Plaunol B

Details

• Internal ID: c74d5012-0fd5-40d5-b68a-4a79427d985a
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1R,5'S,8S,9S,12R)-5'-(furan-3-yl)-12-(hydroxymethyl)-10-methylidenespiro[2-oxatricyclo[6.3.1.04,12]dodec-4-ene-9,3'-oxolane]-2',3-dione
• SMILES (Canonical): C=C1CC2C3(C(C14CC(OC4=O)C5=COC=C5)CCC=C3C(=O)O2)CO
• SMILES (Isomeric): C=C1C[C@@H]2[C@@]3([C@@H]([C@@]14C[C@H](OC4=O)C5=COC=C5)CCC=C3C(=O)O2)CO
• InChI: InChI=1S/C20H20O6/c1-11-7-16-20(10-21)13(17(22)26-16)3-2-4-15(20)19(11)8-14(25-18(19)23)12-5-6-24-9-12/h3,5-6,9,14-16,21H,1-2,4,7-8,10H2/t14-,15+,16+,19+,20-/m0/s1
• InChI Key: GQRWYOWPTLFVDK-AFJOWOCMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.12598835 g/mol
• Topological Polar Surface Area (TPSA): 86.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.45
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 69749-00-4
• C09166
• CHEBI:8265
• Q27108019
• (1R,5'S,8S,9S,12R)-5'-(furan-3-yl)-12-(hydroxymethyl)-10-methylidenespiro[2-oxatricyclo[6.3.1.04,12]dodec-4-ene-9,3'-oxolane]-2',3-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	-	0.7083	70.83%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8396	83.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8040	80.40%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.6696	66.96%
P-glycoprotein inhibitior	-	0.6665	66.65%
P-glycoprotein substrate	-	0.6779	67.79%
CYP3A4 substrate	+	0.6134	61.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8487	84.87%
CYP3A4 inhibition	-	0.5804	58.04%
CYP2C9 inhibition	-	0.7377	73.77%
CYP2C19 inhibition	-	0.7944	79.44%
CYP2D6 inhibition	-	0.8955	89.55%
CYP1A2 inhibition	-	0.7897	78.97%
CYP2C8 inhibition	+	0.5153	51.53%
CYP inhibitory promiscuity	-	0.7759	77.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.4566	45.66%
Eye corrosion	-	0.9696	96.96%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.7196	71.96%
Skin corrosion	-	0.9435	94.35%
Ames mutagenesis	-	0.5070	50.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6468	64.68%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.8322	83.22%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5973	59.73%
Acute Oral Toxicity (c)	III	0.5191	51.91%
Estrogen receptor binding	+	0.8092	80.92%
Androgen receptor binding	+	0.6086	60.86%
Thyroid receptor binding	-	0.5420	54.20%
Glucocorticoid receptor binding	+	0.6091	60.91%
Aromatase binding	+	0.6666	66.66%
PPAR gamma	+	0.6147	61.47%
Honey bee toxicity	-	0.8160	81.60%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9829	98.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	95.52%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.89%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.96%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.10%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.74%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.51%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.62%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.24%	95.83%

Plants that contains it

• Croton sublyratus
• Petasites radiatus
• Tephroseris kirilowii

Cross-Links

• PubChem: 442074
• NPASS: NPC267984
• LOTUS: LTS0115096
• wikiData: Q27108019