(2S)-2-acetamido-N-[(2R,5S,8S,11S,12S,15S,18S,21R)-2-benzyl-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-15-(2-methylpropyl)-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]pentanediamide

Details

• Internal ID: 8cf8c823-d9ac-4fe6-ac53-1834bd4595c0
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2S)-2-acetamido-N-[(2R,5S,8S,11S,12S,15S,18S,21R)-2-benzyl-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-15-(2-methylpropyl)-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]pentanediamide
• SMILES (Canonical): CC1C(C(=O)NC(C(=O)NC2CCC(N(C2=O)C(C(=O)N(C(C(=O)NC(C(=O)O1)C(C)C)CC3=CC=C(C=C3)O)C)CC4=CC=CC=C4)O)CC(C)C)NC(=O)C(CCC(=O)N)NC(=O)C
• SMILES (Isomeric): C[C@H]1[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)N[C@H](C(=O)O1)C(C)C)CC3=CC=C(C=C3)O)C)CC4=CC=CC=C4)O)CC(C)C)NC(=O)[C@H](CCC(=O)N)NC(=O)C
• InChI: InChI=1S/C46H64N8O12/c1-24(2)21-33-41(60)49-32-18-20-37(58)54(44(32)63)35(23-28-11-9-8-10-12-28)45(64)53(7)34(22-29-13-15-30(56)16-14-29)42(61)51-38(25(3)4)46(65)66-26(5)39(43(62)50-33)52-40(59)31(48-27(6)55)17-19-36(47)57/h8-16,24-26,31-35,37-39,56,58H,17-23H2,1-7H3,(H2,47,57)(H,48,55)(H,49,60)(H,50,62)(H,51,61)(H,52,59)/t26-,31-,32-,33-,34-,35+,37+,38-,39-/m0/s1
• InChI Key: GSMBUVTZXAPMMN-NSIPKKQDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₆₄N₈O₁₂
• Molecular Weight: 921.00 g/mol
• Exact Mass: 920.46436951 g/mol
• Topological Polar Surface Area (TPSA): 296.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): -0.33
• 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	-	0.7204	72.04%
Caco-2	-	0.8733	87.33%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.3489	34.89%
OATP2B1 inhibitior	-	0.5749	57.49%
OATP1B1 inhibitior	+	0.8363	83.63%
OATP1B3 inhibitior	+	0.9240	92.40%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8640	86.40%
BSEP inhibitior	+	0.8138	81.38%
P-glycoprotein inhibitior	+	0.7526	75.26%
P-glycoprotein substrate	+	0.9055	90.55%
CYP3A4 substrate	+	0.7299	72.99%
CYP2C9 substrate	-	0.7984	79.84%
CYP2D6 substrate	-	0.8442	84.42%
CYP3A4 inhibition	-	0.7051	70.51%
CYP2C9 inhibition	-	0.8957	89.57%
CYP2C19 inhibition	-	0.8558	85.58%
CYP2D6 inhibition	-	0.8868	88.68%
CYP1A2 inhibition	-	0.9209	92.09%
CYP2C8 inhibition	+	0.6719	67.19%
CYP inhibitory promiscuity	-	0.9758	97.58%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6114	61.14%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9081	90.81%
Skin irritation	-	0.7904	79.04%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4208	42.08%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8897	88.97%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6860	68.60%
Acute Oral Toxicity (c)	III	0.6226	62.26%
Estrogen receptor binding	+	0.8342	83.42%
Androgen receptor binding	+	0.7153	71.53%
Thyroid receptor binding	+	0.5957	59.57%
Glucocorticoid receptor binding	+	0.5786	57.86%
Aromatase binding	+	0.6186	61.86%
PPAR gamma	+	0.8087	80.87%
Honey bee toxicity	-	0.7118	71.18%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8436	84.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.86%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.53%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	98.23%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.11%	91.11%
CHEMBL5103	Q969S8	Histone deacetylase 10	96.24%	90.08%
CHEMBL221	P23219	Cyclooxygenase-1	94.69%	90.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	94.32%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	94.23%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.22%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.18%	95.56%
CHEMBL3837	P07711	Cathepsin L	93.91%	96.61%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	93.66%	97.64%
CHEMBL4072	P07858	Cathepsin B	92.40%	93.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.85%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.25%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.99%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.70%	93.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.61%	89.67%
CHEMBL1949	P62937	Cyclophilin A	88.07%	98.57%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.52%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.93%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.34%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.06%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.92%	89.00%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	84.32%	95.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.22%	100.00%
CHEMBL259	P32245	Melanocortin receptor 4	82.47%	95.38%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.36%	89.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.11%	91.19%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	81.64%	96.03%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.46%	85.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.45%	96.47%

Plants that contains it

• Rauvolfia littoralis

Cross-Links

• PubChem: 163185256
• LOTUS: LTS0134951
• wikiData: Q105229057