Rimosamide A

Details

• Internal ID: 6e8dbb99-8ac7-4d5e-be78-d1eeb6303af3
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides
• IUPAC Name: (3S)-3-[(2S,3R)-3-acetyloxy-1-[(2S)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl]-3-[(2S)-2-[[2-(2-methylpropanoylamino)acetyl]amino]-3-phenylpropanoyl]oxypropanoic acid
• SMILES (Canonical): CCC(C)C(C(=O)N1CCC(C1C(CC(=O)O)OC(=O)C(CC2=CC=CC=C2)NC(=O)CNC(=O)C(C)C)OC(=O)C)N
• SMILES (Isomeric): CCC(C)[C@@H](C(=O)N1CC[C@H]([C@H]1[C@H](CC(=O)O)OC(=O)[C@H](CC2=CC=CC=C2)NC(=O)CNC(=O)C(C)C)OC(=O)C)N
• InChI: InChI=1S/C30H44N4O9/c1-6-18(4)26(31)29(40)34-13-12-22(42-19(5)35)27(34)23(15-25(37)38)43-30(41)21(14-20-10-8-7-9-11-20)33-24(36)16-32-28(39)17(2)3/h7-11,17-18,21-23,26-27H,6,12-16,31H2,1-5H3,(H,32,39)(H,33,36)(H,37,38)/t18?,21-,22+,23-,26-,27-/m0/s1
• InChI Key: OOZXZLMNWFHGNB-NZEUKUFQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₄N₄O₉
• Molecular Weight: 604.70 g/mol
• Exact Mass: 604.31082899 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.78
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 15

Synonyms

• (3S)-3-[(2S,3R)-3-acetyloxy-1-[(2S)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl]-3-[(2S)-2-[[2-(2-methylpropanoylamino)acetyl]amino]-3-phenylpropanoyl]oxypropanoic acid
• (3S)-3-((2S,3R)-3-(Acetyloxy)-1-((2S)-2-amino-3-methylpentanoyl)pyrrolidin-2-yl)-3-(((2S)-2-((1-hydroxy-2-((1-hydroxy-2-methylpropylidene)amino)ethylidene)amino)-3-phenylpropanoyl)oxy)propanoate
• (3S)-3-((2S,3R)-3-acetyloxy-1-((2S)-2-amino-3-methylpentanoyl)pyrrolidin-2-yl)-3-((2S)-2-((2-(2-methylpropanoylamino)acetyl)amino)-3-phenylpropanoyl)oxypropanoic acid
• (3S)-3-[(2S,3R)-3-(Acetyloxy)-1-[(2S)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl]-3-{[(2S)-2-({1-hydroxy-2-[(1-hydroxy-2-methylpropylidene)amino]ethylidene}amino)-3-phenylpropanoyl]oxy}propanoate
• RefChem:179472
• CHEBI:218990

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7552	75.52%
Caco-2	-	0.8432	84.32%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4743	47.43%
OATP2B1 inhibitior	-	0.7079	70.79%
OATP1B1 inhibitior	+	0.8816	88.16%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8977	89.77%
P-glycoprotein inhibitior	+	0.7883	78.83%
P-glycoprotein substrate	+	0.7612	76.12%
CYP3A4 substrate	+	0.6876	68.76%
CYP2C9 substrate	-	0.7970	79.70%
CYP2D6 substrate	-	0.8054	80.54%
CYP3A4 inhibition	-	0.7594	75.94%
CYP2C9 inhibition	-	0.8717	87.17%
CYP2C19 inhibition	-	0.8153	81.53%
CYP2D6 inhibition	-	0.9139	91.39%
CYP1A2 inhibition	-	0.9177	91.77%
CYP2C8 inhibition	+	0.5487	54.87%
CYP inhibitory promiscuity	-	0.9330	93.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6290	62.90%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9429	94.29%
Skin irritation	-	0.7968	79.68%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7100	71.00%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.6177	61.77%
skin sensitisation	-	0.9003	90.03%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7235	72.35%
Acute Oral Toxicity (c)	III	0.6016	60.16%
Estrogen receptor binding	+	0.7877	78.77%
Androgen receptor binding	+	0.6403	64.03%
Thyroid receptor binding	+	0.5378	53.78%
Glucocorticoid receptor binding	+	0.7653	76.53%
Aromatase binding	+	0.5391	53.91%
PPAR gamma	+	0.7439	74.39%
Honey bee toxicity	-	0.8040	80.40%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.4012	40.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.95%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	99.72%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.36%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.98%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	95.56%	97.21%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	94.80%	98.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.87%	94.45%
CHEMBL220	P22303	Acetylcholinesterase	93.65%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	92.42%	90.20%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	91.95%	89.33%
CHEMBL204	P00734	Thrombin	91.90%	96.01%
CHEMBL1914	P06276	Butyrylcholinesterase	91.65%	95.00%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	90.99%	96.67%
CHEMBL2535	P11166	Glucose transporter	88.84%	98.75%
CHEMBL230	P35354	Cyclooxygenase-2	88.79%	89.63%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	88.63%	97.64%
CHEMBL340	P08684	Cytochrome P450 3A4	88.61%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.40%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.34%	95.89%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.87%	94.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.81%	93.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.43%	97.14%
CHEMBL3837	P07711	Cathepsin L	86.74%	96.61%
CHEMBL5028	O14672	ADAM10	86.40%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.67%	95.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.46%	95.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.17%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.59%	96.95%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	82.55%	95.48%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.34%	95.89%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.96%	86.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.16%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 146684521
• LOTUS: LTS0078446
• wikiData: Q105195887