0.8634	86.34%
CYP inhibitory promiscuity	-	0.9161	91.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6550	65.50%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.7937	79.37%
Skin irritation	-	0.5753	57.53%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7965	79.65%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5426	54.26%
skin sensitisation	-	0.8765	87.65%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4994	49.94%
Estrogen receptor binding	-	0.7916	79.16%
Androgen receptor binding	-	0.6016	60.16%
Thyroid receptor binding	-	0.7167	71.67%
Glucocorticoid receptor binding	+	0.6456	64.56%
Aromatase binding	-	0.7622	76.22%
PPAR gamma	-	0.6026	60.26%
Honey bee toxicity	-	0.8817	88.17%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9684	96.84%

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	93.02%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.25%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.11%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	85.90%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.68%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.11%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.26%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.20%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.71%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.03%	86.33%

Plants that contains it

• Salvia miltiorrhiza

Cross-Links

• PubChem: 10333019
• NPASS: NPC276305