(3aR,7S,8aS)-6-[(1R,3S)-1,3-dihydroxybutyl]-7-methyl-3-methylidene-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: cbed880e-4b9d-4643-ab8b-237fdb2226a3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3aR,7S,8aS)-6-[(1R,3S)-1,3-dihydroxybutyl]-7-methyl-3-methylidene-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• SMILES (Canonical): CC1CC2C(CC=C1C(CC(C)O)O)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@H]2[C@H](CC=C1[C@@H](C[C@H](C)O)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H22O4/c1-8-6-14-12(10(3)15(18)19-14)5-4-11(8)13(17)7-9(2)16/h4,8-9,12-14,16-17H,3,5-7H2,1-2H3/t8-,9-,12+,13+,14-/m0/s1
• InChI Key: TVKYSIIBPQZNFW-HWLKSRQQSA-N
• Popularity: 0 references 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: 1.30
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9399	93.99%
Caco-2	+	0.7063	70.63%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4261	42.61%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.8983	89.83%
OATP1B3 inhibitior	+	0.9558	95.58%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8459	84.59%
P-glycoprotein inhibitior	-	0.9219	92.19%
P-glycoprotein substrate	-	0.7238	72.38%
CYP3A4 substrate	+	0.5424	54.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8270	82.70%
CYP3A4 inhibition	-	0.5540	55.40%
CYP2C9 inhibition	-	0.8656	86.56%
CYP2C19 inhibition	-	0.7811	78.11%
CYP2D6 inhibition	-	0.9321	93.21%
CYP1A2 inhibition	-	0.7392	73.92%
CYP2C8 inhibition	-	0.8601	86.01%
CYP inhibitory promiscuity	-	0.8084	80.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5604	56.04%
Eye corrosion	-	0.9771	97.71%
Eye irritation	-	0.5402	54.02%
Skin irritation	-	0.6157	61.57%
Skin corrosion	-	0.9243	92.43%
Ames mutagenesis	-	0.8170	81.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6115	61.15%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.7352	73.52%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6743	67.43%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6340	63.40%
Acute Oral Toxicity (c)	II	0.3960	39.60%
Estrogen receptor binding	-	0.6125	61.25%
Androgen receptor binding	-	0.5930	59.30%
Thyroid receptor binding	+	0.5895	58.95%
Glucocorticoid receptor binding	-	0.5106	51.06%
Aromatase binding	-	0.8228	82.28%
PPAR gamma	-	0.6007	60.07%
Honey bee toxicity	-	0.8724	87.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9776	97.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.38%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.96%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.99%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.74%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.16%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.11%	96.09%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.79%	96.37%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.20%	93.56%

Plants that contains it

• Xanthium spinosum

Cross-Links

• PubChem: 163189341
• LOTUS: LTS0142914
• wikiData: Q105265376