Megacerotonic acid

Details

• Internal ID: 0f1c0326-e365-42d8-87da-c690fb78314a
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: (2R,3R,4Z)-3-(3,4-dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid
• SMILES (Canonical): C1=CC(=CC=C1C=C2C(C(OC2=O)C(=O)O)C3=CC(=C(C=C3)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C\2/[C@H]([C@@H](OC2=O)C(=O)O)C3=CC(=C(C=C3)O)O)O
• InChI: InChI=1S/C18H14O7/c19-11-4-1-9(2-5-11)7-12-15(16(17(22)23)25-18(12)24)10-3-6-13(20)14(21)8-10/h1-8,15-16,19-21H,(H,22,23)/b12-7-/t15-,16-/m1/s1
• InChI Key: ARPWMKRUUOTSGU-BXCZJDEJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₄O₇
• Molecular Weight: 342.30 g/mol
• Exact Mass: 342.07395278 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• (2R,3R,4Z)-3-(3,4-Dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9712	97.12%
Caco-2	-	0.9189	91.89%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8182	81.82%
OATP2B1 inhibitior	-	0.5769	57.69%
OATP1B1 inhibitior	+	0.9299	92.99%
OATP1B3 inhibitior	+	0.8951	89.51%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5934	59.34%
P-glycoprotein inhibitior	-	0.8679	86.79%
P-glycoprotein substrate	-	0.9618	96.18%
CYP3A4 substrate	-	0.5454	54.54%
CYP2C9 substrate	-	0.7982	79.82%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.8467	84.67%
CYP2C9 inhibition	+	0.7497	74.97%
CYP2C19 inhibition	+	0.5866	58.66%
CYP2D6 inhibition	-	0.8970	89.70%
CYP1A2 inhibition	+	0.6035	60.35%
CYP2C8 inhibition	+	0.5060	50.60%
CYP inhibitory promiscuity	+	0.7186	71.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8843	88.43%
Carcinogenicity (trinary)	Non-required	0.4468	44.68%
Eye corrosion	-	0.9876	98.76%
Eye irritation	+	0.6812	68.12%
Skin irritation	-	0.6329	63.29%
Skin corrosion	-	0.9262	92.62%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7554	75.54%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	+	0.5317	53.17%
skin sensitisation	-	0.6549	65.49%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.5795	57.95%
Acute Oral Toxicity (c)	III	0.4450	44.50%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.7267	72.67%
Thyroid receptor binding	+	0.5251	52.51%
Glucocorticoid receptor binding	+	0.6032	60.32%
Aromatase binding	-	0.6605	66.05%
PPAR gamma	+	0.5487	54.87%
Honey bee toxicity	-	0.8392	83.92%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9974	99.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.87%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.00%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.91%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.89%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.43%	99.15%
CHEMBL3194	P02766	Transthyretin	90.06%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.96%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.53%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.45%	99.23%
CHEMBL2581	P07339	Cathepsin D	81.41%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.92%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.01%	99.17%

Plants that contains it

• Megaceros flagellaris

Cross-Links

• PubChem: 14729377
• LOTUS: LTS0212876
• wikiData: Q104917506