Izenamide B

Details

• Internal ID: 3fc0912e-4791-4008-8f48-d0adacf01199
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides
• IUPAC Name: methyl (2S)-1-[(2R)-2-[[(2S)-2-[[(2S,3S)-2-[[(3S,4S)-3-hydroxy-4-[[(2R,3S)-2-[(2S)-2-hydroxy-3-methylbutanoyl]oxy-3-methylpentanoyl]amino]-6-methylheptanoyl]amino]-3-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
• SMILES (Canonical): CCC(C)C(C(=O)NC(C)C(=O)N(C)C(CC1=CC=CC=C1)C(=O)N2CCCC2C(=O)OC)NC(=O)CC(C(CC(C)C)NC(=O)C(C(C)CC)OC(=O)C(C(C)C)O)O
• SMILES (Isomeric): CC[C@H](C)[C@@H](C(=O)N[C@@H](C)C(=O)N(C)[C@H](CC1=CC=CC=C1)C(=O)N2CCC[C@H]2C(=O)OC)NC(=O)C[C@@H]([C@H](CC(C)C)NC(=O)[C@@H]([C@@H](C)CC)OC(=O)[C@H](C(C)C)O)O
• InChI: InChI=1S/C44H71N5O11/c1-12-27(7)36(47-35(51)24-34(50)31(22-25(3)4)46-40(54)38(28(8)13-2)60-44(58)37(52)26(5)6)39(53)45-29(9)41(55)48(10)33(23-30-18-15-14-16-19-30)42(56)49-21-17-20-32(49)43(57)59-11/h14-16,18-19,25-29,31-34,36-38,50,52H,12-13,17,20-24H2,1-11H3,(H,45,53)(H,46,54)(H,47,51)/t27-,28-,29-,31-,32-,33+,34-,36-,37-,38+/m0/s1
• InChI Key: XLJBQXZXIWSYHO-FSWQITBWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₁N₅O₁₁
• Molecular Weight: 846.10 g/mol
• Exact Mass: 845.51500810 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 23

Synonyms

• DTXSID501319338
• methyl (2S)-1-((2R)-2-(((2S)-2-(((2S,3S)-2-(((3S,4S)-3-hydroxy-4-(((2R,3S)-2-((2S)-2-hydroxy-3-methylbutanoyl)oxy-3-methylpentanoyl)amino)-6-methylheptanoyl)amino)-3-methylpentanoyl)amino)propanoyl)-methylamino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate
• methyl (2S)-1-[(2R)-2-[[(2S)-2-[[(2S,3S)-2-[[(3S,4S)-3-hydroxy-4-[[(2R,3S)-2-[(2S)-2-hydroxy-3-methylbutanoyl]oxy-3-methylpentanoyl]amino]-6-methylheptanoyl]amino]-3-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
• RefChem:150259
• DTXCID801748764
• methyl N-(((3R)-2-((3R,4R)-3-hydroxy-4-((2S,3S)-2-(((S)-2-hydroxy-3-methylbutanoyl)oxy)-3-methylpentanamido)-6-methylheptanamido)-3-methylpentanoyl)-D-alanyl)-N-methyl-D-phenylalanyl-L-prolinate
• CHEMBL4161264
• CHEBI:209997
• BDBM50361186

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5252	52.52%
Caco-2	-	0.8653	86.53%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6909	69.09%
OATP2B1 inhibitior	-	0.7150	71.50%
OATP1B1 inhibitior	+	0.8545	85.45%
OATP1B3 inhibitior	+	0.8986	89.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8725	87.25%
P-glycoprotein inhibitior	+	0.7498	74.98%
P-glycoprotein substrate	+	0.8623	86.23%
CYP3A4 substrate	+	0.7316	73.16%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8175	81.75%
CYP3A4 inhibition	-	0.6464	64.64%
CYP2C9 inhibition	-	0.8267	82.67%
CYP2C19 inhibition	-	0.7977	79.77%
CYP2D6 inhibition	-	0.9097	90.97%
CYP1A2 inhibition	-	0.8925	89.25%
CYP2C8 inhibition	+	0.6389	63.89%
CYP inhibitory promiscuity	-	0.8886	88.86%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6784	67.84%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9084	90.84%
Skin irritation	-	0.8027	80.27%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3913	39.13%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.8958	89.58%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.4591	45.91%
Acute Oral Toxicity (c)	III	0.6638	66.38%
Estrogen receptor binding	+	0.8428	84.28%
Androgen receptor binding	+	0.7252	72.52%
Thyroid receptor binding	+	0.6007	60.07%
Glucocorticoid receptor binding	+	0.7508	75.08%
Aromatase binding	+	0.5776	57.76%
PPAR gamma	+	0.7898	78.98%
Honey bee toxicity	-	0.7315	73.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8972	89.72%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2581	P07339	Cathepsin D	270 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3837	P07711	Cathepsin L	99.16%	96.61%
CHEMBL221	P23219	Cyclooxygenase-1	98.83%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.17%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	96.52%	89.63%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	95.49%	98.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.45%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	91.20%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.11%	93.56%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	90.98%	97.64%
CHEMBL2514	O95665	Neurotensin receptor 2	90.48%	100.00%
CHEMBL4072	P07858	Cathepsin B	90.12%	93.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.33%	95.56%
CHEMBL3202	P48147	Prolyl endopeptidase	89.09%	90.65%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.74%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.61%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.26%	96.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.03%	100.00%
CHEMBL1255126	O15151	Protein Mdm4	85.69%	90.20%
CHEMBL4588	P22894	Matrix metalloproteinase 8	85.55%	94.66%
CHEMBL2535	P11166	Glucose transporter	85.37%	98.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.30%	100.00%
CHEMBL204	P00734	Thrombin	84.99%	96.01%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	84.97%	98.24%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.75%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.82%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.69%	97.09%
CHEMBL5028	O14672	ADAM10	83.27%	97.50%
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	82.03%	92.17%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	81.91%	96.67%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	81.40%	89.33%
CHEMBL237	P41145	Kappa opioid receptor	81.30%	98.10%

Plants that contains it

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Cross-Links

• PubChem: 139590075
• LOTUS: LTS0077315
• wikiData: Q104203250