9a-Hydroxy-3,8a-dimethyl-5-methylene-4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one

Details

• Internal ID: 97d7e0b2-d805-4710-b26a-b7b280d1157a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4aS,8aS,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-4,4a,6,9-tetrahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2CC3C(=C)CC=CC3(CC2(OC1=O)O)C
• SMILES (Isomeric): CC1=C2C[C@H]3C(=C)CC=C[C@@]3(C[C@@]2(OC1=O)O)C
• InChI: InChI=1S/C15H18O3/c1-9-5-4-6-14(3)8-15(17)12(7-11(9)14)10(2)13(16)18-15/h4,6,11,17H,1,5,7-8H2,2-3H3/t11-,14+,15-/m0/s1
• InChI Key: VMGUBSLDEXOUMH-GLQYFDAESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.48
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 9a-Hydroxy-3,8a-dimethyl-5-methylene-4,4a,5,6,9,9a-hexahydronaphtho[2,3- b]furan-2(8aH)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6383	63.83%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6159	61.59%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8662	86.62%
OATP1B3 inhibitior	+	0.9325	93.25%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.7222	72.22%
P-glycoprotein inhibitior	-	0.9357	93.57%
P-glycoprotein substrate	-	0.8362	83.62%
CYP3A4 substrate	+	0.6046	60.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8742	87.42%
CYP3A4 inhibition	-	0.5847	58.47%
CYP2C9 inhibition	-	0.9039	90.39%
CYP2C19 inhibition	-	0.8248	82.48%
CYP2D6 inhibition	-	0.9607	96.07%
CYP1A2 inhibition	-	0.7357	73.57%
CYP2C8 inhibition	-	0.7967	79.67%
CYP inhibitory promiscuity	-	0.9150	91.50%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4538	45.38%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.8830	88.30%
Skin irritation	+	0.5132	51.32%
Skin corrosion	-	0.9132	91.32%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3698	36.98%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.7783	77.83%
skin sensitisation	-	0.6387	63.87%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6808	68.08%
Acute Oral Toxicity (c)	I	0.2642	26.42%
Estrogen receptor binding	-	0.7147	71.47%
Androgen receptor binding	+	0.5941	59.41%
Thyroid receptor binding	+	0.5241	52.41%
Glucocorticoid receptor binding	-	0.6362	63.62%
Aromatase binding	-	0.7333	73.33%
PPAR gamma	+	0.5677	56.77%
Honey bee toxicity	-	0.8771	87.71%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9961	99.61%

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	96.61%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.13%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.18%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.61%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.85%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.14%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.00%	96.09%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.77%	82.38%
CHEMBL3401	O75469	Pregnane X receptor	80.52%	94.73%

Plants that contains it

• Commiphora myrrha
• Lindera aggregata
• Lophophora williamsii
• Ophiopogon intermedius
• Porophyllum ruderale
• Traversia baccharoides

Cross-Links

• PubChem: 101938021
• NPASS: NPC114718
• LOTUS: LTS0270659
• wikiData: Q105288976