(3R,3aS,7R,9S,10Z,11aR)-7,9-dihydroxy-10-(hydroxymethyl)-3-methyl-6-methylidene-3,3a,4,5,7,8,9,11a-octahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 241b77a6-74f3-4800-bc40-520c1775aae4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3R,3aS,7R,9S,10Z,11aR)-7,9-dihydroxy-10-(hydroxymethyl)-3-methyl-6-methylidene-3,3a,4,5,7,8,9,11a-octahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2CCC(=C)C(CC(C(=CC2OC1=O)CO)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]2CCC(=C)[C@@H](C[C@@H](/C(=C\[C@@H]2OC1=O)/CO)O)O
• InChI: InChI=1S/C15H22O5/c1-8-3-4-11-9(2)15(19)20-14(11)5-10(7-16)13(18)6-12(8)17/h5,9,11-14,16-18H,1,3-4,6-7H2,2H3/b10-5-/t9-,11+,12-,13+,14+/m1/s1
• InChI Key: DXKDMYPOFFBVQD-WWZLGEPXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.54
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9555	95.55%
Caco-2	-	0.6192	61.92%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6202	62.02%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6113	61.13%
BSEP inhibitior	-	0.9465	94.65%
P-glycoprotein inhibitior	-	0.9362	93.62%
P-glycoprotein substrate	-	0.7865	78.65%
CYP3A4 substrate	+	0.5624	56.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	-	0.8461	84.61%
CYP2C9 inhibition	-	0.9162	91.62%
CYP2C19 inhibition	-	0.8629	86.29%
CYP2D6 inhibition	-	0.9114	91.14%
CYP1A2 inhibition	-	0.6947	69.47%
CYP2C8 inhibition	-	0.8879	88.79%
CYP inhibitory promiscuity	-	0.8910	89.10%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7063	70.63%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9036	90.36%
Skin irritation	-	0.6332	63.32%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	-	0.6078	60.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.7068	70.68%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.8657	86.57%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.5950	59.50%
Acute Oral Toxicity (c)	III	0.5307	53.07%
Estrogen receptor binding	+	0.6691	66.91%
Androgen receptor binding	-	0.5569	55.69%
Thyroid receptor binding	-	0.4924	49.24%
Glucocorticoid receptor binding	+	0.7551	75.51%
Aromatase binding	-	0.6487	64.87%
PPAR gamma	-	0.7182	71.82%
Honey bee toxicity	-	0.8759	87.59%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9176	91.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.52%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.47%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.17%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.99%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.53%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.55%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.69%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.81%	89.00%
CHEMBL2581	P07339	Cathepsin D	81.38%	98.95%
CHEMBL1871	P10275	Androgen Receptor	80.52%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.05%	95.89%

Plants that contains it

• Chrysanthemum naktongense

Cross-Links

• PubChem: 56968798
• LOTUS: LTS0254288
• wikiData: Q104991042