(1R,3aR,5S,8S,8aS,9S,9aS)-9-hydroxy-1,5,8-trimethyl-1,3a,4,5,8,8a,9,9a-octahydroazuleno[6,5-b]furan-2,7-dione

Details

• Internal ID: bcc0bffe-49f0-44a1-adc7-5b24fd7d9515
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (1R,3aR,5S,8S,8aS,9S,9aS)-9-hydroxy-1,5,8-trimethyl-1,3a,4,5,8,8a,9,9a-octahydroazuleno[6,5-b]furan-2,7-dione
• SMILES (Canonical): CC1CC2C(C(C(=O)O2)C)C(C3C1=CC(=O)C3C)O
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@@H]([C@H](C(=O)O2)C)[C@H]([C@@H]3C1=CC(=O)[C@H]3C)O
• InChI: InChI=1S/C15H20O4/c1-6-4-11-13(8(3)15(18)19-11)14(17)12-7(2)10(16)5-9(6)12/h5-8,11-14,17H,4H2,1-3H3/t6-,7+,8+,11+,12-,13+,14-/m0/s1
• InChI Key: VHTBTVRLPXVBLM-TYOVXKSESA-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): 63.60 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9790	97.90%
Caco-2	+	0.5784	57.84%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5868	58.68%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.9079	90.79%
OATP1B3 inhibitior	+	0.9540	95.40%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9017	90.17%
P-glycoprotein inhibitior	-	0.8820	88.20%
P-glycoprotein substrate	-	0.8107	81.07%
CYP3A4 substrate	+	0.5192	51.92%
CYP2C9 substrate	-	0.7791	77.91%
CYP2D6 substrate	-	0.8897	88.97%
CYP3A4 inhibition	-	0.8585	85.85%
CYP2C9 inhibition	-	0.8299	82.99%
CYP2C19 inhibition	-	0.8719	87.19%
CYP2D6 inhibition	-	0.9528	95.28%
CYP1A2 inhibition	-	0.5617	56.17%
CYP2C8 inhibition	-	0.9560	95.60%
CYP inhibitory promiscuity	-	0.9194	91.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Danger	0.4544	45.44%
Eye corrosion	-	0.9512	95.12%
Eye irritation	-	0.9517	95.17%
Skin irritation	-	0.5475	54.75%
Skin corrosion	-	0.8852	88.52%
Ames mutagenesis	-	0.7037	70.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4797	47.97%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6408	64.08%
skin sensitisation	-	0.7499	74.99%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7136	71.36%
Acute Oral Toxicity (c)	II	0.5160	51.60%
Estrogen receptor binding	-	0.5956	59.56%
Androgen receptor binding	-	0.5282	52.82%
Thyroid receptor binding	-	0.6765	67.65%
Glucocorticoid receptor binding	-	0.7768	77.68%
Aromatase binding	-	0.8703	87.03%
PPAR gamma	-	0.8227	82.27%
Honey bee toxicity	-	0.8728	87.28%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9213	92.13%

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	95.32%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.61%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.70%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.38%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.29%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.98%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.77%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.70%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.74%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.36%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.16%	99.23%

Plants that contains it

• Geigeria aspera

Cross-Links

• PubChem: 163044850
• LOTUS: LTS0058362
• wikiData: Q105286608