(4S)-5-[[(2S,5S,8S,11R,12S,15S,18S,21R)-2-butyl-21-hydroxy-5,15-bis[(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]amino]-4-(hexanoylamino)-5-oxopentanoic acid

Details

• Internal ID: 7b816099-68fb-4439-9122-e04ed8e2d5b1
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (4S)-5-[[(2S,5S,8S,11R,12S,15S,18S,21R)-2-butyl-21-hydroxy-5,15-bis[(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]amino]-4-(hexanoylamino)-5-oxopentanoic acid
• SMILES (Canonical): CCCCCC(=O)NC(CCC(=O)O)C(=O)NC1C(OC(=O)C(NC(=O)C(N(C(=O)C(N2C(CCC(C2=O)NC(=O)C(NC1=O)CC3=CC=C(C=C3)O)O)CCCC)C)CC4=CC=C(C=C4)O)C(C)C)C
• SMILES (Isomeric): CCCCCC(=O)N[C@@H](CCC(=O)O)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@@H](NC1=O)CC3=CC=C(C=C3)O)O)CCCC)C)CC4=CC=C(C=C4)O)C(C)C)C
• InChI: InChI=1S/C50H71N7O14/c1-7-9-11-13-39(60)51-34(23-25-41(62)63)44(64)55-43-29(5)71-50(70)42(28(3)4)54-46(66)38(27-31-16-20-33(59)21-17-31)56(6)49(69)37(12-10-8-2)57-40(61)24-22-35(48(57)68)52-45(65)36(53-47(43)67)26-30-14-18-32(58)19-15-30/h14-21,28-29,34-38,40,42-43,58-59,61H,7-13,22-27H2,1-6H3,(H,51,60)(H,52,65)(H,53,67)(H,54,66)(H,55,64)(H,62,63)/t29-,34+,35+,36+,37+,38+,40-,42+,43+/m1/s1
• InChI Key: FDGKXYTYNOAXMH-YEZRCUTOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₁N₇O₁₄
• Molecular Weight: 994.10 g/mol
• Exact Mass: 993.50589996 g/mol
• Topological Polar Surface Area (TPSA): 310.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 18

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5576	55.76%
Caco-2	-	0.8672	86.72%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5061	50.61%
OATP2B1 inhibitior	-	0.7165	71.65%
OATP1B1 inhibitior	+	0.8110	81.10%
OATP1B3 inhibitior	+	0.9040	90.40%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8890	88.90%
BSEP inhibitior	+	0.9345	93.45%
P-glycoprotein inhibitior	+	0.7445	74.45%
P-glycoprotein substrate	+	0.8860	88.60%
CYP3A4 substrate	+	0.7236	72.36%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	-	0.8595	85.95%
CYP3A4 inhibition	-	0.6017	60.17%
CYP2C9 inhibition	-	0.8770	87.70%
CYP2C19 inhibition	-	0.8374	83.74%
CYP2D6 inhibition	-	0.8515	85.15%
CYP1A2 inhibition	-	0.9278	92.78%
CYP2C8 inhibition	+	0.7293	72.93%
CYP inhibitory promiscuity	-	0.9619	96.19%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6424	64.24%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9038	90.38%
Skin irritation	-	0.7939	79.39%
Skin corrosion	-	0.9272	92.72%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3643	36.43%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8957	89.57%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7388	73.88%
Acute Oral Toxicity (c)	III	0.6664	66.64%
Estrogen receptor binding	+	0.8365	83.65%
Androgen receptor binding	+	0.7194	71.94%
Thyroid receptor binding	+	0.5781	57.81%
Glucocorticoid receptor binding	+	0.5550	55.50%
Aromatase binding	+	0.5804	58.04%
PPAR gamma	+	0.7814	78.14%
Honey bee toxicity	-	0.7666	76.66%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5815	58.15%
Fish aquatic toxicity	+	0.9638	96.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.94%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	99.06%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	98.02%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.97%	96.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	97.70%	90.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.13%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.02%	91.11%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	94.59%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	93.93%	93.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	93.71%	93.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	92.68%	92.08%
CHEMBL4072	P07858	Cathepsin B	92.59%	93.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.62%	90.71%
CHEMBL236	P41143	Delta opioid receptor	90.56%	99.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.51%	95.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	90.48%	82.38%
CHEMBL5255	O00206	Toll-like receptor 4	90.47%	92.50%
CHEMBL1949	P62937	Cyclophilin A	90.26%	98.57%
CHEMBL4608	P33032	Melanocortin receptor 5	89.59%	97.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.40%	89.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.68%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.57%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.51%	97.14%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	86.89%	97.64%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	86.31%	95.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.25%	99.23%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.00%	90.93%
CHEMBL4588	P22894	Matrix metalloproteinase 8	86.00%	94.66%
CHEMBL4644	P41968	Melanocortin receptor 3	85.44%	99.52%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.39%	85.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.38%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.58%	97.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.40%	89.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.01%	97.25%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.90%	100.00%
CHEMBL3891	P07384	Calpain 1	83.17%	93.04%
CHEMBL259	P32245	Melanocortin receptor 4	82.73%	95.38%
CHEMBL2514	O95665	Neurotensin receptor 2	81.46%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.99%	96.47%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.58%	97.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.07%	100.00%

Plants that contains it

• Hagenia abyssinica

Cross-Links

• PubChem: 163103950
• LOTUS: LTS0178400
• wikiData: Q105375116