Lyciumin B

Details

• Internal ID: 4a304183-c9e3-4858-acc7-f10c43b177d9
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Cyclic peptides
• IUPAC Name: 11-(hydroxymethyl)-2-[[3-(1H-indol-3-yl)-2-[[1-(5-oxopyrrolidine-2-carbonyl)pyrrolidine-2-carbonyl]amino]propanoyl]amino]-3,6,9,12-tetraoxo-5-propan-2-yl-1,4,7,10,13-pentazatricyclo[14.6.1.017,22]tricosa-16(23),17,19,21-tetraene-14-carboxylic acid
• SMILES (Canonical): CC(C)C1C(=O)NCC(=O)NC(C(=O)NC(CC2=CN(C(C(=O)N1)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C5CCCN5C(=O)C6CCC(=O)N6)C7=CC=CC=C27)C(=O)O)CO
• SMILES (Isomeric): CC(C)C1C(=O)NCC(=O)NC(C(=O)NC(CC2=CN(C(C(=O)N1)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C5CCCN5C(=O)C6CCC(=O)N6)C7=CC=CC=C27)C(=O)O)CO
• InChI: InChI=1S/C44H52N10O11/c1-22(2)36-41(61)46-19-35(57)48-31(21-55)39(59)50-30(44(64)65)17-24-20-54(32-11-6-4-9-26(24)32)37(42(62)51-36)52-38(58)29(16-23-18-45-27-10-5-3-8-25(23)27)49-40(60)33-12-7-15-53(33)43(63)28-13-14-34(56)47-28/h3-6,8-11,18,20,22,28-31,33,36-37,45,55H,7,12-17,19,21H2,1-2H3,(H,46,61)(H,47,56)(H,48,57)(H,49,60)(H,50,59)(H,51,62)(H,52,58)(H,64,65)
• InChI Key: BWRVBFMWWHWLBW-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₅₂N₁₀O₁₁
• Molecular Weight: 896.90 g/mol
• Exact Mass: 896.38170251 g/mol
• Topological Polar Surface Area (TPSA): 302.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): -1.41
• H-Bond Acceptor: 11
• H-Bond Donor: 10
• Rotatable Bonds: 10

Synonyms

• 125756-66-3
• 11-(hydroxymethyl)-2-[[3-(1H-indol-3-yl)-2-[[1-(5-oxopyrrolidine-2-carbonyl)pyrrolidine-2-carbonyl]amino]propanoyl]amino]-3,6,9,12-tetraoxo-5-propan-2-yl-1,4,7,10,13-pentazatricyclo[14.6.1.017,22]tricosa-16(23),17,19,21-tetraene-14-carboxylic acid
• 11-(hydroxymethyl)-2-((3-(1H-indol-3-yl)-2-((1-(5-oxopyrrolidine-2-carbonyl)pyrrolidine-2-carbonyl)amino)propanoyl)amino)-3,6,9,12-tetraoxo-5-propan-2-yl-1,4,7,10,13-pentazatricyclo(14.6.1.017,22)tricosa-16(23),17,19,21-tetraene-14-carboxylic acid
• RefChem:154592
• orb1691862
• SCHEMBL29471760
• CHEBI:185794
• AKOS040756590
• DA-75211

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8770	87.70%
Caco-2	-	0.8772	87.72%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4508	45.08%
OATP2B1 inhibitior	-	0.7107	71.07%
OATP1B1 inhibitior	+	0.8406	84.06%
OATP1B3 inhibitior	+	0.9310	93.10%
MATE1 inhibitior	-	0.8647	86.47%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9187	91.87%
P-glycoprotein inhibitior	+	0.7516	75.16%
P-glycoprotein substrate	+	0.8668	86.68%
CYP3A4 substrate	+	0.7445	74.45%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.8542	85.42%
CYP3A4 inhibition	-	0.8920	89.20%
CYP2C9 inhibition	-	0.8094	80.94%
CYP2C19 inhibition	-	0.8201	82.01%
CYP2D6 inhibition	-	0.9430	94.30%
CYP1A2 inhibition	-	0.8993	89.93%
CYP2C8 inhibition	+	0.7066	70.66%
CYP inhibitory promiscuity	-	0.7903	79.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6524	65.24%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9086	90.86%
Skin irritation	-	0.7797	77.97%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4776	47.76%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.6133	61.33%
skin sensitisation	-	0.8843	88.43%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7309	73.09%
Acute Oral Toxicity (c)	III	0.6116	61.16%
Estrogen receptor binding	+	0.8264	82.64%
Androgen receptor binding	+	0.5590	55.90%
Thyroid receptor binding	+	0.5983	59.83%
Glucocorticoid receptor binding	+	0.5620	56.20%
Aromatase binding	+	0.6275	62.75%
PPAR gamma	+	0.7632	76.32%
Honey bee toxicity	-	0.6906	69.06%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5349	53.49%
Fish aquatic toxicity	+	0.7718	77.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.80%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	99.21%	93.99%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	98.99%	97.64%
CHEMBL5103	Q969S8	Histone deacetylase 10	98.98%	90.08%
CHEMBL333	P08253	Matrix metalloproteinase-2	98.88%	96.31%
CHEMBL3310	Q96DB2	Histone deacetylase 11	98.84%	88.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.69%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	97.23%	93.10%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.99%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.92%	91.11%
CHEMBL3524	P56524	Histone deacetylase 4	95.46%	92.97%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	95.05%	98.24%
CHEMBL1937	Q92769	Histone deacetylase 2	94.91%	94.75%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	94.72%	90.71%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	94.69%	96.39%
CHEMBL4040	P28482	MAP kinase ERK2	94.19%	83.82%
CHEMBL213	P08588	Beta-1 adrenergic receptor	93.77%	95.56%
CHEMBL3837	P07711	Cathepsin L	93.44%	96.61%
CHEMBL321	P14780	Matrix metalloproteinase 9	93.34%	92.12%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.77%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.59%	89.00%
CHEMBL4073	P09237	Matrix metalloproteinase 7	91.43%	97.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	91.29%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.10%	99.23%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	90.77%	98.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.71%	95.89%
CHEMBL4588	P22894	Matrix metalloproteinase 8	90.32%	94.66%
CHEMBL259	P32245	Melanocortin receptor 4	89.17%	95.38%
CHEMBL261	P00915	Carbonic anhydrase I	89.14%	96.76%
CHEMBL5028	O14672	ADAM10	87.85%	97.50%
CHEMBL255	P29275	Adenosine A2b receptor	87.70%	98.59%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.60%	95.83%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.15%	97.09%
CHEMBL217	P14416	Dopamine D2 receptor	86.94%	95.62%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	86.87%	99.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.01%	82.69%
CHEMBL4644	P41968	Melanocortin receptor 3	85.96%	99.52%
CHEMBL4208	P20618	Proteasome component C5	84.69%	90.00%
CHEMBL332	P03956	Matrix metalloproteinase-1	84.48%	94.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.28%	92.62%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	83.87%	91.81%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.37%	96.47%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.16%	97.25%
CHEMBL1914	P06276	Butyrylcholinesterase	81.89%	95.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.71%	94.45%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	81.64%	97.50%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.57%	90.95%
CHEMBL2535	P11166	Glucose transporter	81.56%	98.75%
CHEMBL3384	Q16512	Protein kinase N1	81.02%	80.71%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.90%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.56%	85.14%

Plants that contains it

• Lycium chinense

Cross-Links

• PubChem: 14430292
• LOTUS: LTS0124077
• wikiData: Q104402519