(3aR,4S,6aR,8S,9S,9aR,9bR)-4,8-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: b4059a94-6caa-4bc5-8625-9d86e0b3fb00
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,4S,6aR,8S,9S,9aR,9bR)-4,8-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C(CC2C1C3C(C(CC2=C)O)C(=C)C(=O)O3)O
• SMILES (Isomeric): C[C@@H]1[C@H](C[C@@H]2[C@H]1[C@@H]3[C@@H]([C@H](CC2=C)O)C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H20O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7,9-14,16-17H,1,3-5H2,2H3/t7-,9+,10+,11+,12+,13-,14-/m1/s1
• InChI Key: FHYQPZNZWJKLKK-FUCUMGKVSA-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): 66.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.4888	48.88%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4601	46.01%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.8532	85.32%
OATP1B3 inhibitior	+	0.9548	95.48%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9533	95.33%
P-glycoprotein inhibitior	-	0.9007	90.07%
P-glycoprotein substrate	-	0.7616	76.16%
CYP3A4 substrate	+	0.5389	53.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.8246	82.46%
CYP2C9 inhibition	-	0.9112	91.12%
CYP2C19 inhibition	-	0.8194	81.94%
CYP2D6 inhibition	-	0.9450	94.50%
CYP1A2 inhibition	-	0.6285	62.85%
CYP2C8 inhibition	-	0.9397	93.97%
CYP inhibitory promiscuity	-	0.9134	91.34%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9425	94.25%
Carcinogenicity (trinary)	Non-required	0.4981	49.81%
Eye corrosion	-	0.9431	94.31%
Eye irritation	+	0.5602	56.02%
Skin irritation	-	0.5268	52.68%
Skin corrosion	-	0.8590	85.90%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6504	65.04%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.8158	81.58%
skin sensitisation	-	0.7348	73.48%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6097	60.97%
Acute Oral Toxicity (c)	III	0.4038	40.38%
Estrogen receptor binding	+	0.6542	65.42%
Androgen receptor binding	-	0.4852	48.52%
Thyroid receptor binding	-	0.5485	54.85%
Glucocorticoid receptor binding	+	0.7148	71.48%
Aromatase binding	-	0.7091	70.91%
PPAR gamma	-	0.7787	77.87%
Honey bee toxicity	-	0.7051	70.51%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9515	95.15%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.35%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.62%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.71%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.70%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.34%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.11%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.04%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.86%	95.50%
CHEMBL2581	P07339	Cathepsin D	80.37%	98.95%

Plants that contains it

• Centaurea behen

Cross-Links

• PubChem: 14378125
• LOTUS: LTS0176998
• wikiData: Q104995514