Erythro-carolignan E

Details

• Internal ID: 3131c42b-f7a4-4bd5-b5aa-c1eeca9dc006
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: 3-[4-[(1S,2S)-1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxypropan-2-yl]oxy-3-methoxyphenyl]propyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)CCCOC(=O)C=CC2=CC(=C(C=C2)O)OC)OC(COC(=O)C=CC3=CC(=C(C=C3)O)OC)C(C4=CC(=C(C=C4)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CCCOC(=O)/C=C/C2=CC(=C(C=C2)O)OC)O[C@@H](COC(=O)/C=C/C3=CC(=C(C=C3)O)OC)[C@H](C4=CC(=C(C=C4)O)OC)O
• InChI: InChI=1S/C40H42O13/c1-47-33-20-26(7-13-29(33)41)10-17-38(44)51-19-5-6-25-9-16-32(36(22-25)50-4)53-37(40(46)28-12-15-31(43)35(23-28)49-3)24-52-39(45)18-11-27-8-14-30(42)34(21-27)48-2/h7-18,20-23,37,40-43,46H,5-6,19,24H2,1-4H3/b17-10+,18-11+/t37-,40-/m0/s1
• InChI Key: CXFBVHGWTGTGBR-QYQWMRSMSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₂O₁₃
• Molecular Weight: 730.80 g/mol
• Exact Mass: 730.26254139 g/mol
• Topological Polar Surface Area (TPSA): 180.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.76
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 18

Synonyms

• threo-Carolignan E
• CHEMBL3589244
• CHEBI:70673
• 3-[4-[(1S,2S)-1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxypropan-2-yl]oxy-3-methoxyphenyl]propyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• Q27139005
• 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, 3-[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]-3-methoxyphenyl]propyl ester, (2E)-
• 3-[4-[(1S,2S)-2-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-1-[[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]oxymethyl]ethoxy]-3-methoxy-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	+	0.9510	95.10%
Caco-2	-	0.8609	86.09%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8800	88.00%
OATP2B1 inhibitior	+	0.5730	57.30%
OATP1B1 inhibitior	+	0.8721	87.21%
OATP1B3 inhibitior	+	0.8850	88.50%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9877	98.77%
P-glycoprotein inhibitior	+	0.8312	83.12%
P-glycoprotein substrate	+	0.6302	63.02%
CYP3A4 substrate	+	0.6472	64.72%
CYP2C9 substrate	-	0.6017	60.17%
CYP2D6 substrate	-	0.8072	80.72%
CYP3A4 inhibition	-	0.7839	78.39%
CYP2C9 inhibition	+	0.5959	59.59%
CYP2C19 inhibition	-	0.6338	63.38%
CYP2D6 inhibition	-	0.8942	89.42%
CYP1A2 inhibition	+	0.6476	64.76%
CYP2C8 inhibition	+	0.8127	81.27%
CYP inhibitory promiscuity	-	0.8204	82.04%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.7924	79.24%
Carcinogenicity (trinary)	Non-required	0.7007	70.07%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9137	91.37%
Skin irritation	-	0.9099	90.99%
Skin corrosion	-	0.9722	97.22%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8210	82.10%
Micronuclear	-	0.6467	64.67%
Hepatotoxicity	-	0.7321	73.21%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.9381	93.81%
Acute Oral Toxicity (c)	III	0.7741	77.41%
Estrogen receptor binding	+	0.8542	85.42%
Androgen receptor binding	+	0.8187	81.87%
Thyroid receptor binding	+	0.6404	64.04%
Glucocorticoid receptor binding	+	0.7703	77.03%
Aromatase binding	+	0.5700	57.00%
PPAR gamma	+	0.7272	72.72%
Honey bee toxicity	-	0.8405	84.05%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9721	97.21%

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	99.14%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.82%	86.33%
CHEMBL2581	P07339	Cathepsin D	97.39%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.96%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.53%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.60%	94.45%
CHEMBL3194	P02766	Transthyretin	91.88%	90.71%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.47%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.18%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.29%	90.71%
CHEMBL2535	P11166	Glucose transporter	89.10%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.13%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.92%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.70%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.56%	95.56%
CHEMBL1255126	O15151	Protein Mdm4	85.53%	90.20%
CHEMBL4208	P20618	Proteasome component C5	84.98%	90.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.70%	89.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.42%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.05%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.30%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.62%	95.89%

Plants that contains it

• Abelmoschus ficulneus
• Durio carinatus
• Hibiscus cannabinus
• Hibiscus taiwanensis

Cross-Links

• PubChem: 5274622
• NPASS: NPC143120
• ChEMBL: CHEMBL3589244
• LOTUS: LTS0041647
• wikiData: Q27139005