2alpha,5alpha-Dihydroxy-11alphaH-eudesma-4(15)-en-12,8beta-olide

Details

• Internal ID: b8a07ee8-2df3-4854-b677-6c683e5a544d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aR,4aR,7S,8aR,9aR)-4a,7-dihydroxy-3,8a-dimethyl-5-methylidene-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CC3(C(=C)CC(CC3(CC2OC1=O)C)O)O
• SMILES (Isomeric): C[C@H]1[C@H]2C[C@]3(C(=C)C[C@@H](C[C@@]3(C[C@H]2OC1=O)C)O)O
• InChI: InChI=1S/C15H22O4/c1-8-4-10(16)5-14(3)7-12-11(6-15(8,14)18)9(2)13(17)19-12/h9-12,16,18H,1,4-7H2,2-3H3/t9-,10-,11+,12+,14+,15+/m0/s1
• InChI Key: KGJUZQMPTQIFAB-IDMWBNCISA-N
• Popularity: 1 reference 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: 1.10
• Atomic LogP (AlogP): 1.41
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 2alpha,5alpha-Dihydroxy-11alphaH-eudesma-4(15)-en-12,8beta-olide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9928	99.28%
Caco-2	+	0.6134	61.34%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6849	68.49%
OATP2B1 inhibitior	-	0.8510	85.10%
OATP1B1 inhibitior	+	0.9080	90.80%
OATP1B3 inhibitior	+	0.8815	88.15%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9159	91.59%
P-glycoprotein inhibitior	-	0.9372	93.72%
P-glycoprotein substrate	-	0.7669	76.69%
CYP3A4 substrate	+	0.5810	58.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8542	85.42%
CYP3A4 inhibition	-	0.5247	52.47%
CYP2C9 inhibition	-	0.9322	93.22%
CYP2C19 inhibition	-	0.8756	87.56%
CYP2D6 inhibition	-	0.9464	94.64%
CYP1A2 inhibition	-	0.8151	81.51%
CYP2C8 inhibition	-	0.9304	93.04%
CYP inhibitory promiscuity	-	0.8660	86.60%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5058	50.58%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8571	85.71%
Skin irritation	+	0.5439	54.39%
Skin corrosion	-	0.9192	91.92%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7181	71.81%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.6482	64.82%
skin sensitisation	-	0.6841	68.41%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.7911	79.11%
Acute Oral Toxicity (c)	III	0.4579	45.79%
Estrogen receptor binding	+	0.7886	78.86%
Androgen receptor binding	+	0.5792	57.92%
Thyroid receptor binding	+	0.5768	57.68%
Glucocorticoid receptor binding	+	0.7421	74.21%
Aromatase binding	+	0.5953	59.53%
PPAR gamma	-	0.6677	66.77%
Honey bee toxicity	-	0.8185	81.85%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9973	99.73%

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	94.57%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.54%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.17%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.95%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.85%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.78%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.60%	94.45%
CHEMBL299	P17252	Protein kinase C alpha	81.50%	98.03%
CHEMBL2581	P07339	Cathepsin D	80.89%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.24%	94.80%

Plants that contains it

• Carpesium faberi
• Carpesium macrocephalum

Cross-Links

• PubChem: 53323206
• NPASS: NPC147272
• LOTUS: LTS0167253
• wikiData: Q105140809