[(2R)-3-[[(2R)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-2,8-bis[(2S)-butan-2-yl]-21-hydroxy-15-[2-(4-hydroxyphenyl)ethyl]-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-(4-hydroxyphenyl)-1-oxobutan-2-yl]amino]-2-methoxy-3-oxopropyl] hydrogen sulfate

Details

• Internal ID: 89a2ea57-f17b-4da4-9675-5c97f8d1f782
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: [(2R)-3-[[(2R)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-2,8-bis[(2S)-butan-2-yl]-21-hydroxy-15-[2-(4-hydroxyphenyl)ethyl]-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-(4-hydroxyphenyl)-1-oxobutan-2-yl]amino]-2-methoxy-3-oxopropyl] hydrogen sulfate
• 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=CC=C3)C)C(C)CC)O)CCC4=CC=C(C=C4)O)NC(=O)C(CCC5=CC=C(C=C5)O)NC(=O)C(COS(=O)(=O)O)OC)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=CC=C3)C)[C@@H](C)CC)O)CCC4=CC=C(C=C4)O)NC(=O)[C@@H](CCC5=CC=C(C=C5)O)NC(=O)[C@@H](COS(=O)(=O)O)OC)C
• InChI: InChI=1S/C55H75N7O17S/c1-8-31(3)45-55(73)79-33(5)46(60-49(67)40(26-20-35-17-23-38(64)24-18-35)56-51(69)43(77-7)30-78-80(74,75)76)52(70)57-39(25-19-34-15-21-37(63)22-16-34)48(66)58-41-27-28-44(65)62(53(41)71)47(32(4)9-2)54(72)61(6)42(50(68)59-45)29-36-13-11-10-12-14-36/h10-18,21-24,31-33,39-47,63-65H,8-9,19-20,25-30H2,1-7H3,(H,56,69)(H,57,70)(H,58,66)(H,59,68)(H,60,67)(H,74,75,76)/t31-,32-,33+,39-,40+,41-,42-,43+,44+,45-,46-,47-/m0/s1
• InChI Key: IPSPUQFSLMOERD-ANWWLRMESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₇₅N₇O₁₇S
• Molecular Weight: 1138.30 g/mol
• Exact Mass: 1137.49401512 g/mol
• Topological Polar Surface Area (TPSA): 354.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 1.34
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 20

Synonyms

• DTXSID401335442
• 239088-24-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6668	66.68%
Caco-2	-	0.8661	86.61%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Lysosomes	0.3465	34.65%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8132	81.32%
OATP1B3 inhibitior	+	0.9125	91.25%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9083	90.83%
P-glycoprotein inhibitior	+	0.7480	74.80%
P-glycoprotein substrate	+	0.8819	88.19%
CYP3A4 substrate	+	0.7455	74.55%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.8471	84.71%
CYP3A4 inhibition	-	0.8397	83.97%
CYP2C9 inhibition	-	0.7637	76.37%
CYP2C19 inhibition	-	0.7606	76.06%
CYP2D6 inhibition	-	0.8595	85.95%
CYP1A2 inhibition	-	0.7867	78.67%
CYP2C8 inhibition	+	0.7811	78.11%
CYP inhibitory promiscuity	-	0.9358	93.58%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.5535	55.35%
Carcinogenicity (trinary)	Non-required	0.6001	60.01%
Eye corrosion	-	0.9787	97.87%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.7709	77.09%
Skin corrosion	-	0.9166	91.66%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6601	66.01%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6147	61.47%
skin sensitisation	-	0.8476	84.76%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.4792	47.92%
Acute Oral Toxicity (c)	III	0.5973	59.73%
Estrogen receptor binding	+	0.7986	79.86%
Androgen receptor binding	+	0.7563	75.63%
Thyroid receptor binding	+	0.6056	60.56%
Glucocorticoid receptor binding	+	0.7014	70.14%
Aromatase binding	+	0.5878	58.78%
PPAR gamma	+	0.8220	82.20%
Honey bee toxicity	-	0.6357	63.57%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9396	93.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.88%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.82%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.99%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	96.81%	95.93%
CHEMBL4072	P07858	Cathepsin B	96.30%	93.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	96.26%	97.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	95.96%	90.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.82%	94.45%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	94.27%	97.64%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	93.97%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.97%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.23%	97.09%
CHEMBL3837	P07711	Cathepsin L	92.12%	96.61%
CHEMBL1801	P00747	Plasminogen	92.07%	92.44%
CHEMBL255	P29275	Adenosine A2b receptor	91.58%	98.59%
CHEMBL333	P08253	Matrix metalloproteinase-2	90.89%	96.31%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.22%	93.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.42%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.96%	99.17%
CHEMBL4588	P22894	Matrix metalloproteinase 8	88.85%	94.66%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.50%	93.03%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.75%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.35%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.29%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.19%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.89%	96.38%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.10%	92.67%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.30%	82.38%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	82.56%	95.34%
CHEMBL340	P08684	Cytochrome P450 3A4	82.52%	91.19%
CHEMBL4393	P39900	Matrix metalloproteinase 12	81.65%	92.22%
CHEMBL2094135	Q96BI3	Gamma-secretase	81.34%	98.05%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	81.34%	95.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.45%	97.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.43%	91.11%

Plants that contains it

• Elsholtzia bodinieri
• Ipomoea purpurea

Cross-Links

• PubChem: 10701454
• NPASS: NPC289980
• LOTUS: LTS0073953
• wikiData: Q105117472