N-(phenylacetyl)-L-phenylalanyl-N-[(3R,6S,9S,14S,17S,18R)-6-(2-amino-2-oxoethyl)-3,18-dimethyl-9,14-bis(2-methylpropyl)-2,5,8,11,12,13,16-heptaoxo-1-oxa-4,7,10,15-tetraazacyclooctadecan-17-yl]-L-threoninamide

Details

• Internal ID: 7810b234-3fcd-4b19-bd42-8bd8e0d11ff4
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2S,3R)-N-[(3R,6S,9S,14S,17S,18R)-6-(2-amino-2-oxoethyl)-3,18-dimethyl-9,14-bis(2-methylpropyl)-2,5,8,11,12,13,16-heptaoxo-1-oxa-4,7,10,15-tetrazacyclooctadec-17-yl]-3-hydroxy-2-[[(2S)-3-phenyl-2-[(2-phenylacetyl)amino]propanoyl]amino]butanamide
• SMILES (Canonical): CC1C(C(=O)NC(C(=O)C(=O)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O1)C)CC(=O)N)CC(C)C)CC(C)C)NC(=O)C(C(C)O)NC(=O)C(CC2=CC=CC=C2)NC(=O)CC3=CC=CC=C3
• SMILES (Isomeric): C[C@@H]1[C@@H](C(=O)N[C@H](C(=O)C(=O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)O1)C)CC(=O)N)CC(C)C)CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)CC3=CC=CC=C3
• InChI: InChI=1S/C46H62N8O13/c1-23(2)18-30-38(58)39(59)45(65)52-31(19-24(3)4)41(61)51-33(22-34(47)56)40(60)48-25(5)46(66)67-27(7)37(44(64)50-30)54-43(63)36(26(6)55)53-42(62)32(20-28-14-10-8-11-15-28)49-35(57)21-29-16-12-9-13-17-29/h8-17,23-27,30-33,36-37,55H,18-22H2,1-7H3,(H2,47,56)(H,48,60)(H,49,57)(H,50,64)(H,51,61)(H,52,65)(H,53,62)(H,54,63)/t25-,26-,27-,30+,31+,32+,33+,36+,37+/m1/s1
• InChI Key: RLFDHDLZRRLOSI-VFLTUTPWSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₆₂N₈O₁₃
• Molecular Weight: 935.00 g/mol
• Exact Mass: 934.44363406 g/mol
• Topological Polar Surface Area (TPSA): 327.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): -1.68
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 16

Synonyms

• CHEBI:66494
• YM 47141
• RefChem:934435
• 157951-38-7
• N-(phenylacetyl)-L-phenylalanyl-N-[(3R,6S,9S,14S,17S,18R)-6-(2-amino-2-oxoethyl)-3,18-dimethyl-9,14-bis(2-methylpropyl)-2,5,8,11,12,13,16-heptaoxo-1-oxa-4,7,10,15-tetraazacyclooctadecan-17-yl]-L-threoninamide
• Q27135097

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4868	48.68%
Caco-2	-	0.8691	86.91%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.3420	34.20%
OATP2B1 inhibitior	-	0.5739	57.39%
OATP1B1 inhibitior	+	0.8317	83.17%
OATP1B3 inhibitior	+	0.9217	92.17%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9818	98.18%
BSEP inhibitior	+	0.8992	89.92%
P-glycoprotein inhibitior	+	0.7463	74.63%
P-glycoprotein substrate	+	0.8435	84.35%
CYP3A4 substrate	+	0.6809	68.09%
CYP2C9 substrate	-	0.6049	60.49%
CYP2D6 substrate	-	0.8392	83.92%
CYP3A4 inhibition	-	0.6835	68.35%
CYP2C9 inhibition	-	0.9205	92.05%
CYP2C19 inhibition	-	0.9044	90.44%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.9303	93.03%
CYP2C8 inhibition	+	0.6391	63.91%
CYP inhibitory promiscuity	-	0.9458	94.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8000	80.00%
Carcinogenicity (trinary)	Non-required	0.6155	61.55%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9047	90.47%
Skin irritation	-	0.8100	81.00%
Skin corrosion	-	0.9465	94.65%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4049	40.49%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8772	87.72%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6868	68.68%
Acute Oral Toxicity (c)	III	0.6220	62.20%
Estrogen receptor binding	+	0.8001	80.01%
Androgen receptor binding	+	0.7415	74.15%
Thyroid receptor binding	+	0.5942	59.42%
Glucocorticoid receptor binding	+	0.6322	63.22%
Aromatase binding	+	0.6442	64.42%
PPAR gamma	+	0.7629	76.29%
Honey bee toxicity	-	0.7512	75.12%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.7549	75.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.77%	98.95%
CHEMBL3837	P07711	Cathepsin L	99.43%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.50%	95.56%
CHEMBL1255126	O15151	Protein Mdm4	96.46%	90.20%
CHEMBL221	P23219	Cyclooxygenase-1	93.80%	90.17%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	93.03%	88.42%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.15%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.86%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.13%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.10%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.34%	93.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.31%	96.47%
CHEMBL2535	P11166	Glucose transporter	87.43%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	87.25%	94.73%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	86.59%	97.64%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	85.68%	97.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.91%	97.09%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	83.57%	95.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.42%	85.31%
CHEMBL230	P35354	Cyclooxygenase-2	82.69%	89.63%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.13%	93.03%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 70678745
• LOTUS: LTS0233178
• wikiData: Q27135097