Paliurine B

Details

• Internal ID: 199afb25-7f45-4aa8-9679-6766e8a96f80
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Cyclic peptides
• IUPAC Name: (2S,3S)-N-[(2S)-1-[(3S,7S,10S,13E)-10-[(2S)-butan-2-yl]-16-methoxy-8,11-dioxo-2-oxa-6,9,12-triazatricyclo[13.3.1.03,7]nonadeca-1(19),13,15,17-tetraen-6-yl]-1-oxo-3-phenylpropan-2-yl]-3-methyl-2-(methylamino)pentanamide
• SMILES (Canonical): CCC(C)C1C(=O)NC=CC2=C(C=CC(=C2)OC3CCN(C3C(=O)N1)C(=O)C(CC4=CC=CC=C4)NC(=O)C(C(C)CC)NC)OC
• SMILES (Isomeric): CC[C@H](C)[C@H]1C(=O)N/C=C/C2=C(C=CC(=C2)O[C@H]3CCN([C@@H]3C(=O)N1)C(=O)[C@H](CC4=CC=CC=C4)NC(=O)[C@H]([C@@H](C)CC)NC)OC
• InChI: InChI=1S/C36H49N5O6/c1-7-22(3)30(37-5)34(43)39-27(20-24-12-10-9-11-13-24)36(45)41-19-17-29-32(41)35(44)40-31(23(4)8-2)33(42)38-18-16-25-21-26(47-29)14-15-28(25)46-6/h9-16,18,21-23,27,29-32,37H,7-8,17,19-20H2,1-6H3,(H,38,42)(H,39,43)(H,40,44)/b18-16+/t22-,23-,27-,29-,30-,31-,32-/m0/s1
• InChI Key: CDQIHKYZYILDAS-AMRSUGGNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₉N₅O₆
• Molecular Weight: 647.80 g/mol
• Exact Mass: 647.36828430 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 3.04
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 11

Synonyms

• 149183-88-0
• (2S,3S)-N-[(2S)-1-[(3S,7S,10S,13E)-10-[(2S)-Butan-2-yl]-16-methoxy-8,11-dioxo-2-oxa-6,9,12-triazatricyclo[13.3.1.03,7]nonadeca-1(19),13,15,17-tetraen-6-yl]-1-oxo-3-phenylpropan-2-yl]-3-methyl-2-(methylamino)pentanamide
• L-Isoleucine, N-methyl-L-isoleucyl-L-phenylalanyl-3-(3-(2-aminoethenyl)-4-methoxyphenoxy)prolyl-, cyclic (4-3)-peptide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9075	90.75%
Caco-2	-	0.8229	82.29%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7006	70.06%
OATP2B1 inhibitior	+	0.8605	86.05%
OATP1B1 inhibitior	+	0.8506	85.06%
OATP1B3 inhibitior	+	0.9093	90.93%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9907	99.07%
P-glycoprotein inhibitior	+	0.8777	87.77%
P-glycoprotein substrate	+	0.8504	85.04%
CYP3A4 substrate	+	0.7147	71.47%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.7698	76.98%
CYP3A4 inhibition	+	0.8019	80.19%
CYP2C9 inhibition	-	0.7663	76.63%
CYP2C19 inhibition	-	0.7092	70.92%
CYP2D6 inhibition	-	0.8199	81.99%
CYP1A2 inhibition	-	0.8396	83.96%
CYP2C8 inhibition	+	0.6724	67.24%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5580	55.80%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9413	94.13%
Skin irritation	-	0.8008	80.08%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7583	75.83%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.6626	66.26%
skin sensitisation	-	0.8968	89.68%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.5881	58.81%
Acute Oral Toxicity (c)	III	0.6382	63.82%
Estrogen receptor binding	+	0.7633	76.33%
Androgen receptor binding	+	0.6759	67.59%
Thyroid receptor binding	+	0.6292	62.92%
Glucocorticoid receptor binding	+	0.7689	76.89%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7861	78.61%
Honey bee toxicity	-	0.7593	75.93%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5526	55.26%
Fish aquatic toxicity	+	0.9499	94.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.66%	98.95%
CHEMBL3837	P07711	Cathepsin L	99.47%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.45%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.20%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	95.60%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.96%	95.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	94.49%	98.33%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	93.65%	97.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.92%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	91.46%	90.20%
CHEMBL4208	P20618	Proteasome component C5	90.55%	90.00%
CHEMBL4588	P22894	Matrix metalloproteinase 8	89.06%	94.66%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.89%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.77%	89.50%
CHEMBL221	P23219	Cyclooxygenase-1	87.53%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.09%	94.45%
CHEMBL2535	P11166	Glucose transporter	86.98%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.01%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.16%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.15%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.99%	93.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.40%	93.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.03%	91.11%
CHEMBL5028	O14672	ADAM10	81.30%	97.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.22%	96.21%
CHEMBL340	P08684	Cytochrome P450 3A4	81.16%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.10%	90.71%
CHEMBL209	P07477	Trypsin I	80.86%	90.00%
CHEMBL4393	P39900	Matrix metalloproteinase 12	80.78%	92.22%
CHEMBL220	P22303	Acetylcholinesterase	80.64%	94.45%

Plants that contains it

• Paliurus ramosissimus

Cross-Links

• PubChem: 101063132
• LOTUS: LTS0215326
• wikiData: Q104955017