(S)-(+)-Gentiolactone

Details

• Internal ID: f8d4c680-90d6-4bc5-8d6a-20bf574e22be
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives > Dihydropyranones
• IUPAC Name: (4S)-4-ethyl-4-hydroxy-5,6-dihydro-1H-pyrano[3,4-c]pyran-3,8-dione
• SMILES (Canonical): CCC1(C2=C(COC1=O)C(=O)OCC2)O
• SMILES (Isomeric): CC[C@@]1(C2=C(COC1=O)C(=O)OCC2)O
• InChI: InChI=1S/C10H12O5/c1-2-10(13)7-3-4-14-8(11)6(7)5-15-9(10)12/h13H,2-5H2,1H3/t10-/m0/s1
• InChI Key: YOWUDEPRYODFBZ-JTQLQIEISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.20 g/mol
• Exact Mass: 212.06847348 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.07
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9488	94.88%
Caco-2	+	0.5525	55.25%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8892	88.92%
OATP2B1 inhibitior	-	0.8425	84.25%
OATP1B1 inhibitior	+	0.9341	93.41%
OATP1B3 inhibitior	+	0.9454	94.54%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7276	72.76%
BSEP inhibitior	-	0.9599	95.99%
P-glycoprotein inhibitior	-	0.9620	96.20%
P-glycoprotein substrate	-	0.9352	93.52%
CYP3A4 substrate	-	0.5553	55.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8809	88.09%
CYP3A4 inhibition	-	0.9126	91.26%
CYP2C9 inhibition	-	0.9221	92.21%
CYP2C19 inhibition	-	0.8668	86.68%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.9105	91.05%
CYP2C8 inhibition	-	0.9590	95.90%
CYP inhibitory promiscuity	-	0.9630	96.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4810	48.10%
Eye corrosion	-	0.9864	98.64%
Eye irritation	+	0.8557	85.57%
Skin irritation	-	0.5929	59.29%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	+	0.6163	61.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.6885	68.85%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.7428	74.28%
skin sensitisation	-	0.8650	86.50%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.7307	73.07%
Acute Oral Toxicity (c)	III	0.5649	56.49%
Estrogen receptor binding	-	0.6400	64.00%
Androgen receptor binding	+	0.6274	62.74%
Thyroid receptor binding	-	0.8170	81.70%
Glucocorticoid receptor binding	-	0.5653	56.53%
Aromatase binding	-	0.7603	76.03%
PPAR gamma	-	0.8009	80.09%
Honey bee toxicity	-	0.9357	93.57%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8929	89.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	91.42%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.88%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.85%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.61%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.64%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.89%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.48%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.92%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	81.19%	89.63%

Plants that contains it

• Gentiana crassa subsp. rigescens
• Gentiana manshurica
• Gentiana scabra

Cross-Links

• PubChem: 11052961
• NPASS: NPC156749