Gyrophoric acid

Details

• Internal ID: fd043e67-b59f-4fe8-925a-1f14e45939e7
• Taxonomy: Phenylpropanoids and polyketides > Depsides and depsidones
• IUPAC Name: 4-[4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoyl]oxy-2-hydroxy-6-methylbenzoic acid
• SMILES (Canonical): CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)OC3=CC(=C(C(=C3)C)C(=O)O)O)O)O)O
• SMILES (Isomeric): CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)OC3=CC(=C(C(=C3)C)C(=O)O)O)O)O)O
• InChI: InChI=1S/C24H20O10/c1-10-4-13(25)7-16(26)20(10)23(31)34-15-6-12(3)21(18(28)9-15)24(32)33-14-5-11(2)19(22(29)30)17(27)8-14/h4-9,25-28H,1-3H3,(H,29,30)
• InChI Key: ATQPZSQVWCPVGV-UHFFFAOYSA-N
• Popularity: 147 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₀O₁₀
• Molecular Weight: 468.40 g/mol
• Exact Mass: 468.10564683 g/mol
• Topological Polar Surface Area (TPSA): 171.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• 548-89-0
• GYROPHORICACID
• NSC646006
• BAQ44A6C6H
• 4-[4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoyl]oxy-2-hydroxy-6-methylbenzoic acid
• UNII-BAQ44A6C6H
• 4-(4-(2,4-DIHYDROXY-6-METHYLBENZOYL)OXY-2-HYDROXY-6-METHYLBENZOYL)OXY-2-HYDROXY-6-METHYLBENZOIC ACID
• beta-Resorcylic acid, 6-methyl-, 4-(6-methyl-beta-resorcylate) 4-(6-methyl-beta-resorcylate); NSC 646006
• starbld0009598
• SpecPlus_000292
• Spectrum2_000208
• Spectrum4_000891
• Spectrum5_001823
• KBioGR_001322
• MLS000563513
• DivK1c_006388
• SPBio_000195
• CHEMBL470648
• SCHEMBL3800330
• KBio1_001332
• DTXSID30203289
• CHEBI:144159
• HMS2271K07
• HY-N3985
• CCG-40001
• STL564987
• AKOS015965527
• NSC-646006
• NCGC00247583-01
• AC-20252
• Benzoic acid, 4-((2,4-dihydroxy-6-methylbenzoyl)oxy)-2-hydroxy-6-methyl-, 4-carboxy-3-hydroxy-5-methylphenyl ester
• FS-10004
• NCI60_015819
• SMR000387062
• CS-0024568
• Q2244355
• B0005-124431
• -Resorcylic acid, 6-methyl-, 4-(6-methyl--resorcylate) 4-(6-methyl--resorcylate); NSC 646006
• 4-[4-(2,4-dihydroxy-6-methyl-benzoyl)oxy-2-hydroxy-6-methyl-benzoyl]oxy-2-hydroxy-6-methyl-benzoic acid
• 4-{[(4-{[(2,4-dihydroxy-6-methylphenyl)carbonyl]oxy}-2-hydroxy-6-methylphenyl)carbonyl]oxy}-2-hydroxy-6-methylbenzoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9506	95.06%
Caco-2	-	0.6338	63.38%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8895	88.95%
OATP2B1 inhibitior	-	0.5712	57.12%
OATP1B1 inhibitior	+	0.9640	96.40%
OATP1B3 inhibitior	-	0.5000	50.00%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5358	53.58%
P-glycoprotein inhibitior	+	0.5913	59.13%
P-glycoprotein substrate	-	0.9702	97.02%
CYP3A4 substrate	-	0.5814	58.14%
CYP2C9 substrate	-	0.6130	61.30%
CYP2D6 substrate	-	0.9089	90.89%
CYP3A4 inhibition	-	0.7914	79.14%
CYP2C9 inhibition	-	0.5787	57.87%
CYP2C19 inhibition	-	0.8708	87.08%
CYP2D6 inhibition	-	0.9003	90.03%
CYP1A2 inhibition	-	0.6210	62.10%
CYP2C8 inhibition	-	0.6769	67.69%
CYP inhibitory promiscuity	-	0.6703	67.03%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7356	73.56%
Carcinogenicity (trinary)	Non-required	0.7275	72.75%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.6631	66.31%
Skin irritation	-	0.8220	82.20%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8845	88.45%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.9158	91.58%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.5170	51.70%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5884	58.84%
Acute Oral Toxicity (c)	III	0.5364	53.64%
Estrogen receptor binding	+	0.8301	83.01%
Androgen receptor binding	+	0.6161	61.61%
Thyroid receptor binding	+	0.5352	53.52%
Glucocorticoid receptor binding	+	0.7498	74.98%
Aromatase binding	+	0.6760	67.60%
PPAR gamma	+	0.7434	74.34%
Honey bee toxicity	-	0.7720	77.20%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9943	99.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3194	P02766	Transthyretin	91.66%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.54%	99.15%
CHEMBL4208	P20618	Proteasome component C5	89.65%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.33%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.00%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.25%	96.09%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.42%	94.42%
CHEMBL3401	O75469	Pregnane X receptor	84.39%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.10%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.84%	99.17%
CHEMBL2581	P07339	Cathepsin D	83.77%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	82.24%	96.12%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	81.66%	95.70%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 135728
• LOTUS: LTS0257395
• wikiData: Q2244355