Gonioheptolide A

Details

• Internal ID: 0237d064-e7f9-4265-97d8-3deb15e258f2
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: methyl (3R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-phenyloxolan-2-yl]-3-hydroxypropanoate
• InChI: InChI=1S/C14H18O6/c1-19-10(16)7-9(15)14-12(18)11(17)13(20-14)8-5-3-2-4-6-8/h2-6,9,11-15,17-18H,7H2,1H3/t9-,11+,12+,13-,14+/m1/s1
• InChI Key: YCKKAXDZPAQYOF-YTLQFRNZSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₆
• Molecular Weight: 282.29 g/mol
• Exact Mass: 282.11033829 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• (-)-gonioheptolide A
• CHEMBL592727
• Methyl (3R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-phenyloxolan-2-yl]-3-hydroxypropanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7016	70.16%
Caco-2	-	0.5245	52.45%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6897	68.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9352	93.52%
OATP1B3 inhibitior	+	0.9399	93.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9408	94.08%
P-glycoprotein inhibitior	-	0.8815	88.15%
P-glycoprotein substrate	-	0.8822	88.22%
CYP3A4 substrate	-	0.5283	52.83%
CYP2C9 substrate	-	0.8047	80.47%
CYP2D6 substrate	-	0.8075	80.75%
CYP3A4 inhibition	-	0.9102	91.02%
CYP2C9 inhibition	-	0.8789	87.89%
CYP2C19 inhibition	-	0.8259	82.59%
CYP2D6 inhibition	-	0.8970	89.70%
CYP1A2 inhibition	-	0.8682	86.82%
CYP2C8 inhibition	-	0.7837	78.37%
CYP inhibitory promiscuity	-	0.7732	77.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9311	93.11%
Carcinogenicity (trinary)	Non-required	0.6216	62.16%
Eye corrosion	-	0.9814	98.14%
Eye irritation	-	0.9477	94.77%
Skin irritation	-	0.6787	67.87%
Skin corrosion	-	0.9290	92.90%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4558	45.58%
Micronuclear	-	0.5323	53.23%
Hepatotoxicity	-	0.5943	59.43%
skin sensitisation	-	0.8702	87.02%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6639	66.39%
Acute Oral Toxicity (c)	III	0.6349	63.49%
Estrogen receptor binding	-	0.6947	69.47%
Androgen receptor binding	-	0.6541	65.41%
Thyroid receptor binding	-	0.6708	67.08%
Glucocorticoid receptor binding	-	0.7663	76.63%
Aromatase binding	-	0.8311	83.11%
PPAR gamma	-	0.5571	55.71%
Honey bee toxicity	-	0.9108	91.08%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.6504	65.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.74%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.98%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	96.28%	90.17%
CHEMBL2581	P07339	Cathepsin D	93.42%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.31%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	90.71%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.49%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	86.86%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.62%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.17%	96.00%
CHEMBL5028	O14672	ADAM10	84.83%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.91%	86.33%

Plants that contains it

• Goniothalamus giganteus

Cross-Links

• PubChem: 9993900
• LOTUS: LTS0159455
• wikiData: Q105346339