Petiolin A

Details

• Internal ID: ac2fb9e6-bb4f-4e10-852c-6f3847eae336
• Taxonomy: Organoheterocyclic compounds > Pyrans
• IUPAC Name: 5-hydroxy-2,8,8-trimethyl-2-(4-methylpent-3-enyl)-6-(2-methylpropanoyl)chromen-7-one
• SMILES (Canonical): CC(C)C(=O)C1=C(C2=C(C(C1=O)(C)C)OC(C=C2)(C)CCC=C(C)C)O
• SMILES (Isomeric): CC(C)C(=O)C1=C(C2=C(C(C1=O)(C)C)OC(C=C2)(C)CCC=C(C)C)O
• InChI: InChI=1S/C22H30O4/c1-13(2)9-8-11-22(7)12-10-15-18(24)16(17(23)14(3)4)19(25)21(5,6)20(15)26-22/h9-10,12,14,24H,8,11H2,1-7H3
• InChI Key: WCWBRLFAEDFKAR-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.50 g/mol
• Exact Mass: 358.21440943 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.98
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• CHEMBL496291

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	+	0.7596	75.96%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7200	72.00%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.7654	76.54%
OATP1B3 inhibitior	+	0.9565	95.65%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.4500	45.00%
P-glycoprotein inhibitior	-	0.6011	60.11%
P-glycoprotein substrate	-	0.7606	76.06%
CYP3A4 substrate	+	0.5870	58.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8791	87.91%
CYP3A4 inhibition	-	0.5334	53.34%
CYP2C9 inhibition	-	0.8617	86.17%
CYP2C19 inhibition	-	0.9374	93.74%
CYP2D6 inhibition	-	0.9202	92.02%
CYP1A2 inhibition	-	0.7199	71.99%
CYP2C8 inhibition	-	0.7806	78.06%
CYP inhibitory promiscuity	-	0.8629	86.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6281	62.81%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9073	90.73%
Skin irritation	+	0.5353	53.53%
Skin corrosion	-	0.8753	87.53%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3982	39.82%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.6135	61.35%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5723	57.23%
Acute Oral Toxicity (c)	III	0.7372	73.72%
Estrogen receptor binding	+	0.7732	77.32%
Androgen receptor binding	-	0.6081	60.81%
Thyroid receptor binding	+	0.7067	70.67%
Glucocorticoid receptor binding	+	0.7083	70.83%
Aromatase binding	+	0.6870	68.70%
PPAR gamma	+	0.8132	81.32%
Honey bee toxicity	-	0.8679	86.79%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9197	91.97%

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	99.02%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.55%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	94.77%	94.73%
CHEMBL2581	P07339	Cathepsin D	93.46%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.68%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.19%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.09%	96.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	88.27%	83.57%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.91%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	87.74%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.15%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.10%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.31%	99.17%

Plants that contains it

• Hypericum pseudopetiolatum

Cross-Links

• PubChem: 44576700
• LOTUS: LTS0000253
• wikiData: Q105302134