10-epi-Lithospermic acid

Details

• Internal ID: 06decf19-6ca0-459a-a04e-e3d03b87b5bd
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3S)-4-[(E)-3-[(1S)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=C3C(C(OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@@H](C(=O)O)OC(=O)/C=C/C2=C3[C@@H]([C@H](OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)O)O)O
• InChI: InChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/b8-4+/t20-,23-,24+/m0/s1
• InChI Key: UJZQBMQZMKFSRV-WDMOTZMRSA-N
• Popularity: 47 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₂O₁₂
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.11112613 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.77
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 10-epi-Lithospermic acid
• 28831-65-4
• AKOS037514725

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9386	93.86%
Caco-2	-	0.9389	93.89%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7277	72.77%
OATP2B1 inhibitior	-	0.5636	56.36%
OATP1B1 inhibitior	+	0.8846	88.46%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7009	70.09%
P-glycoprotein inhibitior	+	0.6664	66.64%
P-glycoprotein substrate	-	0.7342	73.42%
CYP3A4 substrate	+	0.6189	61.89%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.8393	83.93%
CYP3A4 inhibition	-	0.8491	84.91%
CYP2C9 inhibition	+	0.6147	61.47%
CYP2C19 inhibition	-	0.6025	60.25%
CYP2D6 inhibition	-	0.9293	92.93%
CYP1A2 inhibition	-	0.7427	74.27%
CYP2C8 inhibition	+	0.7255	72.55%
CYP inhibitory promiscuity	-	0.6058	60.58%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.4149	41.49%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8339	83.39%
Skin irritation	-	0.7352	73.52%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	+	0.5046	50.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.6687	66.87%
Micronuclear	+	0.8218	82.18%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8114	81.14%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.9101	91.01%
Acute Oral Toxicity (c)	III	0.3187	31.87%
Estrogen receptor binding	+	0.7686	76.86%
Androgen receptor binding	+	0.8095	80.95%
Thyroid receptor binding	+	0.5414	54.14%
Glucocorticoid receptor binding	+	0.6262	62.62%
Aromatase binding	-	0.6596	65.96%
PPAR gamma	+	0.6196	61.96%
Honey bee toxicity	-	0.6508	65.08%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9934	99.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3729	P22748	Carbonic anhydrase IV	101.2 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	268.3 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	4.8 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.51%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.93%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.75%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.30%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	92.97%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.87%	86.33%
CHEMBL233	P35372	Mu opioid receptor	91.28%	97.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.17%	95.56%
CHEMBL3194	P02766	Transthyretin	91.12%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.79%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.87%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.09%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.16%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.88%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.85%	99.15%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.52%	95.17%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.95%	95.71%
CHEMBL236	P41143	Delta opioid receptor	82.91%	99.35%
CHEMBL340	P08684	Cytochrome P450 3A4	82.56%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	82.45%	90.17%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.87%	89.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.07%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.79%	94.62%

Plants that contains it

• Arnebia euchroma
• Arnebia guttata
• Heliotropium sarmentosum
• Isodon rubescens
• Lithospermum erythrorhizon
• Lithospermum ruderale
• Mentha arvensis
• Mentha canadensis
• Origanum vulgare
• Salvia cavaleriei
• Salvia chinensis
• Salvia miltiorrhiza
• Salvia przewalskii

Cross-Links

• PubChem: 95359683
• NPASS: NPC47489
• LOTUS: LTS0059529
• wikiData: Q104393190