(3aR,5Z,9Z,11aS)-6,10-bis(hydroxymethyl)-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: d5a3e29a-4c50-4f19-894c-b4b20ede05eb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aR,5Z,9Z,11aS)-6,10-bis(hydroxymethyl)-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): C=C1C2CC=C(CCC=C(CC2OC1=O)CO)CO
• SMILES (Isomeric): C=C1[C@H]2C/C=C(/CC/C=C(/C[C@@H]2OC1=O)\CO)\CO
• InChI: InChI=1S/C15H20O4/c1-10-13-6-5-11(8-16)3-2-4-12(9-17)7-14(13)19-15(10)18/h4-5,13-14,16-17H,1-3,6-9H2/b11-5-,12-4-/t13-,14+/m1/s1
• InChI Key: BIWFCYHZMKXRAY-UEDUBJLOSA-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: 0.50
• Atomic LogP (AlogP): 1.50
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9500	95.00%
Caco-2	+	0.5715	57.15%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7620	76.20%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.9096	90.96%
OATP1B3 inhibitior	+	0.9551	95.51%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6820	68.20%
BSEP inhibitior	-	0.9335	93.35%
P-glycoprotein inhibitior	-	0.9323	93.23%
P-glycoprotein substrate	-	0.9256	92.56%
CYP3A4 substrate	-	0.5257	52.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8091	80.91%
CYP3A4 inhibition	-	0.9183	91.83%
CYP2C9 inhibition	-	0.9043	90.43%
CYP2C19 inhibition	-	0.7963	79.63%
CYP2D6 inhibition	-	0.8935	89.35%
CYP1A2 inhibition	-	0.7449	74.49%
CYP2C8 inhibition	-	0.7265	72.65%
CYP inhibitory promiscuity	-	0.8926	89.26%
UGT catelyzed	-	0.7638	76.38%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6573	65.73%
Eye corrosion	-	0.9448	94.48%
Eye irritation	+	0.7109	71.09%
Skin irritation	-	0.7700	77.00%
Skin corrosion	-	0.9307	93.07%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8541	85.41%
Hepatotoxicity	+	0.6050	60.50%
skin sensitisation	-	0.8239	82.39%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6471	64.71%
Acute Oral Toxicity (c)	III	0.5547	55.47%
Estrogen receptor binding	-	0.5673	56.73%
Androgen receptor binding	-	0.5737	57.37%
Thyroid receptor binding	-	0.6607	66.07%
Glucocorticoid receptor binding	+	0.6711	67.11%
Aromatase binding	-	0.6576	65.76%
PPAR gamma	-	0.5883	58.83%
Honey bee toxicity	-	0.8219	82.19%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8758	87.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.18%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.04%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.47%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.69%	95.56%
CHEMBL2581	P07339	Cathepsin D	81.42%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.25%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.21%	100.00%
CHEMBL4208	P20618	Proteasome component C5	80.18%	90.00%

Plants that contains it

• Mikania cordifolia

Cross-Links

• PubChem: 163003029
• LOTUS: LTS0147160
• wikiData: Q104936835