Gelastatin A

Details

• Internal ID: 0a780a63-73b6-4eb8-8bf6-f710afc1e0ab
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives > Dihydropyranones
• IUPAC Name: 3-[(5E)-5-[(2E,4E)-hexa-2,4-dienylidene]-2-oxopyran-3-yl]propanoic acid
• SMILES (Canonical): CC=CC=CC=C1COC(=O)C(=C1)CCC(=O)O
• SMILES (Isomeric): C/C=C/C=C/C=C\1/COC(=O)C(=C1)CCC(=O)O
• InChI: InChI=1S/C14H16O4/c1-2-3-4-5-6-11-9-12(7-8-13(15)16)14(17)18-10-11/h2-6,9H,7-8,10H2,1H3,(H,15,16)/b3-2+,5-4+,11-6+
• InChI Key: ACFXHMLFZGREFW-JCESNKCLSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.27 g/mol
• Exact Mass: 248.10485899 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 3-[(5E)-5-[(2E,4E)-hexa-2,4-dienylidene]-2-oxopyran-3-yl]propanoic acid
• 3-((5E)-5-((2E,4E)-hexa-2,4-dienylidene)-2-oxopyran-3-yl)propanoic acid
• RefChem:142821
• SCHEMBL10021375
• CHEBI:200481

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9496	94.96%
Caco-2	+	0.6100	61.00%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8967	89.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8875	88.75%
OATP1B3 inhibitior	+	0.9597	95.97%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6011	60.11%
P-glycoprotein inhibitior	-	0.9830	98.30%
P-glycoprotein substrate	-	0.8969	89.69%
CYP3A4 substrate	-	0.5211	52.11%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8975	89.75%
CYP3A4 inhibition	-	0.9537	95.37%
CYP2C9 inhibition	-	0.9455	94.55%
CYP2C19 inhibition	-	0.8958	89.58%
CYP2D6 inhibition	-	0.9179	91.79%
CYP1A2 inhibition	-	0.9290	92.90%
CYP2C8 inhibition	-	0.8935	89.35%
CYP inhibitory promiscuity	-	0.9837	98.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9128	91.28%
Carcinogenicity (trinary)	Non-required	0.7529	75.29%
Eye corrosion	-	0.9332	93.32%
Eye irritation	-	0.5959	59.59%
Skin irritation	-	0.6306	63.06%
Skin corrosion	-	0.9344	93.44%
Ames mutagenesis	+	0.5377	53.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.4431	44.31%
Micronuclear	-	0.8341	83.41%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.7688	76.88%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.7421	74.21%
Acute Oral Toxicity (c)	III	0.6973	69.73%
Estrogen receptor binding	+	0.6254	62.54%
Androgen receptor binding	+	0.5497	54.97%
Thyroid receptor binding	-	0.6506	65.06%
Glucocorticoid receptor binding	-	0.4836	48.36%
Aromatase binding	+	0.5747	57.47%
PPAR gamma	-	0.5744	57.44%
Honey bee toxicity	-	0.9682	96.82%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	+	0.7339	73.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.21%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.67%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.05%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.03%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.73%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	84.62%	89.63%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.13%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	83.98%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.86%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10198812
• LOTUS: LTS0068668
• wikiData: Q77278904