Demethylcarolignan E

Details

• Internal ID: da725003-567c-48ce-b341-722daf9749a3
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: 3-[3-hydroxy-4-[(1S,2S)-1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxypropan-2-yl]oxyphenyl]propyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCCCC2=CC(=C(C=C2)OC(COC(=O)C=CC3=CC(=C(C=C3)O)OC)C(C4=CC(=C(C=C4)O)OC)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OCCCC2=CC(=C(C=C2)O[C@@H](COC(=O)/C=C/C3=CC(=C(C=C3)O)OC)[C@H](C4=CC(=C(C=C4)O)OC)O)O)O
• InChI: InChI=1S/C39H40O13/c1-47-33-20-25(6-12-28(33)40)9-16-37(44)50-18-4-5-24-8-15-32(31(43)19-24)52-36(39(46)27-11-14-30(42)35(22-27)49-3)23-51-38(45)17-10-26-7-13-29(41)34(21-26)48-2/h6-17,19-22,36,39-43,46H,4-5,18,23H2,1-3H3/b16-9+,17-10+/t36-,39-/m0/s1
• InChI Key: GSGRJWMOIKUHLN-DZOJLRKVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₀O₁₃
• Molecular Weight: 716.70 g/mol
• Exact Mass: 716.24689133 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.46
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 17

Synonyms

• 873694-46-3
• 3-[3-hydroxy-4-[(1S,2S)-1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxypropan-2-yl]oxyphenyl]propyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• (7S,8S)-Demethylcarolignan E
• CHEMBL3589243
• HY-N7589
• CS-0134413
• 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, 3-[3-hydroxy-4-[[(1S,2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-[[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]oxy]methyl]ethyl]oxy]phenyl]propyl ester, (2E)-
• 3-[3-hydroxy-4-[(1S,2S)-2-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-1-[[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]oxymethyl]ethoxy]phenyl]propyl (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8933	89.33%
Caco-2	-	0.8729	87.29%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8807	88.07%
OATP2B1 inhibitior	+	0.5721	57.21%
OATP1B1 inhibitior	+	0.8799	87.99%
OATP1B3 inhibitior	+	0.9074	90.74%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9538	95.38%
P-glycoprotein inhibitior	+	0.8125	81.25%
P-glycoprotein substrate	+	0.5693	56.93%
CYP3A4 substrate	+	0.6401	64.01%
CYP2C9 substrate	-	0.6017	60.17%
CYP2D6 substrate	-	0.8072	80.72%
CYP3A4 inhibition	-	0.8158	81.58%
CYP2C9 inhibition	+	0.6165	61.65%
CYP2C19 inhibition	-	0.6097	60.97%
CYP2D6 inhibition	-	0.8777	87.77%
CYP1A2 inhibition	+	0.7298	72.98%
CYP2C8 inhibition	+	0.7522	75.22%
CYP inhibitory promiscuity	-	0.7757	77.57%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7924	79.24%
Carcinogenicity (trinary)	Non-required	0.6941	69.41%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9131	91.31%
Skin irritation	-	0.8968	89.68%
Skin corrosion	-	0.9675	96.75%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8066	80.66%
Micronuclear	-	0.6667	66.67%
Hepatotoxicity	-	0.7321	73.21%
skin sensitisation	-	0.8850	88.50%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.9142	91.42%
Acute Oral Toxicity (c)	III	0.7381	73.81%
Estrogen receptor binding	+	0.8205	82.05%
Androgen receptor binding	+	0.8193	81.93%
Thyroid receptor binding	+	0.5906	59.06%
Glucocorticoid receptor binding	+	0.7170	71.70%
Aromatase binding	+	0.5490	54.90%
PPAR gamma	+	0.7252	72.52%
Honey bee toxicity	-	0.8302	83.02%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9738	97.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.12%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.95%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.06%	96.00%
CHEMBL2581	P07339	Cathepsin D	96.34%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.10%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.09%	99.17%
CHEMBL3194	P02766	Transthyretin	94.76%	90.71%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.31%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.63%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.83%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.90%	95.56%
CHEMBL4208	P20618	Proteasome component C5	87.75%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.54%	89.00%
CHEMBL2535	P11166	Glucose transporter	87.04%	98.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.70%	96.95%
CHEMBL1255126	O15151	Protein Mdm4	85.24%	90.20%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.00%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.64%	97.21%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.10%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.48%	86.92%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.24%	80.78%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.05%	90.24%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.56%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.25%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.62%	89.50%

Plants that contains it

• Abelmoschus ficulneus
• Hibiscus taiwanensis

Cross-Links

• PubChem: 5274621
• LOTUS: LTS0141810
• wikiData: Q105017133