(3S)-3-acetamido-4-[[(2R,5S,8S,11R,12S,15S,18R,21R)-2-benzyl-8-[(2S)-butan-2-yl]-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-4-oxobutanoic acid

Details

• Internal ID: 7a1f2fae-600b-44f0-aad4-68f08c7c8c67
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (3S)-3-acetamido-4-[[(2R,5S,8S,11R,12S,15S,18R,21R)-2-benzyl-8-[(2S)-butan-2-yl]-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-4-oxobutanoic acid
• SMILES (Canonical): CCC(C)C1C(=O)OC(C(C(=O)NC(C(=O)NC2CCC(N(C2=O)C(C(=O)N(C(C(=O)N1)CC3=CC=C(C=C3)O)C)CC4=CC=CC=C4)O)CCCN=C(N)N)NC(=O)C(CC(=O)O)NC(=O)C)C
• SMILES (Isomeric): CC[C@H](C)[C@H]1C(=O)O[C@@H]([C@@H](C(=O)N[C@H](C(=O)N[C@@H]2CC[C@H](N(C2=O)[C@@H](C(=O)N([C@H](C(=O)N1)CC3=CC=C(C=C3)O)C)CC4=CC=CC=C4)O)CCCN=C(N)N)NC(=O)[C@H](CC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C46H64N10O13/c1-6-24(2)37-45(68)69-25(3)38(54-40(63)32(23-36(60)61)50-26(4)57)42(65)51-30(13-10-20-49-46(47)48)39(62)52-31-18-19-35(59)56(43(31)66)34(22-27-11-8-7-9-12-27)44(67)55(5)33(41(64)53-37)21-28-14-16-29(58)17-15-28/h7-9,11-12,14-17,24-25,30-35,37-38,58-59H,6,10,13,18-23H2,1-5H3,(H,50,57)(H,51,65)(H,52,62)(H,53,64)(H,54,63)(H,60,61)(H4,47,48,49)/t24-,25+,30-,31+,32-,33-,34+,35+,37-,38-/m0/s1
• InChI Key: WCCRMFNYIYCRFM-MYONFRKVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₆₄N₁₀O₁₃
• Molecular Weight: 965.10 g/mol
• Exact Mass: 964.46543213 g/mol
• Topological Polar Surface Area (TPSA): 355.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -1.72
• H-Bond Acceptor: 13
• H-Bond Donor: 10
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7735	77.35%
Caco-2	-	0.8737	87.37%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4225	42.25%
OATP2B1 inhibitior	-	0.7146	71.46%
OATP1B1 inhibitior	+	0.8094	80.94%
OATP1B3 inhibitior	+	0.9252	92.52%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9453	94.53%
P-glycoprotein inhibitior	+	0.7473	74.73%
P-glycoprotein substrate	+	0.8949	89.49%
CYP3A4 substrate	+	0.7364	73.64%
CYP2C9 substrate	-	0.5923	59.23%
CYP2D6 substrate	-	0.8510	85.10%
CYP3A4 inhibition	-	0.8653	86.53%
CYP2C9 inhibition	-	0.8266	82.66%
CYP2C19 inhibition	-	0.7828	78.28%
CYP2D6 inhibition	-	0.8677	86.77%
CYP1A2 inhibition	-	0.8699	86.99%
CYP2C8 inhibition	+	0.7477	74.77%
CYP inhibitory promiscuity	-	0.9893	98.93%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6126	61.26%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.9056	90.56%
Skin irritation	-	0.7749	77.49%
Skin corrosion	-	0.9279	92.79%
Ames mutagenesis	-	0.5128	51.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4258	42.58%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8509	85.09%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.7342	73.42%
Acute Oral Toxicity (c)	III	0.5383	53.83%
Estrogen receptor binding	+	0.8202	82.02%
Androgen receptor binding	+	0.7081	70.81%
Thyroid receptor binding	+	0.6141	61.41%
Glucocorticoid receptor binding	+	0.5574	55.74%
Aromatase binding	+	0.6238	62.38%
PPAR gamma	+	0.7786	77.86%
Honey bee toxicity	-	0.7073	70.73%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8050	80.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.91%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.39%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.13%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.11%	99.17%
CHEMBL3837	P07711	Cathepsin L	95.53%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.32%	94.45%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	94.07%	97.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.76%	95.56%
CHEMBL4072	P07858	Cathepsin B	93.56%	93.67%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	93.50%	90.93%
CHEMBL221	P23219	Cyclooxygenase-1	93.03%	90.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.66%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	92.42%	90.08%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	91.66%	93.00%
CHEMBL3776	Q14790	Caspase-8	90.15%	97.06%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.76%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.04%	97.09%
CHEMBL4588	P22894	Matrix metalloproteinase 8	86.43%	94.66%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.68%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.67%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	85.44%	95.93%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.12%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.12%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.72%	97.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.04%	90.71%
CHEMBL255	P29275	Adenosine A2b receptor	83.91%	98.59%
CHEMBL4644	P41968	Melanocortin receptor 3	82.94%	99.52%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.93%	99.23%
CHEMBL259	P32245	Melanocortin receptor 4	82.93%	95.38%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162903507
• LOTUS: LTS0039545
• wikiData: Q105301304