Halicylindramide D

Details

• Internal ID: b38a5046-4c9d-463e-a3a5-2ca3dcb496ab
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2S)-3-[[(3R,9R,12S,15S,16R)-3-(2-amino-2-oxoethyl)-12-(3-amino-3-oxopropyl)-9-benzyl-13,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-15-yl]amino]-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-3-(4-bromophenyl)-2-[[(2R)-2-formamidopropanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-oxopropane-1-sulfonic acid
• InChI: InChI=1S/C73H100BrN19O20S/c1-37(2)58(90-69(106)59(38(3)4)89-67(104)54-20-14-28-93(54)70(107)50(87-61(98)39(5)82-36-94)30-42-21-23-44(74)24-22-42)68(105)86-49(31-43-33-80-46-18-12-11-17-45(43)46)64(101)84-47(19-13-27-79-73(77)78)63(100)88-52(35-114(110,111)112)65(102)91-60-40(6)113-72(109)51(32-56(76)96)83-57(97)34-81-62(99)48(29-41-15-9-8-10-16-41)85-66(103)53(25-26-55(75)95)92(7)71(60)108/h8-12,15-18,21-24,33,36-40,47-54,58-60,80H,13-14,19-20,25-32,34-35H2,1-7H3,(H2,75,95)(H2,76,96)(H,81,99)(H,82,94)(H,83,97)(H,84,101)(H,85,103)(H,86,105)(H,87,98)(H,88,100)(H,89,104)(H,90,106)(H,91,102)(H4,77,78,79)(H,110,111,112)/t39-,40-,47+,48-,49-,50+,51-,52-,53+,54+,58+,59-,60+/m1/s1
• InChI Key: LCUFSEOEZNOMTE-HUKYMJEXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₇₃H₁₀₀BrN₁₉O₂₀S
• Molecular Weight: 1675.70 g/mol
• Exact Mass: 1673.62961 g/mol
• Topological Polar Surface Area (TPSA): 614.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -4.06
• H-Bond Acceptor: 20
• H-Bond Donor: 18
• Rotatable Bonds: 36

Synonyms

• 172548-80-0
• RefChem:145056
• (2S)-3-(((3R,9R,12S,15S,16R)-3-(2-amino-2-oxoethyl)-12-(3-amino-3-oxopropyl)-9-benzyl-13,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-15-yl)amino)-2-(((2S)-2-(((2R)-2-(((2S)-2-(((2R)-2-(((2S)-1-((2S)-3-(4-bromophenyl)-2-(((2R)-2-formamidopropanoyl)amino)propanoyl)pyrrolidine-2-carbonyl)amino)-3-methylbutanoyl)amino)-3-methylbutanoyl)amino)-3-(1H-indol-3-yl)propanoyl)amino)-5-carbamimidamidopentanoyl)amino)-3-oxopropane-1-sulfonic acid
• (2S)-N-((2R)-1-((2S)-1-((2R)-1-((2S)-1-((2S)-1-(((3R,9R,12S,15S,16R)-9-benzyl-5,8,11-trihydroxy-3-(2-hydroxy-2-iminoethyl)-12-(3-hydroxy-3-iminopropyl)-13,16-dimethyl-2,14-dioxo-1-oxa-4,7,10,13-tetrazacyclohexadeca-4,7,10-trien-15-yl)imino)-1-hydroxy-3-sulfopropan-2-yl)imino-5-carbamimidamido-1-hydroxypentan-2-yl)imino-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)imino-1-hydroxy-3-methylbutan-2-yl)imino-1-hydroxy-3-methylbutan-2-yl)-1-((2S)-3-(4-bromophenyl)-2-(((2R)-1-hydroxy-2-(hydroxymethylideneamino)propylidene)amino)propanoyl)pyrrolidine-2-carboximidic acid
• CHEMBL1208206

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7234	72.34%
Caco-2	-	0.8628	86.28%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Lysosomes	0.4145	41.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8048	80.48%
OATP1B3 inhibitior	+	0.9269	92.69%
MATE1 inhibitior	-	0.6844	68.44%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9626	96.26%
P-glycoprotein inhibitior	+	0.7420	74.20%
P-glycoprotein substrate	+	0.8795	87.95%
CYP3A4 substrate	+	0.7649	76.49%
CYP2C9 substrate	-	0.5985	59.85%
CYP2D6 substrate	-	0.8371	83.71%
CYP3A4 inhibition	-	0.7042	70.42%
CYP2C9 inhibition	-	0.7140	71.40%
CYP2C19 inhibition	-	0.6721	67.21%
CYP2D6 inhibition	-	0.8475	84.75%
CYP1A2 inhibition	-	0.7115	71.15%
CYP2C8 inhibition	+	0.8393	83.93%
CYP inhibitory promiscuity	-	0.8540	85.40%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5100	51.00%
Carcinogenicity (trinary)	Non-required	0.5626	56.26%
Eye corrosion	-	0.9762	97.62%
Eye irritation	-	0.8954	89.54%
Skin irritation	-	0.7557	75.57%
Skin corrosion	-	0.9091	90.91%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7274	72.74%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5599	55.99%
skin sensitisation	-	0.8264	82.64%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8550	85.50%
Acute Oral Toxicity (c)	III	0.5717	57.17%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.6950	69.50%
Thyroid receptor binding	+	0.7982	79.82%
Glucocorticoid receptor binding	+	0.8320	83.20%
Aromatase binding	+	0.8147	81.47%
PPAR gamma	+	0.7840	78.40%
Honey bee toxicity	-	0.6116	61.16%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9690	96.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.90%	98.95%
CHEMBL333	P08253	Matrix metalloproteinase-2	99.84%	96.31%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	99.75%	98.33%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	99.74%	97.64%
CHEMBL3837	P07711	Cathepsin L	99.30%	96.61%
CHEMBL5103	Q969S8	Histone deacetylase 10	99.28%	90.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	99.17%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.95%	96.09%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	98.85%	91.81%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	98.04%	88.42%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.97%	91.11%
CHEMBL321	P14780	Matrix metalloproteinase 9	97.50%	92.12%
CHEMBL2514	O95665	Neurotensin receptor 2	97.37%	100.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	97.26%	97.31%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	97.14%	93.00%
CHEMBL4588	P22894	Matrix metalloproteinase 8	97.13%	94.66%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	96.70%	82.38%
CHEMBL4644	P41968	Melanocortin receptor 3	96.09%	99.52%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	95.97%	95.00%
CHEMBL4123	P30989	Neurotensin receptor 1	95.85%	96.67%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	95.83%	85.00%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	95.62%	98.24%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	95.56%	93.10%
CHEMBL3310	Q96DB2	Histone deacetylase 11	95.43%	88.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	95.41%	96.90%
CHEMBL1293287	P14735	Insulin-degrading enzyme	95.33%	88.10%
CHEMBL259	P32245	Melanocortin receptor 4	95.21%	95.38%
CHEMBL261	P00915	Carbonic anhydrase I	94.73%	96.76%
CHEMBL3729	P22748	Carbonic anhydrase IV	94.40%	99.23%
CHEMBL4393	P39900	Matrix metalloproteinase 12	94.06%	92.22%
CHEMBL4777	P25929	Neuropeptide Y receptor type 1	93.94%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.84%	99.23%
CHEMBL4040	P28482	MAP kinase ERK2	93.51%	83.82%
CHEMBL4227	P25090	Lipoxin A4 receptor	93.41%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	93.31%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.13%	95.89%
CHEMBL3524	P56524	Histone deacetylase 4	93.11%	92.97%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.31%	89.00%
CHEMBL4801	P29466	Caspase-1	92.12%	96.85%
CHEMBL2179	P04062	Beta-glucocerebrosidase	91.91%	85.31%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.70%	94.45%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	90.60%	96.11%
CHEMBL1801	P00747	Plasminogen	90.53%	92.44%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.33%	97.09%
CHEMBL4073	P09237	Matrix metalloproteinase 7	90.32%	97.56%
CHEMBL340	P08684	Cytochrome P450 3A4	90.05%	91.19%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	89.77%	97.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.53%	97.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.68%	93.03%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	88.67%	96.03%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	88.16%	96.28%
CHEMBL1937	Q92769	Histone deacetylase 2	88.12%	94.75%
CHEMBL255	P29275	Adenosine A2b receptor	87.95%	98.59%
CHEMBL4608	P33032	Melanocortin receptor 5	87.95%	97.00%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	87.41%	100.00%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	86.94%	95.34%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	86.86%	92.32%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	86.47%	96.25%
CHEMBL1075317	P61964	WD repeat-containing protein 5	85.61%	96.33%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	85.45%	100.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	85.27%	98.05%
CHEMBL2535	P11166	Glucose transporter	84.89%	98.75%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.48%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.84%	96.00%
CHEMBL5500	Q92831	Histone acetyltransferase PCAF	82.54%	91.96%
CHEMBL5028	O14672	ADAM10	82.37%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.91%	93.56%
CHEMBL1900	P15121	Aldose reductase	81.69%	92.38%
CHEMBL1921	P47901	Vasopressin V1b receptor	81.14%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.74%	99.17%
CHEMBL2327	P21452	Neurokinin 2 receptor	80.67%	98.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.65%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.55%	94.00%
CHEMBL5646	Q6L5J4	FML2_HUMAN	80.06%	100.00%

Plants that contains it

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Cross-Links

• PubChem: 16131321
• LOTUS: LTS0255023
• wikiData: Q105149992