(Z)-N-[(2S)-1-[[(2S)-1-[[(2S,3S)-1,3-dihydroxy-5-[[(2S)-1-[[(3S,6S,11R)-3-[(4-hydroxyphenyl)methyl]-4-methyl-2,5,8-trioxo-6-propan-2-yl-1-oxa-4,7-diazacyclododec-9-en-11-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]dec-3-enamide

Details

• Internal ID: 478d800a-7271-4a31-bade-2895a2346f2d
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (Z)-N-[(2S)-1-[[(2S)-1-[[(2S,3S)-1,3-dihydroxy-5-[[(2S)-1-[[(3S,6S,11R)-3-[(4-hydroxyphenyl)methyl]-4-methyl-2,5,8-trioxo-6-propan-2-yl-1-oxa-4,7-diazacyclododec-9-en-11-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]dec-3-enamide
• SMILES (Canonical): CCCCCCC=CCC(=O)NC(CO)C(=O)NC(C(C)C)C(=O)NC(CO)C(CC(=O)NC(C(C)C)C(=O)NC1COC(=O)C(N(C(=O)C(NC(=O)C=C1)C(C)C)C)CC2=CC=C(C=C2)O)O
• SMILES (Isomeric): CCCCCC/C=C\CC(=O)N[C@@H](CO)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CO)[C@H](CC(=O)N[C@@H](C(C)C)C(=O)N[C@H]1COC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)C=C1)C(C)C)C)CC2=CC=C(C=C2)O)O
• InChI: InChI=1S/C48H75N7O13/c1-9-10-11-12-13-14-15-16-38(60)50-35(26-57)44(63)54-42(29(4)5)46(65)51-34(25-56)37(59)24-40(62)53-41(28(2)3)45(64)49-32-19-22-39(61)52-43(30(6)7)47(66)55(8)36(48(67)68-27-32)23-31-17-20-33(58)21-18-31/h14-15,17-22,28-30,32,34-37,41-43,56-59H,9-13,16,23-27H2,1-8H3,(H,49,64)(H,50,60)(H,51,65)(H,52,61)(H,53,62)(H,54,63)/b15-14-,22-19?/t32-,34+,35+,36+,37+,41+,42+,43+/m1/s1
• InChI Key: MGOHJFNPHUCXQI-ZOZVJHEXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₅N₇O₁₃
• Molecular Weight: 958.10 g/mol
• Exact Mass: 957.54228547 g/mol
• Topological Polar Surface Area (TPSA): 302.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 0.40
• H-Bond Acceptor: 13
• H-Bond Donor: 10
• Rotatable Bonds: 25

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7518	75.18%
Caco-2	-	0.8627	86.27%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4675	46.75%
OATP2B1 inhibitior	-	0.8523	85.23%
OATP1B1 inhibitior	+	0.8030	80.30%
OATP1B3 inhibitior	+	0.8837	88.37%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9520	95.20%
P-glycoprotein inhibitior	+	0.7411	74.11%
P-glycoprotein substrate	+	0.8601	86.01%
CYP3A4 substrate	+	0.7311	73.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8731	87.31%
CYP3A4 inhibition	+	0.8683	86.83%
CYP2C9 inhibition	-	0.8877	88.77%
CYP2C19 inhibition	-	0.8629	86.29%
CYP2D6 inhibition	-	0.8895	88.95%
CYP1A2 inhibition	-	0.9246	92.46%
CYP2C8 inhibition	+	0.7877	78.77%
CYP inhibitory promiscuity	-	0.9407	94.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6134	61.34%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9006	90.06%
Skin irritation	-	0.7781	77.81%
Skin corrosion	-	0.9249	92.49%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6717	67.17%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.6830	68.30%
skin sensitisation	-	0.8691	86.91%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6590	65.90%
Acute Oral Toxicity (c)	III	0.6506	65.06%
Estrogen receptor binding	+	0.8100	81.00%
Androgen receptor binding	+	0.7211	72.11%
Thyroid receptor binding	+	0.5844	58.44%
Glucocorticoid receptor binding	+	0.6557	65.57%
Aromatase binding	+	0.6280	62.80%
PPAR gamma	+	0.7946	79.46%
Honey bee toxicity	-	0.7825	78.25%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6515	65.15%
Fish aquatic toxicity	+	0.9219	92.19%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3891	P07384	Calpain 1	3 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.99%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	99.19%	99.17%
CHEMBL5103	Q969S8	Histone deacetylase 10	98.47%	90.08%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.44%	91.11%
CHEMBL4072	P07858	Cathepsin B	97.92%	93.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.35%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.67%	94.45%
CHEMBL4588	P22894	Matrix metalloproteinase 8	95.13%	94.66%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	95.07%	93.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.40%	92.08%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	94.23%	90.71%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	94.09%	93.10%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.25%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.02%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	90.26%	89.67%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	90.25%	96.90%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.25%	97.29%
CHEMBL236	P41143	Delta opioid receptor	87.64%	99.35%
CHEMBL1781	P11387	DNA topoisomerase I	87.27%	97.00%
CHEMBL220	P22303	Acetylcholinesterase	87.06%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.51%	93.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.14%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.51%	95.56%
CHEMBL3776	Q14790	Caspase-8	85.15%	97.06%
CHEMBL2514	O95665	Neurotensin receptor 2	85.00%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.88%	89.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.35%	97.09%
CHEMBL3837	P07711	Cathepsin L	83.72%	96.61%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.91%	92.86%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.12%	100.00%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	81.01%	92.29%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	80.80%	89.33%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.78%	85.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.68%	88.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.22%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.13%	96.47%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139583633
• LOTUS: LTS0088109
• wikiData: Q75064825