(3s,6s,9s,12r)-6-[(1-Methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-3-sec-butyl-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone

Details

• Internal ID: 426cf6fd-cbfc-4a54-a514-baa8f4d05b1d
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone
• SMILES (Canonical): CCC(C)C1C(=O)N2CCCCC2C(=O)NC(C(=O)NC(C(=O)N1)CC3=CN(C4=CC=CC=C43)OC)CCCCCC(=O)CC
• SMILES (Isomeric): CCC(C)[C@H]1C(=O)N2CCCC[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC3=CN(C4=CC=CC=C43)OC)CCCCCC(=O)CC
• InChI: InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22?,26-,27-,29+,30-/m0/s1
• InChI Key: JWOGUUIOCYMBPV-LQJYRIKDSA-N
• Popularity: 120 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₉N₅O₆
• Molecular Weight: 623.80 g/mol
• Exact Mass: 623.36828430 g/mol
• Topological Polar Surface Area (TPSA): 139.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 12

Synonyms

• SCHEMBL19605498
• BDBM25142
• CHEBI:125423
• Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinexcarbonyl]
• BRD-A63989068-001-01-2
• Q27216040
• (3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxy-3-indolyl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone
• (3S,6S,9S,15aR)-9-[(2R)-butan-2-yl]-6-[(1-methoxy-1H-indol-3-yl)methyl]-3-(6-oxooctyl)-tetradecahydro-1H-pyrido[1,2-a][,,,]cyclododecane-1,4,7,10-tetrone
• 6-Sec-Butyl-9-(1-methoxy-1H-indol-3-ylmethyl)-12-(6-oxo-octyl)-decahydro-4a,7,10,13-tetraaza-benzocyclododecene-5,8,11,14-tetraone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9260	92.60%
Caco-2	-	0.8236	82.36%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6065	60.65%
OATP2B1 inhibitior	-	0.5684	56.84%
OATP1B1 inhibitior	+	0.8558	85.58%
OATP1B3 inhibitior	+	0.9270	92.70%
MATE1 inhibitior	-	0.7435	74.35%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9444	94.44%
P-glycoprotein inhibitior	+	0.8049	80.49%
P-glycoprotein substrate	+	0.8258	82.58%
CYP3A4 substrate	+	0.6943	69.43%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8265	82.65%
CYP3A4 inhibition	+	0.6375	63.75%
CYP2C9 inhibition	-	0.6322	63.22%
CYP2C19 inhibition	-	0.7007	70.07%
CYP2D6 inhibition	-	0.7521	75.21%
CYP1A2 inhibition	-	0.8623	86.23%
CYP2C8 inhibition	+	0.6151	61.51%
CYP inhibitory promiscuity	-	0.7380	73.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.5850	58.50%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9447	94.47%
Skin irritation	-	0.7826	78.26%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6587	65.87%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.5824	58.24%
skin sensitisation	-	0.8830	88.30%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5699	56.99%
Acute Oral Toxicity (c)	III	0.6376	63.76%
Estrogen receptor binding	+	0.7622	76.22%
Androgen receptor binding	+	0.5440	54.40%
Thyroid receptor binding	+	0.5189	51.89%
Glucocorticoid receptor binding	+	0.7279	72.79%
Aromatase binding	+	0.5552	55.52%
PPAR gamma	+	0.7189	71.89%
Honey bee toxicity	-	0.8013	80.13%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9504	95.04%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	150 nM	IC50	via Super-PRED
CHEMBL325	Q13547	Histone deacetylase 1	0.04 nM	Ki	via Super-PRED
CHEMBL1937	Q92769	Histone deacetylase 2	0.12 nM	Ki	via Super-PRED
CHEMBL1829	O15379	Histone deacetylase 3	0.26 nM	Ki	via Super-PRED
CHEMBL2111363	O15379	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	1.5 nM	Ki	via Super-PRED
CHEMBL1865	Q9UBN7	Histone deacetylase 6	123.4 nM	Ki	via Super-PRED
CHEMBL3192	Q9BY41	Histone deacetylase 8	49 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.71%	96.09%
CHEMBL2581	P07339	Cathepsin D	99.23%	98.95%
CHEMBL3524	P56524	Histone deacetylase 4	99.08%	92.97%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.01%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	97.63%	94.45%
CHEMBL5103	Q969S8	Histone deacetylase 10	97.40%	90.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.96%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.15%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.64%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.05%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	91.26%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.25%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.81%	82.69%
CHEMBL240	Q12809	HERG	87.98%	89.76%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.92%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.43%	89.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.38%	82.38%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	87.25%	97.64%
CHEMBL2443	P49862	Kallikrein 7	86.53%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	85.22%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.99%	85.14%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	83.86%	98.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.80%	89.62%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.53%	97.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.46%	91.71%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.11%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.53%	99.17%

Plants that contains it

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Cross-Links

• PubChem: 467801
• LOTUS: LTS0254939
• wikiData: Q27216040