Lyciumin C

Details

• Internal ID: c7e954bf-23d4-40bd-a94f-5bb01a15a1f0
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: methyl (2R,5S,8S,11S,14S)-8-benzyl-11-(hydroxymethyl)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-1-[(2S)-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-carboxylate
• SMILES (Canonical): CC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CC2=CN(C(C(=O)N1)NC(=O)C(CC3=CC=C(C=C3)O)NC(=O)C4CCCN4C(=O)C5CCC(=O)N5)C6=CC=CC=C26)C(=O)OC)CO)CC7=CC=CC=C7
• SMILES (Isomeric): CC(C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CC2=CN([C@H](C(=O)N1)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@@H]4CCCN4C(=O)[C@@H]5CCC(=O)N5)C6=CC=CC=C26)C(=O)OC)CO)CC7=CC=CC=C7
• InChI: InChI=1S/C50H59N9O12/c1-27(2)41-47(67)53-34(22-28-10-5-4-6-11-28)43(63)55-37(26-60)45(65)54-36(50(70)71-3)24-30-25-59(38-13-8-7-12-32(30)38)42(48(68)56-41)57-44(64)35(23-29-15-17-31(61)18-16-29)52-46(66)39-14-9-21-58(39)49(69)33-19-20-40(62)51-33/h4-8,10-13,15-18,25,27,33-37,39,41-42,60-61H,9,14,19-24,26H2,1-3H3,(H,51,62)(H,52,66)(H,53,67)(H,54,65)(H,55,63)(H,56,68)(H,57,64)/t33-,34-,35-,36-,37-,39-,41-,42+/m0/s1
• InChI Key: HCCOYHQCWLIMRA-HDNCMCGHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₅₉N₉O₁₂
• Molecular Weight: 978.10 g/mol
• Exact Mass: 977.42831835 g/mol
• Topological Polar Surface Area (TPSA): 296.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): -0.48
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

• Liciumin C methyl
• CHEMBL505660
• CHEBI:185740
• methyl (2R,5S,8S,11S,14S)-8-benzyl-11-(hydroxymethyl)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-1-[(2S)-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-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8051	80.51%
Caco-2	-	0.8763	87.63%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4657	46.57%
OATP2B1 inhibitior	-	0.5733	57.33%
OATP1B1 inhibitior	+	0.8335	83.35%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.7238	72.38%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9587	95.87%
P-glycoprotein inhibitior	+	0.7522	75.22%
P-glycoprotein substrate	+	0.8713	87.13%
CYP3A4 substrate	+	0.7555	75.55%
CYP2C9 substrate	+	0.6005	60.05%
CYP2D6 substrate	-	0.8363	83.63%
CYP3A4 inhibition	-	0.7096	70.96%
CYP2C9 inhibition	-	0.7132	71.32%
CYP2C19 inhibition	-	0.7212	72.12%
CYP2D6 inhibition	-	0.8780	87.80%
CYP1A2 inhibition	-	0.8854	88.54%
CYP2C8 inhibition	+	0.7570	75.70%
CYP inhibitory promiscuity	+	0.5121	51.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6317	63.17%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9053	90.53%
Skin irritation	-	0.7908	79.08%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6501	65.01%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.5928	59.28%
skin sensitisation	-	0.8918	89.18%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7442	74.42%
Acute Oral Toxicity (c)	III	0.6204	62.04%
Estrogen receptor binding	+	0.8275	82.75%
Androgen receptor binding	+	0.6654	66.54%
Thyroid receptor binding	+	0.5614	56.14%
Glucocorticoid receptor binding	+	0.5582	55.82%
Aromatase binding	+	0.6216	62.16%
PPAR gamma	+	0.7643	76.43%
Honey bee toxicity	-	0.6695	66.95%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.6850	68.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.94%	98.95%
CHEMBL5103	Q969S8	Histone deacetylase 10	99.19%	90.08%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	99.06%	97.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.41%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	97.92%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.22%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	97.03%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.24%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	96.21%	91.71%
CHEMBL3837	P07711	Cathepsin L	96.15%	96.61%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.45%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	95.41%	95.89%
CHEMBL3310	Q96DB2	Histone deacetylase 11	92.57%	88.56%
CHEMBL3524	P56524	Histone deacetylase 4	91.58%	92.97%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.55%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.89%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	90.04%	83.82%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	89.79%	93.10%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	89.10%	98.24%
CHEMBL1937	Q92769	Histone deacetylase 2	88.40%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.44%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	86.80%	91.19%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	86.80%	92.67%
CHEMBL4644	P41968	Melanocortin receptor 3	86.44%	99.52%
CHEMBL2535	P11166	Glucose transporter	85.82%	98.75%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.43%	89.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.18%	85.14%
CHEMBL259	P32245	Melanocortin receptor 4	85.17%	95.38%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.77%	95.83%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.38%	93.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.38%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.24%	82.69%
CHEMBL5314	Q06418	Tyrosine-protein kinase receptor TYRO3	84.17%	96.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.86%	95.71%
CHEMBL1921	P47901	Vasopressin V1b receptor	83.67%	92.50%
CHEMBL4208	P20618	Proteasome component C5	83.43%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.36%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.92%	89.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.86%	96.47%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.72%	94.66%
CHEMBL217	P14416	Dopamine D2 receptor	82.00%	95.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.63%	90.95%
CHEMBL4777	P25929	Neuropeptide Y receptor type 1	81.40%	96.67%
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	81.23%	97.43%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.77%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.62%	100.00%
CHEMBL4393	P39900	Matrix metalloproteinase 12	80.53%	92.22%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.33%	94.23%

Plants that contains it

• Celosia argentea
• Lycium barbarum
• Lycium chinense

Cross-Links

• PubChem: 44584331
• NPASS: NPC285343
• LOTUS: LTS0259364
• wikiData: Q105025606