Acyclolaxaphycin B

Details

• Internal ID: d7070053-828e-44b6-93f8-e01fcc1de822
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (2R,3S)-2-[[(2S)-2-[[(3R)-3-[[(2S,3R)-2-[[(2R)-2-[[(2S)-1-[(2S,3R)-2-[[(2R,3R)-4-amino-2-[[(2S,3S)-2-[[(2S)-5-amino-2-[[(2R,3S)-2-[[(2S)-2-aminopropanoyl]amino]-3-hydroxy-4-methylpentanoyl]amino]-5-oxopentanoyl]-methylamino]-3-methylpentanoyl]amino]-3-hydroxy-4-oxobutanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]decanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxy-4-methylpentanoic acid
• SMILES (Canonical): CCCCCCCC(CC(=O)NC(C(C)C)C(=O)NC(C(C(C)C)O)C(=O)O)NC(=O)C(C(C)O)NC(=O)C(CC(C)C)NC(=O)C1CCCN1C(=O)C(C(C)O)NC(=O)C(C(C(=O)N)O)NC(=O)C(C(C)CC)N(C)C(=O)C(CCC(=O)N)NC(=O)C(C(C(C)C)O)NC(=O)C(C)N
• SMILES (Isomeric): CCCCCCC[C@H](CC(=O)N[C@@H](C(C)C)C(=O)N[C@H]([C@H](C(C)C)O)C(=O)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H]([C@H](C(=O)N)O)NC(=O)[C@H]([C@@H](C)CC)N(C)C(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]([C@H](C(C)C)O)NC(=O)[C@H](C)N
• InChI: InChI=1S/C65H116N14O20/c1-16-18-19-20-21-23-38(29-43(83)72-44(31(5)6)58(91)77-49(65(98)99)52(85)33(9)10)69-59(92)45(36(13)80)73-56(89)40(28-30(3)4)71-57(90)41-24-22-27-79(41)64(97)46(37(14)81)74-61(94)48(53(86)54(68)87)76-62(95)50(34(11)17-2)78(15)63(96)39(25-26-42(67)82)70-60(93)47(51(84)32(7)8)75-55(88)35(12)66/h30-41,44-53,80-81,84-86H,16-29,66H2,1-15H3,(H2,67,82)(H2,68,87)(H,69,92)(H,70,93)(H,71,90)(H,72,83)(H,73,89)(H,74,94)(H,75,88)(H,76,95)(H,77,91)(H,98,99)/t34-,35-,36+,37+,38+,39-,40+,41-,44-,45-,46-,47+,48+,49+,50-,51-,52-,53+/m0/s1
• InChI Key: ARBTXEGGGLHUPG-FYHKVEBYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₅H₁₁₆N₁₄O₂₀
• Molecular Weight: 1413.70 g/mol
• Exact Mass: 1412.84903214 g/mol
• Topological Polar Surface Area (TPSA): 553.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -3.99
• H-Bond Acceptor: 20
• H-Bond Donor: 18
• Rotatable Bonds: 45

Synonyms

• RefChem:109614
• (2R,3S)-2-(((2S)-2-(((3R)-3-(((2S,3R)-2-(((2R)-2-(((2S)-1-((2S,3R)-2-(((2R,3R)-4-amino-2-(((2S,3S)-2-(((2S)-5-amino-2-(((2R,3S)-2-(((2S)-2-aminopropanoyl)amino)-3-hydroxy-4-methylpentanoyl)amino)-5-oxopentanoyl)-methylamino)-3-methylpentanoyl)amino)-3-hydroxy-4-oxobutanoyl)amino)-3-hydroxybutanoyl)pyrrolidine-2-carbonyl)amino)-4-methylpentanoyl)amino)-3-hydroxybutanoyl)amino)decanoyl)amino)-3-methylbutanoyl)amino)-3-hydroxy-4-methylpentanoic acid
• (2R,3S)-2-((S)-2-((R)-3-((2S,3R)-2-((R)-2-((S)-1-(((2R,3R)-4-amino-2-((2S,3S)-2-((S)-5-amino-2-((2R,3S)-2-((S)-2-aminopropanamido)-3-hydroxy-4-methylpentanamido)-N-methyl-5-oxopentanamido)-3-methylpentanamido)-3-hydroxy-4-oxobutanoyl)-L-threonyl)pyrrolidine-2-carboxamido)-4-methylpentanamido)-3-hydroxybutanamido)decanamido)-3-methylbutanamido)-3-hydroxy-4-methylpentanoic acid
• (2R,3S)-2-[[(2S)-2-[[(3R)-3-[[(2S,3R)-2-[[(2R)-2-[[(2S)-1-[(2S,3R)-2-[[(2R,3R)-4-amino-2-[[(2S,3S)-2-[[(2S)-5-amino-2-[[(2R,3S)-2-[[(2S)-2-aminopropanoyl]amino]-3-hydroxy-4-methylpentanoyl]amino]-5-oxopentanoyl]-methylamino]-3-methylpentanoyl]amino]-3-hydroxy-4-oxobutanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]decanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxy-4-methylpentanoic acid
• CHEBI:227771
• DTXSID001046530

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6363	63.63%
Caco-2	-	0.8610	86.10%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5171	51.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8270	82.70%
OATP1B3 inhibitior	+	0.9017	90.17%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9292	92.92%
P-glycoprotein inhibitior	+	0.7417	74.17%
P-glycoprotein substrate	+	0.8495	84.95%
CYP3A4 substrate	+	0.7463	74.63%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.8151	81.51%
CYP3A4 inhibition	-	0.8617	86.17%
CYP2C9 inhibition	-	0.8889	88.89%
CYP2C19 inhibition	-	0.8705	87.05%
CYP2D6 inhibition	-	0.9344	93.44%
CYP1A2 inhibition	-	0.8978	89.78%
CYP2C8 inhibition	+	0.7015	70.15%
CYP inhibitory promiscuity	-	0.9832	98.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6427	64.27%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.8957	89.57%
Skin irritation	-	0.7977	79.77%
Skin corrosion	-	0.9161	91.61%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6807	68.07%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.5409	54.09%
skin sensitisation	-	0.8839	88.39%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7197	71.97%
Acute Oral Toxicity (c)	III	0.6688	66.88%
Estrogen receptor binding	+	0.6404	64.04%
Androgen receptor binding	+	0.7138	71.38%
Thyroid receptor binding	+	0.6416	64.16%
Glucocorticoid receptor binding	+	0.7411	74.11%
Aromatase binding	+	0.7610	76.10%
PPAR gamma	+	0.7952	79.52%
Honey bee toxicity	-	0.7448	74.48%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5189	51.89%
Fish aquatic toxicity	+	0.6471	64.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3837	P07711	Cathepsin L	99.96%	96.61%
CHEMBL2581	P07339	Cathepsin D	99.88%	98.95%
CHEMBL237	P41145	Kappa opioid receptor	99.43%	98.10%
CHEMBL2514	O95665	Neurotensin receptor 2	99.16%	100.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	99.16%	98.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	98.71%	93.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.47%	95.17%
CHEMBL4018	P49146	Neuropeptide Y receptor type 2	98.46%	98.94%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	98.36%	91.81%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.29%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	98.25%	90.17%
CHEMBL220	P22303	Acetylcholinesterase	98.08%	94.45%
CHEMBL4123	P30989	Neurotensin receptor 1	97.78%	96.67%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	97.49%	92.38%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	96.81%	97.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	96.77%	96.47%
CHEMBL4625	Q07817	Apoptosis regulator Bcl-X	96.72%	99.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.64%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	96.42%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	95.62%	100.00%
CHEMBL4801	P29466	Caspase-1	95.59%	96.85%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	95.46%	98.24%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	95.43%	95.52%
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	95.42%	97.43%
CHEMBL340	P08684	Cytochrome P450 3A4	94.56%	91.19%
CHEMBL230	P35354	Cyclooxygenase-2	94.55%	89.63%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	94.14%	100.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	94.13%	93.10%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	94.10%	97.64%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	94.09%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.91%	97.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	93.67%	92.86%
CHEMBL3176	O43603	Galanin receptor 2	93.38%	98.89%
CHEMBL3468	P55210	Caspase-7	93.08%	95.68%
CHEMBL4588	P22894	Matrix metalloproteinase 8	92.62%	94.66%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.49%	97.21%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	92.34%	97.29%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	92.02%	97.86%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.52%	96.95%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	91.48%	88.42%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.45%	90.71%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	91.14%	95.00%
CHEMBL274	P51681	C-C chemokine receptor type 5	90.92%	98.77%
CHEMBL283	P08254	Matrix metalloproteinase 3	90.90%	97.29%
CHEMBL3776	Q14790	Caspase-8	90.81%	97.06%
CHEMBL4777	P25929	Neuropeptide Y receptor type 1	90.56%	96.67%
CHEMBL5103	Q969S8	Histone deacetylase 10	90.54%	90.08%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	90.47%	96.00%
CHEMBL236	P41143	Delta opioid receptor	90.16%	99.35%
CHEMBL238	Q01959	Dopamine transporter	90.11%	95.88%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	88.21%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.59%	94.33%
CHEMBL3202	P48147	Prolyl endopeptidase	87.48%	90.65%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	87.10%	96.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.85%	95.50%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	86.82%	96.03%
CHEMBL2094135	Q96BI3	Gamma-secretase	86.51%	98.05%
CHEMBL3629	P68400	Casein kinase II alpha	85.86%	98.89%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.49%	90.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.42%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	85.29%	90.20%
CHEMBL5500	Q92831	Histone acetyltransferase PCAF	85.00%	91.96%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	84.60%	83.14%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.48%	82.38%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.24%	97.14%
CHEMBL1991	O14920	Inhibitor of nuclear factor kappa B kinase beta subunit	84.06%	97.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.80%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.50%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.32%	97.25%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	83.25%	92.32%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.21%	96.90%
CHEMBL3018	Q9Y5Y6	Matriptase	83.13%	98.33%
CHEMBL3691	Q13822	Autotaxin	82.10%	96.39%
CHEMBL206	P03372	Estrogen receptor alpha	81.88%	97.64%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	81.81%	95.36%
CHEMBL1873	P00750	Tissue-type plasminogen activator	81.75%	93.33%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	81.29%	90.24%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.16%	96.37%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.04%	97.47%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	80.84%	96.11%
CHEMBL299	P17252	Protein kinase C alpha	80.41%	98.03%
CHEMBL4071	P08311	Cathepsin G	80.27%	94.64%
CHEMBL4198	P98170	Inhibitor of apoptosis protein 3	80.23%	97.79%
CHEMBL228	P31645	Serotonin transporter	80.19%	95.51%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 155801635
• LOTUS: LTS0169715
• wikiData: Q104203043