(2R)-N-[(2R,5R,8R,11R,12R,18R,21S)-2-benzyl-15-ethylidene-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-[[(2R)-2-(butanoylamino)propanoyl]amino]-3-methylbutanamide

Details

• Internal ID: b908d07f-26ef-46fb-aa07-f42f651907e4
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2R)-N-[(2R,5R,8R,11R,12R,18R,21S)-2-benzyl-15-ethylidene-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-[[(2R)-2-(butanoylamino)propanoyl]amino]-3-methylbutanamide
• SMILES (Canonical): CCCC(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC1C(OC(=O)C(NC(=O)C(N(C(=O)C(N2C(CCC(C2=O)NC(=O)C(=CC)NC1=O)O)CC3=CC=CC=C3)C)CC4=CC=C(C=C4)O)C(C)C)C
• SMILES (Isomeric): CCCC(=O)N[C@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H]1[C@H](OC(=O)[C@H](NC(=O)[C@H](N(C(=O)[C@H](N2[C@H](CC[C@H](C2=O)NC(=O)C(=CC)NC1=O)O)CC3=CC=CC=C3)C)CC4=CC=C(C=C4)O)C(C)C)C
• InChI: InChI=1S/C49H68N8O12/c1-10-15-37(59)50-28(7)42(61)53-39(26(3)4)45(64)55-41-29(8)69-49(68)40(27(5)6)54-44(63)35(24-31-18-20-32(58)21-19-31)56(9)48(67)36(25-30-16-13-12-14-17-30)57-38(60)23-22-34(47(57)66)52-43(62)33(11-2)51-46(41)65/h11-14,16-21,26-29,34-36,38-41,58,60H,10,15,22-25H2,1-9H3,(H,50,59)(H,51,65)(H,52,62)(H,53,61)(H,54,63)(H,55,64)/t28-,29-,34-,35-,36-,38+,39-,40-,41-/m1/s1
• InChI Key: KROYJVUBAIMQLZ-IQKOZBLYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₆₈N₈O₁₂
• Molecular Weight: 961.10 g/mol
• Exact Mass: 960.49566963 g/mol
• Topological Polar Surface Area (TPSA): 282.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 0.84
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6539	65.39%
Caco-2	-	0.8682	86.82%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5582	55.82%
OATP2B1 inhibitior	-	0.5774	57.74%
OATP1B1 inhibitior	+	0.7832	78.32%
OATP1B3 inhibitior	+	0.9116	91.16%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8640	86.40%
BSEP inhibitior	+	0.9480	94.80%
P-glycoprotein inhibitior	+	0.7458	74.58%
P-glycoprotein substrate	+	0.8820	88.20%
CYP3A4 substrate	+	0.7342	73.42%
CYP2C9 substrate	+	0.5951	59.51%
CYP2D6 substrate	-	0.8713	87.13%
CYP3A4 inhibition	+	0.5995	59.95%
CYP2C9 inhibition	-	0.8136	81.36%
CYP2C19 inhibition	-	0.7537	75.37%
CYP2D6 inhibition	-	0.8614	86.14%
CYP1A2 inhibition	-	0.8613	86.13%
CYP2C8 inhibition	+	0.7574	75.74%
CYP inhibitory promiscuity	-	0.9052	90.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5696	56.96%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9039	90.39%
Skin irritation	-	0.7755	77.55%
Skin corrosion	-	0.9205	92.05%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4702	47.02%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8724	87.24%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6722	67.22%
Acute Oral Toxicity (c)	III	0.6374	63.74%
Estrogen receptor binding	+	0.8338	83.38%
Androgen receptor binding	+	0.7190	71.90%
Thyroid receptor binding	+	0.6003	60.03%
Glucocorticoid receptor binding	+	0.6215	62.15%
Aromatase binding	+	0.6301	63.01%
PPAR gamma	+	0.7986	79.86%
Honey bee toxicity	-	0.7070	70.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9690	96.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.89%	98.95%
CHEMBL4072	P07858	Cathepsin B	98.94%	93.67%
CHEMBL5103	Q969S8	Histone deacetylase 10	98.54%	90.08%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.16%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.75%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.79%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.59%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.81%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	93.19%	93.00%
CHEMBL221	P23219	Cyclooxygenase-1	92.34%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.18%	89.00%
CHEMBL255	P29275	Adenosine A2b receptor	91.49%	98.59%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.33%	99.23%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	89.94%	90.93%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	88.30%	97.64%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.59%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.29%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.84%	95.89%
CHEMBL333	P08253	Matrix metalloproteinase-2	85.61%	96.31%
CHEMBL268	P43235	Cathepsin K	85.36%	96.85%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.34%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.37%	97.09%
CHEMBL1949	P62937	Cyclophilin A	83.93%	98.57%
CHEMBL4588	P22894	Matrix metalloproteinase 8	83.60%	94.66%
CHEMBL3891	P07384	Calpain 1	83.19%	93.04%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.09%	93.03%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.97%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.42%	85.14%
CHEMBL4393	P39900	Matrix metalloproteinase 12	80.39%	92.22%
CHEMBL2535	P11166	Glucose transporter	80.20%	98.75%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 146684874
• LOTUS: LTS0185086
• wikiData: Q105145150