Psoromic acid

Details

• Internal ID: ce1ffe1c-3c99-45b1-b0b5-3663c882f18b
• Taxonomy: Phenylpropanoids and polyketides > Depsides and depsidones
• IUPAC Name: 10-formyl-9-hydroxy-3-methoxy-4,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-1-carboxylic acid
• SMILES (Canonical): CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C(=CC(=C3C)OC)C(=O)O)C=O)O
• SMILES (Isomeric): CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C(=CC(=C3C)OC)C(=O)O)C=O)O
• InChI: InChI=1S/C18H14O8/c1-7-4-11(20)10(6-19)15-13(7)18(23)26-14-8(2)12(24-3)5-9(17(21)22)16(14)25-15/h4-6,20H,1-3H3,(H,21,22)
• InChI Key: FUCWJKJZOHOLEO-UHFFFAOYSA-N
• Popularity: 82 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₄O₈
• Molecular Weight: 358.30 g/mol
• Exact Mass: 358.06886740 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.85
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• Parellic acid
• 7299-11-8
• NSC-92186
• Psoromic acid (parellic acid)
• PSOROMICACID
• CHEMBL176570
• NSC92186
• NSC 92186
• 4-Formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid
• 11H-Dibenzo(b,e)(1,4)dioxepin-6-carboxylic acid, 4-formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-
• 4-formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-6-carboxylic acid
• Parellic acid, 3
• Spectrum_000493
• SpecPlus_000286
• Spectrum2_000214
• Spectrum3_000160
• Spectrum4_001484
• Spectrum5_000187
• NCIOpen2_009926
• BSPBio_001900
• KBioGR_002087
• KBioSS_000973
• cid_23725
• MLS000563148
• DivK1c_006382
• SPBio_000227
• SCHEMBL2113679
• CHEBI:92074
• KBio1_001326
• KBio2_000973
• KBio2_003541
• KBio2_006109
• KBio3_001120
• DTXSID70223264
• FUCWJKJZOHOLEO-UHFFFAOYSA-N
• HMS2268L13
• BDBM50056939
• CCG-38361
• MFCD00046941
• 4-Formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxodibenzo[b,f]1,4-dioxepin-6-carboxylic acid
• NCGC00178916-01
• 10-formyl-9-hydroxy-3-methoxy-4,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-1-carboxylic acid
• LS-60972
• SMR000470881
• FT-0700762
• Q27163869
• 10-formyl-9-hydroxy-3-methoxy-4,7-dimethyl-6-oxo-1-benzo[b][1,4]benzodioxepincarboxylic acid
• 10-formyl-9-hydroxy-3-methoxy-4,7-dimethyl-6-oxo-benzo[b][1,4]benzodioxepine-1-carboxylic acid
• 10-formyl-9-hydroxy-6-keto-3-methoxy-4,7-dimethyl-benzo[b][1,4]benzodioxepin-1-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9372	93.72%
Caco-2	+	0.6202	62.02%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6579	65.79%
OATP2B1 inhibitior	-	0.7132	71.32%
OATP1B1 inhibitior	+	0.7301	73.01%
OATP1B3 inhibitior	-	0.4458	44.58%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7055	70.55%
P-glycoprotein inhibitior	-	0.6719	67.19%
P-glycoprotein substrate	-	0.8879	88.79%
CYP3A4 substrate	-	0.5399	53.99%
CYP2C9 substrate	+	0.5789	57.89%
CYP2D6 substrate	-	0.8829	88.29%
CYP3A4 inhibition	-	0.8783	87.83%
CYP2C9 inhibition	-	0.9470	94.70%
CYP2C19 inhibition	-	0.9283	92.83%
CYP2D6 inhibition	-	0.9204	92.04%
CYP1A2 inhibition	-	0.8242	82.42%
CYP2C8 inhibition	+	0.5690	56.90%
CYP inhibitory promiscuity	-	0.8502	85.02%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.4942	49.42%
Eye corrosion	-	0.9848	98.48%
Eye irritation	+	0.8915	89.15%
Skin irritation	-	0.7585	75.85%
Skin corrosion	-	0.9666	96.66%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6809	68.09%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.5927	59.27%
skin sensitisation	-	0.9167	91.67%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5146	51.46%
Acute Oral Toxicity (c)	II	0.6478	64.78%
Estrogen receptor binding	+	0.8337	83.37%
Androgen receptor binding	-	0.5749	57.49%
Thyroid receptor binding	-	0.6086	60.86%
Glucocorticoid receptor binding	+	0.5632	56.32%
Aromatase binding	+	0.5468	54.68%
PPAR gamma	+	0.6433	64.33%
Honey bee toxicity	-	0.8823	88.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.9697	96.97%

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	98.80%	95.56%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	96.96%	98.11%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.19%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.95%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.24%	95.50%
CHEMBL2535	P11166	Glucose transporter	87.93%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.77%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.33%	99.23%
CHEMBL3194	P02766	Transthyretin	86.99%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.31%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.42%	94.45%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.22%	94.42%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.71%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.67%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.51%	96.21%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.53%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	81.96%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	81.74%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.67%	97.36%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.97%	96.00%

Plants that contains it

• Adiantum capillus-veneris
• Cephalocroton cordofanus
• Givotia madagascariensis

Cross-Links

• PubChem: 23725
• NPASS: NPC10576
• ChEMBL: CHEMBL176570
• LOTUS: LTS0185474
• wikiData: Q27163869