[(3aR,4S,6Z,10Z,11aR)-6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate

Details

• Internal ID: 13af9552-e3d9-48a0-9d15-58a3491cd6c9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4S,6Z,10Z,11aR)-6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC(=C)C(=O)OC1CC(=CCCC(=CC2C1C(=C)C(=O)O2)CO)CO
• SMILES (Isomeric): CC(=C)C(=O)O[C@H]1C/C(=C/CC/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/CO)/CO
• InChI: InChI=1S/C19H24O6/c1-11(2)18(22)24-15-7-13(9-20)5-4-6-14(10-21)8-16-17(15)12(3)19(23)25-16/h5,8,15-17,20-21H,1,3-4,6-7,9-10H2,2H3/b13-5-,14-8-/t15-,16+,17+/m0/s1
• InChI Key: CXDFJLQIPUJSIX-YINPGZOOSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.59
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9300	93.00%
Caco-2	-	0.6710	67.10%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8264	82.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9118	91.18%
OATP1B3 inhibitior	+	0.9594	95.94%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.7570	75.70%
BSEP inhibitior	-	0.7792	77.92%
P-glycoprotein inhibitior	-	0.7359	73.59%
P-glycoprotein substrate	-	0.6787	67.87%
CYP3A4 substrate	+	0.6127	61.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.8919	89.19%
CYP2C9 inhibition	-	0.8784	87.84%
CYP2C19 inhibition	-	0.8095	80.95%
CYP2D6 inhibition	-	0.9078	90.78%
CYP1A2 inhibition	-	0.6853	68.53%
CYP2C8 inhibition	-	0.7095	70.95%
CYP inhibitory promiscuity	-	0.8619	86.19%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.6470	64.70%
Eye corrosion	-	0.9635	96.35%
Eye irritation	-	0.7212	72.12%
Skin irritation	-	0.7429	74.29%
Skin corrosion	-	0.9364	93.64%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3843	38.43%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8600	86.00%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6302	63.02%
Acute Oral Toxicity (c)	III	0.5150	51.50%
Estrogen receptor binding	-	0.5273	52.73%
Androgen receptor binding	-	0.5442	54.42%
Thyroid receptor binding	-	0.5769	57.69%
Glucocorticoid receptor binding	+	0.6122	61.22%
Aromatase binding	-	0.5680	56.80%
PPAR gamma	-	0.5277	52.77%
Honey bee toxicity	-	0.7052	70.52%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9271	92.71%

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	98.56%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.65%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.80%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.00%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.87%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.07%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.39%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.27%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.06%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.59%	97.09%

Plants that contains it

• Gymnanthemum pectorale
• Jurinea albicaulis
• Jurinea eriobasis
• Jurinea leptoloba

Cross-Links

• PubChem: 102090434
• LOTUS: LTS0237401
• wikiData: Q104397232