Lobaric Acid

Details

• Internal ID: 8f44f900-c5bc-4073-93ce-a11a11834779
• Taxonomy: Phenylpropanoids and polyketides > Depsides and depsidones
• IUPAC Name: 3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylic acid
• InChI: InChI=1S/C25H28O8/c1-4-6-8-9-15-21(24(28)29)18(27)13-20-23(15)32-19-12-14(31-3)11-16(17(26)10-7-5-2)22(19)25(30)33-20/h11-13,27H,4-10H2,1-3H3,(H,28,29)
• InChI Key: JHEWMLHQNRHTQX-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₈
• Molecular Weight: 456.50 g/mol
• Exact Mass: 456.17841785 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 6.10
• Atomic LogP (AlogP): 5.53
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

• 522-53-2
• 3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylic acid
• DTXSID30200238
• 3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo(b)(1,4)benzodioxepine-2-carboxylic acid
• RefChem:153858
• DTXCID30122729
• Usnetic acid
• 8-Hydroxy-3-methoxy-11-oxo-1-pentanoyl-6-pentyl-11H-dibenzo[b,E][1,4]dioxepine-7-carboxylic acid
• CHEMBL551842
• Lobraric acid
• lobutoic Acid
• Stereocaulic acid
• Lobaric acid(aS)
• 11H-Dibenzo(b,e)(1,4)dioxepin-7-carboxylic acid, 8-hydroxy-3-methoxy-11-oxo-1-(1-oxopentyl)-6-pentyl-
• 11H-Dibenzo[b,e][1,4]dioxepin-7-carboxylic acid, 8-hydroxy-3-methoxy-11-oxo-1-(1-oxopentyl)-6-pentyl-
• Spectrum_000626
• Spectrum2_000310
• Spectrum3_001177
• Spectrum4_001443
• Spectrum5_000025
• BSPBio_002793
• KBioGR_001925
• KBioSS_001106
• SPECTRUM300018
• cid_73157
• MLS001049101
• REGID_for_CID_73157
• SPBio_000280
• orb1737683
• SCHEMBL3910434
• SCHEMBL29431924
• SCHEMBL29788372
• CHEBI:93548
• KBio2_001106
• KBio2_003674
• KBio2_006242
• KBio3_002293
• JHEWMLHQNRHTQX-UHFFFAOYSA-N
• HMS2271L13
• NP335
• AAA52253
• BDBM50294526
• CCG-38587
• MFCD00597234
• STL578212
• AKOS015969735
• SDCCGMLS-0066497.P001
• NCGC00095570-01
• NCGC00095570-02
• SMR000386933
• HY-117085
• CS-0063676
• SR-01000758235
• SR-01000758235-2
• BRD-K88849294-001-02-1
• BRD-K88849294-001-08-8
• Q27165242
• 11H-Dibenzo[b,e][1,4]dioxepin-7-carboxylic acid, 8-hydroxy-3-methoxy-11-oxo-6-pentyl-1-valeryl-
• 3-hydroxy-9-methoxy-6-oxo-7-(1-oxopentyl)-1-pentyl-2-benzo[b][1,4]benzodioxepincarboxylic acid
• 3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentyl-benzo[b][1,4]benzodioxepine-2-carboxylic acid
• 8-Hydroxy-3-methoxy-11-oxo-1-pentanoyl-6-pentyl-11H-dibenzo[b,E][1,4]dioxepine-7-carboxylic acid #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8309	83.09%
Caco-2	-	0.6012	60.12%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6125	61.25%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	-	0.7738	77.38%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7936	79.36%
P-glycoprotein inhibitior	+	0.6115	61.15%
P-glycoprotein substrate	-	0.6990	69.90%
CYP3A4 substrate	+	0.6032	60.32%
CYP2C9 substrate	+	0.8036	80.36%
CYP2D6 substrate	-	0.8592	85.92%
CYP3A4 inhibition	-	0.7594	75.94%
CYP2C9 inhibition	-	0.8060	80.60%
CYP2C19 inhibition	-	0.7398	73.98%
CYP2D6 inhibition	-	0.8885	88.85%
CYP1A2 inhibition	-	0.6677	66.77%
CYP2C8 inhibition	+	0.7920	79.20%
CYP inhibitory promiscuity	-	0.7751	77.51%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6757	67.57%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.6328	63.28%
Skin irritation	-	0.7763	77.63%
Skin corrosion	-	0.9244	92.44%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4680	46.80%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5141	51.41%
skin sensitisation	-	0.8849	88.49%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7936	79.36%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4636	46.36%
Acute Oral Toxicity (c)	III	0.4277	42.77%
Estrogen receptor binding	+	0.7671	76.71%
Androgen receptor binding	+	0.6391	63.91%
Thyroid receptor binding	-	0.6229	62.29%
Glucocorticoid receptor binding	+	0.8351	83.51%
Aromatase binding	+	0.6057	60.57%
PPAR gamma	+	0.7483	74.83%
Honey bee toxicity	-	0.8743	87.43%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5050	50.50%
Fish aquatic toxicity	+	0.9917	99.17%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	39810.7 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	4540 nM	IC50	PMID: 24900447
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	39810.7 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	25118.9 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	28183.8 nM	Potency	via CMAUP
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	870 nM; 800 nM	IC50; IC50	PMID: 19362837; via Super-PRED
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	724.44 nM	IC50	PMID: 23571415
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	1621.81 nM	IC50	PMID: 23571415

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.87%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.47%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.52%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.63%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.28%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.16%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.96%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.46%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.98%	91.71%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.70%	92.08%
CHEMBL1907	P15144	Aminopeptidase N	85.79%	93.31%
CHEMBL230	P35354	Cyclooxygenase-2	85.32%	89.63%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.19%	95.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.25%	93.99%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.06%	92.62%
CHEMBL4208	P20618	Proteasome component C5	81.84%	90.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.80%	82.38%
CHEMBL2535	P11166	Glucose transporter	80.49%	98.75%

Plants that contains it

• Helleborus niger

Cross-Links

• PubChem: 73157
• NPASS: NPC300984
• ChEMBL: CHEMBL551842
• LOTUS: LTS0164103
• wikiData: Q27165242