(3aR,4S,9aS,9bR)-4-hydroxy-6,9-dimethyl-3-methylidene-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: a281ae33-b0b8-48b0-9fb5-37ce475d30ce
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,4S,9aS,9bR)-4-hydroxy-6,9-dimethyl-3-methylidene-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=C2CC=C(C2C3C(C(C1)O)C(=C)C(=O)O3)C
• SMILES (Isomeric): CC1=C2CC=C([C@@H]2[C@@H]3[C@@H]([C@H](C1)O)C(=C)C(=O)O3)C
• InChI: InChI=1S/C15H18O3/c1-7-4-5-10-8(2)6-11(16)13-9(3)15(17)18-14(13)12(7)10/h4,11-14,16H,3,5-6H2,1-2H3/t11-,12-,13+,14+/m0/s1
• InChI Key: ANSNHOYHRRPFIU-IGQOVBAYSA-N
• Popularity: 0 references 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: 1.10
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 3
• 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	+	0.9962	99.62%
Caco-2	+	0.6674	66.74%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4411	44.11%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.9281	92.81%
OATP1B3 inhibitior	+	0.9537	95.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9620	96.20%
P-glycoprotein inhibitior	-	0.9034	90.34%
P-glycoprotein substrate	-	0.8247	82.47%
CYP3A4 substrate	+	0.5082	50.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.7629	76.29%
CYP2C9 inhibition	-	0.9239	92.39%
CYP2C19 inhibition	-	0.8647	86.47%
CYP2D6 inhibition	-	0.9465	94.65%
CYP1A2 inhibition	-	0.5169	51.69%
CYP2C8 inhibition	-	0.9182	91.82%
CYP inhibitory promiscuity	-	0.9371	93.71%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5126	51.26%
Eye corrosion	-	0.9423	94.23%
Eye irritation	-	0.6603	66.03%
Skin irritation	+	0.4936	49.36%
Skin corrosion	-	0.8839	88.39%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7032	70.32%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.8495	84.95%
skin sensitisation	-	0.6265	62.65%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.8523	85.23%
Acute Oral Toxicity (c)	III	0.3847	38.47%
Estrogen receptor binding	-	0.7639	76.39%
Androgen receptor binding	+	0.5752	57.52%
Thyroid receptor binding	-	0.6900	69.00%
Glucocorticoid receptor binding	-	0.5204	52.04%
Aromatase binding	-	0.8233	82.33%
PPAR gamma	-	0.6695	66.95%
Honey bee toxicity	-	0.7644	76.44%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9758	97.58%

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	91.36%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.69%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.90%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	88.90%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.14%	99.23%
CHEMBL2581	P07339	Cathepsin D	85.59%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.32%	89.00%

Plants that contains it

• Picradeniopsis oppositifolia
• Stevia myriadenia

Cross-Links

• PubChem: 14829040
• LOTUS: LTS0160357
• wikiData: Q104915380