Tasiamide F

Details

• Internal ID: 17364c21-1611-438b-854c-794c71bdf061
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: methyl (2S)-1-[(2R)-2-[[2-[[(2S,3S)-2-[[(3S,4S)-4-[[(2S)-5-amino-2-[[(2S,3S)-2-[[(2S)-2-hydroxypropanoyl]amino]-3-methylpentanoyl]-methylamino]-5-oxopentanoyl]amino]-3-hydroxy-5-phenylpentanoyl]amino]-3-methylpentanoyl]amino]acetyl]-methylamino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
• SMILES (Canonical): CCC(C)C(C(=O)NCC(=O)N(C)C(CC1=CC=CC=C1)C(=O)N2CCCC2C(=O)OC)NC(=O)CC(C(CC3=CC=CC=C3)NC(=O)C(CCC(=O)N)N(C)C(=O)C(C(C)CC)NC(=O)C(C)O)O
• SMILES (Isomeric): CC[C@H](C)[C@@H](C(=O)NCC(=O)N(C)[C@H](CC1=CC=CC=C1)C(=O)N2CCC[C@H]2C(=O)OC)NC(=O)C[C@@H]([C@H](CC3=CC=CC=C3)NC(=O)[C@H](CCC(=O)N)N(C)C(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](C)O)O
• InChI: InChI=1S/C50H74N8O12/c1-9-30(3)43(47(66)52-29-42(63)56(6)38(27-34-20-15-12-16-21-34)48(67)58-25-17-22-37(58)50(69)70-8)54-41(62)28-39(60)35(26-33-18-13-11-14-19-33)53-46(65)36(23-24-40(51)61)57(7)49(68)44(31(4)10-2)55-45(64)32(5)59/h11-16,18-21,30-32,35-39,43-44,59-60H,9-10,17,22-29H2,1-8H3,(H2,51,61)(H,52,66)(H,53,65)(H,54,62)(H,55,64)/t30-,31-,32-,35-,36-,37-,38+,39-,43-,44-/m0/s1
• InChI Key: CJLWKFUIIJXJBZ-PMQPHXACSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₄N₈O₁₂
• Molecular Weight: 979.20 g/mol
• Exact Mass: 978.54261983 g/mol
• Topological Polar Surface Area (TPSA): 287.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 27

Synonyms

• methyl (2S)-1-[(2R)-2-[[2-[[(2S,3S)-2-[[(3S,4S)-4-[[(2S)-5-amino-2-[[(2S,3S)-2-[[(2S)-2-hydroxypropanoyl]amino]-3-methylpentanoyl]-methylamino]-5-oxopentanoyl]amino]-3-hydroxy-5-phenylpentanoyl]amino]-3-methylpentanoyl]amino]acetyl]-methylamino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
• (2S)-2-((2S,3S)-2-(((2S)-1,2-dihydroxypropylidene)amino)-N,3-dimethylpentanamido)-N-((2S,3S)-3-hydroxy-4-(((1S,2S)-1-(((((2R)-1-((2S)-2-(methoxycarbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)(methyl)carbamoyl)methyl)-C-hydroxycarbonimidoyl)-2-methylbutyl)-C-hydroxycarbonimidoyl)-1-phenylbutan-2-yl)pentanediimidate
• (2S)-2-[(2S,3S)-2-{[(2S)-1,2-dihydroxypropylidene]amino}-N,3-dimethylpentanamido]-N-[(2S,3S)-3-hydroxy-4-{[(1S,2S)-1-[({[(2R)-1-[(2S)-2-(methoxycarbonyl)pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl](methyl)carbamoyl}methyl)-C-hydroxycarbonimidoyl]-2-methylbutyl]-C-hydroxycarbonimidoyl}-1-phenylbutan-2-yl]pentanediimidate
• methyl (2S)-1-((2R)-2-((2-(((2S,3S)-2-(((3S,4S)-4-(((2S)-5-amino-2-(((2S,3S)-2-(((2S)-2-hydroxypropanoyl)amino)-3-methylpentanoyl)-methylamino)-5-oxopentanoyl)amino)-3-hydroxy-5-phenylpentanoyl)amino)-3-methylpentanoyl)amino)acetyl)-methylamino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate
• RefChem:187481
• 3-((1S,2R,3R,4R,6S)-4-chloro-2-isocyano-3-methyl-6-(prop-1-en-2-yl)-3-vinylcyclohexyl)-1H-indole
• CHEMBL3813928
• CHEBI:219993
• BDBM50178261

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5787	57.87%
Caco-2	-	0.8660	86.60%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4518	45.18%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.8413	84.13%
OATP1B3 inhibitior	+	0.9220	92.20%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9641	96.41%
P-glycoprotein inhibitior	+	0.7465	74.65%
P-glycoprotein substrate	+	0.8422	84.22%
CYP3A4 substrate	+	0.7382	73.82%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8214	82.14%
CYP3A4 inhibition	+	0.5678	56.78%
CYP2C9 inhibition	-	0.7989	79.89%
CYP2C19 inhibition	-	0.7781	77.81%
CYP2D6 inhibition	-	0.8456	84.56%
CYP1A2 inhibition	-	0.9031	90.31%
CYP2C8 inhibition	+	0.6223	62.23%
CYP inhibitory promiscuity	-	0.8626	86.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6430	64.30%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9013	90.13%
Skin irritation	-	0.7972	79.72%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6733	67.33%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.6689	66.89%
skin sensitisation	-	0.9005	90.05%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6418	64.18%
Acute Oral Toxicity (c)	III	0.6663	66.63%
Estrogen receptor binding	+	0.8255	82.55%
Androgen receptor binding	+	0.7219	72.19%
Thyroid receptor binding	+	0.6165	61.65%
Glucocorticoid receptor binding	+	0.6738	67.38%
Aromatase binding	+	0.5859	58.59%
PPAR gamma	+	0.8152	81.52%
Honey bee toxicity	-	0.7002	70.02%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8607	86.07%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4822	P56817	Beta-secretase 1	690 nM	IC50	via Super-PRED
CHEMBL2581	P07339	Cathepsin D	57 nM	IC50	via Super-PRED
CHEMBL3092	P14091	Cathepsin E	23 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.20%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	98.82%	90.17%
CHEMBL204	P00734	Thrombin	95.40%	96.01%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	95.37%	98.33%
CHEMBL2514	O95665	Neurotensin receptor 2	95.02%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	93.17%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.11%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	93.06%	89.63%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.41%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	92.21%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.82%	97.09%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	91.10%	98.24%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.45%	93.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.22%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.91%	97.14%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	88.95%	97.64%
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	88.49%	92.17%
CHEMBL1255126	O15151	Protein Mdm4	88.00%	90.20%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.78%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.04%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.33%	95.89%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	85.95%	96.03%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	85.74%	96.67%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	85.62%	95.52%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.35%	82.38%
CHEMBL4447	Q9Y337	Kallikrein 5	83.48%	87.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.40%	100.00%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	82.42%	89.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.38%	93.03%
CHEMBL4588	P22894	Matrix metalloproteinase 8	80.60%	94.66%
CHEMBL3837	P07711	Cathepsin L	80.58%	96.61%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.58%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.47%	95.50%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	80.16%	95.00%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.00%	86.67%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 127050883
• LOTUS: LTS0224251
• wikiData: Q104961363