2-amino-4,6-dimethyl-3-oxo-1-N-[(3R,6S,7R,10S,16S)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propan-2-yl)-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-9-N-[(3R,6S,7R,16S)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propan-2-yl)-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]phenoxazine-1,9-dicarboxamide

Details

• Internal ID: e8acd43f-0dde-4931-80be-2464d7831f5a
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: 2-amino-4,6-dimethyl-3-oxo-1-N-[(3R,6S,7R,10S,16S)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propan-2-yl)-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-9-N-[(3R,6S,7R,16S)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propan-2-yl)-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]phenoxazine-1,9-dicarboxamide
• SMILES (Canonical): CC1C(C(=O)NC(C(=O)N2CCCC2C(=O)N(CC(=O)N(C(C(=O)O1)C(C)C)C)C)C(C)C)NC(=O)C3=C4C(=C(C=C3)C)OC5=C(C(=O)C(=C(C5=N4)C(=O)NC6C(OC(=O)C(N(C(=O)CN(C(=O)C7CCCN7C(=O)C(NC6=O)C(C)C)C)C)C(C)C)C)N)C
• SMILES (Isomeric): C[C@@H]1[C@@H](C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N(CC(=O)N([C@H](C(=O)O1)C(C)C)C)C)C(C)C)NC(=O)C3=C(C(=O)C(=C4C3=NC5=C(C=CC(=C5O4)C)C(=O)N[C@H]6[C@H](OC(=O)C(N(C(=O)CN(C(=O)[C@@H]7CCCN7C(=O)[C@H](NC6=O)C(C)C)C)C)C(C)C)C)C)N
• InChI: InChI=1S/C62H86N12O16/c1-27(2)42-59(84)73-23-17-19-36(73)57(82)69(13)25-38(75)71(15)48(29(5)6)61(86)88-33(11)44(55(80)65-42)67-53(78)35-22-21-31(9)51-46(35)64-47-40(41(63)50(77)32(10)52(47)90-51)54(79)68-45-34(12)89-62(87)49(30(7)8)72(16)39(76)26-70(14)58(83)37-20-18-24-74(37)60(85)43(28(3)4)66-56(45)81/h21-22,27-30,33-34,36-37,42-45,48-49H,17-20,23-26,63H2,1-16H3,(H,65,80)(H,66,81)(H,67,78)(H,68,79)/t33-,34-,36+,37+,42-,43-,44+,45+,48?,49+/m1/s1
• InChI Key: RJURFGZVJUQBHK-HUZQGMAJSA-N
• Popularity: 18,957 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₂H₈₆N₁₂O₁₆
• Molecular Weight: 1255.40 g/mol
• Exact Mass: 1254.62847470 g/mol
• Topological Polar Surface Area (TPSA): 356.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 0.73
• H-Bond Acceptor: 18
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• 50-76-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6825	68.25%
Caco-2	-	0.8566	85.66%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Nucleus	0.3958	39.58%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8023	80.23%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9698	96.98%
P-glycoprotein inhibitior	+	0.7454	74.54%
P-glycoprotein substrate	+	0.8649	86.49%
CYP3A4 substrate	+	0.7064	70.64%
CYP2C9 substrate	+	0.7925	79.25%
CYP2D6 substrate	-	0.8524	85.24%
CYP3A4 inhibition	-	0.8614	86.14%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.6524	65.24%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6015	60.15%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.8969	89.69%
Skin irritation	-	0.7807	78.07%
Skin corrosion	-	0.9344	93.44%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7455	74.55%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.9092	90.92%
skin sensitisation	-	0.8785	87.85%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.6418	64.18%
Acute Oral Toxicity (c)	I	0.8168	81.68%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.6319	63.19%
Glucocorticoid receptor binding	+	0.6981	69.81%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.8709	87.09%
Honey bee toxicity	-	0.7581	75.81%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9078	90.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	31.6 nM	Potency	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	251.2 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	316.2 nM; 354.8 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.82%	99.23%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	93.93%	93.65%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	93.62%	90.71%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	92.81%	81.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL3837	P07711	Cathepsin L	89.17%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.04%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.84%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.76%	94.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.70%	93.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.10%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.99%	97.09%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.32%	82.38%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.73%	90.08%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.31%	90.93%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.73%	96.67%

Plants that contains it

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Cross-Links

• PubChem: 131954673
• LOTUS: LTS0199470
• wikiData: Q104401916