(3S,3aS,6Z,10Z,11aS)-6,10-bis(hydroxymethyl)-3-methyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: 200e1bf2-7980-45fe-8a0e-624296beadc9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aS,6Z,10Z,11aS)-6,10-bis(hydroxymethyl)-3-methyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2CCC(=CCCC(=CC2OC1=O)CO)CO
• SMILES (Isomeric): C[C@H]1[C@@H]2CC/C(=C/CC/C(=C/[C@H]2OC1=O)/CO)/CO
• InChI: InChI=1S/C15H22O4/c1-10-13-6-5-11(8-16)3-2-4-12(9-17)7-14(13)19-15(10)18/h3,7,10,13-14,16-17H,2,4-6,8-9H2,1H3/b11-3-,12-7-/t10-,13-,14+/m0/s1
• InChI Key: FZXDIRFGXUFCPH-OMTBHUEDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.58
• 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	+	0.9709	97.09%
Caco-2	+	0.7045	70.45%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7259	72.59%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.9237	92.37%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6320	63.20%
BSEP inhibitior	-	0.8543	85.43%
P-glycoprotein inhibitior	-	0.9280	92.80%
P-glycoprotein substrate	-	0.8368	83.68%
CYP3A4 substrate	+	0.5087	50.87%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.8233	82.33%
CYP2C9 inhibition	-	0.8542	85.42%
CYP2C19 inhibition	-	0.7861	78.61%
CYP2D6 inhibition	-	0.8577	85.77%
CYP1A2 inhibition	-	0.5140	51.40%
CYP2C8 inhibition	-	0.9308	93.08%
CYP inhibitory promiscuity	-	0.7925	79.25%
UGT catelyzed	-	0.7638	76.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6121	61.21%
Eye corrosion	-	0.9734	97.34%
Eye irritation	-	0.8455	84.55%
Skin irritation	-	0.6840	68.40%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.6178	61.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.6775	67.75%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8295	82.95%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7010	70.10%
Acute Oral Toxicity (c)	III	0.5514	55.14%
Estrogen receptor binding	+	0.5446	54.46%
Androgen receptor binding	-	0.5683	56.83%
Thyroid receptor binding	-	0.6688	66.88%
Glucocorticoid receptor binding	+	0.6832	68.32%
Aromatase binding	-	0.7837	78.37%
PPAR gamma	-	0.6952	69.52%
Honey bee toxicity	-	0.9201	92.01%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9487	94.87%

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	97.63%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.64%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.18%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.85%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.32%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.03%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.41%	100.00%
CHEMBL2581	P07339	Cathepsin D	86.87%	98.95%
CHEMBL4072	P07858	Cathepsin B	80.46%	93.67%

Plants that contains it

• Ixeris tamagawaensis

Cross-Links

• PubChem: 163193681
• LOTUS: LTS0245748
• wikiData: Q105005225