Rel-Neamphamide B

Details

• Internal ID: 2d84ed12-a04c-43fb-8b6c-7da427fe68e1
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: 4-[[(2R,3R,4S)-4-[[(2S)-4-amino-2-[[(2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoyl]amino]-4-oxobutanoyl]amino]-7-(diaminomethylideneamino)-2,3-dihydroxyheptanoyl]amino]-N'-[(3R,6S,9S,12R,15R,18R,19R,22S)-6-(3-amino-3-oxopropyl)-12-[3-(diaminomethylideneamino)propyl]-15-[(1S)-1-hydroxyethyl]-3-[(R)-(4-hydroxyphenyl)-methoxymethyl]-7,19-dimethyl-9-(2-methylpropyl)-2,5,8,11,14,17,21-heptaoxo-20-oxa-1,4,7,10,13,16-hexazabicyclo[20.4.0]hexacosan-18-yl]-2,3-dimethylpentanediamide
• SMILES (Canonical): CC1C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)N2CCCCC2C(=O)O1)C(C3=CC=C(C=C3)O)OC)CCC(=O)N)C)CC(C)C)CCCN=C(N)N)C(C)O)NC(=O)C(C(C)C(C)C(=O)N)NC(=O)C(C(C(CCCN=C(N)N)NC(=O)C(CC(=O)N)NC(=O)C(C)C(C(C)CC(C)C)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@@H](C(=O)N2CCCC[C@H]2C(=O)O1)[C@@H](C3=CC=C(C=C3)O)OC)CCC(=O)N)C)CC(C)C)CCCN=C(N)N)[C@H](C)O)NC(=O)C(C(C)C(C)C(=O)N)NC(=O)[C@@H]([C@@H]([C@H](CCCN=C(N)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C)[C@@H]([C@H](C)CC(C)C)O)O)O
• InChI: InChI=1S/C71H119N19O21/c1-32(2)29-34(5)54(95)37(8)59(99)83-44(31-49(73)94)61(101)81-42(17-15-26-79-70(75)76)55(96)56(97)66(106)85-50(35(6)36(7)58(74)98)63(103)87-52-39(10)111-69(109)47-19-13-14-28-90(47)68(108)53(57(110-12)40-20-22-41(92)23-21-40)88-62(102)46(24-25-48(72)93)89(11)67(107)45(30-33(3)4)84-60(100)43(18-16-27-80-71(77)78)82-64(104)51(38(9)91)86-65(52)105/h20-23,32-39,42-47,50-57,91-92,95-97H,13-19,24-31H2,1-12H3,(H2,72,93)(H2,73,94)(H2,74,98)(H,81,101)(H,82,104)(H,83,99)(H,84,100)(H,85,106)(H,86,105)(H,87,103)(H,88,102)(H4,75,76,79)(H4,77,78,80)/t34-,35?,36?,37-,38+,39-,42+,43-,44+,45+,46+,47+,50?,51-,52-,53-,54-,55-,56-,57-/m1/s1
• InChI Key: CTBZWDZNRDQPPS-SZKMIYDASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₇₁H₁₁₉N₁₉O₂₁
• Molecular Weight: 1574.80 g/mol
• Exact Mass: 1573.88279188 g/mol
• Topological Polar Surface Area (TPSA): 668.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -6.05
• H-Bond Acceptor: 23
• H-Bond Donor: 20
• Rotatable Bonds: 36

Synonyms

• RefChem:178805
• 4-(((2R,3R,4S)-4-(((2S)-4-amino-2-(((2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoyl)amino)-4-oxobutanoyl)amino)-7-(diaminomethylideneamino)-2,3-dihydroxyheptanoyl)amino)-N'-((3R,6S,9S,12R,15R,18R,19R,22S)-6-(3-amino-3-oxopropyl)-12-(3-(diaminomethylideneamino)propyl)-15-((1S)-1-hydroxyethyl)-3-((R)-(4-hydroxyphenyl)-methoxymethyl)-7,19-dimethyl-9-(2-methylpropyl)-2,5,8,11,14,17,21-heptaoxo-20-oxa-1,4,7,10,13,16-hexazabicyclo(20.4.0)hexacosan-18-yl)-2,3-dimethylpentanediamide
• 4-[[(2R,3R,4S)-4-[[(2S)-4-amino-2-[[(2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoyl]amino]-4-oxobutanoyl]amino]-7-(diaminomethylideneamino)-2,3-dihydroxyheptanoyl]amino]-N'-[(3R,6S,9S,12R,15R,18R,19R,22S)-6-(3-amino-3-oxopropyl)-12-[3-(diaminomethylideneamino)propyl]-15-[(1S)-1-hydroxyethyl]-3-[(R)-(4-hydroxyphenyl)-methoxymethyl]-7,19-dimethyl-9-(2-methylpropyl)-2,5,8,11,14,17,21-heptaoxo-20-oxa-1,4,7,10,13,16-hexazabicyclo[20.4.0]hexacosan-18-yl]-2,3-dimethylpentanediamide
• CHEMBL2208229

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7800	78.00%
Caco-2	-	0.8604	86.04%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.4287	42.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8035	80.35%
OATP1B3 inhibitior	+	0.9284	92.84%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9405	94.05%
P-glycoprotein inhibitior	+	0.7418	74.18%
P-glycoprotein substrate	+	0.8911	89.11%
CYP3A4 substrate	+	0.7597	75.97%
CYP2C9 substrate	-	0.6128	61.28%
CYP2D6 substrate	-	0.8120	81.20%
CYP3A4 inhibition	-	0.9318	93.18%
CYP2C9 inhibition	-	0.8159	81.59%
CYP2C19 inhibition	-	0.8321	83.21%
CYP2D6 inhibition	-	0.8827	88.27%
CYP1A2 inhibition	-	0.8898	88.98%
CYP2C8 inhibition	+	0.8420	84.20%
CYP inhibitory promiscuity	-	0.9900	99.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6140	61.40%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.8954	89.54%
Skin irritation	-	0.7610	76.10%
Skin corrosion	-	0.9249	92.49%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7164	71.64%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.5169	51.69%
skin sensitisation	-	0.8467	84.67%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.7593	75.93%
Acute Oral Toxicity (c)	III	0.5329	53.29%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.7544	75.44%
Thyroid receptor binding	+	0.7637	76.37%
Glucocorticoid receptor binding	+	0.8246	82.46%
Aromatase binding	+	0.8135	81.35%
PPAR gamma	+	0.7795	77.95%
Honey bee toxicity	-	0.6229	62.29%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8173	81.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.93%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.82%	96.09%
CHEMBL3837	P07711	Cathepsin L	99.72%	96.61%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.65%	91.11%
CHEMBL2094135	Q96BI3	Gamma-secretase	97.65%	98.05%
CHEMBL4777	P25929	Neuropeptide Y receptor type 1	96.99%	96.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.56%	97.09%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	95.61%	88.42%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.57%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	95.16%	90.71%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	95.03%	96.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.77%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.83%	95.56%
CHEMBL4588	P22894	Matrix metalloproteinase 8	93.61%	94.66%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	92.42%	90.93%
CHEMBL5103	Q969S8	Histone deacetylase 10	91.97%	90.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.43%	94.45%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	91.39%	97.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.20%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.65%	100.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	89.85%	98.33%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	89.84%	91.81%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.57%	93.03%
CHEMBL255	P29275	Adenosine A2b receptor	89.43%	98.59%
CHEMBL2514	O95665	Neurotensin receptor 2	89.36%	100.00%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	89.12%	95.00%
CHEMBL333	P08253	Matrix metalloproteinase-2	89.01%	96.31%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	88.22%	96.11%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	88.14%	96.90%
CHEMBL236	P41143	Delta opioid receptor	87.92%	99.35%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.91%	93.00%
CHEMBL332	P03956	Matrix metalloproteinase-1	87.71%	94.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.17%	89.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.71%	99.23%
CHEMBL226	P30542	Adenosine A1 receptor	86.68%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	86.63%	91.19%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.31%	85.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.98%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.86%	85.14%
CHEMBL2535	P11166	Glucose transporter	85.54%	98.75%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	85.15%	97.31%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.54%	82.38%
CHEMBL259	P32245	Melanocortin receptor 4	84.14%	95.38%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.77%	92.88%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.37%	99.15%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.19%	90.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.09%	95.89%
CHEMBL206	P03372	Estrogen receptor alpha	83.04%	97.64%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.79%	94.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.61%	89.00%
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	82.56%	97.43%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.55%	97.25%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.15%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.04%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.00%	95.50%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.22%	85.83%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.92%	96.47%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.86%	100.00%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	80.76%	83.14%
CHEMBL4330	Q9NS75	Cysteinyl leukotriene receptor 2	80.20%	98.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 71461528
• LOTUS: LTS0027856
• wikiData: Q104969701