Diffractaic Acid

Details

• Internal ID: f8e9aaa9-d83f-4fe9-9c82-f5a732e70d84
• Taxonomy: Phenylpropanoids and polyketides > Depsides and depsidones
• IUPAC Name: 4-(2,4-dimethoxy-3,6-dimethylbenzoyl)oxy-2-hydroxy-3,6-dimethylbenzoic acid
• InChI: InChI=1S/C20H22O7/c1-9-8-14(11(3)17(21)15(9)19(22)23)27-20(24)16-10(2)7-13(25-5)12(4)18(16)26-6/h7-8,21H,1-6H3,(H,22,23)
• InChI Key: MIJKZXWOOXIEEU-UHFFFAOYSA-N
• Popularity: 35 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₇
• Molecular Weight: 374.40 g/mol
• Exact Mass: 374.13655304 g/mol
• Topological Polar Surface Area (TPSA): 102.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 3.56
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 436-32-8
• 4-(2,4-dimethoxy-3,6-dimethylbenzoyl)oxy-2-hydroxy-3,6-dimethylbenzoic acid
• NSC-685595
• PD86RC383X
• DTXSID40195883
• NSC-5901
• Benzoic acid, 2,4-dimethoxy-3,6-dimethyl-, 4-carboxy-3-hydroxy-2,5-dimethylphenyl ester
• beta-Resorcylic acid, 3,6-dimethyl-, 4-(2,4-dimethoxy-3,6-dimethylbenzoate)
• RefChem:920174
• DTXCID80118374
• Diffractic acid
• Dirbizomic acid
• Dirhizomic acid
• DIFFRACTOIC ACID
• DIFFRACTANIC ACID
• Difractaic acid
• NSC5901
• NSC685595
• NSC 5901; NSC 685595
• DiffracticAcid
• 4-(2,4-dimethoxy-3,6-dimethyl-benzoyl)oxy-2-hydroxy-3,6-dimethyl-benzoic acid
• NSC 5901
• NSC 685595
• BRN 2915070
• Diffractasaure
• DIFFRATIC ACID
• Spectrum_000043
• SpecPlus_000832
• Spectrum2_000730
• Spectrum3_001103
• Spectrum4_001934
• Spectrum5_000723
• UNII-PD86RC383X
• BSPBio_002806
• KBioGR_002309
• KBioSS_000423
• 3-10-00-01544 (Beilstein Handbook Reference)
• MLS001049104
• DivK1c_006928
• SPECTRUM1504118
• SPBio_000660
• CHEMBL367741
• orb1303148
• SCHEMBL3459615
• KBio1_001872
• KBio2_000423
• KBio2_002991
• KBio2_005559
• KBio3_002026
• CHEBI:107634
• HY-N2399
• CCG-39676
• MFCD01684770
• STL564827
• AKOS015969704
• NCGC00095683-01
• NCGC00095683-02
• NCGC00095683-03
• AC-34168
• DA-72757
• MS-26050
• SMR000386936
• XD165792
• CS-0022601
• SR-01000758212
• SR-01000758212-2
• BRD-K51370144-001-02-3
• BRD-K51370144-001-06-4
• Q27185958
• 4-(2,4-Dimethoxy-3,6-dimethylphenylcarbonyloxy)-2-hydroxy-3,6-dimethylbenzoic acid
• 4-[(2,4-dimethoxy-3,6-dimethylphenyl)-oxomethoxy]-2-hydroxy-3,6-dimethylbenzoic acid
• 4-{[(2,4-dimethoxy-3,6-dimethylphenyl)carbonyl]oxy}-2-hydroxy-3,6-dimethylbenzoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9450	94.50%
Caco-2	+	0.7618	76.18%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8663	86.63%
OATP2B1 inhibitior	-	0.7207	72.07%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5549	55.49%
P-glycoprotein inhibitior	-	0.6484	64.84%
P-glycoprotein substrate	-	0.8970	89.70%
CYP3A4 substrate	-	0.5394	53.94%
CYP2C9 substrate	-	0.6089	60.89%
CYP2D6 substrate	-	0.8933	89.33%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.7343	73.43%
CYP2C19 inhibition	-	0.8817	88.17%
CYP2D6 inhibition	-	0.8907	89.07%
CYP1A2 inhibition	-	0.6138	61.38%
CYP2C8 inhibition	+	0.5635	56.35%
CYP inhibitory promiscuity	-	0.6980	69.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7156	71.56%
Carcinogenicity (trinary)	Non-required	0.7193	71.93%
Eye corrosion	-	0.9856	98.56%
Eye irritation	+	0.6022	60.22%
Skin irritation	-	0.8241	82.41%
Skin corrosion	-	0.9491	94.91%
Ames mutagenesis	-	0.6164	61.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6094	60.94%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.6569	65.69%
skin sensitisation	-	0.9583	95.83%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.6059	60.59%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9023	90.23%
Acute Oral Toxicity (c)	II	0.6323	63.23%
Estrogen receptor binding	+	0.8601	86.01%
Androgen receptor binding	+	0.5395	53.95%
Thyroid receptor binding	-	0.5165	51.65%
Glucocorticoid receptor binding	+	0.5937	59.37%
Aromatase binding	+	0.6530	65.30%
PPAR gamma	+	0.7237	72.37%
Honey bee toxicity	-	0.8777	87.77%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	19952.6 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1741189	P55789	FAD-linked sulfhydryl oxidase ALR	784 nM	AC50	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	707.9 nM; 707.9 nM; 562.3 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	10000 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	22387.2 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.80%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.50%	95.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.74%	97.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.57%	86.33%
CHEMBL3194	P02766	Transthyretin	87.48%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.04%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.72%	96.09%
CHEMBL1255126	O15151	Protein Mdm4	85.96%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.69%	99.17%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.66%	94.42%
CHEMBL2581	P07339	Cathepsin D	83.12%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.70%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.10%	89.00%

Plants that contains it

• Allium cepa
• Illicium difengpi

Cross-Links

• PubChem: 94870
• NPASS: NPC233267
• ChEMBL: CHEMBL367741
• LOTUS: LTS0256505
• wikiData: Q27185958