Erysubin E

Details

• Internal ID: 07676f2f-dab7-4cb2-86a5-5e9241fbdbb8
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (2S,11S)-17,17-dimethyl-8-(3-methylbut-2-enyl)-4,12,18-trioxapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-1(13),5(10),6,8,14(19),15,20-heptaene-2,7-diol
• SMILES (Canonical): CC(=CCC1=CC2=C(C=C1O)OCC3(C2OC4=C3C=CC5=C4C=CC(O5)(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=CC2=C(C=C1O)OC[C@@]3([C@H]2OC4=C3C=CC5=C4C=CC(O5)(C)C)O)C
• InChI: InChI=1S/C25H26O5/c1-14(2)5-6-15-11-17-21(12-19(15)26)28-13-25(27)18-7-8-20-16(22(18)29-23(17)25)9-10-24(3,4)30-20/h5,7-12,23,26-27H,6,13H2,1-4H3/t23-,25+/m0/s1
• InChI Key: CMHGFGMNRHHGSN-UKILVPOCSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₅
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.17802393 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.80
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CHEMBL1086764
• D0M7ZZ
• BDBM50311581
• 3,3-Dimethyl-11-(3-methyl-but-2-enyl)-3H,12bH-4,8,13-trioxa-dibenzo[a,i]fluorene-6b,10-diol
• 3H,7H-pyrano[2',3':6,7]benzofuro[3,2-c][1]benzopyran-6b,10(12bH)-diol, 3,3-dimethyl-11-(3-methyl-2-butenyl)-, (6bS,12bS)-
• InChI=1/C25H26O5/c1-14(2)5-6-15-11-17-21(12-19(15)26)28-13-25(27)18-7-8-20-16(22(18)29-23(17)25)9-10-24(3,4)30-20/h5,7-12,23,26-27H,6,13H2,1-4H3/t23-,25+/m0/s
• rel-(6bR,12bR)-3,3-dimethyl-11-(3-methylbut-2-en-1-yl)-3H,7H-chromeno[6',5':4,5]furo[3,2-c]chromene-6b,10(12bH)-diol (non-preferred name)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.5335	53.35%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7401	74.01%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8801	88.01%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9109	91.09%
P-glycoprotein inhibitior	+	0.7898	78.98%
P-glycoprotein substrate	+	0.5979	59.79%
CYP3A4 substrate	+	0.6282	62.82%
CYP2C9 substrate	-	0.6095	60.95%
CYP2D6 substrate	+	0.3517	35.17%
CYP3A4 inhibition	-	0.8599	85.99%
CYP2C9 inhibition	-	0.5210	52.10%
CYP2C19 inhibition	+	0.5827	58.27%
CYP2D6 inhibition	-	0.7894	78.94%
CYP1A2 inhibition	+	0.6651	66.51%
CYP2C8 inhibition	+	0.4716	47.16%
CYP inhibitory promiscuity	+	0.5924	59.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5846	58.46%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.7134	71.34%
Skin irritation	-	0.7528	75.28%
Skin corrosion	-	0.9304	93.04%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.6837	68.37%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6184	61.84%
Acute Oral Toxicity (c)	III	0.5526	55.26%
Estrogen receptor binding	+	0.9062	90.62%
Androgen receptor binding	+	0.6934	69.34%
Thyroid receptor binding	+	0.7461	74.61%
Glucocorticoid receptor binding	+	0.8936	89.36%
Aromatase binding	+	0.7312	73.12%
PPAR gamma	+	0.8764	87.64%
Honey bee toxicity	-	0.8142	81.42%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9648	96.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	8800 nM	IC50	PMID: 19836230

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.78%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.67%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.55%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	93.87%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.65%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.64%	93.40%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.80%	100.00%
CHEMBL2581	P07339	Cathepsin D	90.59%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	88.36%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.28%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.78%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	86.75%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.42%	97.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.10%	95.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.80%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.77%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.18%	85.14%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	83.34%	97.88%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.41%	93.10%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.34%	85.30%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.08%	85.49%
CHEMBL4208	P20618	Proteasome component C5	81.07%	90.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.91%	89.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.90%	99.15%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.67%	90.24%

Plants that contains it

• Erythrina abyssinica
• Erythrina abyssinica
• Erythrina suberosa
• Erythrina variegata

Cross-Links

• PubChem: 637080
• NPASS: NPC20829
• ChEMBL: CHEMBL1086764
• LOTUS: LTS0018794
• wikiData: Q104964538