Fascicularone B

Details

• Internal ID: 9c59fdaf-823b-451d-a696-01d2f0afffe0
• Taxonomy: Organoheterocyclic compounds > Lactones
• IUPAC Name: (1S,2R,3S,6S,7S,10R,12R)-1,10-dihydroxy-2,5,5,12-tetramethyl-8-oxatetracyclo[5.5.0.02,10.03,6]dodecan-9-one
• SMILES (Canonical): CC1CC2(C(=O)OC3C1(C2(C4C3C(C4)(C)C)C)O)O
• SMILES (Isomeric): C[C@@H]1C[C@@]2(C(=O)O[C@@H]3[C@]1([C@]2([C@@H]4[C@H]3C(C4)(C)C)C)O)O
• InChI: InChI=1S/C15H22O4/c1-7-5-14(17)11(16)19-10-9-8(6-12(9,2)3)13(14,4)15(7,10)18/h7-10,17-18H,5-6H2,1-4H3/t7-,8+,9-,10+,13+,14+,15-/m1/s1
• InChI Key: JHJQFYPUGZHONZ-PCHBDJRGSA-N
• Popularity: 1 reference 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: 1.70
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• (1S,2R,3S,6S,7S,10R,12R)-1,10-Dihydroxy-2,5,5,12-tetramethyl-8-oxatetracyclo[5.5.0.02,10.03,6]dodecan-9-one
• (1S,2R,3S,6S,7S,10R,12R)-1,10-dihydroxy-2,5,5,12-tetramethyl-8-oxatetracyclo(5.5.0.02,10.03,6)dodecan-9-one
• RefChem:139982
• 681027-88-3
• CHEBI:202568

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8954	89.54%
Caco-2	+	0.6585	65.85%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4845	48.45%
OATP2B1 inhibitior	-	0.8501	85.01%
OATP1B1 inhibitior	+	0.9181	91.81%
OATP1B3 inhibitior	+	0.9407	94.07%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9067	90.67%
P-glycoprotein inhibitior	-	0.9086	90.86%
P-glycoprotein substrate	-	0.8744	87.44%
CYP3A4 substrate	+	0.5520	55.20%
CYP2C9 substrate	+	0.6063	60.63%
CYP2D6 substrate	-	0.8136	81.36%
CYP3A4 inhibition	-	0.8116	81.16%
CYP2C9 inhibition	-	0.8875	88.75%
CYP2C19 inhibition	-	0.8587	85.87%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.7476	74.76%
CYP2C8 inhibition	-	0.9586	95.86%
CYP inhibitory promiscuity	-	0.9818	98.18%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6331	63.31%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.8627	86.27%
Skin irritation	-	0.5848	58.48%
Skin corrosion	-	0.8704	87.04%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7125	71.25%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.6002	60.02%
skin sensitisation	-	0.8023	80.23%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7573	75.73%
Acute Oral Toxicity (c)	III	0.4238	42.38%
Estrogen receptor binding	+	0.7529	75.29%
Androgen receptor binding	+	0.6422	64.22%
Thyroid receptor binding	+	0.5693	56.93%
Glucocorticoid receptor binding	-	0.5994	59.94%
Aromatase binding	-	0.6031	60.31%
PPAR gamma	-	0.7072	70.72%
Honey bee toxicity	-	0.9071	90.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8010	80.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.00%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.09%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.04%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.27%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.67%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.89%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.79%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.43%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.91%	93.04%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.38%	96.61%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 12149381
• LOTUS: LTS0256787
• wikiData: Q77372156