Goniobutenolide A

Details

• Internal ID: 273f403c-28e3-4e63-88ac-4c50a6e4f985
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (5E)-5-[(2S,3R)-2,3-dihydroxy-3-phenylpropylidene]furan-2-one
• SMILES (Canonical): C1=CC=C(C=C1)C(C(C=C2C=CC(=O)O2)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)[C@H]([C@H](/C=C/2\C=CC(=O)O2)O)O
• InChI: InChI=1S/C13H12O4/c14-11(8-10-6-7-12(15)17-10)13(16)9-4-2-1-3-5-9/h1-8,11,13-14,16H/b10-8+/t11-,13+/m0/s1
• InChI Key: XDLSRIVPCBODNQ-YRFMYUJQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.23 g/mol
• Exact Mass: 232.07355886 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.08
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• Goniobutenolide B
• CHEMBL3775075
• (5E)-5-[(2S,3R)-2,3-Dihydroxy-3-phenylpropylidene]furan-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9553	95.53%
Caco-2	+	0.6606	66.06%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6437	64.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9479	94.79%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9222	92.22%
P-glycoprotein inhibitior	-	0.9207	92.07%
P-glycoprotein substrate	-	0.9716	97.16%
CYP3A4 substrate	-	0.6522	65.22%
CYP2C9 substrate	-	0.6120	61.20%
CYP2D6 substrate	-	0.8516	85.16%
CYP3A4 inhibition	-	0.8707	87.07%
CYP2C9 inhibition	-	0.8986	89.86%
CYP2C19 inhibition	-	0.8508	85.08%
CYP2D6 inhibition	-	0.9580	95.80%
CYP1A2 inhibition	-	0.6013	60.13%
CYP2C8 inhibition	-	0.9413	94.13%
CYP inhibitory promiscuity	-	0.7560	75.60%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8419	84.19%
Carcinogenicity (trinary)	Non-required	0.4724	47.24%
Eye corrosion	-	0.8643	86.43%
Eye irritation	+	0.8190	81.90%
Skin irritation	+	0.6030	60.30%
Skin corrosion	-	0.9035	90.35%
Ames mutagenesis	-	0.7491	74.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.8169	81.69%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5335	53.35%
skin sensitisation	-	0.6405	64.05%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.4630	46.30%
Acute Oral Toxicity (c)	IV	0.5009	50.09%
Estrogen receptor binding	-	0.5411	54.11%
Androgen receptor binding	-	0.6638	66.38%
Thyroid receptor binding	-	0.5443	54.43%
Glucocorticoid receptor binding	-	0.6280	62.80%
Aromatase binding	-	0.5178	51.78%
PPAR gamma	+	0.5255	52.55%
Honey bee toxicity	-	0.8678	86.78%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.8920	89.20%

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	94.12%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.22%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.66%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.94%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.63%	94.08%
CHEMBL3401	O75469	Pregnane X receptor	85.64%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.64%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.39%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.99%	85.14%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.96%	94.23%
CHEMBL3902	P09211	Glutathione S-transferase Pi	81.85%	93.81%

Plants that contains it

• Goniothalamus amuyon
• Goniothalamus borneensis
• Goniothalamus giganteus
• Gymnacranthera farquhariana var. paniculata
• Lysimachia monelli
• Ornithogalum thyrsoides

Cross-Links

• PubChem: 11770317
• NPASS: NPC82426
• ChEMBL: CHEMBL3775075
• LOTUS: LTS0071573
• wikiData: Q105325826