Xeromphalinone A

Details

• Internal ID: 1dc3386a-f810-441e-af12-47c82d036d03
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1S,3R,7R,8R,11S)-8-(hydroxymethyl)-5,5-dimethyl-9-methylidene-12-oxatetracyclo[6.4.0.01,11.03,7]dodecan-10-one
• SMILES (Canonical): CC1(CC2CC34C(O3)C(=O)C(=C)C4(C2C1)CO)C
• SMILES (Isomeric): CC1(C[C@@H]2C[C@]34[C@H](O3)C(=O)C(=C)[C@]4([C@@H]2C1)CO)C
• InChI: InChI=1S/C15H20O3/c1-8-11(17)12-15(18-12)5-9-4-13(2,3)6-10(9)14(8,15)7-16/h9-10,12,16H,1,4-7H2,2-3H3/t9-,10-,12-,14+,15-/m1/s1
• InChI Key: ARNIZSCCRGQMAQ-DTFMEENKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.70
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• ARNIZSCCRGQMAQ-DTFMEENKSA-
• CHEBI:208683
• (1S,3R,7R,8R,11S)-8-(hydroxymethyl)-5,5-dimethyl-9-methylidene-12-oxatetracyclo[6.4.0.01,11.03,7]dodecan-10-one
• InChI=1/C15H20O3/c1-8-11(17)12-15(18-12)5-9-4-13(2,3)6-10(9)14(8,15)7-16/h9-10,12,16H,1,4-7H2,2-3H3/t9-,10-,12-,14+,15-/m1/s1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9705	97.05%
Caco-2	+	0.7346	73.46%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6846	68.46%
OATP2B1 inhibitior	-	0.8502	85.02%
OATP1B1 inhibitior	+	0.9300	93.00%
OATP1B3 inhibitior	+	0.9584	95.84%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9217	92.17%
P-glycoprotein inhibitior	-	0.9397	93.97%
P-glycoprotein substrate	-	0.8601	86.01%
CYP3A4 substrate	+	0.5443	54.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8405	84.05%
CYP3A4 inhibition	-	0.7873	78.73%
CYP2C9 inhibition	-	0.7931	79.31%
CYP2C19 inhibition	-	0.7638	76.38%
CYP2D6 inhibition	-	0.9283	92.83%
CYP1A2 inhibition	-	0.7380	73.80%
CYP2C8 inhibition	-	0.8799	87.99%
CYP inhibitory promiscuity	-	0.8338	83.38%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6273	62.73%
Eye corrosion	-	0.9779	97.79%
Eye irritation	-	0.6830	68.30%
Skin irritation	-	0.6788	67.88%
Skin corrosion	-	0.9261	92.61%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7678	76.78%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.6432	64.32%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.7110	71.10%
Acute Oral Toxicity (c)	III	0.5209	52.09%
Estrogen receptor binding	+	0.8105	81.05%
Androgen receptor binding	+	0.6168	61.68%
Thyroid receptor binding	-	0.5244	52.44%
Glucocorticoid receptor binding	+	0.6362	63.62%
Aromatase binding	+	0.5244	52.44%
PPAR gamma	-	0.5757	57.57%
Honey bee toxicity	-	0.9109	91.09%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9109	91.09%

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	94.88%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.99%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.83%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	88.66%	90.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.29%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.24%	97.09%
CHEMBL2581	P07339	Cathepsin D	83.24%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.09%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.65%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	80.40%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 46217876
• LOTUS: LTS0028078
• wikiData: Q104917438